Helices F-G are important for the substrate specificities of CYP3A7

Drug Metabolism and Disposition

Volumn 35, Issue 3, 2007, Pages 484-492

  Torimoto, Nao ^a   Ishii, Itsuko ^a,c   Toyama, Ken Ichi ^a   Hata, Masayuki ^a   Tanaka, Kanako ^a   Shimomura, Hitoshi ^a   Nakamura, Hiroyoshi ^a   Ariyoshi, Noritaka ^a   Ohmori, Shigeru ^b   Kitada, Mitsukazu ^a  

^a CHIBA UNIVERSITY HOSPITAL   (Japan)

^b SHINSHU UNIVERSITY HOSPITAL   (Japan)

^c CHIBA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; CYTOCHROME P450 3A; CYTOCHROME P450 3A4; CYTOCHROME P450 3A7; ERYTHROMYCIN; NEVIRAPINE; PRASTERONE SULFATE; TESTOSTERONE; TRIAZOLAM;

ARTICLE; CHIMERA; COMPARATIVE STUDY; CONTROLLED STUDY; CRYSTAL STRUCTURE; DRUG METABOLISM; ENZYME KINETICS; ENZYME SPECIFICITY; HUMAN; HUMAN TISSUE; HYDROXYLATION; PRIORITY JOURNAL; SITE DIRECTED MUTAGENESIS;

AMINO ACID SEQUENCE; ARYL HYDROCARBON HYDROXYLASES; CYTOCHROME P-450 ENZYME SYSTEM; DEHYDROEPIANDROSTERONE; DEHYDROEPIANDROSTERONE SULFATE; HYDROXYLATION; MODELS, CHEMICAL; MOLECULAR SEQUENCE DATA; MUTAGENESIS, SITE-DIRECTED; MUTANT CHIMERIC PROTEINS; PROTEIN CONFORMATION; SEQUENCE ALIGNMENT; SUBSTRATE SPECIFICITY;

EID: 33847379777     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.106.011304     Document Type: Article

References (38)

