Paul Ortiz De Montellano, PhD

Title(s)Professor, Pharmaceutical Chemistry
SchoolSchool of Pharmacy
Address1700 4th St
San Francisco CA 94158
Phone415-476-2903
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    Collapse Biography 
    Collapse Education and Training
    Massachusetts Institute of TechnologyB.S.1964Chemistry
    Harvard UniversityM.A., Ph.D.1968Chemistry
    Eidgenossische Technische Hochschule, ZurichPostdoc1969Chemistry

    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 Research 
    Collapse Research Activities and Funding
    Oxygen Sensors and P450 Monooxygenases in Mycobacertium tuberculosis
    NIH R01AI074824Sep 1, 2007 - Jan 31, 2019
    Role: Principal Investigator
    2000 GORDON CONFERENCE ON TETRAPYRROLES
    NIH R13DK058032Jul 1, 2000 - Jun 30, 2001
    Role: Principal Investigator
    Structure Biology and Targeted Drug Design for AIDS
    NIH P01GM056531Sep 1, 1997 - Aug 31, 2007
    Role: Principal Investigator
    STRUCTURAL BIOLOGY AND TARGETED DRUG DESIGN FOR AIDS
    NIH P01GM039552Sep 1, 1987 - Aug 31, 1997
    Role: Co-Investigator
    LIVER CORE CENTER
    NIH P30AM026743Jul 1, 1985 - Jun 30, 1990
    Role: Co-Investigator
    BIOCHEMISTRY AND HEPATIC TOXICITY OF CARBON RADICALS
    NIH R01GM032488Jul 1, 1983 - Jun 30, 2009
    Role: Principal Investigator
    Bio-Organic Biomedical Mass Spectrometry Resource
    NIH P41RR001614Mar 1, 1982 - May 31, 2015
    Role: Co-Investigator
    Hemoprotein Oxidation and Heme Catabolism
    NIH R01DK030297Jan 1, 1982 - Jun 30, 2014
    Role: Principal Investigator
    HEMOLYTIC ANEMIA AND ABNORMAL HEME CATABOLITES
    NIH R01AM030297Jan 1, 1982 - Dec 31, 1989
    Role: Principal Investigator
    Mechanism, Specificity, and Inhibition of Cytochrome P450
    NIH R01GM025515Jul 1, 1978 - Jun 30, 2016
    Role: Principal Investigator
    SELECTIVE DESTRUCTION OF CYTOCHROME P450 BY DRUGS
    NIH R37GM025515Jul 1, 1978 - Jun 30, 1999
    Role: Principal Investigator
    Resource for Biocomputing, Visualization, and Informatics
    NIH/NCRR P41RR001081Jun 1, 1976 - Sep 14, 2012
    Role: Co-Investigator

    Collapse ORNG Applications 
    Collapse Global Health
    Collapse Academic Senate

    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. to make corrections and additions.
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    1. Acetylenes: cytochrome P450 oxidation and mechanism-based enzyme inactivation. Drug Metab Rev. 2019 05; 51(2):162-177. Ortiz de Montellano PR. PMID: 31203694.
      View in: PubMed   Mentions: 1     Fields:    Translation:HumansAnimalsCells
    2. Xanthates: Metabolism by Flavoprotein-Containing Monooxygenases and Antimycobacterial Activity. Drug Metab Dispos. 2018 08; 46(8):1091-1095. Yanev SG, Stoyanova TD, Valcheva VV, Ortiz de Montellano PR. PMID: 29777023.
      View in: PubMed   Mentions:    Fields:    Translation:HumansCells
    3. Potential drug targets in the Mycobacterium tuberculosis cytochrome P450 system. J Inorg Biochem. 2018 03; 180:235-245. Ortiz de Montellano PR. PMID: 29352597.
      View in: PubMed   Mentions: 8     Fields:    Translation:Cells
    4. A New Step in the Treatment of Sickle Cell DiseasePublished as part of the Biochemistry series "Biochemistry to Bedside". Biochemistry. 2018 02 06; 57(5):470-471. Ortiz de Montellano PR. PMID: 29172465.
      View in: PubMed   Mentions: 3     Fields:    Translation:HumansAnimals
    5. Crystal structures of the CO and NOBound DosS GAF-A domain and implications for DosS signaling in Mycobacterium tuberculosis. Arch Biochem Biophys. 2016 Dec 15; 612:1-8. Madrona Y, Waddling CA, Ortiz de Montellano PR. PMID: 27729224.
      View in: PubMed   Mentions: 3     Fields:    Translation:Cells
    6. Distal Hydrogen-bonding Interactions in Ligand Sensing and Signaling by Mycobacterium tuberculosis DosS. J Biol Chem. 2016 07 29; 291(31):16100-11. Basudhar D, Madrona Y, Yukl ET, Sivaramakrishnan S, Nishida CR, Moënne-Loccoz P, Ortiz de Montellano PR. PMID: 27235395.
