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    Paul Ortiz De Montellano, PhD

    TitleProfessor
    SchoolUCSF School of Pharmacy
    DepartmentPharmaceutical Chemistry
    Address600 16th Street
    San Francisco CA 94158
    Phone415-476-2903
    vCardDownload vCard

      Collapse Biography 
      Collapse Education and Training
      Massachusetts Institute of TechnologyB.S.Chemistry1964
      Harvard UniversityM.A., Ph.D.Chemistry1968
      Eidgenossische Technische Hochschule, ZurichPostdocChemistry1969
      Collapse Awards and Honors
      Harvard University1966 - 1968NIH Graduate Fellowship
      ETH Switzerland1968 - 1969NATO Postdoctoral Fellow
      1978 - 1992Alfred P. Sloan Research Fellow
      UCSF School of Pharmacy1985Joseph M. Long Foundation Prize for Excellence in Teaching
      UCSF1988Academic Senate Award for Distinction in Teaching
      UCSF1990125 Most Outstanding People
      1990International Society for Neutron Capture Therapy Award for Excellence in Research
      1988Elected Fellow, American Association for the Advancement of Scie
      1989 - 1999MERIT Grant Award, National Institutes of Health
      Université René Descartes, Paris, France1993 - 1994Rhône-Poulenc Professor
      1994Bernard B. Brodie Award in Drug Metabolism, American Society for Pharmacology and Experimental Thera
      UCSF School of Pharmacy2006 - 2013Dean’s Recognition for Excellence in Teaching
      2003Ingelheim Boehringer Lecture Award, Division of Chemical Toxicology, 226th American Chemical Society
      2006Volwiler Research Achievement Award, American Association of Colleges of Pharmacy
      2007RT Williams Distinguished Scientific Achievement Award, International Society for the Study of Xenob
      UCSF2009Champion of Diversity Award

      Collapse Overview 
      Collapse Overview
      Heme-containing proteins are critical for the function of essentially all life forms. In humans, they are involved in respiration, the synthesis of hormones and other vital molecules, the elimination of drugs, and various signaling pathways. My laboratory has investigated the structure, mechanism, biochemistry and role of heme proteins for many years. We have focused particularly on the human cytochrome P450, peroxidase, and heme oxygenase enzymes. Our contributions in this area include crystal structures of bacterial P450 enzymes and the human heme oxygenase, clarification of the mechanism of cytochrome P450 enzymes, the development of methods for the mechanism-based inactivation of P450 enzymes, and more recently studies of human cytochrome P450 enzymes that are selectively expressed in cancer cells and are potentially useful in the activation of anticancer drugs. We currently also work on two classes of heme proteins in Mycobacterium tuberculosis, the causative agent of tuberculosis: (a) the twenty cytochrome P450 enzymes, some of which potential targets for anti-tuberculosis drugs, and (b) the gas sensor that initiates the dormant, persistent stage of tuberculosis that is difficult to eradicate and which can be reactivated when the immune system is compromised.

      The studies in my laboratory employ a diversity of techniques, including organic synthesis, molecular biology, enzymology, and multiple spectroscopic techniques. We frequently collaborate with laboratories that have complementary expertise in organic synthesis, X-ray crystallography, NMR, or resonance Raman spectroscopy.


      Collapse ORNG Applications 
      Collapse Awarded Grants
      Collapse Global Health

      Collapse Bibliographic 
      Collapse Publications
      Publications listed below are automatically derived from MEDLINE/PubMed and other sources, which might result in incorrect or missing publications. Researchers can login to make corrections and additions, or contact us for help.
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      1. Basudhar D, Madrona Y, Yukl ET, Sivaramakrishnan S, Nishida CR, Moënne-Loccoz P, Ortiz de Montellano PR. Distal Hydrogen-bonding Interactions in Ligand Sensing and Signaling by Mycobacterium tuberculosis DosS. J Biol Chem. 2016 Jul 29; 291(31):16100-11. PMID: 27235395.
        View in: PubMed
      2. Zhao Y, Wan D, Yang J, Hammock BD, Ortiz de Montellano PR. Catalytic Activities of Tumor-Specific Human Cytochrome P450 CYP2W1 Toward Endogenous Substrates. Drug Metab Dispos. 2016 May; 44(5):771-80. PMID: 26936974.
        View in: PubMed
      3. Frank DJ, Zhao Y, Wong SH, Basudhar D, De Voss JJ, Ortiz de Montellano PR. Cholesterol Analogs with Degradation-resistant Alkyl Side Chains Are Effective Mycobacterium tuberculosis Growth Inhibitors. J Biol Chem. 2016 Apr 1; 291(14):7325-33. PMID: 26833565.
        View in: PubMed
      4. Frank DJ, Waddling CA, La M, Ortiz de Montellano PR. Cytochrome P450 125A4, the Third Cholesterol C-26 Hydroxylase from Mycobacterium smegmatis. Biochemistry. 2015 Nov 24; 54(46):6909-16. PMID: 26522442; PMCID: PMC4660985 [Available on 11/01/16].
      5. Ortiz de Montellano PR. Heme and I. J Biol Chem. 2015 Sep 4; 290(36):21833-44. PMID: 26195628; PMCID: PMC4571939 [Available on 09/04/16].
      6. Conner KP, Cruce AA, Krzyaniak MD, Schimpf AM, Frank DJ, Ortiz de Montellano P, Atkins WM, Bowman MK. Drug modulation of water-heme interactions in low-spin P450 complexes of CYP2C9d and CYP125A1. Biochemistry. 2015 Feb 10; 54(5):1198-207. PMID: 25591012; PMCID: PMC4437715.
      7. Frank DJ, Madrona Y, Ortiz de Montellano PR. Cholesterol ester oxidation by mycobacterial cytochrome P450. J Biol Chem. 2014 Oct 31; 289(44):30417-25. PMID: 25210044; PMCID: PMC4215225.
      8. Varfaj F, Zulkifli SN, Park HG, Challinor VL, De Voss JJ, Ortiz de Montellano PR. Carbon-carbon bond cleavage in activation of the prodrug nabumetone. Drug Metab Dispos. 2014 May; 42(5):828-38. PMID: 24584631; PMCID: PMC3989788.
      9. Conner KP, Schimpf AM, Cruce AA, McLean KJ, Munro AW, Frank DJ, Krzyaniak MD, Ortiz de Montellano P, Bowman MK, Atkins WM. Strength of axial water ligation in substrate-free cytochrome P450s is isoform dependent. Biochemistry. 2014 Mar 11; 53(9):1428-34. PMID: 24576089; PMCID: PMC3985942.
      10. Nishida CR, Everett S, Ortiz de Montellano PR. Specificity determinants of CYP1B1 estradiol hydroxylation. Mol Pharmacol. 2013 Sep; 84(3):451-8. PMID: 23821647; PMCID: PMC3876821.
      11. García-Fernández E, Frank DJ, Galán B, Kells PM, Podust LM, García JL, Ortiz de Montellano PR. A highly conserved mycobacterial cholesterol catabolic pathway. Environ Microbiol. 2013 Aug; 15(8):2342-59. PMID: 23489718; PMCID: PMC3706556.
      12. Ortiz de Montellano PR. Cytochrome P450-activated prodrugs. Future Med Chem. 2013 Feb; 5(2):213-28. PMID: 23360144; PMCID: PMC3697796.
      13. Meitzler JL, Hinde S, Bánfi B, Nauseef WM, Ortiz de Montellano PR. Conserved cysteine residues provide a protein-protein interaction surface in dual oxidase (DUOX) proteins. J Biol Chem. 2013 Mar 8; 288(10):7147-57. PMID: 23362256; PMCID: PMC3591624.
      14. Aicart-Ramos C, Valhondo Falcón M, Ortiz de Montellano PR, Rodriguez-Crespo I. Covalent attachment of heme to the protein moiety in an insect E75 nitric oxide sensor. Biochemistry. 2012 Sep 18; 51(37):7403-16. PMID: 22946928; PMCID: PMC3448046.
      15. Varfaj F, Lampe JN, Ortiz de Montellano PR. Role of cysteine residues in heme binding to human heme oxygenase-2 elucidated by two-dimensional NMR spectroscopy. J Biol Chem. 2012 Oct 12; 287(42):35181-91. PMID: 22923613; PMCID: PMC3471713.
      16. Johnston JB, Singh AA, Clary AA, Chen CK, Hayes PY, Chow S, De Voss JJ, Ortiz de Montellano PR. Substrate analog studies of the ?-regiospecificity of Mycobacterium tuberculosis cholesterol metabolizing cytochrome P450 enzymes CYP124A1, CYP125A1 and CYP142A1. Bioorg Med Chem. 2012 Jul 1; 20(13):4064-81. PMID: 22647881; PMCID: PMC3376231.
      17. Sivaramakrishnan S, Ouellet H, Matsumura H, Guan S, Moënne-Loccoz P, Burlingame AL, Ortiz de Montellano PR. Proximal ligand electron donation and reactivity of the cytochrome P450 ferric-peroxo anion. J Am Chem Soc. 2012 Apr 18; 134(15):6673-84. PMID: 22444582; PMCID: PMC3329582.
      18. Vos MH, Bouzhir-Sima L, Lambry JC, Luo H, Eaton-Rye JJ, Ioanoviciu A, Ortiz de Montellano PR, Liebl U. Ultrafast ligand dynamics in the heme-based GAF sensor domains of the histidine kinases DosS and DosT from Mycobacterium tuberculosis. Biochemistry. 2012 Jan 10; 51(1):159-66. PMID: 22142262; PMCID: PMC3254832.
      19. Meitzler JL, Ortiz de Montellano PR. Structural stability and heme binding potential of the truncated human dual oxidase 2 (DUOX2) peroxidase domain. Arch Biochem Biophys. 2011 Aug 15; 512(2):197-203. PMID: 21704604; PMCID: PMC3139011.
      20. Sivaramakrishnan S, Ouellet H, Du J, McLean KJ, Medzihradszky KF, Dawson JH, Munro AW, Ortiz de Montellano PR. A novel intermediate in the reaction of seleno CYP119 with m-chloroperbenzoic acid. Biochemistry. 2011 Apr 12; 50(14):3014-24. PMID: 21381758; PMCID: PMC3071435.
      21. Yukl ET, Ioanoviciu A, Sivaramakrishnan S, Nakano MM, Ortiz de Montellano PR, Moënne-Loccoz P. Nitric oxide dioxygenation reaction in DevS and the initial response to nitric oxide in Mycobacterium tuberculosis. Biochemistry. 2011 Feb 15; 50(6):1023-8. PMID: 21250657; PMCID: PMC3079480.
      22. Ouellet H, Kells PM, Ortiz de Montellano PR, Podust LM. Reverse type I inhibitor of Mycobacterium tuberculosis CYP125A1. Bioorg Med Chem Lett. 2011 Jan 1; 21(1):332-7. PMID: 21109436; PMCID: PMC3011832.
      23. Ortiz de Montellano PR, Nelson SD. Rearrangement reactions catalyzed by cytochrome P450s. Arch Biochem Biophys. 2011 Mar 1; 507(1):95-110. PMID: 20971058; PMCID: PMC3039701.
      24. Meitzler JL, Brandman R, Ortiz de Montellano PR. Perturbed heme binding is responsible for the blistering phenotype associated with mutations in the Caenorhabditis elegans dual oxidase 1 (DUOX1) peroxidase domain. J Biol Chem. 2010 Dec 24; 285(52):40991-1000. PMID: 20947510; PMCID: PMC3003398.
      25. Nishida CR, Ortiz de Montellano PR. Bioactivation of antituberculosis thioamide and thiourea prodrugs by bacterial and mammalian flavin monooxygenases. Chem Biol Interact. 2011 Jun 30; 192(1-2):21-5. PMID: 20863819; PMCID: PMC3033498.
      26. Johnston JB, Ouellet H, Ortiz de Montellano PR. Functional redundancy of steroid C26-monooxygenase activity in Mycobacterium tuberculosis revealed by biochemical and genetic analyses. J Biol Chem. 2010 Nov 19; 285(47):36352-60. PMID: 20843794; PMCID: PMC2978563.
      27. Johnston JB, Ouellet H, Podust LM, Ortiz de Montellano PR. Structural control of cytochrome P450-catalyzed ?-hydroxylation. Arch Biochem Biophys. 2011 Mar 1; 507(1):86-94. PMID: 20727847; PMCID: PMC2997901.