1. Aoyama T, Yamano S, Waxman DJ, Lapenson DP, Meyer UA, Fisher R, Tyndale R, Inaba T, Werner K, et al. (1989) Cytochrome P-450 hPCN3, a novel cytochrome P-450 IIIA gene product that is differentially expressed in adult human liver. cDNA and deduced amino acid sequence and distinct specificities of cDNA-expressed hPCN1 and hPCN3 for the metabolism of steroid hormones and cyclosporine. J Biol Chem 264:10388-10395.
2. Beaune PH, Umbenhauer DR, Bork RW, Lloyd RS, and Guengerich FP (1986) Isolation and sequence determination of a cDNA clone related to human cytochrome P-450 nifedipine oxidase. Proc Natl Acad Sci USA 83:8064-8068.
3. Bork RW, Muto T, Beaune PH, Srivastava PK, Lloyd RS, and Guengerich FP (1989) Characterization of mRNA species related to human liver cytochrome P-450 nifedipine oxidase and the regulation of catalytic activity. J Biol Chem 264:910-919.
4. Case DA, Pearlman DA, Caldwell JW, Cheatham TE III, Ross WS, Simmerling CL, Darden TA, Merz KM, Stanton RV, Cheng AL, et al. (1999). AMBER 6, University of California, San Francisco.
5. Domanski TL, He YA, Harlow GR, and Halpert JR (2000) Dual role of human cytochrome P450 3A4 residue Phe-304 in substrate specificity and cooperativity. J Pharmacol Exp Ther 293:585-591.
6. Ekroos M and Sjögren T (2006) Structural basis for ligand promiscuity in cytochrome P450 3A4. Proc Natl Acad Sci USA 103:13682-13687.
7. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Zakrzewski VG, Montgomery JA Jr, Stratmann RE, Burant JC, et al. (2001) Gaussian 98, revision A. 11.1, Gaussian, Inc., Pittsburgh PA.
8. Gonzalez FJ, Schmid BJ, Umeno M, Mcbride OW, Hardwick JP, Meyer UA, Gelboin HV, and Idle JR (1988) Human P450PCN1: sequence, chromosome localization, and direct evidence through cDNA expression that P450PCN1 is nifedipine oxidase. DNA 7:79-86.
9. Guengerich FP, Wang P, and Davidson NK (1982) Estimation of isoenzymes of microsomal cytochrome P-450 in rats, rabbits and humans using immunochemical staining coupled with sodium dodecyl sulfate-polyacrylamide gel electrophoresis. Biochemistry 21:1698-1706.
10. Hashimoto H, Toide T, Kitamura R, Fujita M, Tagawa S, Itoh S, and Kamataki T (1993) Gene structure of CYP3A4, an adult-specific form of cytochrome P450 in human livers, and its transcriptional control. Eur J Biochem 218:585-595.
11. Hata M, Hirano Y, Hoshino T, and Tsuda M (2001) Monooxygenation mechanism by cytochrome P450. J Am Chem Soc 123:6410-6416.
12. Itoh S, Yanagimoto T, Tagawa S, Hashimoto H, Kitamura R, Nakajima Y, Okouchi T, Fujimoto S, Uchino J, and Kamataki T (1992) Genomic organization of human fetal specific P-450IIIA7 (cytochrome P-450HFLa)-related gene(s) and interaction of transcriptional regulatory factor with its DNA element in the 5′ flanking region. Biochim Biophys Acta 1130:133-138.
13. Jorgensen WL, Chandrasekhar J, and Madura JD (1983) Composition of simple potential functions for simulating liquid water. J Chem Phys 79:926-935.
14. Kedzie KM, Balfour CA, Escobar GY, Grimm SW, He, Y.-A., Pepperl DJ, Regan JW, Stevens JC, and Halpert JR (1991) Molecular basis for a functionally unique cytochrome P450IIB1 variant. J Biol Chem 266:22515-22521.
15. Kitada M, Kamataki T, Itahashi K, Rikihisa T, Kato R, and Kanakubo Y (1985a) Immunochemical examinations of cytochrome P-450 in various tissues of human fetuses using antibodies to human fetal cytochrome P-450, P-450 HFLa. Biochem Biophys Res Commun 131:1154-1159.
16. Kitada M, Kamataki T, Itahashi K, Rikihisa T, Kato R, and Kanakubo Y (1985b) Purification and properties of cytochrome P450 from homogenates of human fetal livers. Arch Biochem Biophys 241:275-280.
17. Kitada M, Kamataki T, Itahashi K, Rikihisa T, and Kanakubo Y (1987) P-450 HFLa, a form of cytochrome P-450 purified from human fetal livers, is the 16α-hydroxylase of dehydroepiandrosterone 3-sulfate. J Biol Chem 262:13534-13537.
18. Komori M, Nishio K, Ohi H, Kitada M, and Kamataki T (1989) Molecular cloning and sequence analysis of cDNA containing the entire coding region for human fetal liver cytochrome P-450. J Biochem (Tokyo) 105:161-163.