      View in: PubMed   Mentions: 2     Fields:    Translation:Cells
    7. Catalytic Activities of Tumor-Specific Human Cytochrome P450 CYP2W1 Toward Endogenous Substrates. Drug Metab Dispos. 2016 May; 44(5):771-80. Zhao Y, Wan D, Yang J, Hammock BD, Ortiz de Montellano PR. PMID: 26936974.
      View in: PubMed   Mentions: 3     Fields:    Translation:HumansCells
    8. Cholesterol Analogs with Degradation-resistant Alkyl Side Chains Are Effective Mycobacterium tuberculosis Growth Inhibitors. J Biol Chem. 2016 Apr 01; 291(14):7325-33. Frank DJ, Zhao Y, Wong SH, Basudhar D, De Voss JJ, Ortiz de Montellano PR. PMID: 26833565; PMCID: PMC4817165.
      View in: PubMed   Mentions: 4     Fields:    Translation:Cells
    9. Cytochrome P450 125A4, the Third Cholesterol C-26 Hydroxylase from Mycobacterium smegmatis. Biochemistry. 2015 Nov 24; 54(46):6909-16. Frank DJ, Waddling CA, La M, Ortiz de Montellano PR. PMID: 26522442.
      View in: PubMed   Mentions: 2     Fields:    Translation:Cells
    10. Heme and I. J Biol Chem. 2015 Sep 04; 290(36):21833-44. Ortiz de Montellano PR. PMID: 26195628.
      View in: PubMed   Mentions: 1     Fields:    
    11. Drug modulation of water-heme interactions in low-spin P450 complexes of CYP2C9d and CYP125A1. Biochemistry. 2015 Feb 10; 54(5):1198-207. Conner KP, Cruce AA, Krzyaniak MD, Schimpf AM, Frank DJ, Ortiz de Montellano P, Atkins WM, Bowman MK. PMID: 25591012.
      View in: PubMed   Mentions: 6     Fields:    Translation:HumansCells
    12. Cholesterol ester oxidation by mycobacterial cytochrome P450. J Biol Chem. 2014 Oct 31; 289(44):30417-30425. Frank DJ, Madrona Y, Ortiz de Montellano PR. PMID: 25210044.
      View in: PubMed   Mentions: 10     Fields:    Translation:Cells
    13. Carbon-carbon bond cleavage in activation of the prodrug nabumetone. Drug Metab Dispos. 2014 May; 42(5):828-38. Varfaj F, Zulkifli SN, Park HG, Challinor VL, De Voss JJ, Ortiz de Montellano PR. PMID: 24584631; PMCID: PMC3989788.
      View in: PubMed   Mentions: 5     Fields:    Translation:HumansCells
    14. Strength of axial water ligation in substrate-free cytochrome P450s is isoform dependent. Biochemistry. 2014 Mar 11; 53(9):1428-34. Conner KP, Schimpf AM, Cruce AA, McLean KJ, Munro AW, Frank DJ, Krzyaniak MD, Ortiz de Montellano P, Bowman MK, Atkins WM. PMID: 24576089.
      View in: PubMed   Mentions: 10     Fields:    
    15. Specificity determinants of CYP1B1 estradiol hydroxylation. Mol Pharmacol. 2013 Sep; 84(3):451-8. Nishida CR, Everett S, Ortiz de Montellano PR. PMID: 23821647; PMCID: PMC3876821.
      View in: PubMed   Mentions: 15     Fields:    Translation:HumansAnimalsCells
    16. A highly conserved mycobacterial cholesterol catabolic pathway. Environ Microbiol. 2013 Aug; 15(8):2342-59. García-Fernández E, Frank DJ, Galán B, Kells PM, Podust LM, García JL, Ortiz de Montellano PR. PMID: 23489718.
      View in: PubMed   Mentions: 13     Fields:    Translation:Cells
    17. Cytochrome P450-activated prodrugs. Future Med Chem. 2013 Feb; 5(2):213-28. Ortiz de Montellano PR. PMID: 23360144.
      View in: PubMed   Mentions: 21     Fields:    Translation:HumansAnimals
    18. Conserved cysteine residues provide a protein-protein interaction surface in dual oxidase (DUOX) proteins. J Biol Chem. 2013 Mar 08; 288(10):7147-57. Meitzler JL, Hinde S, Bánfi B, Nauseef WM, Ortiz de Montellano PR. PMID: 23362256; PMCID: PMC3591624.
      View in: PubMed   Mentions: 17     Fields:    Translation:HumansAnimalsCells
    19. Covalent attachment of heme to the protein moiety in an insect E75 nitric oxide sensor. Biochemistry. 2012 Sep 18; 51(37):7403-16. Aicart-Ramos C, Valhondo Falcón M, Ortiz de Montellano PR, Rodriguez-Crespo I. PMID: 22946928; PMCID: PMC3448046.
      View in: PubMed   Mentions: 7     Fields:    Translation:HumansAnimalsCells
    20. 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. Varfaj F, Lampe JN, Ortiz de Montellano PR. PMID: 22923613; PMCID: PMC3471713.