      28. Ortiz de Montellano PR. Hydrocarbon hydroxylation by cytochrome P450 enzymes. Chem Rev. 2010 Feb 10; 110(2):932-48. PMID: 19769330; PMCID: PMC2820140.
      29. Peng D, Ogura H, Zhu W, Ma LH, Evans JP, Ortiz de Montellano PR, La Mar GN. Coupling of the distal hydrogen bond network to the exogenous ligand in substrate-bound, resting state human heme oxygenase. Biochemistry. 2009 Dec 1; 48(47):11231-42. PMID: 19842713; PMCID: PMC3008551.
      30. Johnston JB, Kells PM, Podust LM, Ortiz de Montellano PR. Biochemical and structural characterization of CYP124: a methyl-branched lipid omega-hydroxylase from Mycobacterium tuberculosis. Proc Natl Acad Sci U S A. 2009 Dec 8; 106(49):20687-92. PMID: 19933331.
        View in: PubMed
      31. Evans JP, Kandel S, Ortiz de Montellano PR. Isocyanides inhibit human heme oxygenases at the verdoheme stage. Biochemistry. 2009 Sep 22; 48(37):8920-8. PMID: 19694439; PMCID: PMC2857669.
      32. Ouellet H, Johnston JB, Ortiz de Montellano PR. The Mycobacterium tuberculosis cytochrome P450 system. Arch Biochem Biophys. 2010 Jan 1; 493(1):82-95. PMID: 19635450; PMCID: PMC2812603.
      33. Ioanoviciu A, Meharenna YT, Poulos TL, Ortiz de Montellano PR. DevS oxy complex stability identifies this heme protein as a gas sensor in Mycobacterium tuberculosis dormancy. Biochemistry. 2009 Jun 30; 48(25):5839-48. PMID: 19463006; PMCID: PMC2756985.
      34. Dey A, Jiang Y, Ortiz de Montellano P, Hodgson KO, Hedman B, Solomon EI. S K-edge XAS and DFT calculations on cytochrome P450: covalent and ionic contributions to the cysteine-Fe bond and their contribution to reactivity. J Am Chem Soc. 2009 Jun 10; 131(22):7869-78. PMID: 19438234; PMCID: PMC2734335.
      35. Meitzler JL, Ortiz de Montellano PR. Caenorhabditis elegans and human dual oxidase 1 (DUOX1) "peroxidase" domains: insights into heme binding and catalytic activity. J Biol Chem. 2009 Jul 10; 284(28):18634-43. PMID: 19460756; PMCID: PMC2707201.
      36. Kim D, Ortiz de Montellano PR. Tricistronic overexpression of cytochrome P450cam, putidaredoxin, and putidaredoxin reductase provides a useful cell-based catalytic system. Biotechnol Lett. 2009 Sep; 31(9):1427-31. PMID: 19458919; PMCID: PMC2844094.
      37. Ogura H, Evans JP, Peng D, Satterlee JD, Ortiz de Montellano PR, La Mar GN. The orbital ground state of the azide-substrate complex of human heme oxygenase is an indicator of distal H-bonding: implications for the enzyme mechanism. Biochemistry. 2009 Apr 14; 48(14):3127-37. PMID: 19243105; PMCID: PMC2676937.
      38. Jiang Y, Ortiz de Montellano PR. Cooperative effects on radical recombination in CYP3A4-catalyzed oxidation of the radical clock beta-thujone. Chembiochem. 2009 Mar 2; 10(4):650-3. PMID: 19189363; PMCID: PMC2709176.
      39. Ouellet H, Lang J, Couture M, Ortiz de Montellano PR. Reaction of Mycobacterium tuberculosis cytochrome P450 enzymes with nitric oxide. Biochemistry. 2009 Feb 10; 48(5):863-72. PMID: 19146393; PMCID: PMC2681326.
      40. Jiang Y, Sivaramakrishnan S, Hayashi T, Cohen S, Moënne-Loccoz P, Shaik S, Ortiz de Montellano PR. Calculated and experimental spin state of seleno cytochrome P450. Angew Chem Int Ed Engl. 2009; 48(39):7193-5. PMID: 19718734; PMCID: PMC2848667.
      41. Lampe JN, Floor SN, Gross JD, Nishida CR, Jiang Y, Trnka MJ, Ortiz de Montellano PR. Ligand-induced conformational heterogeneity of cytochrome P450 CYP119 identified by 2D NMR spectroscopy with the unnatural amino acid (13)C-p-methoxyphenylalanine. J Am Chem Soc. 2008 Dec 3; 130(48):16168-9. PMID: 18998650; PMCID: PMC2645923.
      42. Podust LM, Ioanoviciu A, Ortiz de Montellano PR. 2.3 A X-ray structure of the heme-bound GAF domain of sensory histidine kinase DosT of Mycobacterium tuberculosis. Biochemistry. 2008 Nov 25; 47(47):12523-31. PMID: 18980385; PMCID: PMC2645934.
      43. Jiang Y, Trnka MJ, Medzihradszky KF, Ouellet H, Wang Y, Ortiz de Montellano PR. Covalent heme attachment to the protein in human heme oxygenase-1 with selenocysteine replacing the His25 proximal iron ligand. J Inorg Biochem. 2009 Mar; 103(3):316-25. PMID: 19135260; PMCID: PMC2762215.
      44. Nishida CR, Ortiz de Montellano PR. Reductive heme-dependent activation of the n-oxide prodrug AQ4N by nitric oxide synthase. J Med Chem. 2008 Aug 28; 51(16):5118-20. PMID: 18681417; PMCID: PMC2730118.
      45. Jiang Y, Ortiz de Montellano PR. Selenolate complexes of CYP101 and the heme-bound hHO-1/H25A proximal cavity mutant. Inorg Chem. 2008 May 5; 47(9):3480-2. PMID: 18376820; PMCID: PMC2727152.
      46. Kim D, Heo YS, Ortiz de Montellano PR. Efficient catalytic turnover of cytochrome P450(cam) is supported by a T252N mutation. Arch Biochem Biophys. 2008 Jun 1; 474(1):150-6. PMID: 18359283; PMCID: PMC2577879.
      47. Ortiz de Montellano PR. Mechanism and role of covalent heme binding in the CYP4 family of P450 enzymes and the mammalian peroxidases. Drug Metab Rev. 2008; 40(3):405-26. PMID: 18642140.
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      48. He X, Alian A, Ortiz de Montellano PR. Inhibition of the Mycobacterium tuberculosis enoyl acyl carrier protein reductase InhA by arylamides. Bioorg Med Chem. 2007 Nov 1; 15(21):6649-58. PMID: 17723305; PMCID: PMC2020492.
      49. Kim D, Cryle MJ, De Voss JJ, Ortiz de Montellano PR. Functional expression and characterization of cytochrome P450 52A21 from Candida albicans. Arch Biochem Biophys. 2007 Aug 15; 464(2):213-20. PMID: 17400174; PMCID: PMC1993549.
      50. Huang L, Ortiz de Montellano PR. Arthromyces ramosus peroxidase produces two chlorinating species. Biochem Biophys Res Commun. 2007 Apr 6; 355(2):581-6. PMID: 17303078; PMCID: PMC1852486.
      51. Austin RN, Deng D, Jiang Y, Luddy K, van Beilen JB, Ortiz de Montellano PR, Groves JT. The diagnostic substrate bicyclohexane reveals a radical mechanism for bacterial cytochrome P450 in whole cells. Angew Chem Int Ed Engl. 2006 Dec 11; 45(48):8192-4. PMID: 17103473.
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      52. Verras A, Ortiz de Montellano PR. Protein dynamics and imidazole binding in cytochrome P450 enzymes. Biochem Soc Trans. 2006 Dec; 34(Pt 6):1170-2. PMID: 17073778.
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      53. He X, Alian A, Stroud R, Ortiz de Montellano PR. Pyrrolidine carboxamides as a novel class of inhibitors of enoyl acyl carrier protein reductase from Mycobacterium tuberculosis. J Med Chem. 2006 Oct 19; 49(21):6308-23. PMID: 17034137; PMCID: PMC2517584.
      54. Huang L, Wojciechowski G, Ortiz de Montellano PR. Role of heme-protein covalent bonds in mammalian peroxidases. Protection of the heme by a single engineered heme-protein link in horseradish peroxidase. J Biol Chem. 2006 Jul 14; 281(28):18983-8. PMID: 16651262.
        View in: PubMed
      55. Qian L, Ortiz de Montellano PR. Oxidative activation of thiacetazone by the Mycobacterium tuberculosis flavin monooxygenase EtaA and human FMO1 and FMO3. Chem Res Toxicol. 2006 Mar; 19(3):443-9. PMID: 16544950; PMCID: PMC2533439.
      56. Jiang Y, He X, Ortiz de Montellano PR. Radical intermediates in the catalytic oxidation of hydrocarbons by bacterial and human cytochrome P450 enzymes. Biochemistry. 2006 Jan 17; 45(2):533-42. PMID: 16401082; PMCID: PMC2566308.
      57. Wang J, Evans JP, Ogura H, La Mar GN, Ortiz de Montellano PR. Alteration of the regiospecificity of human heme oxygenase-1 by unseating of the heme but not disruption of the distal hydrogen bonding network. Biochemistry. 2006 Jan 10; 45(1):61-73. PMID: 16388581; PMCID: PMC2507887.
      58. Zhu W, Li Y, Wang J, Ortiz de Montellano PR, La Mar GN. Solution NMR study of environmental effects on substrate seating in human heme oxygenase: influence of polypeptide truncation, substrate modification and axial ligand. J Inorg Biochem. 2006 Jan; 100(1):97-107. PMID: 16337271.
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      59. Huang L, Ortiz de Montellano PR. Heme-protein covalent bonds in peroxidases and resistance to heme modification during halide oxidation. Arch Biochem Biophys. 2006 Feb 1; 446(1):77-83. PMID: 16375846.
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      60. Ghiladi RA, Medzihradszky KF, Ortiz de Montellano PR. Role of the Met-Tyr-Trp cross-link in Mycobacterium tuberculosis catalase-peroxidase (KatG) as revealed by KatG(M255I). Biochemistry. 2005 Nov 22; 44(46):15093-105. PMID: 16285713.
        View in: PubMed
      61. Wojciechowski G, Huang L, Ortiz de Montellano PR. Autocatalytic modification of the prosthetic heme of horseradish but not lactoperoxidase by thiocyanate oxidation products. A role for heme-protein covalent cross-linking. J Am Chem Soc. 2005 Nov 16; 127(45):15871-9. PMID: 16277530.
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      62. Ghiladi RA, Medzihradszky KF, Rusnak FM, Ortiz de Montellano PR. Correlation between isoniazid resistance and superoxide reactivity in mycobacterium tuberculosis KatG. J Am Chem Soc. 2005 Sep 28; 127(38):13428-42. PMID: 16173777.
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      63. Nishida CR, Ortiz de Montellano PR. Thermophilic cytochrome P450 enzymes. Biochem Biophys Res Commun. 2005 Dec 9; 338(1):437-45. PMID: 16139791.
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      64. Huang L, Wojciechowski G, Ortiz de Montellano PR. Prosthetic heme modification during halide ion oxidation. Demonstration of chloride oxidation by horseradish peroxidase. J Am Chem Soc. 2005 Apr 20; 127(15):5345-53. PMID: 15826172.
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      65. Ghiladi RA, Knudsen GM, Medzihradszky KF, Ortiz de Montellano PR. The Met-Tyr-Trp cross-link in Mycobacterium tuberculosis catalase-peroxidase (KatG): autocatalytic formation and effect on enzyme catalysis and spectroscopic properties. J Biol Chem. 2005 Jun 17; 280(24):22651-63. PMID: 15840564.
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      66. Cryle MJ, Ortiz de Montellano PR, De Voss JJ. Cyclopropyl containing fatty acids as mechanistic probes for cytochromes P450. J Org Chem. 2005 Apr 1; 70(7):2455-69. PMID: 15787531.
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      67. Limburg J, LeBrun LA, Ortiz de Montellano PR. The P450cam G248E mutant covalently binds its prosthetic heme group. Biochemistry. 2005 Mar 15; 44(10):4091-9. PMID: 15751986.
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      68. Puchkaev AV, Ortiz de Montellano PR. The Sulfolobus solfataricus electron donor partners of thermophilic CYP119: an unusual non-NAD(P)H-dependent cytochrome P450 system. Arch Biochem Biophys. 2005 Feb 1; 434(1):169-77. PMID: 15629120.