19. Lacroix D, Sonnier M, Moncion A, Cheron G, and Cresteil T (1997) Expression of CYP3A in the human liver-evidence that the shift between CYP3A7 and CYP3A4 occurs immediately after birth. Eur J Biochem 247:625-634.
20. Lowry OH, Rosebrough NJ, Farr AL, and Randall RJ (1951) Protein measurement with the Folin phenol reagent. J Biol Chem 193:265-279.
21. Miura T, Komori M, Iwasaki M, Kurosumi K, Ohta H, Ohmori S, Kitada M, and Kamataki T (1988) Sex-related difference in oxidative metabolism of testosterone and erythromycin by hamster liver microsomes. FEBS Lett 231:183-186.
22. Nakamura H, Nakasa H, Ishii I, Ariyoshi N, Igarashi T, Ohmori S, and Kitada M (2002) Effects of endogenous steroids on CYP3A4-mediated drug metabolism by human liver microsomes. Drug Metab Dispos 30:534-540.
23. Nakamura H, Torimoto N, Ishii I, Ariyoshi N, Nakasa H, Ohmori S, and Kitada M (2003) CYP3A4 and CYP3A7-mediated carbamazepine 10,11-epoxidation are activated by differential endogenous steroids. Drug Metab Dispos 31:432-438.
24. Nelson DR, Koymans L, Kamataki T, Stegeman JJ, Feyereisen R, Waxman DJ, Waterman MR, Gotoh O, Coon MJ, Estabrook RW, et al. (1996) P450 superfamily: update on new sequences, gene mapping, accession numbers and nomenclature. Pharmacogenetics 6:1-42.
25. Ohmori S, Nakasa H, Asanome K, Kurose Y, Ishii I, Hosokawa M, and Kitada M (1998) Differential catalytic properties in metabolism of endogenous and exogenous substrates among CYP3A enzymes expressed in COS-7 cells. Biochim Biophys Acta 1380:297-304.
26. Omura T, and Sato R (1964) The carbon monoxide-binding pigment of liver microsomes. II. Solubilization, purification, and properties. J Biol Chem 239:2370-2385.
27. Pearce RE, Gotschall RR, Kearns GL, and Leeder JS (2001) Cytochrome P450 involvement in the biotransformation of cisapride and racemic norcisapride in vitro: differential activity of individual human CYP3A isoforms. Drug Metab Dispos 29:1548-1554.
28. Pearlman DA, Case DA, Caldwell JW, Ross WS, Cheatham TE 3rd, Seibel GL, Singh UC, Weiner PK, and Kollman PA (1995). AMBER 4.1, University of California, San Francisco.
29. Phillips AH and Langdon RJ (1962) Hepatic triphosphopyridine nucleotide-cytochrome c reductase: isolation, characterization, and kinetic studies. J Biol Chem 237:2652-2790.
30. Saito T, Takahashi Y, Hashimoto H, and Kamataki T (2001) Novel transcriptional regulation of the human CYP3A7 gene by Sp1 and Sp3 through nuclear factor κB-like element. J Biol Chem 276:38010-38022.
31. 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.
32. Shimada T, Yamazaki H, Mimura M, Inui Y, and Guengerich FP (1994) Interindividual variations in human liver cytochrome P-450 enzymes involved in the oxidation of drugs, carcinogens and toxic chemicals: studies with liver microsomes of 30 Japanese and 30 Caucasians. J Pharmacol Exp Ther 270:414-423.
33. Shimada T, Yamazaki H, Mimura M, Wakamiya N, Ueng YF, Guengerich FP, and Inui Y (1996) Characterization of microsomal cytochrome P450 enzymes involved in the oxidation of xenobiotic chemicals in human fetal liver and adult lungs. Drug Metab Dispos 24:515-522.
34. Torimoto N, Ishii I, Hata M, Nakamura H, Imada H, Ariyoshi N, Ohmori S, Igarashi T, and Kitada M (2003) Direct interaction between substrates and endogenous steroids in the active site may change the activity of CYP3A4. Biochemistry 42:15068-15077.
35. Weiner SJ, Kollman PA, Nguyen DT, and Case DA (1986) An all-atom force field for simulations of proteins and nuclei acid. J Comput Chem 7:230-252.
36. Williams JA, Ring BJ, Cantrell VE, Jones DR, Eckstein J, Ruterbories K, Hamman MA, Hall SD, and Wrighton SA (2002) Comparative metabolic capabilities of CYP3A4, CYP3A5, and CYP3A7. Drug Metab Dispos 30:883-891.
37. Williams PA, Cosme J, Vinkovi DM, Ward A, Angove HC, Day PJ, Vonrhein C, Tickle IJ, and Jhoti H (2004) Crystal structures of human cytochrome P450 3A4 bound to metyrapone and progesterone, Science (Wash DC) 305:683-686.
38. 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 2.05Å resolution, J Biol Chem 279:38091-38094.