      View in: PubMed   Mentions: 16     Fields:    Translation:HumansCells
    21. Substrate analog studies of the ?-regiospecificity of Mycobacterium tuberculosis cholesterol metabolizing cytochrome P450 enzymes CYP124A1, CYP125A1 and CYP142A1. Bioorg Med Chem. 2012 Jul 01; 20(13):4064-81. Johnston JB, Singh AA, Clary AA, Chen CK, Hayes PY, Chow S, De Voss JJ, Ortiz de Montellano PR. PMID: 22647881; PMCID: PMC3376231.
      View in: PubMed   Mentions: 5     Fields:    Translation:Cells
    22. Proximal ligand electron donation and reactivity of the cytochrome P450 ferric-peroxo anion. J Am Chem Soc. 2012 Apr 18; 134(15):6673-84. Sivaramakrishnan S, Ouellet H, Matsumura H, Guan S, Moënne-Loccoz P, Burlingame AL, Ortiz de Montellano PR. PMID: 22444582.
      View in: PubMed   Mentions: 9     Fields:    Translation:Cells
    23. 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. Vos MH, Bouzhir-Sima L, Lambry JC, Luo H, Eaton-Rye JJ, Ioanoviciu A, Ortiz de Montellano PR, Liebl U. PMID: 22142262; PMCID: PMC3254832.
      View in: PubMed   Mentions: 9     Fields:    Translation:Cells
    24. 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. Meitzler JL, Ortiz de Montellano PR. PMID: 21704604; PMCID: PMC3139011.
      View in: PubMed   Mentions: 11     Fields:    Translation:HumansCells
    25. A novel intermediate in the reaction of seleno CYP119 with m-chloroperbenzoic acid. Biochemistry. 2011 Apr 12; 50(14):3014-24. Sivaramakrishnan S, Ouellet H, Du J, McLean KJ, Medzihradszky KF, Dawson JH, Munro AW, Ortiz de Montellano PR. PMID: 21381758.
      View in: PubMed   Mentions: 6     Fields:    Translation:Cells
    26. Nitric oxide dioxygenation reaction in DevS and the initial response to nitric oxide in Mycobacterium tuberculosis. Biochemistry. 2011 Feb 15; 50(6):1023-8. Yukl ET, Ioanoviciu A, Sivaramakrishnan S, Nakano MM, Ortiz de Montellano PR, Moënne-Loccoz P. PMID: 21250657; PMCID: PMC3079480.
      View in: PubMed   Mentions: 11     Fields:    Translation:Cells
    27. Reverse type I inhibitor of Mycobacterium tuberculosis CYP125A1. Bioorg Med Chem Lett. 2011 Jan 01; 21(1):332-7. Ouellet H, Kells PM, Ortiz de Montellano PR, Podust LM. PMID: 21109436.
      View in: PubMed   Mentions: 10     Fields:    Translation:Cells
    28. Rearrangement reactions catalyzed by cytochrome P450s. Arch Biochem Biophys. 2011 Mar 01; 507(1):95-110. Ortiz de Montellano PR, Nelson SD. PMID: 20971058; PMCID: PMC3039701.
      View in: PubMed   Mentions: 11     Fields:    Translation:HumansAnimalsCells
    29. 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. Meitzler JL, Brandman R, Ortiz de Montellano PR. PMID: 20947510.
      View in: PubMed   Mentions: 15     Fields:    Translation:HumansAnimalsCells
    30. Bioactivation of antituberculosis thioamide and thiourea prodrugs by bacterial and mammalian flavin monooxygenases. Chem Biol Interact. 2011 Jun 30; 192(1-2):21-5. Nishida CR, Ortiz de Montellano PR. PMID: 20863819; PMCID: PMC3033498.
      View in: PubMed   Mentions: 14     Fields:    Translation:HumansCells
    31. 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. Johnston JB, Ouellet H, Ortiz de Montellano PR. PMID: 20843794; PMCID: PMC2978563.
      View in: PubMed   Mentions: 35     Fields:    Translation:Cells
    32. Structural control of cytochrome P450-catalyzed ?-hydroxylation. Arch Biochem Biophys. 2011 Mar 01; 507(1):86-94. Johnston JB, Ouellet H, Podust LM, Ortiz de Montellano PR. PMID: 20727847.
      View in: PubMed   Mentions: 18     Fields:    Translation:HumansAnimalsCells
    33. Hydrocarbon hydroxylation by cytochrome P450 enzymes. Chem Rev. 2010 Feb 10; 110(2):932-48. Ortiz de Montellano PR. PMID: 19769330.
      View in: PubMed   Mentions: 162     Fields:    Translation:Cells
    34. Coupling of the distal hydrogen bond network to the exogenous ligand in substrate-bound, resting state human heme oxygenase. Biochemistry. 2009 Dec 01; 48(47):11231-42. Peng D, Ogura H, Zhu W, Ma LH, Evans JP, Ortiz de Montellano PR, La Mar GN. PMID: 19842713; PMCID: PMC3008551.
      View in: PubMed   Mentions: 3     Fields:    Translation:HumansCells
    35. Biochemical and structural characterization of CYP124: a methyl-branched lipid omega-hydroxylase from Mycobacterium tuberculosis. Proc Natl Acad Sci U S A. 2009 Dec 08; 106(49):20687-92. Johnston JB, Kells PM, Podust LM, Ortiz de Montellano PR. PMID: 19933331.
