Synthesis of novel Se-substituted selenocysteine derivatives as potential kidney selective prodrugs of biologically active selenol compounds: Evaluation of kinetics of β-elimination reactions in rat renal cytosol

Journal of Medicinal Chemistry

Volumn 39, Issue 10, 1996, Pages 2040-2046

  Andreadou, Ioanna ^a   Menge, Wiro M P B ^a   Commandeur, Jan N M ^a   Worthington, Eduard A ^a   Vermeiden, Nico P E ^a  

^a VU UNIVERSITY AMSTERDAM   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

LYASE; PRODRUG; SELENOCYSTEINE;

ARTICLE; CYTOSOL; DRUG ACTIVATION; DRUG DESIGN; DRUG SELECTIVITY; DRUG SYNTHESIS; DRUG TARGETING; ENZYME KINETICS;

ANIMALS; ANTINEOPLASTIC AGENTS; BIOTRANSFORMATION; CARBON-SULFUR LYASES; CHEMOPREVENTION; CYTOSOL; KIDNEY; LYASES; MALE; PRODRUGS; RATS; RATS, WISTAR; SELENOCYSTEINE; SUBSTRATE SPECIFICITY;

EID: 0029977773     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm950750x     Document Type: Article

References (30)

1. Vadhanavikit, S.; Ip, C.; Ganther, H. E. Metabolites of sodium selenite and methylated selenium compounds administered at cancer chemoprevention levels in the rat. Xenobiotica 1993, 23, 731-745.
2. Thompson, H. J.; Wilson, A.; Lu, J.; Singh, M.; Jiang, C.; Upadyaya, P.; Bayoumy, E.; Ip, C. Comparison of the effects of an organic and an inorganic form of selenium on a mammary carcinoma cell line. Carcinogenesis 1994, 15, 183-186.
3. Bayoumy, K. E. Effects of organoselenium compounds on induction of mouse forestomach tumors by benzo(a)pyrene. Cancer Res. 1985, 45, 3631-3635.
4. Hwang, I. Y.; Elfarra, A. Cysteine S-conjugates may act as kidney selective prodrugs: Formation of 6-mercaptopurine by the renal metabolism of S-(6-purinyl)-L-cysteine. J. Pharmacol. Exp. Ther. 1989, 251, 448-453.
5. Elfarra, A.; Hwang, I. Y. Targeting of 6-mercaptopurine to the kidneys. Metabolism and kidney-selectivity of S-(6-purinyl)-L-cysteine analogs in rats. Drug Metab. Dispos. 1993, 21, 841-845.
6. Commandeur, J. N. M.; Stijntjes, G. J.; Vermeulen, N. P. E. Enzymes and transport systems involved in the formation and disposition of glutathione S-conjugates. Role in bioactivation and detoxication mechanisms of xenobiotics. Pharmacol. Rev. 1995, 47, 271-330.
7. Nelson, J. A.; Pan, B. F.; Swanson, D. A.; Elfarra, A. A. Cysteine conjugate beta-lyase activity in human renal carcinomas. Cancer Biochem. Biophys. 1995, 14, 257-263.
8. Baldew, G. S.; Van der Hamer, C. J. A.; Los, G. ; Vermeulen, N. P. E.; De Goeij, J.J. M.; McVie, J. G. Selenium-induced protection against cisplatin nephrotoxicity in mice and rats. Cancer Res. 1989, 49, 3020-3023.
9. Vermeulen, N. P. E.; Baldew, G. S.; Los, G.; McVie, J. G.; De Goeij, J. J. M. Reduction of cisplatin nephrotoxicity by sodium selenite. Lack of interaction at the pharmacokinetic level of both compounds. Drug Metab. Dispos. 1993, 21, 30-36.
10. Ip, C.; Hayes, C.; Budnick, R. M.; Ganther, H. E. Chemical form of selenium, critical metabolites and cancer prevention. Cancer Res. 1991, 51, 595-609.
11. 4. J. Biol.Chem. 1995, 270, 180-188.