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      69. Salinas M, Wang J, Rosa de Sagarra M, Martín D, Rojo AI, Martin-Perez J, Ortiz de Montellano PR, Cuadrado A. Protein kinase Akt/PKB phosphorylates heme oxygenase-1 in vitro and in vivo. FEBS Lett. 2004 Dec 3; 578(1-2):90-4. PMID: 15581622.
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      70. Ogura H, Nishida CR, Hoch UR, Perera R, Dawson JH, Ortiz de Montellano PR. EpoK, a cytochrome P450 involved in biosynthesis of the anticancer agents epothilones A and B. Substrate-mediated rescue of a P450 enzyme. Biochemistry. 2004 Nov 23; 43(46):14712-21. PMID: 15544342.
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      71. Wang J, Lad L, Poulos TL, Ortiz de Montellano PR. Regiospecificity determinants of human heme oxygenase: differential NADPH- and ascorbate-dependent heme cleavage by the R183E mutant. J Biol Chem. 2005 Jan 28; 280(4):2797-806. PMID: 15525643.
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      72. Lad L, Ortiz de Montellano PR, Poulos TL. Crystal structures of ferrous and ferrous-NO forms of verdoheme in a complex with human heme oxygenase-1: catalytic implications for heme cleavage. J Inorg Biochem. 2004 Nov; 98(11):1686-95. PMID: 15522396.
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      73. Huang L, Colas C, Ortiz de Montellano PR. Oxidation of carboxylic acids by horseradish peroxidase results in prosthetic heme modification and inactivation. J Am Chem Soc. 2004 Oct 13; 126(40):12865-73. PMID: 15469283.
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      74. He X, Ortiz de Montellano PR. Alpha- and beta-thujone radical rearrangements and isomerizations. A new radical clock. J Org Chem. 2004 Aug 20; 69(17):5684-9. PMID: 15307740.
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      75. Koshkin A, Zhou XT, Kraus CN, Brenner JM, Bandyopadhyay P, Kuntz ID, Barry CE, Ortiz de Montellano PR. Inhibition of Mycobacterium tuberculosis AhpD, an element of the peroxiredoxin defense against oxidative stress. Antimicrob Agents Chemother. 2004 Jul; 48(7):2424-30. PMID: 15215090; PMCID: PMC434156.
      76. Verras A, Kuntz ID, Ortiz de Montellano PR. Computer-assisted design of selective imidazole inhibitors for cytochrome p450 enzymes. J Med Chem. 2004 Jul 1; 47(14):3572-9. PMID: 15214784.
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      77. Koshkin A, Knudsen GM, Ortiz De Montellano PR. Intermolecular interactions in the AhpC/AhpD antioxidant defense system of Mycobacterium tuberculosis. Arch Biochem Biophys. 2004 Jul 1; 427(1):41-7. PMID: 15178486.
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      78. Serber Z, Straub W, Corsini L, Nomura AM, Shimba N, Craik CS, Ortiz de Montellano P, Dötsch V. Methyl groups as probes for proteins and complexes in in-cell NMR experiments. J Am Chem Soc. 2004 Jun 9; 126(22):7119-25. PMID: 15174883.
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      79. Marnett AB, Nomura AM, Shimba N, Ortiz de Montellano PR, Craik CS. Communication between the active sites and dimer interface of a herpesvirus protease revealed by a transition-state inhibitor. Proc Natl Acad Sci U S A. 2004 May 4; 101(18):6870-5. PMID: 15118083; PMCID: PMC406434.
      80. Ghiladi RA, Cabelli DE, Ortiz de Montellano PR. Superoxide reactivity of KatG: insights into isoniazid resistance pathways in TB. J Am Chem Soc. 2004 Apr 21; 126(15):4772-3. PMID: 15080669.
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      81. Lardinois OM, Ortiz de Montellano PR. Autoreduction of ferryl myoglobin: discrimination among the three tyrosine and two tryptophan residues as electron donors. Biochemistry. 2004 Apr 20; 43(15):4601-10. PMID: 15078107.
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      82. Lad L, Friedman J, Li H, Bhaskar B, Ortiz de Montellano PR, Poulos TL. Crystal structure of human heme oxygenase-1 in a complex with biliverdin. Biochemistry. 2004 Apr 6; 43(13):3793-801. PMID: 15049686.
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      83. Cryle MJ, Stuthe JM, Ortiz de Montellano PR, De Voss JJ. Cyclopropyl fatty acids implicate a radical but not a cation as an intermediate in P450BM3-catalysed hydroxylations. Chem Commun (Camb). 2004 Mar 7; (5):512-3. PMID: 14973583.
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      84. Purdy MM, Koo LS, Ortiz de Montellano PR, Klinman JP. Steady-state kinetic investigation of cytochrome P450cam: interaction with redox partners and reaction with molecular oxygen. Biochemistry. 2004 Jan 13; 43(1):271-81. PMID: 14705955.
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      85. Xu F, Falck JR, Ortiz de Montellano PR, Kroetz DL. Catalytic activity and isoform-specific inhibition of rat cytochrome p450 4F enzymes. J Pharmacol Exp Ther. 2004 Mar; 308(3):887-95. PMID: 14634044.
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      86. Li Y, Syvitski RT, Auclair K, Ortiz de Montellano P, La Mar GN. Solution 1H, 15N NMR spectroscopic characterization of substrate-bound, cyanide-inhibited human heme oxygenase: water occupation of the distal cavity. J Am Chem Soc. 2003 Nov 5; 125(44):13392-403. PMID: 14583035.
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      87. Nagano S, Li H, Shimizu H, Nishida C, Ogura H, Ortiz de Montellano PR, Poulos TL. Crystal structures of epothilone D-bound, epothilone B-bound, and substrate-free forms of cytochrome P450epoK. J Biol Chem. 2003 Nov 7; 278(45):44886-93. PMID: 12933799.
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      88. Lad L, Wang J, Li H, Friedman J, Bhaskar B, Ortiz de Montellano PR, Poulos TL. Crystal structures of the ferric, ferrous, and ferrous-NO forms of the Asp140Ala mutant of human heme oxygenase-1: catalytic implications. J Mol Biol. 2003 Jul 11; 330(3):527-38. PMID: 12842469.
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      89. Lardinois OM, Ortiz de Montellano PR. Intra- and intermolecular transfers of protein radicals in the reactions of sperm whale myoglobin with hydrogen peroxide. J Biol Chem. 2003 Sep 19; 278(38):36214-26. PMID: 12855712.
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      90. Knudsen GM, Nishida CR, Mooney SD, Ortiz de Montellano PR. Nitric-oxide synthase (NOS) reductase domain models suggest a new control element in endothelial NOS that attenuates calmodulin-dependent activity. J Biol Chem. 2003 Aug 22; 278(34):31814-24. PMID: 12805387.
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      91. Colas C, Ortiz de Montellano PR. Autocatalytic radical reactions in physiological prosthetic heme modification. Chem Rev. 2003 Jun; 103(6):2305-32. PMID: 12797831.
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      92. Koshkin A, Nunn CM, Djordjevic S, Ortiz de Montellano PR. The mechanism of Mycobacterium tuberculosis alkylhydroperoxidase AhpD as defined by mutagenesis, crystallography, and kinetics. J Biol Chem. 2003 Aug 8; 278(32):29502-8. PMID: 12761216.
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      93. Gunther MR, Tschirret-Guth RA, Lardinois OM, Ortiz de Montellano PR. Tryptophan-14 is the preferred site of DBNBS spin trapping in the self-peroxidation reaction of sperm whale metmyoglobin with a single equivalent of hydrogen peroxide. Chem Res Toxicol. 2003 May; 16(5):652-60. PMID: 12755595.
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      94. Auclair K, Huang HW, Moënne-Loccoz P, Ortiz de Montellano PR. Cloning and expression of a heme binding protein from the genome of Saccharomyces cerevisiae. Protein Expr Purif. 2003 Apr; 28(2):340-9. PMID: 12699699.
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      95. Puchkaev AV, Koo LS, Ortiz de Montellano PR. Aromatic stacking as a determinant of the thermal stability of CYP119 from Sulfolobus solfataricus. Arch Biochem Biophys. 2003 Jan 1; 409(1):52-8. PMID: 12464244.
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      96. Lad L, Schuller DJ, Shimizu H, Friedman J, Li H, Ortiz de Montellano PR, Poulos TL. Comparison of the heme-free and -bound crystal structures of human heme oxygenase-1. J Biol Chem. 2003 Mar 7; 278(10):7834-43. PMID: 12500973.
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      97. Syvitski RT, Li Y, Auclair K, Ortiz De Montellano PR, La Mar GN. 1H NMR detection of immobilized water molecules within a strong distal hydrogen-bonding network of substrate-bound human heme oxygenase-1. J Am Chem Soc. 2002 Dec 4; 124(48):14296-7. PMID: 12452690.
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      98. Wang J, Lu S, Moënne-Loccoz P, Ortiz de Montellano PR. Interaction of nitric oxide with human heme oxygenase-1. J Biol Chem. 2003 Jan 24; 278(4):2341-7. PMID: 12433915.
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      99. Puchkaev AV, Wakagi T, Ortiz de Montellano PR. CYP119 plus a Sulfolobus tokodaii strain 7 ferredoxin and 2-oxoacid:ferredoxin oxidoreductase constitute a high-temperature cytochrome P450 catalytic system. J Am Chem Soc. 2002 Oct 30; 124(43):12682-3. PMID: 12392414.
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      100. de Ropp JS, Sham S, Asokan A, Newmyer S, Ortiz de Montellano PR, La Mar GN. Influence of the distal his in imparting imidazolate character to the proximal his in heme peroxidase: (1)h NMR spectroscopic study of cyanide-inhibited his42-->ala horseradish peroxidase. J Am Chem Soc. 2002 Sep 18; 124(37):11029-37. PMID: 12224950.
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      101. Xu F, Straub WO, Pak W, Su P, Maier KG, Yu M, Roman RJ, Ortiz De Montellano PR, Kroetz DL. Antihypertensive effect of mechanism-based inhibition of renal arachidonic acid omega-hydroxylase activity. Am J Physiol Regul Integr Comp Physiol. 2002 Sep; 283(3):R710-20. PMID: 12185006.
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      102. Nishida CR, Knudsen G, Straub W, Ortiz de Montellano PR. Electron supply and catalytic oxidation of nitrogen by cytochrome P450 and nitric oxide synthase. Drug Metab Rev. 2002 Aug; 34(3):479-501. PMID: 12214661.
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      103. Ortiz de Montellano PR, De Voss JJ. Oxidizing species in the mechanism of cytochrome P450. Nat Prod Rep. 2002 Aug; 19(4):477-93. PMID: 12195813.
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      104. Li Y, Syvitski RT, Auclair K, Wilks A, Ortiz De Montellano PR, La Mar GN. Solution NMR characterization of an unusual distal H-bond network in the active site of the cyanide-inhibited, human heme oxygenase complex of the symmetric substrate, 2,4-dimethyldeuterohemin. J Biol Chem. 2002 Sep 6; 277(36):33018-31. PMID: 12070167.
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      105. Auclair K, Hu Z, Little DM, Ortiz De Montellano PR, Groves JT. Revisiting the mechanism of P450 enzymes with the radical clocks norcarane and spiro[2,5]octane. J Am Chem Soc. 2002 May 29; 124(21):6020-7. PMID: 12022835.
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      106. Koo LS, Immoos CE, Cohen MS, Farmer PJ, Ortiz de Montellano PR. Enhanced electron transfer and lauric acid hydroxylation by site-directed mutagenesis of CYP119. J Am Chem Soc. 2002 May 22; 124(20):5684-91. PMID: 12010041.
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      107. Hawkes DB, Adams GW, Burlingame AL, Ortiz de Montellano PR, De Voss JJ. Cytochrome P450(cin) (CYP176A), isolation, expression, and characterization. J Biol Chem. 2002 Aug 2; 277(31):27725-32. PMID: 12016226.
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      108. LeBrun LA, Xu F, Kroetz DL, Ortiz de Montellano PR. Covalent attachment of the heme prosthetic group in the CYP4F cytochrome P450 family. Biochemistry. 2002 May 7; 41(18):5931-7. PMID: 11980497.