      View in: PubMed   Mentions: 31     Fields:    Translation:Cells
    36. Isocyanides inhibit human heme oxygenases at the verdoheme stage. Biochemistry. 2009 Sep 22; 48(37):8920-8. Evans JP, Kandel S, Ortiz de Montellano PR. PMID: 19694439.
      View in: PubMed   Mentions: 3     Fields:    Translation:HumansAnimalsCells
    37. The Mycobacterium tuberculosis cytochrome P450 system. Arch Biochem Biophys. 2010 Jan 01; 493(1):82-95. Ouellet H, Johnston JB, Ortiz de Montellano PR. PMID: 19635450; PMCID: PMC2812603.
      View in: PubMed   Mentions: 36     Fields:    Translation:Cells
    38. DevS oxy complex stability identifies this heme protein as a gas sensor in Mycobacterium tuberculosis dormancy. Biochemistry. 2009 Jun 30; 48(25):5839-48. Ioanoviciu A, Meharenna YT, Poulos TL, Ortiz de Montellano PR. PMID: 19463006.
      View in: PubMed   Mentions: 18     Fields:    Translation:Cells
    39. 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. Dey A, Jiang Y, Ortiz de Montellano P, Hodgson KO, Hedman B, Solomon EI. PMID: 19438234; PMCID: PMC2734335.
      View in: PubMed   Mentions: 10     Fields:    
    40. Tricistronic overexpression of cytochrome P450cam, putidaredoxin, and putidaredoxin reductase provides a useful cell-based catalytic system. Biotechnol Lett. 2009 Sep; 31(9):1427-31. Kim D, Ortiz de Montellano PR. PMID: 19458919; PMCID: PMC2844094.
      View in: PubMed   Mentions: 4     Fields:    Translation:Cells
    41. 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. Meitzler JL, Ortiz de Montellano PR. PMID: 19460756; PMCID: PMC2707201.
      View in: PubMed   Mentions: 40     Fields:    Translation:HumansAnimalsCells
    42. 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. Ogura H, Evans JP, Peng D, Satterlee JD, Ortiz de Montellano PR, La Mar GN. PMID: 19243105; PMCID: PMC2676937.
      View in: PubMed   Mentions: 3     Fields:    Translation:HumansCells
    43. Cooperative effects on radical recombination in CYP3A4-catalyzed oxidation of the radical clock beta-thujone. Chembiochem. 2009 Mar 02; 10(4):650-3. Jiang Y, Ortiz de Montellano PR. PMID: 19189363.
      View in: PubMed   Mentions: 3     Fields:    Translation:HumansCells
    44. Reaction of Mycobacterium tuberculosis cytochrome P450 enzymes with nitric oxide. Biochemistry. 2009 Feb 10; 48(5):863-72. Ouellet H, Lang J, Couture M, Ortiz de Montellano PR. PMID: 19146393; PMCID: PMC2681326.
      View in: PubMed   Mentions: 25     Fields:    Translation:AnimalsCells
    45. Calculated and experimental spin state of seleno cytochrome P450. Angew Chem Int Ed Engl. 2009; 48(39):7193-5. Jiang Y, Sivaramakrishnan S, Hayashi T, Cohen S, Moënne-Loccoz P, Shaik S, Ortiz de Montellano PR. PMID: 19718734.
      View in: PubMed   Mentions: 7     Fields:    
    46. 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 03; 130(48):16168-9. Lampe JN, Floor SN, Gross JD, Nishida CR, Jiang Y, Trnka MJ, Ortiz de Montellano PR. PMID: 18998650.
      View in: PubMed   Mentions: 18     Fields:    Translation:Cells
    47. 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. Podust LM, Ioanoviciu A, Ortiz de Montellano PR. PMID: 18980385.
      View in: PubMed   Mentions: 36     Fields:    Translation:Cells
    48. 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. Jiang Y, Trnka MJ, Medzihradszky KF, Ouellet H, Wang Y, Ortiz de Montellano PR. PMID: 19135260.
      View in: PubMed   Mentions: 4     Fields:    Translation:Humans
    49. Reductive heme-dependent activation of the n-oxide prodrug AQ4N by nitric oxide synthase. J Med Chem. 2008 Aug 28; 51(16):5118-20. Nishida CR, Ortiz de Montellano PR. PMID: 18681417.
      View in: PubMed   Mentions: 9     Fields:    Translation:Cells
    50. Selenolate complexes of CYP101 and the heme-bound hHO-1/H25A proximal cavity mutant. Inorg Chem. 2008 May 05; 47(9):3480-2. Jiang Y, Ortiz de Montellano PR. PMID: 18376820; PMCID: PMC2727152.
      View in: PubMed   Mentions: 3     Fields:    Translation:Humans
    51. Efficient catalytic turnover of cytochrome P450(cam) is supported by a T252N mutation. Arch Biochem Biophys. 2008 Jun 01; 474(1):150-6. Kim D, Heo YS, Ortiz de Montellano PR. PMID: 18359283; PMCID: PMC2577879.
