Differential mechanisms for the inhibition of human cytochrome P450 1A2 by apigenin and genistein

Journal of Biochemical and Molecular Toxicology

Volumn 24, Issue 4, 2010, Pages 230-234

  Shimada, Hideaki ^a   Eto, Masashi ^b   Ohtaguro, Misa ^c   Ohtsubo, Michihiro ^c   Mizukami, Yosuke ^c   Ide, Tsuyoshi ^c   Imamura, Yorishige ^a  

^a KUMAMOTO UNIVERSITY   (Japan)

^b TOKAI UNIVERSITY   (Japan)

^c Food Science Laboratory   (Japan)

Author keywords

Apigenin; CYP1A2; Docking simulation; Genistein; Inhibitory potency

Indexed keywords

ALPHA NAPHTHOFLAVONE; APIGENIN; CHRYSIN; CYTOCHROME P450 1A2; GALANGIN; GENISTEIN; HEME; KAEMPFEROL;

ARTICLE; CONFORMATION; CRYSTALLIZATION; ENZYME ACTIVE SITE; ENZYME BINDING; ENZYME INHIBITION; MOLECULAR DOCKING; SIMULATION;

ANTICARCINOGENIC AGENTS; APIGENIN; CYTOCHROME P-450 CYP1A2; ENZYME INHIBITORS; GENISTEIN; HUMANS; MODELS, MOLECULAR; PROTEIN STRUCTURE, TERTIARY;

EID: 77956406103     PISSN: 10956670     EISSN: 10990461     Source Type: Journal    
DOI: 10.1002/jbt.20328     Document Type: Article

References (21)

1. Porter TD, Coon MJ. Cytochrome P-450: multiplicity of isoforms, substrates, and catalytic and regulatory mechanisms. J Biol Chem 1991;266(21):13469-13472.
2. Agundez JAG. Cytochrome P450 gene polymorphism and cancer. Curr Drug Metab 2004;5(3):211-224.
3. Butler MA, Iwasaki M, Guengerich FP, Kadlubar FF. Human cytochrome P-450(PA) (P-450IA2), the phenacetin O-deethylase, is primarily responsible for the hepatic 3-demethylation of caffeine and N-oxidation of carcinogenic arylamines. Proc Natl Acad Sci USA 1989;86(20):7696-7700.
4. Turesky RJ, Constable A, Richoz J, Varga N, Markovic J, Martin MV, Guengerich FP. Activation of heterocyclic aromatic amines by rat and human liver microsomes and by purified rat and human cytochrome P450 1A2. Chem Res Toxicol 1998;11(8):925-936.
5. Lee H, Yeom H, Kim YG, Yoon CN, Jin C, Choi JS, Kim BR, Kim, DH. Structure-related inhibition of human hepatic caffeine N3-demethylation by naturally occurring flavonoids. Biochem Pharmacol 1998;55(9):1369-1375.
6. Iori F, da Fonseca R, João Ramos M, Menziani MC. Theoretical quantitative structure-activity relationships of flavone ligands interacting with cytochrome P450 1A1 and 1A2 isozymes. Bioorg Med Chem 2005;13(14):4366- 4374.
7. Cermak R, Wolffram S. The potential of flavonoids to influence drug metabolism and pharmacokinetics by local gastrointestinal mechanisms. Curr Drug Metab 2006;7(7):729-744.
8. Sansen S, Yano JK, Reynald RL, Schoch GA, Griffin KJ, Stout CD, Johnson EF. Adaptation for the oxidation of polycyclic aromatic hydrocarbons exhibited by the structure of human P450 1A2. J Biol Chem 2007;282(19):14384-14355.
9. Cho US, Park EY, Dong MS, Park BS, Kim K, Kim KH. Tight-binding inhibition by α-naphthoflavone of human cytochrome P450 1A2. Biochim Biophys Acta 2003;1648(1-2):195-202.
10. Morris GM, Goodsell DS, Halliday RS, Huey R, Hart WE, Belew RK, Olson AJ. Automated docking using a Lamarckian genetic algorithm and an empirical binding free energy function. J Comput Chem 1998;19(14):1639-1662.
11. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JA, Jr, Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X, Knox JE, Hratchian HP, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA. Gaussian 03, Revision C.02. Wallingford, CT: Gaussian, Inc.; 2004.
12. Pettersen EF, Goddard TD, Huang CC, Couch GS, Greenblatt DM, Meng EC, Ferrin TE. UCSF Chimera-A visualization system for exploratory research and analysis. J Comput Chem 2004;25(13):1605-1612.
13. Zhai S, Dai P, Friedman FK, Vestal RE. Comparative inhibition of human cytochrome P450 1A1 and 1A2 by flavonoids. Drug Metab Dispos 1998;26(10):989-992.
14. Hodek P, Trefil P, Stiborová M. Flavonoids-potent and versatile biologically active compounds interacting with cytochromes P450. Chem Biol Interact 2002;139(1):1-21.
15. Moon YJ, Wang X, Morris ME. Dietary flavonoids: effects on xenobiotic and carcinogen metabolism. Toxicol In Vitro 2006;20(2):187-210.
16. Shimada T, Yamazaki H, Foroozesh M, Hopkins NE, Alworth WL, Guengerich FP. Selectivity of polycyclic inhibitors for human cytochrome P450s 1A1, 1A2, and 1B1. Chem Res Toxicol 1998;11(9):1048-1056.
17. 1. Food Chem Toxicol 2006;44(9):1474-1484.
18. Breinholt VM, Offord EA, Brouwer C, Nielsen ES, Brøsen K, Friedberg T. In vitro investigation of cytochrome P450-mediated metabolism of dietary flavonoids. Food Chem Toxicol 2002;40(5):609-616.
19. Kulling SE, Honig DM, Metzler M. Oxidative metabolism of the soy isoflavones daidzein and genistein in humans in vitro and in vivo. J Agric Food Chem 2001;49(6):3024-3033.
20. Atherton KM, Mutch E, Ford D. Metabolism of the soyabean isoflavone daidzein by CYP1A2 and the extra-hepatic CYPs 1A1 and 1B1 affects biological activity. Biochem Pharmacol 2006;72(5):624-631.
21. Toprakçí M, Yelekçi K. Docking studies on monoamine oxidase-B inhibitors: estimation of inhibition constants (Ki) of a series of experimentally tested compounds. Bioorg Med Chem Lett 2005;15(20):4438-4446.