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      109. Nunn CM, Djordjevic S, Hillas PJ, Nishida CR, Ortiz de Montellano PR. The crystal structure of Mycobacterium tuberculosis alkylhydroperoxidase AhpD, a potential target for antitubercular drug design. J Biol Chem. 2002 May 31; 277(22):20033-40. PMID: 11914371.
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      110. Zhang Z, Li Y, Stearns RA, Ortiz De Montellano PR, Baillie TA, Tang W. Cytochrome P450 3A4-mediated oxidative conversion of a cyano to an amide group in the metabolism of pinacidil. Biochemistry. 2002 Feb 26; 41(8):2712-8. PMID: 11851418.
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      111. Vannelli TA, Dykman A, Ortiz de Montellano PR. The antituberculosis drug ethionamide is activated by a flavoprotein monooxygenase. J Biol Chem. 2002 Apr 12; 277(15):12824-9. PMID: 11823459.
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      112. LeBrun LA, Hoch U, Ortiz de Montellano PR. Autocatalytic mechanism and consequences of covalent heme attachment in the cytochrome P4504A family. J Biol Chem. 2002 Apr 12; 277(15):12755-61. PMID: 11821421.
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      113. Colas C, Kuo JM, Ortiz de Montellano PR. Asp-225 and glu-375 in autocatalytic attachment of the prosthetic heme group of lactoperoxidase. J Biol Chem. 2002 Mar 1; 277(9):7191-200. PMID: 11756449.
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      114. Rodríguez-Crespo I, Yélamos B, Roncal F, Albar JP, Ortiz de Montellano PR, Gavilanes F. Identification of novel cellular proteins that bind to the LC8 dynein light chain using a pepscan technique. FEBS Lett. 2001 Aug 17; 503(2-3):135-41. PMID: 11513870.
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      115. Auclair K, Moënne-Loccoz P, Ortiz de Montellano PR. Roles of the proximal heme thiolate ligand in cytochrome p450(cam). J Am Chem Soc. 2001 May 30; 123(21):4877-85. PMID: 11457314.
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      116. Asokan A, de Ropp JS, Newmyer SL, Ortiz de Montellano PR, La Mar GN. Solution 1H NMR of the molecular and electronic structure of the heme cavity and substrate binding pocket of high-spin ferric horseradish peroxidase: effect of His42Ala mutation. J Am Chem Soc. 2001 May 9; 123(18):4243-54. PMID: 11457190.
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      117. Tschirret-Guth RA, Koo LS, Hoa GH, Ortiz De Montellano PR. Reversible pressure deformation of a thermophilic cytochrome P450 enzyme (CYP119) and its active-site mutants. J Am Chem Soc. 2001 Apr 18; 123(15):3412-7. PMID: 11472111.
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      118. La Mar GN, Asokan A, Espiritu B, Yeh DC, Auclair K, Ortiz De Montellano PR. Solution 1H NMR of the active site of substrate-bound, cyanide-inhibited human heme oxygenase. comparison to the crystal structure of the water-ligated form. J Biol Chem. 2001 May 11; 276(19):15676-87. PMID: 11297521.
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      119. Hoch U, Ortiz De Montellano PR. Covalently linked heme in cytochrome p4504a fatty acid hydroxylases. J Biol Chem. 2001 Apr 6; 276(14):11339-46. PMID: 11139583.
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      120. Xiang H, Tschirret-Guth RA, Ortiz De Montellano PR. An A245T mutation conveys on cytochrome P450eryF the ability to oxidize alternative substrates. J Biol Chem. 2000 Nov 17; 275(46):35999-6006. PMID: 10956654.
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      121. Liu Y, Koenigs Lightning L, Huang H, Moënne-Loccoz P, Schuller DJ, Poulos TL, Loehr TM, Ortiz de Montellano PR. Replacement of the distal glycine 139 transforms human heme oxygenase-1 into a peroxidase. J Biol Chem. 2000 Nov 3; 275(44):34501-7. PMID: 10942763.
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      122. Yano JK, Koo LS, Schuller DJ, Li H, Ortiz de Montellano PR, Poulos TL. Crystal structure of a thermophilic cytochrome P450 from the archaeon Sulfolobus solfataricus. J Biol Chem. 2000 Oct 6; 275(40):31086-92. PMID: 10859321.
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      123. Hillas PJ, del Alba FS, Oyarzabal J, Wilks A, Ortiz De Montellano PR. The AhpC and AhpD antioxidant defense system of Mycobacterium tuberculosis. J Biol Chem. 2000 Jun 23; 275(25):18801-9. PMID: 10766746.
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      124. Koo LS, Tschirret-Guth RA, Straub WE, Moënne-Loccoz P, Loehr TM, Ortiz de Montellano PR. The active site of the thermophilic CYP119 from Sulfolobus solfataricus. J Biol Chem. 2000 May 12; 275(19):14112-23. PMID: 10799487.
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      125. Aronov AM, Munagala NR, Ortiz De Montellano PR, Kuntz ID, Wang CC. Rational design of selective submicromolar inhibitors of Tritrichomonas foetus hypoxanthine-guanine-xanthine phosphoribosyltransferase. Biochemistry. 2000 Apr 25; 39(16):4684-91. PMID: 10769124.
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      126. Lardinois OM, Ortiz de Montellano PR. EPR spin-trapping of a myeloperoxidase protein radical. Biochem Biophys Res Commun. 2000 Apr 2; 270(1):199-202. PMID: 10733927.
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      127. Tschirret-Guth RA, Koo LS, Ortiz de Montellano PR. Protein control of the formation and decomposition of the CYP119 and CYP101 aryl-iron complexes. J Biol Inorg Chem. 2000 Apr; 5(2):204-12. PMID: 10819465.
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      128. Montellano PR. The mechanism of heme oxygenase. Curr Opin Chem Biol. 2000 Apr; 4(2):221-7. PMID: 10742194.
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      129. Liu Y, Ortiz de Montellano PR. Reaction intermediates and single turnover rate constants for the oxidation of heme by human heme oxygenase-1. J Biol Chem. 2000 Feb 25; 275(8):5297-307. PMID: 10681502.
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      130. Hoch U, Zhang Z, Kroetz DL, Ortiz de Montellano PR. Structural determination of the substrate specificities and regioselectivities of the rat and human fatty acid omega-hydroxylases. Arch Biochem Biophys. 2000 Jan 1; 373(1):63-71. PMID: 10620324.
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      131. Lardinois OM, Medzihradszky KF, Ortiz de Montellano PR. Spin trapping and protein cross-linking of the lactoperoxidase protein radical. J Biol Chem. 1999 Dec 10; 274(50):35441-8. PMID: 10585414.
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      132. Schuller DJ, Wilks A, Ortiz de Montellano PR, Poulos TL. Crystal structure of human heme oxygenase-1. Nat Struct Biol. 1999 Sep; 6(9):860-7. PMID: 10467099.
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      133. Lee H, Ortiz de Montellano PR, McDermott AE. Deuterium magic angle spinning studies of substrates bound to cytochrome P450. Biochemistry. 1999 Aug 17; 38(33):10808-13. PMID: 10451377.
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      134. Pond AE, Roach MP, Sono M, Rux AH, Franzen S, Hu R, Thomas MR, Wilks A, Dou Y, Ikeda-Saito M, Ortiz de Montellano PR, Woodruff WH, Boxer SG, Dawson JH. Assignment of the heme axial ligand(s) for the ferric myoglobin (H93G) and heme oxygenase (H25A) cavity mutants as oxygen donors using magnetic circular dichroism. Biochemistry. 1999 Jun 8; 38(23):7601-8. PMID: 10360958.
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      135. Nishida CR, Ortiz de Montellano PR. Autoinhibition of endothelial nitric-oxide synthase. Identification of an electron transfer control element. J Biol Chem. 1999 May 21; 274(21):14692-8. PMID: 10329664.
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      136. Garner AP, Paine MJ, Rodriguez-Crespo I, Chinje EC, Ortiz De Montellano P, Stratford IJ, Tew DG, Wolf CR. Nitric oxide synthases catalyze the activation of redox cycling and bioreductive anticancer agents. Cancer Res. 1999 Apr 15; 59(8):1929-34. PMID: 10213502.
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      137. Liu Y, Moënne-Loccoz P, Hildebrand DP, Wilks A, Loehr TM, Mauk AG, Ortiz de Montellano PR. Replacement of the proximal histidine iron ligand by a cysteine or tyrosine converts heme oxygenase to an oxidase. Biochemistry. 1999 Mar 23; 38(12):3733-43. PMID: 10090762.
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      138. Zhang Z, Hillas PJ, Ortiz de Montellano PR. Reduction of peroxides and dinitrobenzenes by Mycobacterium tuberculosis thioredoxin and thioredoxin reductase. Arch Biochem Biophys. 1999 Mar 1; 363(1):19-26. PMID: 10049495.
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      139. Chen ZP, Mitchelhill KI, Michell BJ, Stapleton D, Rodriguez-Crespo I, Witters LA, Power DA, Ortiz de Montellano PR, Kemp BE. AMP-activated protein kinase phosphorylation of endothelial NO synthase. FEBS Lett. 1999 Jan 29; 443(3):285-9. PMID: 10025949.
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      140. Halpert JR, Domanski TL, Adali O, Biagini CP, Cosme J, Dierks EA, Johnson EF, Jones JP, Ortiz de Montellano P, Philpot RM, Sibbesen O, Wyatt WK, Zheng Z. Structure-function of cytochromes P450 and flavin-containing monooxygenases: implications for drug metabolism. Drug Metab Dispos. 1998 Dec; 26(12):1223-31. PMID: 9860932.
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      141. Ortiz de Montellano PR, Nishida C, Rodriguez-Crespo I, Gerber N. Nitric oxide synthase structure and electron transfer. Drug Metab Dispos. 1998 Dec; 26(12):1185-9. PMID: 9860925.
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      142. Rodríguez-Crespo I, Straub W, Gavilanes F, Ortiz de Montellano PR. Binding of dynein light chain (PIN) to neuronal nitric oxide synthase in the absence of inhibition. Arch Biochem Biophys. 1998 Nov 15; 359(2):297-304. PMID: 9808772.
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      143. Iwuoha EI, Joseph S, Zhang Z, Smyth MR, Fuhr U, Ortiz de Montellano PR. Drug metabolism biosensors: electrochemical reactivities of cytochrome P450cam immobilised in synthetic vesicular systems. J Pharm Biomed Anal. 1998 Sep 1; 17(6-7):1101-10. PMID: 9884200.
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      144. Zhang Z, Sibbesen O, Johnson RA, Ortiz de Montellano PR. The substrate specificity of cytochrome P450cam. Bioorg Med Chem. 1998 Sep; 6(9):1501-8. PMID: 9801821.
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      145. Schuller DJ, Wilks A, Ortiz de Montellano P, Poulos TL. Crystallization of recombinant human heme oxygenase-1. Protein Sci. 1998 Aug; 7(8):1836-8. PMID: 10082382; PMCID: PMC2144071.
      146. Savenkova MI, Kuo JM, Ortiz de Montellano PR. Improvement of peroxygenase activity by relocation of a catalytic histidine within the active site of horseradish peroxidase. Biochemistry. 1998 Jul 28; 37(30):10828-36. PMID: 9692973.
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      147. Sibbesen O, Zhang Z, Ortiz de Montellano PR. Cytochrome P450cam substrate specificity: relationship between structure and catalytic oxidation of alkylbenzenes. Arch Biochem Biophys. 1998 May 15; 353(2):285-96. PMID: 9606963.
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      148. Savenkova MI, Ortiz de Montellano PR. Horseradish peroxidase: partial rescue of the His-42 --> Ala mutant by a concurrent Asn-70 --> Asp mutation. Arch Biochem Biophys. 1998 Mar 15; 351(2):286-93. PMID: 9514658.
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      149. Gunther MR, Tschirret-Guth RA, Witkowska HE, Fann YC, Barr DP, Ortiz De Montellano PR, Mason RP. Site-specific spin trapping of tyrosine radicals in the oxidation of metmyoglobin by hydrogen peroxide. Biochem J. 1998 Mar 15; 330 ( Pt 3):1293-9. PMID: 9494099; PMCID: PMC1219275.
      150. Nishida CR, Ortiz de Montellano PR. Electron transfer and catalytic activity of nitric oxide synthases. Chimeric constructs of the neuronal, inducible, and endothelial isoforms. J Biol Chem. 1998 Mar 6; 273(10):5566-71. PMID: 9488682.