      View in: PubMed   Mentions: 4     Fields:    Translation:Cells
    52. 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. Ortiz de Montellano PR. PMID: 18642140.
      View in: PubMed   Mentions: 15     Fields:    Translation:HumansAnimalsCells
    53. Inhibition of the Mycobacterium tuberculosis enoyl acyl carrier protein reductase InhA by arylamides. Bioorg Med Chem. 2007 Nov 01; 15(21):6649-58. He X, Alian A, Ortiz de Montellano PR. PMID: 17723305.
      View in: PubMed   Mentions: 12     Fields:    Translation:Cells
    54. Functional expression and characterization of cytochrome P450 52A21 from Candida albicans. Arch Biochem Biophys. 2007 Aug 15; 464(2):213-20. Kim D, Cryle MJ, De Voss JJ, Ortiz de Montellano PR. PMID: 17400174; PMCID: PMC1993549.
      View in: PubMed   Mentions: 12     Fields:    Translation:AnimalsCells
    55. Arthromyces ramosus peroxidase produces two chlorinating species. Biochem Biophys Res Commun. 2007 Apr 06; 355(2):581-6. Huang L, Ortiz de Montellano PR. PMID: 17303078.
      View in: PubMed   Mentions:    Fields:    Translation:AnimalsCells
    56. 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. Austin RN, Deng D, Jiang Y, Luddy K, van Beilen JB, Ortiz de Montellano PR, Groves JT. PMID: 17103473.
      View in: PubMed   Mentions: 9     Fields:    Translation:Cells
    57. 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. He X, Alian A, Stroud R, Ortiz de Montellano PR. PMID: 17034137.
      View in: PubMed   Mentions: 37     Fields:    Translation:Cells
    58. 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. Huang L, Wojciechowski G, Ortiz de Montellano PR. PMID: 16651262.
      View in: PubMed   Mentions: 11     Fields:    Translation:AnimalsCells
    59. 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. Qian L, Ortiz de Montellano PR. PMID: 16544950; PMCID: PMC2533439.
      View in: PubMed   Mentions: 26     Fields:    Translation:HumansCells
    60. Radical intermediates in the catalytic oxidation of hydrocarbons by bacterial and human cytochrome P450 enzymes. Biochemistry. 2006 Jan 17; 45(2):533-42. Jiang Y, He X, Ortiz de Montellano PR. PMID: 16401082.
      View in: PubMed   Mentions: 16     Fields:    Translation:HumansCells
    61. 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. Wang J, Evans JP, Ogura H, La Mar GN, Ortiz de Montellano PR. PMID: 16388581; PMCID: PMC2507887.
      View in: PubMed   Mentions: 12     Fields:    Translation:HumansCells
    62. 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. Zhu W, Li Y, Wang J, Ortiz de Montellano PR, La Mar GN. PMID: 16337271.
      View in: PubMed   Mentions: 5     Fields:    Translation:Humans
    63. Heme-protein covalent bonds in peroxidases and resistance to heme modification during halide oxidation. Arch Biochem Biophys. 2006 Feb 01; 446(1):77-83. Huang L, Ortiz de Montellano PR. PMID: 16375846.
      View in: PubMed   Mentions: 6     Fields:    Translation:Cells
    64. 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. Ghiladi RA, Medzihradszky KF, Ortiz de Montellano PR. PMID: 16285713.
      View in: PubMed   Mentions: 13     Fields:    Translation:Cells
    65. 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. Wojciechowski G, Huang L, Ortiz de Montellano PR. PMID: 16277530.
      View in: PubMed   Mentions: 8     Fields:    Translation:Cells
    66. Correlation between isoniazid resistance and superoxide reactivity in mycobacterium tuberculosis KatG. J Am Chem Soc. 2005 Sep 28; 127(38):13428-42. Ghiladi RA, Medzihradszky KF, Rusnak FM, Ortiz de Montellano PR. PMID: 16173777.
      View in: PubMed   Mentions: 17     Fields:    Translation:Cells
    67. Thermophilic cytochrome P450 enzymes. Biochem Biophys Res Commun. 2005 Dec 09; 338(1):437-45. Nishida CR, Ortiz de Montellano PR. PMID: 16139791.
      View in: PubMed   Mentions: 10     Fields:    Translation:Cells
    68. 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. Huang L, Wojciechowski G, Ortiz de Montellano PR. PMID: 15826172.
      View in: PubMed   Mentions: 9     Fields:    Translation:Cells
    69. 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. Ghiladi RA, Knudsen GM, Medzihradszky KF, Ortiz de Montellano PR. PMID: 15840564.
      View in: PubMed   Mentions: 24     Fields:    Translation:Cells
    70. Cyclopropyl containing fatty acids as mechanistic probes for cytochromes P450. J Org Chem. 2005 Apr 01; 70(7):2455-69. Cryle MJ, Ortiz de Montellano PR, De Voss JJ. PMID: 15787531.
