Synthesis and excretion profile of 1,4-[14C]phenylenebis(methylene)selenocyanate in the rat

Carcinogenesis

Volumn 19, Issue 9, 1998, Pages 1603-1607

  El Bayoumy, Karam ^a   Upadhyaya, Pramod ^a   Sohn, Ock Soon ^a   Rosa, José G ^a   Fiala, Emerich S ^a  

^a AMERICAN HEALTH FOUNDATION   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON 14; GLUCURONIC ACID; ORGANOSELENIUM DERIVATIVE; SELENIUM; SULFATE;

ANIMAL EXPERIMENT; ARTICLE; CHEMOPROPHYLAXIS; CHROMATOGRAPHY; CONTROLLED STUDY; DRUG EXCRETION; DRUG FECES LEVEL; DRUG METABOLISM; DRUG SYNTHESIS; DRUG URINE LEVEL; EXPIRED AIR; FEMALE; INTRAGASTRIC DRUG ADMINISTRATION; NONHUMAN; PRIORITY JOURNAL; RADIOACTIVITY; RAT; STRUCTURE ACTIVITY RELATION;

ANIMALS; ANTINEOPLASTIC AGENTS; CARBON RADIOISOTOPES; FEMALE; ORGANOSELENIUM COMPOUNDS; RATS; SELENIUM;

EID: 0031682306     PISSN: 01433334     EISSN: None     Source Type: Journal    
DOI: 10.1093/carcin/19.9.1603     Document Type: Article

References (32)