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      151. Wilks A, Medzihradszky KF, Ortiz de Montellano PR. Heme oxygenase active-site residues identified by heme-protein cross-linking during reduction of CBrCl3. Biochemistry. 1998 Mar 3; 37(9):2889-96. PMID: 9485440.
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      152. Dierks EA, Davis SC, Ortiz de Montellano PR. Glu-320 and Asp-323 are determinants of the CYP4A1 hydroxylation regiospecificity and resistance to inactivation by 1-aminobenzotriazole. Biochemistry. 1998 Feb 17; 37(7):1839-47. PMID: 9485309.
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      153. Caldera PS, Yu Z, Knegtel RM, McPhee F, Burlingame AL, Craik CS, Kuntz ID, Ortiz de Montellano PR. Alkylation of a catalytic aspartate group of the SIV protease by an epoxide inhibitor. Bioorg Med Chem. 1997 Nov; 5(11):2019-27. PMID: 9416419.
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      154. Torpey J, Ortiz de Montellano PR. Oxidation of alpha-meso-formylmesoheme by heme oxygenase. Electronic control of the reaction regiospecificity. J Biol Chem. 1997 Aug 29; 272(35):22008-14. PMID: 9268339.
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      155. Gerber NC, Nishida CR, Ortiz de Montellano PR. Characterization of human liver inducible nitric oxide synthase expressed in Escherichia coli. Arch Biochem Biophys. 1997 Jul 15; 343(2):249-53. PMID: 9224737.
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      156. Rodríguez-Crespo I, Moënne-Loccoz P, Loehr TM, Ortiz de Montellano PR. Endothelial nitric oxide synthase: modulations of the distal heme site produced by progressive N-terminal deletions. Biochemistry. 1997 Jul 15; 36(28):8530-8. PMID: 9214298.
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      157. Rutenber EE, De Voss JJ, Hoffman L, Stroud RM, Lee KH, Alvarez J, McPhee F, Craik C, Ortiz de Montellano PR. The discovery, characterization and crystallographically determined binding mode of an FMOC-containing inhibitor of HIV-1 protease. Bioorg Med Chem. 1997 Jul; 5(7):1311-20. PMID: 9377091.
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      158. Hühmer AF, Nishida CR, Ortiz de Montellano PR, Schöneich C. Inactivation of the inducible nitric oxide synthase by peroxynitrite. Chem Res Toxicol. 1997 May; 10(5):618-26. PMID: 9168261.
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      159. DePillis GD, Ozaki Si, Kuo JM, Maltby DA, Ortiz de Montellano PR. Autocatalytic processing of heme by lactoperoxidase produces the native protein-bound prosthetic group. J Biol Chem. 1997 Apr 4; 272(14):8857-60. PMID: 9083001.
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      160. Liu Y, Moënne-Loccoz P, Loehr TM, Ortiz de Montellano PR. Heme oxygenase-1, intermediates in verdoheme formation and the requirement for reduction equivalents. J Biol Chem. 1997 Mar 14; 272(11):6909-17. PMID: 9054378.
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      161. Gerber NC, Rodriguez-Crespo I, Nishida CR, Ortiz de Montellano PR. Active site topologies and cofactor-mediated conformational changes of nitric-oxide synthases. J Biol Chem. 1997 Mar 7; 272(10):6285-90. PMID: 9045646.
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      162. DeGray JA, Gunther MR, Tschirret-Guth R, Ortiz de Montellano PR, Mason RP. Peroxidation of a specific tryptophan of metmyoglobin by hydrogen peroxide. J Biol Chem. 1997 Jan 24; 272(4):2359-62. PMID: 8999946.
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      163. Rodríguez-Crespo I, Ortiz de Montellano PR. Human endothelial nitric oxide synthase: expression in Escherichia coli, coexpression with calmodulin, and characterization. Arch Biochem Biophys. 1996 Dec 1; 336(1):151-6. PMID: 8951046.
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      164. Tschirret-Guth RA, Ortiz de Montellano PR. Protein radicals in myoglobin dimerization and myoglobin-catalyzed styrene epoxidation. Arch Biochem Biophys. 1996 Nov 1; 335(1):93-101. PMID: 8914838.
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      165. Torpey J, Ortiz de Montellano PR. Oxidation of the meso-methylmesoheme regioisomers by heme oxygenase. Electronic control of the reaction regiospecificity. J Biol Chem. 1996 Oct 18; 271(42):26067-73. PMID: 8824248.
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      166. Newmyer SL, Sun J, Loehr TM, Ortiz de Montellano PR. Rescue of the horseradish peroxidase His-170-->Ala mutant activity by imidazole: importance of proximal ligand tethering. Biochemistry. 1996 Oct 1; 35(39):12788-95. PMID: 8841121.
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      167. Hawkins BK, Wilks A, Powers LS, Ortiz de Montellano PR, Dawson JH. Ligation of the iron in the heme-heme oxygenase complex: X-ray absorption, electronic absorption and magnetic circular dichroism studies. Biochim Biophys Acta. 1996 Jul 18; 1295(2):165-73. PMID: 8695642.
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      168. Mackman R, Tschirret-Guth RA, Smith G, Hayhurst GP, Ellis SW, Lennard MS, Tucker GT, Wolf CR, Ortiz de Montellano PR. Active-site topologies of human CYP2D6 and its aspartate-301 --> glutamate, asparagine, and glycine mutants. Arch Biochem Biophys. 1996 Jul 1; 331(1):134-40. PMID: 8660692.
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      169. Rodríguez-Crespo I, Gerber NC, Ortiz de Montellano PR. Endothelial nitric-oxide synthase. Expression in Escherichia coli, spectroscopic characterization, and role of tetrahydrobiopterin in dimer formation. J Biol Chem. 1996 May 10; 271(19):11462-7. PMID: 8626704.
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      170. Davis SC, Sui Z, Peterson JA, Ortiz de Montellano PR. Oxidation of omega-oxo fatty acids by cytochrome P450BM-3 (CYP102). Arch Biochem Biophys. 1996 Apr 1; 328(1):35-42. PMID: 8638935.
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      171. Wilks A, Ortiz de Montellano PR, Sun J, Loehr TM. Heme oxygenase (HO-1): His-132 stabilizes a distal water ligand and assists catalysis. Biochemistry. 1996 Jan 23; 35(3):930-6. PMID: 8547275.
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      172. De Voss JJ, Ortiz de Montellano PR. Substrate docking algorithms and the prediction of substrate specificity. Methods Enzymol. 1996; 272:336-47. PMID: 8791793.
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      173. Mackman R, Guo Z, Guengerich FP, Ortiz de Montellano PR. Active site topology of human cytochrome P450 2E1. Chem Res Toxicol. 1996 Jan-Feb; 9(1):223-6. PMID: 8924594.
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      174. Ortiz de Montellano PR. The 1994 Bernard B. Brodie Award Lecture. Structure, mechanism, and inhibition of cytochrome P450. Drug Metab Dispos. 1995 Nov; 23(11):1181-7. PMID: 8591716.
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      175. Pikuleva IA, Mackman RL, Kagawa N, Waterman MR, Ortiz de Montellano PR. Active-site topology of bovine cholesterol side-chain cleavage cytochrome P450 (P450scc) and evidence for interaction of tyrosine 94 with the side chain of cholesterol. Arch Biochem Biophys. 1995 Sep 10; 322(1):189-97. PMID: 7574674.
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      176. Black SM, Ortiz de Montellano PR. Characterization of rat neuronal nitric oxide synthase expressed in Saccharomyces cerevisiae. DNA Cell Biol. 1995 Sep; 14(9):789-94. PMID: 7545403.
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      177. Newmyer SL, Ortiz de Montellano PR. Horseradish peroxidase His-42 --> Ala, His-42 --> Val, and Phe-41 --> Ala mutants. Histidine catalysis and control of substrate access to the heme iron. J Biol Chem. 1995 Aug 18; 270(33):19430-8. PMID: 7642625.
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      178. Miller VP, Goodin DB, Friedman AE, Hartmann C, Ortiz de Montellano PR. Horseradish peroxidase Phe172-->Tyr mutant. Sequential formation of compound I with a porphyrin radical cation and a protein radical. J Biol Chem. 1995 Aug 4; 270(31):18413-9. PMID: 7629167.
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      179. Gerber NC, Ortiz de Montellano PR. Neuronal nitric oxide synthase. Expression in Escherichia coli, irreversible inhibition by phenyldiazene, and active site topology. J Biol Chem. 1995 Jul 28; 270(30):17791-6. PMID: 7543092.
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      180. Miller VP, Tschirret-Guth RA, Ortiz de Montellano PR. Chloroperoxidase-catalyzed benzylic hydroxylation. Arch Biochem Biophys. 1995 Jun 1; 319(2):333-40. PMID: 7786013.
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      181. Ortiz de Montellano PR, Ozaki SI, Newmyer SL, Miller VP, Harmann C. Structural determinants of the catalytic activities of peroxidases. Biochem Soc Trans. 1995 May; 23(2):223-7. PMID: 7672242.
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      182. Wilks A, Black SM, Miller WL, Ortiz de Montellano PR. Expression and characterization of truncated human heme oxygenase (hHO-1) and a fusion protein of hHO-1 with human cytochrome P450 reductase. Biochemistry. 1995 Apr 4; 34(13):4421-7. PMID: 7703255.
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      183. Ortiz de Montellano PR. Arylhydrazines as probes of hemoprotein structure and function. Biochimie. 1995; 77(7-8):581-93. PMID: 8589069.
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      184. Wilks A, Torpey J, Ortiz de Montellano PR. Heme oxygenase (HO-1). Evidence for electrophilic oxygen addition to the porphyrin ring in the formation of alpha-meso-hydroxyheme. J Biol Chem. 1994 Nov 25; 269(47):29553-6. PMID: 7961940.
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      185. Sun J, Loehr TM, Wilks A, Ortiz de Montellano PR. Identification of histidine 25 as the heme ligand in human liver heme oxygenase. Biochemistry. 1994 Nov 22; 33(46):13734-40. PMID: 7947784.
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      186. Fruetel JA, Mackman RL, Peterson JA, Ortiz de Montellano PR. Relationship of active site topology to substrate specificity for cytochrome P450terp (CYP108). J Biol Chem. 1994 Nov 18; 269(46):28815-21. PMID: 7961838.
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      187. Choe YS, Rao SI, Ortiz de Montellano PR. Requirement of a second oxidation equivalent for ferryl oxygen transfer to styrene in the epoxidation catalyzed by myoglobin-H2O2. Arch Biochem Biophys. 1994 Oct; 314(1):126-31. PMID: 7944384.
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      188. Zou AP, Imig JD, Ortiz de Montellano PR, Sui Z, Falck JR, Roman RJ. Effect of P-450 omega-hydroxylase metabolites of arachidonic acid on tubuloglomerular feedback. Am J Physiol. 1994 Jun; 266(6 Pt 2):F934-41. PMID: 8023972.
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      189. Hernández G, Wilks A, Paolesse R, Smith KM, Ortiz de Montellano PR, La Mar GN. Proton NMR investigation of substrate-bound heme oxygenase: evidence for electronic and steric contributions to stereoselective heme cleavage. Biochemistry. 1994 May 31; 33(21):6631-41. PMID: 8204600.
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      190. Imig JD, Zou AP, Ortiz de Montellano PR, Sui Z, Roman RJ. Cytochrome P-450 inhibitors alter afferent arteriolar responses to elevations in pressure. Am J Physiol. 1994 May; 266(5 Pt 2):H1879-85. PMID: 8203587.
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      191. Hiroya K, Murakami Y, Shimizu T, Hatano M, Ortiz de Montellano PR. Differential roles of Glu318 and Thr319 in cytochrome P450 1A2 catalysis supported by NADPH-cytochrome P450 reductase and tert-butyl hydroperoxide. Arch Biochem Biophys. 1994 May 1; 310(2):397-401. PMID: 7910007.
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      192. Salto R, Babé LM, Li J, Rosé JR, Yu Z, Burlingame A, De Voss JJ, Sui Z, Ortiz de Montellano P, Craik CS. In vitro characterization of nonpeptide irreversible inhibitors of HIV proteases. J Biol Chem. 1994 Apr 8; 269(14):10691-8. PMID: 8144659.
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      193. Rao SI, Wilks A, Hamberg M, Ortiz de Montellano PR. The lipoxygenase activity of myoglobin. Oxidation of linoleic acid by the ferryl oxygen rather than protein radical. J Biol Chem. 1994 Mar 11; 269(10):7210-6. PMID: 8125933.