      View in: PubMed   Mentions: 10     Fields:    Translation:Cells
    71. The P450cam G248E mutant covalently binds its prosthetic heme group. Biochemistry. 2005 Mar 15; 44(10):4091-9. Limburg J, LeBrun LA, Ortiz de Montellano PR. PMID: 15751986.
      View in: PubMed   Mentions: 3     Fields:    Translation:HumansAnimalsCells
    72. The Sulfolobus solfataricus electron donor partners of thermophilic CYP119: an unusual non-NAD(P)H-dependent cytochrome P450 system. Arch Biochem Biophys. 2005 Feb 01; 434(1):169-77. Puchkaev AV, Ortiz de Montellano PR. PMID: 15629120.
      View in: PubMed   Mentions: 13     Fields:    Translation:Cells
    73. Protein kinase Akt/PKB phosphorylates heme oxygenase-1 in vitro and in vivo. FEBS Lett. 2004 Dec 03; 578(1-2):90-4. Salinas M, Wang J, Rosa de Sagarra M, Martín D, Rojo AI, Martin-Perez J, Ortiz de Montellano PR, Cuadrado A. PMID: 15581622.
      View in: PubMed   Mentions: 27     Fields:    Translation:HumansAnimalsCells
    74. 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. Ogura H, Nishida CR, Hoch UR, Perera R, Dawson JH, Ortiz de Montellano PR. PMID: 15544342.
      View in: PubMed   Mentions: 22     Fields:    Translation:Cells
    75. 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. Wang J, Lad L, Poulos TL, Ortiz de Montellano PR. PMID: 15525643.
      View in: PubMed   Mentions: 7     Fields:    Translation:HumansCells
    76. 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. Lad L, Ortiz de Montellano PR, Poulos TL. PMID: 15522396.
      View in: PubMed   Mentions: 10     Fields:    Translation:HumansCells
    77. 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. Huang L, Colas C, Ortiz de Montellano PR. PMID: 15469283.
      View in: PubMed   Mentions: 11     Fields:    Translation:Cells
    78. Alpha- and beta-thujone radical rearrangements and isomerizations. A new radical clock. J Org Chem. 2004 Aug 20; 69(17):5684-9. He X, Ortiz de Montellano PR. PMID: 15307740.
      View in: PubMed   Mentions: 3     Fields:    Translation:Cells
    79. Computer-assisted design of selective imidazole inhibitors for cytochrome p450 enzymes. J Med Chem. 2004 Jul 01; 47(14):3572-9. Verras A, Kuntz ID, Ortiz de Montellano PR. PMID: 15214784.
      View in: PubMed   Mentions: 14     Fields:    
    80. Inhibition of Mycobacterium tuberculosis AhpD, an element of the peroxiredoxin defense against oxidative stress. Antimicrob Agents Chemother. 2004 Jul; 48(7):2424-30. Koshkin A, Zhou XT, Kraus CN, Brenner JM, Bandyopadhyay P, Kuntz ID, Barry CE, Ortiz de Montellano PR. PMID: 15215090.
      View in: PubMed   Mentions: 6     Fields:    Translation:AnimalsCells
    81. Intermolecular interactions in the AhpC/AhpD antioxidant defense system of Mycobacterium tuberculosis. Arch Biochem Biophys. 2004 Jul 01; 427(1):41-7. Koshkin A, Knudsen GM, Ortiz De Montellano PR. PMID: 15178486.
      View in: PubMed   Mentions: 14     Fields:    Translation:Cells
    82. Methyl groups as probes for proteins and complexes in in-cell NMR experiments. J Am Chem Soc. 2004 Jun 09; 126(22):7119-25. Serber Z, Straub W, Corsini L, Nomura AM, Shimba N, Craik CS, Ortiz de Montellano P, Dötsch V. PMID: 15174883.
      View in: PubMed   Mentions: 24     Fields:    Translation:Cells
    83. 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 04; 101(18):6870-5. Marnett AB, Nomura AM, Shimba N, Ortiz de Montellano PR, Craik CS. PMID: 15118083.
      View in: PubMed   Mentions: 14     Fields:    Translation:Cells
    84. Superoxide reactivity of KatG: insights into isoniazid resistance pathways in TB. J Am Chem Soc. 2004 Apr 21; 126(15):4772-3. Ghiladi RA, Cabelli DE, Ortiz de Montellano PR. PMID: 15080669.
      View in: PubMed   Mentions: 3     Fields:    Translation:Cells
    85. Autoreduction of ferryl myoglobin: discrimination among the three tyrosine and two tryptophan residues as electron donors. Biochemistry. 2004 Apr 20; 43(15):4601-10. Lardinois OM, Ortiz de Montellano PR. PMID: 15078107.
      View in: PubMed   Mentions: 11     Fields:    Translation:AnimalsCells
    86. Crystal structure of human heme oxygenase-1 in a complex with biliverdin. Biochemistry. 2004 Apr 06; 43(13):3793-801. Lad L, Friedman J, Li H, Bhaskar B, Ortiz de Montellano PR, Poulos TL. PMID: 15049686.
