Publication Cover
Xenobiotica
the fate of foreign compounds in biological systems
Volume 36, 2006 - Issue 8
133
Views
4
CrossRef citations to date
0
Altmetric
Research Article

In vitro metabolism of the epoxide substructure of cryptophycins by cytosolic glutathione S-transferase: Species differences and stereoselectivity

, , &
Pages 659-670 | Received 06 Dec 2005, Published online: 22 Sep 2008

References

  • Al-Awar RS, Ehlhardt WJ, Gottumukkala SV, Martinelli MJ, Moher ED, Moore RE, Munroe JE, Norman BH, Patel VF, Ray JE, Shih C, Toth JE, Vasudevan Vinventors, Eli Lilly and Company, assignee. Cryptophycin compounds. 2004, US patent 6,680,311. 20 January 2004
  • Al-Awar RS, Ray JE, Schultz RM, Andis SL, Kennedy JH, Moore RE, Liang J, Golakoti T, Subbaraju GV, Corbett TH. A convergent approach to cryptophycin 52 analogues: Synthesis and biological evaluation of a novel series of fragment A epoxides and chlorohydrins. Journal of Medical Chemistry 2003; 46: 2985–3007
  • Bai R, Schwartz RE, Kepler JA, Pettit GR, Hamel E. Characterization of the interaction of cryptophycin I with tubulin: Binding in the vinca domain, competitive inhibition of dolastatin 10 binding, and an unusual aggregation reaction. Cancer Research 1996; 56: 4398–4406
  • Barbier P, Gregoire C, Devred F, Sarrazin M, Peyrot V. In vitro effect of cryptophycin 52 on microtubule assembly and tubulin: Molecular modeling of the mechanism of action of a new antimitotic drug. Biochemistry 2001; 40: 13510–13519
  • Commandeur JNM, Stijntjes GJ, Vermeulen NPE. Enzymes and transport systems involved in the formation and disposition of glutathione S-conjugates. Pharmacology Review 1995; 47: 271–330
  • Dannan GA, Guengerich FP. Immunochemical comparison and quantitation of microsomal flavin-containing monooxygenases in various hog, mouse, rat, rabbit, dog, and human tissues. Molecular Pharmacology 1982; 22: 787–794
  • DeGroot MJ, Van der Aar EM, Nieuwenhuizen PJ, Van der Plas RM, Donne-Op den Kelder GM, Commandeur JNM, Vermeulen NPE. A predictive substrate model for rat glutathione S-transferase 4-4. Chemical Research in Toxicology 1995; 8: 649–658
  • DeGroot MJ, Vermeulen NPE, Mullenders DLJ, Donne-Op den Kelder GM. A homology model for rat mu class glutathione S-transferase 4-4. Chemical Research in Toxicology 1996; 9: 28–40
  • Fahey RC, Sundquist AR. Evolution of glutathione metabolism. Advances in Enzymology and Related Areas in Molecular Biology 1991; 64: 1–53
  • Fanucchi MV, Buckpitt AR, Murphy ME, Storms DH, Hammock BD, Plopper CG. Development of phase II xenobiotic metabolizing enzymes in differentiating murine clara cells. Toxicology and Applied Pharmacology 2000; 168: 253–267
  • Fretland AJ, Omiecinski CJ. Epoxide hydrolases: Biochemistry and molecular biology. Chemico-Biological Interactions 2000; 129: 41–59
  • Hayes JD, Strange RC. Glutathione S-transferase polymorphisms and their biological consequences. Pharmacology 2000; 61: 154–166
  • Hiratsuka A, Yokoi A, Iwata H, Watabe T, Satoh K, Hatayama I, Sato K. Glutathione conjugation of styrene 7,8-oxide enantiomers by major glutathione transferase isoenzymes isolated from rat livers. Biochemistry and Pharmacology 1989; 38: 4405–4413
  • Hirsch CF, Liesch JM, Salvatore MJ, Schwartz RE, Sesin DFinventors, Merck and Company, Inc., assignee. Antifungal fermentation product and method. 1990, US patent 4,946,835. 7 August 1990