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      194. De Voss JJ, Sui Z, DeCamp DL, Salto R, Babé LM, Craik CS, Ortiz de Montellano PR. Haloperidol-based irreversible inhibitors of the HIV-1 and HIV-2 proteases. J Med Chem. 1994 Mar 4; 37(5):665-73. PMID: 8126707.
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      195. Zou AP, Imig JD, Kaldunski M, Ortiz de Montellano PR, Sui Z, Roman RJ. Inhibition of renal vascular 20-HETE production impairs autoregulation of renal blood flow. Am J Physiol. 1994 Feb; 266(2 Pt 2):F275-82. PMID: 8141328.
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      196. Zou AP, Ma YH, Sui ZH, Ortiz de Montellano PR, Clark JE, Masters BS, Roman RJ. Effects of 17-octadecynoic acid, a suicide-substrate inhibitor of cytochrome P450 fatty acid omega-hydroxylase, on renal function in rats. J Pharmacol Exp Ther. 1994 Jan; 268(1):474-81. PMID: 8301590.
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      197. Sun J, Wilks A, Ortiz de Montellano PR, Loehr TM. Resonance Raman and EPR spectroscopic studies on heme-heme oxygenase complexes. Biochemistry. 1993 Dec 28; 32(51):14151-7. PMID: 8260499.
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      198. Kaikaus RM, Sui Z, Lysenko N, Wu NY, Ortiz de Montellano PR, Ockner RK, Bass NM. Regulation of pathways of extramitochondrial fatty acid oxidation and liver fatty acid-binding protein by long-chain monocarboxylic fatty acids in hepatocytes. Effect of inhibition of carnitine palmitoyltransferase I. J Biol Chem. 1993 Dec 25; 268(36):26866-71. PMID: 8262919.
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      199. Shirane N, Sui Z, Peterson JA, Ortiz de Montellano PR. Cytochrome P450BM-3 (CYP102): regiospecificity of oxidation of omega-unsaturated fatty acids and mechanism-based inactivation. Biochemistry. 1993 Dec 14; 32(49):13732-41. PMID: 8257708.
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      200. Sui Z, Salto R, Li J, Craik C, Ortiz de Montellano PR. Inhibition of the HIV-1 and HIV-2 proteases by curcumin and curcumin boron complexes. Bioorg Med Chem. 1993 Dec; 1(6):415-22. PMID: 8087563.
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      201. Wilks A, Ortiz de Montellano PR. Rat liver heme oxygenase. High level expression of a truncated soluble form and nature of the meso-hydroxylating species. J Biol Chem. 1993 Oct 25; 268(30):22357-62. PMID: 8226746.
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      202. Rutenber E, Fauman EB, Keenan RJ, Fong S, Furth PS, Ortiz de Montellano PR, Meng E, Kuntz ID, DeCamp DL, Salto R. Structure of a non-peptide inhibitor complexed with HIV-1 protease. Developing a cycle of structure-based drug design. J Biol Chem. 1993 Jul 25; 268(21):15343-6. PMID: 8340363.
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      203. Kaikaus RM, Chan WK, Ortiz de Montellano PR, Bass NM. Mechanisms of regulation of liver fatty acid-binding protein. Mol Cell Biochem. 1993 Jun 9-23; 123(1-2):93-100. PMID: 8232272.
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      204. Burger A, Clark JE, Nishimoto M, Muerhoff AS, Masters BS, Ortiz de Montellano PR. Mechanism-based inhibitors of prostaglandin omega-hydroxylase: (R)- and (S)-12-hydroxy-16-heptadecynoic acid and 2,2-dimethyl-12-hydroxy-16-heptadecynoic acid. J Med Chem. 1993 May 14; 36(10):1418-24. PMID: 8496909.
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      205. Kaikaus RM, Chan WK, Lysenko N, Ray R, Ortiz de Montellano PR, Bass NM. Induction of peroxisomal fatty acid beta-oxidation and liver fatty acid-binding protein by peroxisome proliferators. Mediation via the cytochrome P-450IVA1 omega-hydroxylase pathway. J Biol Chem. 1993 May 5; 268(13):9593-603. PMID: 8486647.
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      206. Harris RZ, Liddell PA, Smith KM, Ortiz de Montellano PR. Catalytic properties of horseradish peroxidase reconstituted with the 8-(hydroxymethyl)- and 8-formylheme derivatives. Biochemistry. 1993 Apr 13; 32(14):3658-63. PMID: 8385486.
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      207. Tuck SF, Hiroya K, Shimizu T, Hatano M, Ortiz de Montellano PR. The cytochrome P450 1A2 active site: topology and perturbations caused by glutamic acid-318 and threonine-319 mutations. Biochemistry. 1993 Mar 16; 32(10):2548-53. PMID: 8095402.
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      208. Masters BS, Clark JE, Roman LJ, Nishimoto M, McCabe TJ, Ortiz de Montellano PR, Plopper CG, Gebremedhin D, Ma YH, Harder DR. Functional aspects of eicosanoid hydroxylation by lung and kidney cytochromes P450. Expression of cDNAs in mammalian cells and E. coli. J Lipid Mediat. 1993 Mar-Apr; 6(1-3):353-60. PMID: 8357994.
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      209. Harris RZ, Newmyer SL, Ortiz de Montellano PR. Horseradish peroxidase-catalyzed two-electron oxidations. Oxidation of iodide, thioanisoles, and phenols at distinct sites. J Biol Chem. 1993 Jan 25; 268(3):1637-45. PMID: 8420938.
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      210. Rao SI, Wilks A, Ortiz de Montellano PR. The roles of His-64, Tyr-103, Tyr-146, and Tyr-151 in the epoxidation of styrene and beta-methylstyrene by recombinant sperm whale myoglobin. J Biol Chem. 1993 Jan 15; 268(2):803-9. PMID: 8419357.
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      211. Tuck SF, Graham-Lorence S, Peterson JA, Ortiz de Montellano PR. Active sites of the cytochrome p450cam (CYP101) F87W and F87A mutants. Evidence for significant structural reorganization without alteration of catalytic regiospecificity. J Biol Chem. 1993 Jan 5; 268(1):269-75. PMID: 8416934.
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      212. Chan WK, Sui Z, Ortiz de Montellano PR. Determinants of protein modification versus heme alkylation: inactivation of cytochrome P450 1A1 by 1-ethynylpyrene and phenylacetylene. Chem Res Toxicol. 1993 Jan-Feb; 6(1):38-45. PMID: 8448348.
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      213. Miller VP, Fruetel JA, Ortiz de Montellano PR. Cytochrome P450cam-catalyzed oxidation of a hypersensitive radical probe. Arch Biochem Biophys. 1992 Nov 1; 298(2):697-702. PMID: 1416998.
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      214. Chang SW, Dutton D, Wang HL, He LS, Stearns R, Hui A, Giacomini KM, Ortiz de Montellano P, Voelkel NF. Intact lung cytochrome P-450 is not required for hypoxic pulmonary vasoconstriction. Am J Physiol. 1992 Oct; 263(4 Pt 1):L446-53. PMID: 1415722.
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      215. Alvarez JC, Ortiz de Montellano PR. Thianthrene 5-oxide as a probe of the electrophilicity of hemoprotein oxidizing species. Biochemistry. 1992 Sep 8; 31(35):8315-22. PMID: 1525169.
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      216. Hartmann C, Ortiz de Montellano PR. Baculovirus expression and characterization of catalytically active horseradish peroxidase. Arch Biochem Biophys. 1992 Aug 15; 297(1):61-72. PMID: 1637184.
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      217. Tuck SF, Ortiz de Montellano PR. Topological mapping of the active sites of cytochromes P4502B1 and P4502B2 by in situ rearrangement of aryl-iron complexes. Biochemistry. 1992 Aug 4; 31(30):6911-6. PMID: 1637824.
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      218. Tuck SF, Aoyama Y, Yoshida Y, Ortiz de Montellano PR. Active site topology of Saccharomyces cerevisiae lanosterol 14 alpha-demethylase (CYP51) and its G310D mutant (cytochrome P-450SG1). J Biol Chem. 1992 Jul 5; 267(19):13175-9. PMID: 1618820.
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      219. Miller VP, DePillis GD, Ferrer JC, Mauk AG, Ortiz de Montellano PR. Monooxygenase activity of cytochrome c peroxidase. J Biol Chem. 1992 May 5; 267(13):8936-42. PMID: 1315745.
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      220. Wilks A, Ortiz de Montellano PR. Intramolecular translocation of the protein radical formed in the reaction of recombinant sperm whale myoglobin with H2O2. J Biol Chem. 1992 May 5; 267(13):8827-33. PMID: 1315742.
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      221. Tuck SF, Peterson JA, Ortiz de Montellano PR. Active site topologies of bacterial cytochromes P450101 (P450cam), P450108 (P450terp), and P450102 (P450BM-3). In situ rearrangement of their phenyl-iron complexes. J Biol Chem. 1992 Mar 15; 267(8):5614-20. PMID: 1544935.
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      222. Ortiz de Montellano PR, Chan WK, Tuck SF, Kaikaus RM, Bass NM, Peterson JA. Mechanism-based probes of the topology and function of fatty acid hydroxylases. FASEB J. 1992 Jan 6; 6(2):695-9. PMID: 1537458.
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      223. Swanson BA, Halpert JR, Bornheim LM, Ortiz de Montellano PR. Topological analysis of the active sites of cytochromes P450IIB4 (rabbit), P450IIB10 (mouse), and P450IIB11 (dog) by in situ rearrangement of phenyl-iron complexes. Arch Biochem Biophys. 1992 Jan; 292(1):42-6. PMID: 1727649.
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      224. Ortiz de Montellano PR. Catalytic sites of hemoprotein peroxidases. Annu Rev Pharmacol Toxicol. 1992; 32:89-107. PMID: 1605582.
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      225. Samokyszyn VM, Ortiz de Montellano PR. Topology of the chloroperoxidase active site: regiospecificity of heme modification by phenylhydrazine and sodium azide. Biochemistry. 1991 Dec 17; 30(50):11646-53. PMID: 1661144.
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      226. Swanson BA, Dutton DR, Lunetta JM, Yang CS, Ortiz de Montellano PR. The active sites of cytochromes P450 IA1, IIB1, IIB2, and IIE1. Topological analysis by in situ rearrangement of phenyl-iron complexes. J Biol Chem. 1991 Oct 15; 266(29):19258-64. PMID: 1918043.
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      227. DePillis GD, Sishta BP, Mauk AG, Ortiz de Montellano PR. Small substrates and cytochrome c are oxidized at different sites of cytochrome c peroxidase. J Biol Chem. 1991 Oct 15; 266(29):19334-41. PMID: 1655784.
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      228. Harris RZ, Wariishi H, Gold MH, Ortiz de Montellano PR. The catalytic site of manganese peroxidase. Regiospecific addition of sodium azide and alkylhydrazines to the heme group. J Biol Chem. 1991 May 15; 266(14):8751-8. PMID: 1851156.
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      229. Choe YS, Ortiz de Montellano PR. Differential additions to the myoglobin prosthetic heme group. Oxidative gamma-meso substitution by alkylhydrazines. J Biol Chem. 1991 May 5; 266(13):8523-30. PMID: 1850746.
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      230. Kauser K, Clark JE, Masters BS, Ortiz de Montellano PR, Ma YH, Harder DR, Roman RJ. Inhibitors of cytochrome P-450 attenuate the myogenic response of dog renal arcuate arteries. Circ Res. 1991 Apr; 68(4):1154-63. PMID: 1901255.
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      231. Ortiz de Montellano PR. Mechanism-based inactivation of cytochrome P450: isolation and characterization of N-alkyl heme adducts. Methods Enzymol. 1991; 206:533-40. PMID: 1784239.
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      232. DeCamp DL, Babé LM, Furth P, Ortiz de Montellano P, Kuntz ID, Craik CS. Structure-based inhibition of HIV-1 protease activity and viral infectivity. Adv Exp Med Biol. 1991; 306:489-92. PMID: 1812747.
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      233. He LS, Chang SW, Ortiz de Montellano P, Burke TJ, Voelkel NF. Lung injury in Fischer but not Sprague-Dawley rats after short-term hyperoxia. Am J Physiol. 1990 Dec; 259(6 Pt 1):L451-8. PMID: 2260676.