1. Wattenberg, L.W. (1985) Chemoprevention of cancer. Cancer Res., 45, 1-8.
2. Boone, C.W., Kelloff, G.J. and Malone, W.E. (1990) Identification of candidate cancer chemopreventive agents and their evaluation in animal models and human clinical trials: a review. Cancer Res., 50, 2-9.
3. El-Bayoumy, K. (1991) The role of selenium in cancer prevention. In DeVita, V.T. Jr, Hellman, S. and Rosenberg, S.A. (eds) Cancer Prevention. J. B. Lippincott Company, Philadelphia, pp. 1-15.
4. El-Bayoumy, K., Upadhyaya, P., Chae, Y.-H., Sohn, O.-S., Rao, C.V., Fiala, E. and Reddy, B.S. (1995) Chemoprevention of cancer by organoselenium compounds. J. Cell. Biochem., 22 (Suppl.), 92-100.
5. Tanaka, T., Makita, H., Kawabata, K., Mori, H. and El-Bayoumy, K. (1997) 1,4-Phenylenebis(methylene)selenocyanate exerts exceptional chemopreventive activity in rat tongue carcinogenesis. Cancer Res., 57, 3644-3648.
6. Ganther, H.E. and Lawrence, J.R. (1997) Chemical transformations of selenium in living organisms. Improved forms of selenium for cancer prevention. Tetrahedron, 53, 12299-12310.
7. Voth-Beach, L.M. and Shrader, D.E. (1986) Graphite furnace atomic absorption spectroscopy: new approaches to matrix modification. Spectroscopy, 1, 49-59.
8. Sohn, O.-S., Blackwell, L., Mathis, J., Asaad, W.W., Reddy, B.S. and El-Bayoumy, K. (1991) Excretion and tissue distribution of selenium following treatment of male F344 rats with benzylselenocyanate or sodium selenite. Drug Metab. Dispos., 19, 865-870.
9. Ganther, H.E., Kraus, R.J. and Foster, S.J. (1986) Trimethylselenonium ion. Method. Enzymol., 143, 195-201.
10. El-Bayoumy, K., Chae, Y.-H., Upadhyaya, P., Meschter, C., Cohen, L.A. and Reddy, B.S. (1992) Inhibition of 7,12-dimethylbenz(a)anthracene-induced tumors and DNA adduct formation in the mammary glands of female Sprague-Dawley rats by the synthetic organoselenium compound 1,4-phenylenebis(methylene)selenocyanate. Cancer Res., 52, 2402-2407.
11. El-Bayoumy, K. (1985) Effects of organoselenium compounds on induction of mouse forestomach tumors by benzo(a)pyrene. Cancer Res., 45, 3631-3635.
12. 14C]benzyl selenocyanate in the F344 rat. Chem. Res. Toxicol., 4, 560-565.
13. Vadhanavikit, S., Ip,C. and Ganther, H.E. (1993) Metabolites of sodium selenite and methylated selenium compounds administered at cancer chemoprevention levels in the rat. Xenobiotica, 23, 731-745.
14. Sohn, O.-S., Li, H., Surace, A., El-Bayoumy, K., Upadhyaya, P. and Fiala, E.S. (1995) Contrasting patterns of selenium excretion by female CD rats treated with chemically related chemopreventive organic selenocyanate componds. Anticancer Res., 15, 1849-1856.
15. Mitchell, R.H. (1976) 2,3,12,13-Tetraselena[4,4]metacyclophane. A disparity with the literature. Can. J. Chem., 54, 238-241.
16. Hojjatie, M., Muralidharan, S. and Freiser, H. (1989) Synthesis and multinuclear NMR characterization of some [3.3]diselena-and [4,4]tetraselenacyclophanes. Tetrahedron, 45, 1611-1622.
17. Ip, C., El-Bayoumy, K., Upadhyaya, P., Ganther, H., Vadhanavikit, S. and Thompson, H. (1994) Comparative effect of inorganic and organic selenocyanate derivatives in mammary cancer chemoprevention. Carcinogenesis, 15, 187-192.
18. Hasegawa, T., Mihara, M., Okuno, T., Nakamuro, K. and Sayato, Y. (1995) Chemical form of selenium-containing metabolite in small intestine and liver of mice following orally administered selenocystine. Arch. Toxicol., 69, 312-317.
19. Hasegawa, T., Okuno, T., Nakamuro, K. and Sayato, Y. (1996) Identification and metabolism of selenocystein-glutathione selenenyl sulfide (CySeSG) in small intestine of mice orally exposed to selenocystine. Arch. Toxicol., 71, 39-44.
20. Clark, E.R. and Al-Turaihi, M.A.S. (1977) The reaction of o-nitro and p-nitrophenyl selenocyanates with arylthiols. J. Organomet. Chem., 134, 181-187.
21. Fischer, H., Terlinden, R., Lohr, J.P. and Römer, A. (1988) A novel biologically active seleno-organic compound. VIII. Biotransformation of ebselen. Xenobiotica, 18, 1347-1359.
22. Ip, C. and Ganther, H. (1988) Efficacy of trimethylselenonium versus selenite in cancer chemoprevention and its modulation by arsenite. Carcinogenesis, 9, 1481-1484.
23. Ip, C., Hayes, C., Budnick, R.M. and Ganther, H.E. (1991) Chemical form of selenium, critical metabolites and cancer prevention. Cancer Res., 51, 595-600.
24. Ip, C. and Ganther, H.E. (1990) Activity of methylated forms of selenium in cancer prevention. Cancer Res., 50, 1206-1211.
25. Ganther, H. (1984) Selenium metabolism and function in man and animals. In Brutter, P and Schramel, P. (eds) Trace Element-Analytical Chemistry in Medicine and Biology, Vol. 3. Walter de Gruyter, Germany, pp. 3-24.
26. Chambers, I., Frampton, J., Goldfarb, P., Affara, N., McBain, W. and Harrison, P.R. (1986) The structure of the mouse glutathione peroxidase gene: the selenocysteine in the active site is encoded by the 'termination' codon, TGA. EMBO J., 5, 1221-1227.
27. Takahashi, K., Akasaka, M., Yamamoto, Y., Kobayashi, C., Mizoguchi, J. and Koyama, J. (1990) Primary structure of human plasma glutathione peroxidase deduced from rDNA sequences. J. Biochem., 108, 145-148.
28. Yoshimura, S., Watanabe, K., Suemizu, H., Onozawa, T., Mizoguchi, J., Tsuda, K., Hatta, H. and Moriuchi, T. (1991) Tissue specific expression of the plasma glutathione-peroxidase gene in rat kidney. J. Biochem., 109, 918-923.
29. Schuckelt, R., Brigelius-Flohe, R., Maiorino, M., Roveri, A., Reumkens, J., Strassburger, W., Usani, F., Wolf, B. and Flohe, L. (1992) Phospholipidhydroperoxide glutathione peroxidase is a selenoenzyme distinct from the classical glutathione peroxidase as evident from rDNA and amino acid sequencing. Free Rad. Res. Commun., 14, 343-361.
30. Berry, M.J., Banu, L. and Larsen, P.R. (1991) Type I iodothyronine deiodinase is a selenocysteine containing enzyme. Nature, 349, 438-440.
31. Arthur, J.R., Nicol, F., Grant, E. and Beckett, G.H. (1991) The effects of selenium deficiency on hepatic type-I iodothyronine deiodinase and protein disulphide isomerase assessed by activity measurements and affinity labelling. Biochem. J., 274, 297-300.
32. Hill, K.E., Lloyd, R.S., Yang, J.-G., Read, R. and Burk, R.F. (1991) The cDNA for rat selenoprotein P contains 10 TGA codons in the open reading frame. J. Biol. Chem., 266, 10050-10053.