Key residues controlling binding of diverse ligands to human cytochrome P450 2A enzymes

Drug Metabolism and Disposition

Volumn 37, Issue 6, 2009, Pages 1319-1327

  DeVore, N M ^a   Smith, B D ^a   Wang, J L ^a   Lushington, G H ^a   Scott, Emily E ^a  

^a UNIVERSITY OF KANSAS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2' METHOXYACETOPHENONE; ACETOPHENONE DERIVATIVE; COUMARIN; CYTOCHROME P450 2A13; CYTOCHROME P450 2A6; CYTOCHROME P450 ISOENZYME; LEUCINE; METHOXSALEN; NICOTINE; PHENETHYL ISOTHIOCYANATE; UNCLASSIFIED DRUG;

AMINO ACID SEQUENCE; ARTICLE; BINDING AFFINITY; BINDING SITE; DRUG METABOLISM; ENZYME ACTIVE SITE; ENZYME SUBSTRATE COMPLEX; HUMAN; LIGAND BINDING; PRIORITY JOURNAL; QUANTITATIVE STRUCTURE ACTIVITY RELATION; SITE DIRECTED MUTAGENESIS;

AMINO ACID SEQUENCE; AMINO ACID SUBSTITUTION; ARYL HYDROCARBON HYDROXYLASES; CATALYTIC DOMAIN; CYTOCHROME P-450 ENZYME SYSTEM; HUMANS; LIGANDS; MICROSOMES, LIVER; MODELS, MOLECULAR; MUTAGENESIS, SITE-DIRECTED; PROTEIN BINDING; PROTEIN CONFORMATION; STEROID HYDROXYLASES; STRUCTURE-ACTIVITY RELATIONSHIP; SUBSTRATE SPECIFICITY;

EID: 66649122018     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.109.026765     Document Type: Article

References (30)

