Mixed-type Inhibition of Human Hepatic Cytochrome P450 1-Catalyzed Ethoxyresorufin O-deethylation by Volatile Allyl Sulfides

  • 발행 : 2005.04.30

초록

Effects of allyl sulfides on kinetic behavior of cytochrome P450 1 (CYP1)-catalyzed ethoxyresorufin O-deethylase (EROD) activity were studied using microsomes from benzo[a]pyrene-treated human hepatoma cells. Apparent $K_m$ and $V_{max}$ values were calculated as $2.8\;{\mu}M$ and $3.0\;{\mu}mol$ resorufin/min/mg protein based on Lineweaver-Burk plot of microsomal EROD activity, respectively. Diallyl disulfide (DADS) and diallyl trisulfide (DATS) affected $K_m$ and $V_{max}$ values of EROD activity and acted as mixed-type inhibitors for CYP1 isozymes. Apparent Ki values of DADS and DATS were calculated as 1.07 and 0.88 mM, respectively, by re-plotting slopes of Lineweaver-Burk plot and inhibitor concentrations.

키워드

참고문헌

  1. Biomed. Pharmacother. v.58 Organosulfur compounds from alliaceae in the prevention of human pathologies Tapiero, H.;Townsend, D.M.;Tew, K.D.
  2. Cancer Res. v.53 Chemoprevention of colon carcinogenesis by organosulfur compounds Reddy, B.S.;Chinthalapally, V.R.;Rivenson, A.;Kellof, G.
  3. Food Sci. Biotechnol. v.13 Antimicrobial activity of alk(en)yl sulfides found in essential oils of garlic and onion Kim, J.W.;Huh, J.E.;Kyung, S.H.;Kyung, K.H.
  4. Cancer Lett. v.131 Antitumor activity of diallyl sulfide on polycyclic aromatic hydrocarbon-induced mouse skin carcino-genesis Singh, A.;Shukla, Y.
  5. Cancer Lett. v.118 Mechanism of differential efficacy of garlic organosulfides in preventing benzo[a]pyrene-induced cancer in mice Srivastava, S.K.;Hu, X.;Xia, H.;Zaren, H.A.;Chatterjee, M.L.;Agarwal, R.;Singh, S.V.
  6. Biosci. Biotech. Biochem. v.65 Modulation of cytochrome P450-mediated bioactivation of benzo[a]pyrene by volatile allyl sulfides in human hepatoma cells Chun, H.S.;Kim, H.J.;Choi, E.H.
  7. Carcinogenesis v.9 Effects of organosulfur compounds from garlic and onions on benzo[a]pyrene-induced neoplasia and glutathione S-transferase activity in the mouse Sparnins, V.L.;Barany, G.;Wattenberg, L.W.
  8. Biotechnol. Lett. v.24 Structure-activity relationships of organosulfur compounds as inhibitors of cytochrome P450 I-mediated activation of benzo[a]pyrene in a human cell model Kim, H.J.;Chun, H.S.
  9. Pharmacogenetics v.5 Cytochrome P450 mediated reactions studied in genetically engineered V79 Chinese hamster cells Doehmer, J.;Holtkamp, D.;Soballa, V.;Raab, G.;Schmalix, W.;Seidel, A.;Greim, H.;Jacob, J.
  10. Mol. Carcinogen. v.10 The role of 12 eDNA-expressed human, rodent, and rabbit cytochrome P450 in the metabolism of benzo[a]pyrene and benzo(a]pyrene trans-7,8-dihydrodiol Shou, M.;Korzekwa, K.R.;Crespi, C.L.;Gonzalez, F.J.;Gelboin, H.V.
  11. Cancer Res. v.54 2-Amino-3,4-dimethylimidazo[4,5-f]quinoline induces and inhibits cytochrome P450 from the 1A subfamily in chick and rat hepatocytes Sinclair, J.F.;Schaeffer, B.K.;Wood, S.G.;Lambrecht, L.K.;Gorman, N.;Bement, W.J.;Smith, E.L.;Sinclair, P.R.;Waldren, C.A.
  12. Biotechnol. Lett. v.23 Use of a cyclodextrin for increased protective activity of volatile allyl sulfides against benzo[a] pyrene-induced toxicity in human cell model Kim, H.J.;Chun, H.S.;Yang, R.
  13. Enzyme and metabolic inhibitors Webb, J.L.
  14. Chem. Res. Toxicol. v.4 Inhibition of cytochrome P450 2E1 by diallyl sulfide and its metabolites Brady, J.F.;Ishizaki, H.;Fukuto, J.M.;Lin, M.C.;Fadel, A.;Gapac, J.M.;Yang, C.S.
  15. J. Pharmacol. Exp. Ther. v.277 Cytochrome P4S0 isoform inhibitors as a tool for the investigation of metabolic reactions catalyzed by human liver microsomes Bourrie, M.;Meunier, V.;Berger, Y.;Fabre, G.
  16. J. Med. Chem. v.26 Analogues of aminoglutethimide: selective inhibition of cholesterol side-chain cleavage Foster, A.B.;Jarman, M.;Leung, C.S.;Rowlands, M.G.;Taylor, G.N.
  17. Comp. Biochem. Phys. v.C 122 Noncompetitive mixed-type inhibition of rainbow trout CYPIA catalytic activity by clotrimazole Levine, S.L.;Oris, J.T.
  18. Carcinogenesis v.18 Expression of CYP1A1 in human adult and fetal tissues and differential inducibility of CYP1B1 and CYP1A1 and Ah receptor ligands in human placenta and cultured cells Hakkola, J.;Pasanen, M.;Pelkonen, O.;Hukkanen, J.;Evisalmi, S.;Anttila, S.;Rane, A.;Mantyla, M.;Purkunen, R.;Saarikoski, S.;Tooming, M.;Raunio, H.
  19. Cancer Res. v.50 Metabolism of 2-acetylaminofluorene and benzo[a]pyrene and activation of food-derived heterocyclic amine mutagens by human cytochrome P-450 McManus, M.E.;Burgess, W.M.;Veronese, M.E.;Huggett, A.;Quattrochi, L.C.;Tukey, R.H.