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      234. Raag R, Swanson BA, Poulos TL, Ortiz de Montellano PR. Formation, crystal structure, and rearrangement of a cytochrome P-450cam iron-phenyl complex. Biochemistry. 1990 Sep 4; 29(35):8119-26. PMID: 2261467.
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      235. DesJarlais RL, Seibel GL, Kuntz ID, Furth PS, Alvarez JC, Ortiz de Montellano PR, DeCamp DL, Babé LM, Craik CS. Structure-based design of nonpeptide inhibitors specific for the human immunodeficiency virus 1 protease. Proc Natl Acad Sci U S A. 1990 Sep; 87(17):6644-8. PMID: 2204060; PMCID: PMC54593.
      236. DePillis GD, Wariishi H, Gold MH, Ortiz de Montellano PR. Inactivation of lignin peroxidase by phenylhydrazine and sodium azide. Arch Biochem Biophys. 1990 Jul; 280(1):217-23. PMID: 2353822.
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      237. Mackie JE, Ortiz de Montellano PR, Grab LA, Marks GS. Effects of 3-(2-phenylethyl)-4-methylsydnone and related sydnones on heme biosynthesis. Biochem Pharmacol. 1990 Jun 1; 39(11):1767-74. PMID: 2344374.
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      238. Ortiz de Montellano PR. Free radical modification of prosthetic heme groups. Pharmacol Ther. 1990; 48(1):95-120. PMID: 2274579.
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      239. DePillis GD, Ortiz de Montellano PR. Substrate oxidation by the heme edge of fungal peroxidases. Reaction of Coprinus macrorhizus peroxidase with hydrazines and sodium azide. Biochemistry. 1989 Sep 19; 28(19):7947-52. PMID: 2611222.
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      240. Ortiz de Montellano PR. Cytochrome P-450 catalysis: radical intermediates and dehydrogenation reactions. Trends Pharmacol Sci. 1989 Sep; 10(9):354-9. PMID: 2690426.
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      241. Catalano CE, Choe YS, Ortiz de Montellano PR. Reactions of the protein radical in peroxide-treated myoglobin. Formation of a heme-protein cross-link. J Biol Chem. 1989 Jun 25; 264(18):10534-41. PMID: 2732236.
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      242. Ator MA, David SK, Ortiz de Montellano PR. Stabilized isoporphyrin intermediates in the inactivation of horseradish peroxidase by alkylhydrazines. J Biol Chem. 1989 Jun 5; 264(16):9250-7. PMID: 2722829.
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      243. Muerhoff AS, Williams DE, Reich NO, CaJacob CA, Ortiz de Montellano PR, Masters BS. Prostaglandin and fatty acid omega- and (omega-1)-oxidation in rabbit lung. Acetylenic fatty acid mechanism-based inactivators as specific inhibitors. J Biol Chem. 1989 Jan 15; 264(2):749-56. PMID: 2910864.
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      244. Ortiz de Montellano PR, Stearns RA. Radical intermediates in the cytochrome P-450-catalyzed oxidation of aliphatic hydrocarbons. Drug Metab Rev. 1989; 20(2-4):183-91. PMID: 2680378.
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      245. Masters BS, Okita RT, Muerhoff AS, Leithauser MT, Gee A, Winquist S, Roerig DL, Clark JE, Murphy RC, Ortiz de Montellano P. Pulmonary P-450-mediated eicosanoid metabolism and regulation in the pregnant rabbit. Adv Prostaglandin Thromboxane Leukot Res. 1989; 19:335-8. PMID: 2526493.
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      246. CaJacob CA, Chan WK, Shephard E, Ortiz de Montellano PR. The catalytic site of rat hepatic lauric acid omega-hydroxylase. Protein versus prosthetic heme alkylation in the omega-hydroxylation of acetylenic fatty acids. J Biol Chem. 1988 Dec 15; 263(35):18640-9. PMID: 3198593.
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      247. Tew D, Ortiz de Montellano PR. The myoglobin protein radical. Coupling of Tyr-103 to Tyr-151 in the H2O2-mediated cross-linking of sperm whale myoglobin. J Biol Chem. 1988 Nov 25; 263(33):17880-6. PMID: 3182873.
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      248. Lee JS, Jacobsen NE, Ortiz de Montellano PR. 4-alkyl radical extrusion in the cytochrome P-450-catalyzed oxidation of 4-alkyl-1,4-dihydropyridines. Biochemistry. 1988 Oct 4; 27(20):7703-10. PMID: 3207701.
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      249. Ortiz de Montellano PR, David SK, Ator MA, Tew D. Mechanism-based inactivation of horseradish peroxidase by sodium azide. Formation of meso-azidoprotoporphyrin IX. Biochemistry. 1988 Jul 26; 27(15):5470-6. PMID: 3179265.
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      250. Lukton D, Mackie JE, Lee JS, Marks GS, Ortiz de Montellano PR. 2,2-Dialkyl-1,2-dihydroquinolines: cytochrome P-450 catalyzed N-alkylporphyrin formation, ferrochelatase inhibition, and induction of 5-aminolevulinic acid synthase activity. Chem Res Toxicol. 1988 Jul-Aug; 1(4):208-15. PMID: 2979733.
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      251. McCluskey SA, Marks GS, Whitney RA, Ortiz de Montellano PR. Differential inhibition of hepatic ferrochelatase by regioisomers of N-butyl-, N-pentyl-, N-hexyl-, and N-isobutylprotoporphyrin IX. Mol Pharmacol. 1988 Jul; 34(1):80-6. PMID: 3393143.
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      252. Grab LA, Swanson BA, Ortiz de Montellano PR. Cytochrome P-450 inactivation by 3-alkylsydnones. Mechanistic implications of N-alkyl and N-alkenyl heme adduct formation. Biochemistry. 1988 Jun 28; 27(13):4805-14. PMID: 2844240.
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      253. Salaün JP, Simon A, Durst F, Reich NO, Ortiz de Montellano PR. Differential inactivation of plant lauric acid omega- and in-chain-hydroxylases by terminally unsaturated fatty acids. Arch Biochem Biophys. 1988 Feb 1; 260(2):540-5. PMID: 3341756.
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      254. Catalano CE, Ortiz de Montellano PR. Oxene transfer, electron abstraction, and cooxidation in the epoxidation of stilbene and 7,8-dihydroxy-7,8-dihydrobenzo[a]pyrene by hemoglobin. Biochemistry. 1987 Dec 15; 26(25):8373-80. PMID: 3442662.
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      255. Ator MA, David SK, Ortiz de Montellano PR. Structure and catalytic mechanism of horseradish peroxidase. Regiospecific meso alkylation of the prosthetic heme group by alkylhydrazines. J Biol Chem. 1987 Nov 5; 262(31):14954-60. PMID: 3667617.
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      256. Ortiz de Montellano PR, Choe YS, DePillis G, Catalano CE. Structure-mechanism relationships in hemoproteins. Oxygenations catalyzed by chloroperoxidase and horseradish peroxidase. J Biol Chem. 1987 Aug 25; 262(24):11641-6. PMID: 3624229.
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      257. Ortiz de Montellano PR, Grab LA. Cooxidation of styrene by horseradish peroxidase and phenols: a biochemical model for protein-mediated cooxidation. Biochemistry. 1987 Aug 25; 26(17):5310-4. PMID: 2823878.
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      258. Komives EA, Ortiz de Montellano PR. Mechanism of oxidation of pi bonds by cytochrome P-450. Electronic requirements of the transition state in the turnover of phenylacetylenes. J Biol Chem. 1987 Jul 15; 262(20):9793-802. PMID: 3597438.
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      259. Ator MA, Ortiz de Montellano PR. Protein control of prosthetic heme reactivity. Reaction of substrates with the heme edge of horseradish peroxidase. J Biol Chem. 1987 Feb 5; 262(4):1542-51. PMID: 3805041.
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      260. Ortiz de Montellano PR, Watanabe MD. Free radical pathways in the in vitro hepatic metabolism of phenelzine. Mol Pharmacol. 1987 Feb; 31(2):213-9. PMID: 3807896.
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      261. Ortiz de Montellano PR, Costa AK. Dissociation of cytochrome P-450 inactivation and induction. Arch Biochem Biophys. 1986 Dec; 251(2):514-24. PMID: 3800382.
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      262. Ortiz de Montellano PR, Grab LA. Cooxidation of styrene by horseradish peroxidase and glutathione. Mol Pharmacol. 1986 Dec; 30(6):666-9. PMID: 3785143.
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      263. McCluskey SA, Marks GS, Sutherland EP, Jacobsen N, Ortiz de Montellano PR. Ferrochelatase-inhibitory activity and N-alkylprotoporphyrin formation with analogues of 3,5-diethoxycarbonyl-1,4-dihydro-2,4,6-trimethylpyridine (DDC) containing extended 4-alkyl groups: implications for the active site of ferrochelatase. Mol Pharmacol. 1986 Oct; 30(4):352-7. PMID: 3762522.
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      264. CaJacob CA, Ortiz de Montellano PR. Mechanism-based in vivo inactivation of lauric acid hydroxylases. Biochemistry. 1986 Aug 12; 25(16):4705-11. PMID: 3490272.
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      265. Reich NO, Ortiz de Montellano PR. Dissociation of increased lauric acid omega-hydroxylase activity from the antilipidemic action of clofibrate. Biochem Pharmacol. 1986 Apr 15; 35(8):1227-33. PMID: 3964299.
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      266. Sutherland EP, Marks GS, Grab LA, Ortiz de Montellano PR. Porphyrinogenic activity and ferrochelatase-inhibitory activity of sydnones in chick embryo liver cells. FEBS Lett. 1986 Mar 3; 197(1-2):17-20. PMID: 3949013.
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      267. Shak S, Reich NO, Goldstein IM, Ortiz de Montellano PR. Leukotriene B4 omega-hydroxylase in human polymorphonuclear leukocytes. Suicidal inactivation by acetylenic fatty acids. J Biol Chem. 1985 Oct 25; 260(24):13023-8. PMID: 2997155.
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      268. Ortiz de Montellano PR, Catalano CE. Epoxidation of styrene by hemoglobin and myoglobin. Transfer of oxidizing equivalents to the protein surface. J Biol Chem. 1985 Aug 5; 260(16):9265-71. PMID: 4019473.
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      269. Ortiz de Montellano PR, Komives EA. Branchpoint for heme alkylation and metabolite formation in the oxidation of arylacetylenes by cytochrome P-450. J Biol Chem. 1985 Mar 25; 260(6):3330-6. PMID: 3972828.
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      270. Ortiz de Montellano PR, Kerr DE. Inactivation of myoglobin by ortho-substituted arylhydrazines. Formation of prosthetic heme aryl-iron but not N-aryl adducts. Biochemistry. 1985 Feb 26; 24(5):1147-52. PMID: 4096894.
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      271. Salaun JP, Reichhart D, Simon A, Durst F, Reich NO, Ortiz de Montellano PR. Autocatalytic inactivation of plant cytochrome P-450 enzymes: selective inactivation of the lauric acid in-chain hydroxylase from Helianthus tuberosus L. by unsaturated substrate analogs. Arch Biochem Biophys. 1984 Jul; 232(1):1-7. PMID: 6742847.
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      272. Ortiz de Montellano PR, Reich NO. Specific inactivation of hepatic fatty acid hydroxylases by acetylenic fatty acids. J Biol Chem. 1984 Apr 10; 259(7):4136-41. PMID: 6706995.
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      273. Ortiz de Montellano PR, Stearns RA, Langry KC. The allylisopropylacetamide and novonal prosthetic heme adducts. Mol Pharmacol. 1984 Mar; 25(2):310-7. PMID: 6700576.
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      274. Ringe D, Petsko GA, Kerr DE, Ortiz de Montellano PR. Reaction of myoglobin with phenylhydrazine: a molecular doorstop. Biochemistry. 1984 Jan 3; 23(1):2-4. PMID: 6691963.
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      275. Ortiz de Montellano PR, Kerr DE. Inactivation of catalase by phenylhydrazine. Formation of a stable aryl-iron heme complex. J Biol Chem. 1983 Sep 10; 258(17):10558-63. PMID: 6885792.
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      276. Ortiz de Montellano PR, Augusto O, Viola F, Kunze KL. Carbon radicals in the metabolism of alkyl hydrazines. J Biol Chem. 1983 Jul 25; 258(14):8623-9. PMID: 6305994.