      View in: PubMed   Mentions: 17     Fields:    Translation:HumansAnimalsCells
    87. Cyclopropyl fatty acids implicate a radical but not a cation as an intermediate in P450BM3-catalysed hydroxylations. Chem Commun (Camb). 2004 Mar 07; (5):512-3. Cryle MJ, Stuthe JM, Ortiz de Montellano PR, De Voss JJ. PMID: 14973583.
      View in: PubMed   Mentions: 2     Fields:    Translation:Cells
    88. Steady-state kinetic investigation of cytochrome P450cam: interaction with redox partners and reaction with molecular oxygen. Biochemistry. 2004 Jan 13; 43(1):271-81. Purdy MM, Koo LS, Ortiz de Montellano PR, Klinman JP. PMID: 14705955.
      View in: PubMed   Mentions: 6     Fields:    Translation:Cells
    89. Catalytic activity and isoform-specific inhibition of rat cytochrome p450 4F enzymes. J Pharmacol Exp Ther. 2004 Mar; 308(3):887-95. Xu F, Falck JR, Ortiz de Montellano PR, Kroetz DL. PMID: 14634044.
      View in: PubMed   Mentions: 19     Fields:    Translation:AnimalsCells
    90. 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 05; 125(44):13392-403. Li Y, Syvitski RT, Auclair K, Ortiz de Montellano P, La Mar GN. PMID: 14583035.
      View in: PubMed   Mentions: 12     Fields:    Translation:HumansCells
    91. Crystal structures of epothilone D-bound, epothilone B-bound, and substrate-free forms of cytochrome P450epoK. J Biol Chem. 2003 Nov 07; 278(45):44886-93. Nagano S, Li H, Shimizu H, Nishida C, Ogura H, Ortiz de Montellano PR, Poulos TL. PMID: 12933799.
      View in: PubMed   Mentions: 23     Fields:    Translation:Cells
    92. 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. Lad L, Wang J, Li H, Friedman J, Bhaskar B, Ortiz de Montellano PR, Poulos TL. PMID: 12842469.
      View in: PubMed   Mentions: 20     Fields:    Translation:HumansCells
    93. 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. Lardinois OM, Ortiz de Montellano PR. PMID: 12855712.
      View in: PubMed   Mentions: 8     Fields:    Translation:AnimalsCells
    94. 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. Knudsen GM, Nishida CR, Mooney SD, Ortiz de Montellano PR. PMID: 12805387.
      View in: PubMed   Mentions: 22     Fields:    Translation:HumansAnimalsCells
    95. Autocatalytic radical reactions in physiological prosthetic heme modification. Chem Rev. 2003 Jun; 103(6):2305-32. Colas C, Ortiz de Montellano PR. PMID: 12797831.
      View in: PubMed   Mentions: 23     Fields:    Translation:HumansCells
    96. The mechanism of Mycobacterium tuberculosis alkylhydroperoxidase AhpD as defined by mutagenesis, crystallography, and kinetics. J Biol Chem. 2003 Aug 08; 278(32):29502-8. Koshkin A, Nunn CM, Djordjevic S, Ortiz de Montellano PR. PMID: 12761216.
      View in: PubMed   Mentions: 17     Fields:    Translation:Cells
    97. 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. Gunther MR, Tschirret-Guth RA, Lardinois OM, Ortiz de Montellano PR. PMID: 12755595.
      View in: PubMed   Mentions: 8     Fields:    Translation:Animals
    98. Cloning and expression of a heme binding protein from the genome of Saccharomyces cerevisiae. Protein Expr Purif. 2003 Apr; 28(2):340-9. Auclair K, Huang HW, Moënne-Loccoz P, Ortiz de Montellano PR. PMID: 12699699.
      View in: PubMed   Mentions: 2     Fields:    Translation:Cells
    99. Aromatic stacking as a determinant of the thermal stability of CYP119 from Sulfolobus solfataricus. Arch Biochem Biophys. 2003 Jan 01; 409(1):52-8. Puchkaev AV, Koo LS, Ortiz de Montellano PR. PMID: 12464244.
      View in: PubMed   Mentions: 11     Fields:    Translation:Cells
    100. Comparison of the heme-free and -bound crystal structures of human heme oxygenase-1. J Biol Chem. 2003 Mar 07; 278(10):7834-43. Lad L, Schuller DJ, Shimizu H, Friedman J, Li H, Ortiz de Montellano PR, Poulos TL. PMID: 12500973.
      View in: PubMed   Mentions: 43     Fields:    Translation:HumansCells
    101. 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 04; 124(48):14296-7. Syvitski RT, Li Y, Auclair K, Ortiz De Montellano PR, La Mar GN. PMID: 12452690.
      View in: PubMed   Mentions: 11     Fields:    Translation:HumansCells
    102. Interaction of nitric oxide with human heme oxygenase-1. J Biol Chem. 2003 Jan 24; 278(4):2341-7. Wang J, Lu S, Moënne-Loccoz P, Ortiz de Montellano PR. PMID: 12433915.
      View in: PubMed   Mentions: 16     Fields:    Translation:HumansAnimalsCells
    103. 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. Puchkaev AV, Wakagi T, Ortiz de Montellano PR. PMID: 12392414.