12. Stevens, J. L.; Robbins, J. D.; Byrd, R. A. A purified cysteine conjugate β-lyase from rat kidney cytosol. J. Biol.Chem. 1986, 261, 15529-15537,
13. Tanaka, H.; Soda, K. Selenocysteine. Methods Enzymol. 1987, 143, 240-243.
14. Stijntjes, G. J. Renal cysteine conjugate β-lyase. Ph.D. Thesis, Vrije Universiteit, Amsterdam, The Netherlands, 1993.
15. Wolfgang, G. H. I.; Gandolfi, A. J.; Stevens, J. L.; Brendel, K. In vitro and in vivo nephrotoxicity of the L- and D-isomers of S-(1,2-dichlorovinyl)-cysteine. Toxicology 1989, 58, 33-42.
16. Walsh, C. T.; Schonbrunn, A.; Abeles, R. H. Studies on the mechanism of action of D-amino acid oxidase. J. Biol. Chem. 1971, 246, 6855-6866.
17. Koide, T.; Itoh, H.; Otaka, A.; Yasui, H.; Kuroda, M.; Esaki, N.; Soda, K.; Fujii, N. Synthetic study of selenocystine-containing peptides. Chem. Pharm. Bull. 1993, 41, 502-506.
18. Nakayasu, K.; Tanaka, A. Cysteine derivates. Jpn. Kokai Tokkyo Koho JP 1985, 60, 258, 161 (85, 258, 161); Chem. Abstr. 1986, 104, P186853z.
19. 75Se] selenocystine. Anal. Biochem. 1984, 137, 205-209.
20. Esaki, N.; Tanaka, H.; Miles, E. W.; Soda, K. Enzymatic synthesis of Se-substituted L-selenocysteine with tryptophan synthase. FEBS Lett. 1983, 161, 207-209.
21. Esaki, N.; Nakamura, T.; Tanaka, H.; Suzuki, T.; Morino, Y.; Soda, K. Enzymatic synthesis of selenocysteine in liver. Biochemistry 1981, 20, 4492-4496.
22. 13C-NMR, no other organic contaminants were present. The elemental analyses gave the correct ratio between C, H, and N. Therefore, it was concluded that contaminants were inorganic salts which cocrystallized under the present conditions.
23. Theodoropoulos, D.; Schwartz, I. L.; Walter, R. Synthesis of selenium-containing peptides. Biochemistry 1967, 6, 3927-3932.
24. Sayuda, K.; Tanaka, H. Selenoaminoacids. Jpn. Kokai Tokkyo Koho 1979, 79, 52,033 (Cl. C12D13/06); Chem. Abstr. 1979, 91, 122166h.
25. Stijntjes, G. J.; Te Koppele, J. M.; Vermeulen, N. P. E. High-performance liquid chromatography fluorescence assay of pyruvic acid to determine cysteine conjugate β-lyase activity: Application to S-1,2-dichlorovinyl-L-cysteine and S-2-benzothiazoyl-L-cysteine. Anal. Biochem. 1992, 206, 334-343.
26. Yamauchi, A.; Stijntjes, G. J.; Commandeur, J. N. M.; Vermeulen, N. P. E. Purification of glutamine transaminase K/ cysteine conjugate β-lyase from rat renal cytosol based on hydrophobic interaction HPLC and gel permeation FPLC. Protein Expr. Purif. 1993, 44, 552-562.
27. Esaki, N.; Nakamura, T.; Tanaka, H.; Suzuki, T.; Morino, Y.; Soda, K. Enzymic synthesis of selenocysteine in the liver. Biochemistry 1981, 20, 4492-4496.
28. Tamura, T.; Oikawa, T.; Ohtaka, A.; Fujii, N.; Esaki, N.; Soda, K. Synthesis and characterization of the selenium analog of glutathione disulfide. Anal. Biochem. 1993, 151-154.
29. Commandeur, J. N. M.; Brakenhoff, J. P. G.; de Kanter, F. J. J.; Vermeulen, N.P. E. Nephrotoxicity of mercapturic acids of three structurally related 2,2-difluoroethylenes in the rat. Biochem. Pharmacol. 1988, 37, 4495-4504.
30. Foster, D. G. Selenophenol. Organic Syntheses; Wiley: New York, 1955; Collect. Vol. No. 3, pp 771-773.