1. Bao Z, He XY, Ding X, Prabhu S, and Hong JY (2005) Metabolism of nicotine and cotinine by human cytochrome P450 2A13. Drug Metab Dispos 33:258-261. (Pubitemid 40216593)
2. Brooks BR, Bruccoleri RE, Olafson BD, States DJ, Swaminathan S, and Karplus M (1983) CHARMM: a program for macromolecular energy, minimization and dynamics calculations. J Comp Chem 4:187-217.
3. DeLano WL (2003) The PyMOL Molecular Graphics System, DeLano Scientific, San Carlos, CA.
4. DeVore NM, Smith BD, Urban MJ, and Scott EE (2008) Key residues controlling phenacetin metabolism by human cytochrome P450 2A enzymes. Drug Metab Dispos 36:2582-2590.
5. Fernandez-Salguero P, Hoffman SM, Cholerton S, Mohrenweiser H, Raunio H, Rautio A, Pelkonen O, Huang JD, Evans WE, and Idle JR (1995) A genetic-polymorphism in coumarin 7-hydroxylation - sequence of the human Cyp2a genes and identification of variant Cyp2a6 alleles. Am J Hum Genet 57:651-660.
6. Fukami T, Nakajima M, Sakai H, Katoh M, and Yokoi T (2007) CYP2A13 metabolizes human CYP1A2 substrates, phenacetin and theophylline. Drug Metab Dispos 35:335-339. (Pubitemid 46333918)
7. He XY, Shen J, Ding X, Lu AY, and Hong JY (2004a) Identification of critical amino acid residues of human CYP2A13 for the metabolic activation of 4-(methylnitrosamino)-1-(3- pyridyl)-1-butanone, a tobacco-specific carcinogen. Drug Metab Dispos 32:1516-1521. (Pubitemid 39564574)
8. 372 as critical amino acid residues for the activity difference between human CYP2A6 and CYP2A13 in coumarin 7-hydroxylation. Arch Biochem Biophys 427:143-153.
9. He XY, Tang L, Wang SL, Cai QS, Wang JS, and Hong JY (2006) Efficient activation of aflatoxin B1 by cytochrome P450 2A13, an enzyme predominantly expressed in human respiratory tract. Int J Cancer 118:2665-2671. (Pubitemid 43673342)
10. Kim D, Wu ZL, and Guengerich FP (2005) Analysis of coumarin 7-hydroxylation activity of cytochrome P450 2A6 using random mutagenesis. J Biol Chem 280:40319-40327. (Pubitemid 41779169)
11. Koenigs LL, Peter RM, Thompson SJ, Rettie AE, and Trager WF (1997) Mechanism-based inactivation of human liver cytochrome P450 2A6 by 8-methoxypsoralen. Drug Metab Dispos 25:1407-1415. (Pubitemid 28010927)
12. Murphy SE, Raulinaitis V, and Brown KM (2005) Nicotine 5′-oxidation and methyl oxidation by P450 2A enzymes. Drug Metab Dispos 33:1166-1173. (Pubitemid 41043760)
13. Ortiz AR, Pisabarro MT, Gago F, and Wade RC (1995) Prediction of drug binding affinities by comparative binding energy analysis. J Med Chem 38:2681-2691.
14. Rarey M, Kramer B, Lengauer T, and Klebe G (1996) A fast flexible docking method using an incremental construction algorithm. J Mol Biol 261:470-489. (Pubitemid 26335901)
15. Schoch GA, Yano JK, Wester MR, Griffin KJ, Stout CD, and Johnson EF (2004) Structure of human microsomal cytochrome P450 2C8: evidence for a peripheral fatty acid binding site. J Biol Chem 279:9497-9503. (Pubitemid 38296017)
16. Scott EE, Spatzenegger M, and Halpert JR (2001) A truncation of 2B subfamily cytochromes P450 yields increased expression levels, increased solubility, and decreased aggregation while retaining function. Arch Biochem Biophys 395:57-68. (Pubitemid 33030143)
17. Smith BD, Sanders JL, Porubsky PR, Lushington GH, Stout CD, and Scott EE (2007) Structure of the human lung cytochrome P450 2A13. J Biol Chem 282:17306-17313. (Pubitemid 47093207)
18. Su T, Bao Z, Zhang QY, Smith TJ, Hong JY, and Ding X (2000) Human cytochrome P450 CYP2A13: predominant expression in the respiratory tract and its high efficiency metabolic activation of a tobacco-specific carcinogen, 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone. Cancer Res 60:5074-5079.
19. Tan W, Chen GF, Xing DY, Song CY, Kadlubar FF, and Lin DX (2001) Frequency of CYP2A6 gene deletion and its relation to risk of lung and esophageal cancer in the Chinese population. Int J Cancer 95:96-101. (Pubitemid 32187080)
20. von Wachenfeldt C, Richardson TH, Cosme J, and Johnson EF (1997) Microsomal P450 2C3 is expressed as a soluble dimer in Escherichia coli following modification of its N-terminus. Arch Biochem Biophys 339:107-114. (Pubitemid 27199760)
21. von Weymarn LB, Chun JA, and Hollenberg PF (2006) Effects of benzyl and phenethyl isothiocyanate on P450s 2A6 and 2A13: potential for chemoprevention in smokers. Carcinogenesis 27:782-790.
22. von Weymarn LB and Murphy SE (2003) CYP2A13-catalysed coumarin metabolism: comparison with CYP2A5 and CYP2A6. Xenobiotica 33:73-81. (Pubitemid 36071764)
23. von Weymarn LB, Zhang QY, Ding X, and Hollenberg PF (2005) Effects of 8-methoxypsoralen on cytochrome P450 2A13. Carcinogenesis 26:621-629. (Pubitemid 41214152)
24. Wang H, Tan W, Hao B, Miao X, Zhou G, He F, and Lin D (2003) Substantial reduction in risk of lung adenocarcinoma associated with genetic polymorphism in CYP2A13, the most active cytochrome P450 for the metabolic activation of tobacco-specific carcinogen NNK. Cancer Research 63:8057-8061. (Pubitemid 37466745)
25. Wester MR, Yano JK, Schoch GA, Yang C, Griffin KJ, Stout CD, and Johnson EF (2004) The structure of human cytochrome P450 2C9 complexed with flurbiprofen at 2.0-A resolution. J Biol Chem 279:35630-35637. (Pubitemid 39100565)
26. Wu ZL, Podust LM, and Guengerich FP (2005) Expansion of substrate specificity of cytochrome P450 2A6 by random and site-directed mutagenesis. J Biol Chem 280:41090-41100. (Pubitemid 41780604)
27. Yamano S, Tatsuno J, and Gonzalez FJ (1990) The CYP2A3 gene product catalyzes coumarin 7-hydroxylation in human liver microsomes. Biochemistry 29:1322-1329. (Pubitemid 20053858)
28. Yano JK, Hsu MH, Griffin KJ, Stout CD, and Johnson EF (2005) Structures of human microsomal cytochrome P450 2A6 complexed with coumarin and methoxsalen. Nat Struct Mol Biol 12:822-823. (Pubitemid 43086258)
29. Yano JK, Wester MR, Schoch GA, Griffin KJ, Stout CD, and Johnson EF (2004) The structure of human microsomal cytochrome P450 3A4 determined by X-ray crystallography to 2.05-A resolution. J Biol Chem 279:38091-38094. (Pubitemid 39295952)
30. Zhu LR, Thomas PE, Lu G, Reuhl KR, Yang GY, Wang LD, Wang SL, Yang CS, He XY, and Hong JY (2006) CYP2A13 in human respiratory tissues and lung cancers: an immunohistochemical study with a new peptide-specific antibody. Drug Metab Dispos 34:1672-1676. (Pubitemid 44427469)