      View in: PubMed   Mentions: 6     Fields:    Translation:Cells
    104. 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. de Ropp JS, Sham S, Asokan A, Newmyer S, Ortiz de Montellano PR, La Mar GN. PMID: 12224950.
      View in: PubMed   Mentions: 5     Fields:    Translation:Cells
    105. Antihypertensive effect of mechanism-based inhibition of renal arachidonic acid omega-hydroxylase activity. . 2002 Sep; 283(3):R710-20. Xu F, Straub WO, Pak W, Su P, Maier KG, Yu M, Roman RJ, Ortiz De Montellano PR, Kroetz DL. PMID: 12185006.
      View in: PubMed   Mentions:
    106. Electron supply and catalytic oxidation of nitrogen by cytochrome P450 and nitric oxide synthase. Drug Metab Rev. 2002 Aug; 34(3):479-501. Nishida CR, Knudsen G, Straub W, Ortiz de Montellano PR. PMID: 12214661.
      View in: PubMed   Mentions:    Fields:    Translation:Cells
    107. Oxidizing species in the mechanism of cytochrome P450. Nat Prod Rep. 2002 Aug; 19(4):477-93. Ortiz de Montellano PR, De Voss JJ. PMID: 12195813.
      View in: PubMed   Mentions: 44     Fields:    Translation:Cells
    108. 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 06; 277(36):33018-31. Li Y, Syvitski RT, Auclair K, Wilks A, Ortiz De Montellano PR, La Mar GN. PMID: 12070167.
      View in: PubMed   Mentions: 16     Fields:    Translation:HumansCells
    109. 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. Auclair K, Hu Z, Little DM, Ortiz De Montellano PR, Groves JT. PMID: 12022835.
      View in: PubMed   Mentions: 29     Fields:    Translation:HumansAnimalsCells
    110. Enhanced electron transfer and lauric acid hydroxylation by site-directed mutagenesis of CYP119. J Am Chem Soc. 2002 May 22; 124(20):5684-91. Koo LS, Immoos CE, Cohen MS, Farmer PJ, Ortiz de Montellano PR. PMID: 12010041.
      View in: PubMed   Mentions: 14     Fields:    Translation:Cells
    111. Cytochrome P450(cin) (CYP176A), isolation, expression, and characterization. J Biol Chem. 2002 Aug 02; 277(31):27725-32. Hawkes DB, Adams GW, Burlingame AL, Ortiz de Montellano PR, De Voss JJ. PMID: 12016226.
      View in: PubMed   Mentions: 22     Fields:    Translation:HumansAnimalsCells
    112. Covalent attachment of the heme prosthetic group in the CYP4F cytochrome P450 family. Biochemistry. 2002 May 07; 41(18):5931-7. LeBrun LA, Xu F, Kroetz DL, Ortiz de Montellano PR. PMID: 11980497.
      View in: PubMed   Mentions: 9     Fields:    Translation:AnimalsCells
    113. 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. Nunn CM, Djordjevic S, Hillas PJ, Nishida CR, Ortiz de Montellano PR. PMID: 11914371.
      View in: PubMed   Mentions: 15     Fields:    Translation:Cells
    114. 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. Zhang Z, Li Y, Stearns RA, Ortiz De Montellano PR, Baillie TA, Tang W. PMID: 11851418.
      View in: PubMed   Mentions: 3     Fields:    Translation:HumansCells
    115. The antituberculosis drug ethionamide is activated by a flavoprotein monooxygenase. J Biol Chem. 2002 Apr 12; 277(15):12824-9. Vannelli TA, Dykman A, Ortiz de Montellano PR. PMID: 11823459.
      View in: PubMed   Mentions: 46     Fields:    Translation:Cells
    116. Autocatalytic mechanism and consequences of covalent heme attachment in the cytochrome P4504A family. J Biol Chem. 2002 Apr 12; 277(15):12755-61. LeBrun LA, Hoch U, Ortiz de Montellano PR. PMID: 11821421.
      View in: PubMed   Mentions: 10     Fields:    Translation:Cells
    117. Asp-225 and glu-375 in autocatalytic attachment of the prosthetic heme group of lactoperoxidase. J Biol Chem. 2002 Mar 01; 277(9):7191-200. Colas C, Kuo JM, Ortiz de Montellano PR. PMID: 11756449.
      View in: PubMed   Mentions: 9     Fields:    Translation:AnimalsCells
    118. The mechanism of heme oxygenase. Curr Opin Chem Biol. 2000 Apr; 4(2):221-7. Montellano PR. PMID: 10742194.
      View in: PubMed   Mentions: 38     Fields:    Translation:HumansAnimalsCells
    119. Nitric oxide synthase structure and electron transfer. Drug Metab Dispos. 1998 Dec; 26(12):1185-9. Ortiz de Montellano PR, Nishida C, Rodriguez-Crespo I, Gerber N. PMID: 9860925.
      View in: PubMed   Mentions: 1     Fields:    Translation:HumansAnimalsCells
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