  • Jolivette LJ, Anders MW. Computational and experimental studies on the distribution of addition and substitution products of the microsomal glutathione transferase 1-catalyzed conjugation of glutathione with fluoroalkenes. Chemical Research in Toxicology 2003; 16: 137–144
  • Josephy PD. Glutathione and detoxication. Molecular toxicology, PD Josephy, B Mannervik, P Ortiz de Montellano. Oxford University Press, New York, NY 1997; 152–186
  • Kim DH, Guengerich FP. Formation of the DNA adduct S-[2-(N7-guanyl)ethyl]glutathione from ethylene dibromide: Effects of modulation of glutathione and glutathione S-transferase levels and lack of a role for sulfation. Carcinogenesis 1990; 11: 419–424
  • Kitteringham NR, Davis C, Howard N, Pirmohamed M, Park BK. Interindividual and interspecies variation in hepatic microsomal epoxide hydrolase activity: Studies with cis-stilbene oxide, carbamazepine 10,11-epoxide and naphthalene. Journal of Pharmacology and Experimental Therapy 1996; 278: 1018–1027
  • Luo G, Guenthner TM. Detoxication of the 2′,3′-epoxide metabolites of allylbenzene and estragole, conjugation with glutathione. Drug Metabolism and Disposition 1994; 22: 731–737
  • Mendrala AL, Langvardt PW, Nitschke KD, Quast JF, Nolan RJ. In vitro kinetics of styrene and styrene oxide metabolism in rat, mouse and human. Archives in Toxicology 1993; 67: 18–27
  • Morgenstern R, DePierre JW. Membrane-bound glutathione transferases. Glutathione conjugation: Its mechanism and biological significance, B Ketterer, HV Sies. Academic Press, London 1988; 157–174
  • Omiecinski CJ, Hassett C, Hosagrahara V. Epoxide hydrolase — polymorphism and role in toxicology. Toxicology Letters 2000; 112: 365–370
  • Panda D, Ananthnarayan V, Larson G, Shih C, Jordan MA, Wilson L. Interaction of the antitumor compound cryptophycin-52 with tubulin. Biochemistry 2000; 39: 14121–14127
  • Parkinson A. Biotransformation of xenobiotics. Casarett and Doull's toxicology the basic science of poisons, 5th ed, CD Klaassen. McGraw-Hill Inc, New York, NY 1996; 113–186
  • Robertson IGC, Jernström B. The enzymatic conjugation of glutathione with bay-region diol-epoxides of benzo[a]pyrene, benz[a]anthracene and chrysene. Carcinogenesis 1986; 7: 1633–1636
  • Salinas AE, Wong MG. Glutathione S-transferases — a review. Current Medical Chemistry 1999; 6: 279–309
  • Sato M, Sasaki M, Oguro T, Kuroiwa Y, Yoshida T. Induction of metallothionein synthesis by glutathione depletion after trans- and cis-stilbene oxide administration in rats. Chemico-Biological Interactions 1995; 98: 15–25
  • Schwartz RE, Hirsch CF, Sesin DF, Flor JE, Chartrain M, Fromcling RE, Harris GH, Salvatore MJ, Liesch JM, Yudin K. Pharmaceuticals from cultured algae. Journal of Industrial Microbiology 1990; 5: 113–124
  • Smith CD, Zhang X, Mooberry SL, Patterson GML, Moore RE. Cryptophycin: A new antimicrotubule agent active against drug-resistant cells. Cancer Research 1994; 54: 3779–3784
  • Sumner SJ, Fennel TR. Review of the metabolic fate of styrene. Critical Reviews in Toxicology 1994; 24: S11–S33
  • Trimurtulu G, Ohtani I, Patterson GML, Moore RE, Corbett TH, Valeriote FA, Demchik L. Total structures of cryptophycins, potent antitumor depsipeptides from the blue-green alga Nostoc sp. Strain GSV224. Journal of the American Chemistry Society 1994; 116: 4729–4737
  • Wagner MM, Paul DC, Shih C, Jordan MA, Wilson L, Williams DC. In vitro pharmacology of cryptophycin 52 (LY355703) in human tumor cell lines. Cancer Chemotherapy and Pharmacology 1999; 43: 115–125

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.