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      277. Kunze KL, Mangold BL, Wheeler C, Beilan HS, Ortiz de Montellano PR. The cytochrome P-450 active site. Regiospecificity of prosthetic heme alkylation by olefins and acetylenes. J Biol Chem. 1983 Apr 10; 258(7):4202-7. PMID: 6833252.
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      278. Ortiz de Montellano PR, Mangold BL, Wheeler C, Kunze KL, Reich NO. Stereochemistry of cytochrome P-450-catalyzed epoxidation and prosthetic heme alkylation. J Biol Chem. 1983 Apr 10; 258(7):4208-13. PMID: 6833253.
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      279. Ortiz de Montellano PR, Kunze KL, Beilan HS. Chiral orientation of prosthetic heme in the cytochrome P-450 active site. J Biol Chem. 1983 Jan 10; 258(1):45-7. PMID: 6848512.
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      280. Augusto O, Beilan HS, Ortiz de Montellano PR. The catalytic mechanism of cytochrome P-450. Spin-trapping evidence for one-electron substrate oxidation. J Biol Chem. 1982 Oct 10; 257(19):11288-95. PMID: 6288676.
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      281. Ortiz de Montellano PR, Beilan HS, Mathews JM. Alkylation of the prosthetic heme in cytochrome P-450 during oxidative metabolism of the sedative-hypnotic ethchlorvynol. J Med Chem. 1982 Oct; 25(10):1174-9. PMID: 7143353.
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      282. Reichhart D, Simon A, Durst F, Mathews JM, Ortiz de Montellano PR. Autocatalytic inactivation of plant cytochrome P-450 enzymes: selective inactivation of cinnamic acid 4-hydroxylase from Helianthus tuberosus by 1-aminobenzotriazole. Arch Biochem Biophys. 1982 Jul; 216(2):522-9. PMID: 7114850.
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      283. Augusto O, Kunze KL, Ortiz de Montellano PR. N-Phenylprotoporphyrin IX formation in the hemoglobin-phenylhydrazine reaction. Evidence for a protein-stabilized iron-phenyl intermediate. J Biol Chem. 1982 Jun 10; 257(11):6231-41. PMID: 7076671.
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      284. Ortiz de Montellano PR, Kunze KL, Beilan HS, Wheeler C. Destruction of cytochrome P-450 by vinyl fluoride, fluroxene, and acetylene. Evidence for a radical intermediate in olefin oxidation. Biochemistry. 1982 Mar 16; 21(6):1331-9. PMID: 6122467.
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      285. Ortiz de Montellano PR, Kunze KL. Cytochrome P-450 inactivation: structure of the prosthetic heme adduct with propyne. Biochemistry. 1981 Dec 8; 20(25):7266-71. PMID: 7317380.
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      286. Ortiz de Montellano PR, Kunze KL, Cole SP, Marks GS. Differential inhibition of hepatic ferrochelatase by the isomers of N-ethylprotoporphyrin IX. Biochem Biophys Res Commun. 1981 Nov 30; 103(2):581-6. PMID: 7332558.
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      287. Silber B, Mico BA, Ortiz de Montellano PR, Dols DM, Riegelman S. In vivo effects of the cytochrome P-450 suicide substrate 2-isopropyl-4-pentenamide (allylisopropylacetamide) on the disposition and metabolic pattern of propranolol. J Pharmacol Exp Ther. 1981 Oct; 219(1):125-33. PMID: 7288600.
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      288. Ortiz de Montellano PR, Mico BA, Mathews JM, Kunze KL, Miwa GT, Lu AY. Selective inactivation of cytochrome P-450 isozymes by suicide substrates. Arch Biochem Biophys. 1981 Sep; 210(2):717-28. PMID: 7305355.
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      289. Augusto O, Ortiz de Montellano PR, Quintanilha A. Spin-trapping of free radicals formed during microsomal metabolism of ethylhydrazine and acetylhydrazine. Biochem Biophys Res Commun. 1981 Aug 31; 101(4):1324-30. PMID: 6272782.
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      290. Ortiz de Montellano PR, Beilan HS, Kunze KL. N-Alkylprotoporphyrin IX formation in 3,5-dicarbethoxy-1,4-dihydrocollidine-treated rats. Transfer of the alkyl group from the substrate to the porphyrin. J Biol Chem. 1981 Jul 10; 256(13):6708-13. PMID: 6894597.
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      291. Ortiz de Montellano PR, Kunze KL. Shift of the acetylenic hydrogen during chemical and enzymatic oxidation of the biphenylacetylene triple bond. Arch Biochem Biophys. 1981 Jul; 209(2):710-2. PMID: 7294821.
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      292. Marks GS, Zimmer SB, Dinizo SE, Mico BA, Kunze KL, Ortiz de Montellano PR. Studies of the porphyrin-inducing activity of ethynyl compounds and conformationally restricted and unrestricted analogues of allylisopropylacetamide in chick embryo liver cell culture. Mol Pharmacol. 1981 Jul; 20(1):206-10. PMID: 7290085.
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      293. Correia MA, Farrell GC, Olson S, Wong JS, Schmid R, Ortiz de Montellano PR, Beilan HS, Kunze KL, Mico BA. Cytochrome P-450 heme moiety. The specific target in drug-induced heme alkylation. J Biol Chem. 1981 Jun 10; 256(11):5466-70. PMID: 7240150.
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      294. Ortiz de Montellano PR, Mathews JM. Autocatalytic alkylation of the cytochrome P-450 prosthetic haem group by 1-aminobenzotriazole. Isolation of an NN-bridged benzyne-protoporphyrin IX adduct. Biochem J. 1981 Jun 1; 195(3):761-4. PMID: 7316983; PMCID: PMC1162949.
      295. Ortiz de Montellano PR, Mathews JM. Inactivation of hepatic cytochrome P-450 by a 1,2,3-benzothiadiazole insecticide synergist. Biochem Pharmacol. 1981 May 15; 30(10):1138-41. PMID: 7259795.
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      296. Ortiz de Montellano PR, Beilan HS, Kunze KL, Mico BA. Destruction of cytochrome P-450 by ethylene. Structure of the resulting prosthetic heme adduct. J Biol Chem. 1981 May 10; 256(9):4395-9. PMID: 7217086.
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      297. Ortiz de Montellano PR, Beilan HS, Kunze KL. N-Methylprotoporphyrin IX: chemical synthesis and identification as the green pigment produced by 3,5-diethoxycarbonyl-1,4-dihydrocollidine treatment. Proc Natl Acad Sci U S A. 1981 Mar; 78(3):1490-4. PMID: 6940170; PMCID: PMC319156.
      298. Ortiz de Montellano PR, Mico BA. Destruction of cytochrome P-450 by allylisopropylacetamide is a suicidal process. Arch Biochem Biophys. 1981 Jan; 206(1):43-50. PMID: 7212720.
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      299. Ortiz de Montellano PR, Kunze KL, Cole SP, Marks GS. Inhibition of hepatic ferrochelatase by the four isomers of N-methylprotoporphyrin IX. Biochem Biophys Res Commun. 1980 Dec 31; 97(4):1436-42. PMID: 6894236.
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      300. Ortiz de Montellano PR, Kunze KL, Mico BA. Destruction of cytochrome P-450 by olefins: N-alkylation of prosthetic heme. Mol Pharmacol. 1980 Nov; 18(3):602-5. PMID: 7464822.
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      301. Ortiz de Montellano PR, Mico BA. Destruction of cytochrome P-450 by ethylene and other olefins. Mol Pharmacol. 1980 Jul; 18(1):128-35. PMID: 7412756.
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      302. Ortiz de Montellano PR, Kunze KL. Self-catalyzed inactivation of hepatic cytochrome P-450 by ethynyl substrates. J Biol Chem. 1980 Jun 25; 255(12):5578-85. PMID: 7380828.
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      303. Ortiz de Montellano PR, Kunze KL. Inactivation of hepatic cytochrome P-450 by allenic substrates. Biochem Biophys Res Commun. 1980 May 30; 94(2):443-9. PMID: 7396909.
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      304. Ortiz de Montellano PR, Yost GS, Mico BA, Dinizo SE, Correia MA, Kumbara H. Destruction of cytochrome P-450 by 2-isopropyl-4-pentenamide and methyl 2-isopropyl-4-pentenoate: mass spectrometric characterization of prosthetic heme adducts and nonparticipation of epoxide metabolites. Arch Biochem Biophys. 1979 Oct 15; 197(2):524-33. PMID: 41487.
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      305. Ortiz de Montellano PR, Beck JP, Ourisson G. Regulation of sterol biosynthesis and lysis of cultured hepatoma cells: inhibition of lanosterol demethylation by hydroxysterols. Biochem Biophys Res Commun. 1979 Oct 12; 90(3):897-903. PMID: 508352.
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      306. Farrell GC, Schmid R, Kunze KL, Ortiz de Montellano PR. Exogenous heme restores in vivo functional capacity of hepatic cytochrome P-450 destroyed by allylisopropylacetamide. Biochem Biophys Res Commun. 1979 Jul 27; 89(2):456-63. PMID: 486175.
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      307. Ortiz de Montellano PR, Kunze KL, Yost GS, Mico BA. Self-catalyzed destruction of cytochrome P-450: covalent binding of ethynyl sterols to prosthetic heme. Proc Natl Acad Sci U S A. 1979 Feb; 76(2):746-9. PMID: 284396; PMCID: PMC383038.
      308. Correia MA, Farrell GC, Schmid R, Ortiz de Montellano PR, Yost GS, Mico BA. Incorporation of exogenous heme into hepatic cytochrome P-450 in vivo. J Biol Chem. 1979 Jan 10; 254(1):15-7. PMID: 758315.
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      309. Ortiz de Montellano PR, Boparai AS. Alphatic 3,4-epoxyalcohols. Metabolism by epoxide hydrase and mutagenic activity. Biochim Biophys Acta. 1978 Dec 18; 544(3):504-13. PMID: 728469.
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      310. Ortiz de Montellano PR, Mico BA, Yost GS. Suicidal inactivation of cytochrome P-450. Formation of a heme-substrate covalent adduct. Biochem Biophys Res Commun. 1978 Jul 14; 83(1):132-7. PMID: 697804.
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      311. Ortiz de Montellano PR, Wei JS, Vinson WA, Castillo R, Boparai AS. Substrate selectivity of squalene synthetase. Biochemistry. 1977 Jun 14; 16(12):2680-5. PMID: 329862.
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      312. Ortiz de Montellano PR, Vinson WA. Fluoroisoprenyl synthesis using ethyl 2-fluoroacetoacetate. J Org Chem. 1977 May 27; 42(11):2013-4. PMID: 864541.
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      313. Ortiz de Montellano PR, Boparai AS. The squalene synthetase active site. Catalytic acceptance of 7- and 11- demethylfarnesyl pyrophosphates. Biochem Biophys Res Commun. 1976 May 23; 76(2):520-5. PMID: 800341.
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      314. Ortiz de Montellano PR, Castillo R, Vinson W, Wei JS. Squalene biosynthesis. Role of the 3-methyl group in farnesyl pyrophosphate. J Am Chem Soc. 1976 May 12; 98(10):3020-1. PMID: 177475.
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      315. Ortiz de Montellano PR, Castillo R, Vinson W, Wei JS. Letter: Squalene synthetase. Differentiation between the two substrate binding sites by a substrate analogue. J Am Chem Soc. 1976 Mar 31; 98(7):2018-9. PMID: 1254859.
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      316. Dean PD, Ortiz de Montellano PR, Bloch K, Corey EJ. A soluble 2,3-oxidosqualene sterol cyclase. J Biol Chem. 1967 Jun 25; 242(12):3014-5. PMID: 6027261.
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      317. Corey EJ, Ortiz de Montellano PR. Enzymic synthesis of beta-amyrin from 2,3-oxidosqualene. J Am Chem Soc. 1967 Jun 21; 89(13):3362-3. PMID: 6042774.
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      318. Corey EJ, Ortiz de Montellano PR, Lin K, Dean PD. 2,3-iminosqualene, a potent inhibitor of the enzymic cyclization of 2,3-oxidosqualene to sterols. J Am Chem Soc. 1967 May 24; 89(11):2797-8. PMID: 6043808.
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      319. Cory EJ, Russey WE, Ortiz de Montellano PR. 2,3-oxidosqualene, an intermediate in the biological synthesis of sterols from squalene. J Am Chem Soc. 1966 Oct 20; 88(20):4750-1. PMID: 5918046.
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