Abstract
A large number of animal studies and epidemiological studies which have been performed in the last decades has revealed that a number of selenium (Se)-containing compounds possess chemopreventive activity. In a meta-analysis from a number of studies comparing the significance of serum Se, retinol, beta-carotene and vitamin E, Se emerged as the factor with the most consistent protective effect (Comstock et al., 1992). On the other hand, geographic analysis and several prospective and case-control studies showed that people with low blood Se had an increased risk of cancer. Recently, a placebo-controlled double-blind study involving 1312 patients with a history in skin cancer showed a much lower prevalence of developing and dying from lung, colon or prostate cancer in the group receiving supplementation of 200 µg Se per day (Clark et al., 1996). A selenized yeast-extract was given to the people of this study. Relative risk of cancer incidence in lung, colon and prostate was reduced to 0.54 (P=0.04), 0.37 (P=0.002) and 0.42 (P=0.03), respectively. The Se-compounds responsible for the chemopreventive effect of selenized yeast still are not completely characterized yet. Selenomethionine accounts for 20% of the Se-containing compounds (Bird et al., 1997). Other compounds identified include selenocystine, Semethylselenocysteine and selenoethionine, representing approximately 20%. However, still 40-50% of the total Se is unidentified.
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References
Andreadou, I., Menge, W. P. B., Commandeur, J. N. M., Worthington, E. A., and Vermeulen, N. P. E., 1996a, Synthesis of novel Se-substituted selenocysteine derivatives as potential kidney selective prodrugs of biologically active selenol compounds: Evaluation of kinetics of beta-elimination reactions in rat renal cytosol.e. 39: 2040–2046.
Andreadou, I., Van De Water, B., Commandeur, J. N. M., Nagelkerke, F. J., and Vermeulen, N. P. E., 1996b, Comparative cytotoxicity of 14 novel selenocysteine Se-conjugates in rat renal proximal tubular cells. Toxicol. Appl. Pharmacol 141: 278–287.
Assmann, A., Briviba K., and Sies, H., 1998, Reduction of methionine selenoxide to selenomethionine by glutathione. Arch. Biochem. Biophys 349: 201–203.
Bird, S.M., Uden, P.C., Tyson, J.F., Block, E. and Denoyer, E., 1997, Speciation of selenoaminoacids and organoselenium compounds in selenium-enriched yeast using high-performance liquid chromatography-inductively coupled plasma mass spectrometry. J. Anal. Atom. Spectrom 12: 785–788.
Chen, G. -P., and Ziegler, D. M., 1994, Liver microsomes and flavin-containing monooxygenase catalyzed oxidation of organic selenium compounds. Arch. Biochem. Biophys 312: 566–572.
Clark, L.C., Combs, G.F., Turnbull, B.W., Slate, E.H., Chalker, D.K., Chow, L.S., Davis, L.S., Glover, R.A., Graham, G.F., Gross, E.G., Krongrad, A., Lesher, J.L., Park, K., Sanders, B.B., Smith, C.L. and Taylor, R., 1996, Effects of selenium supplemention for cancer prevention in patients with carcinoma of the skin. J. Am. Med. Assoc 276: 1957–1985.
Commandeur, J. N. M., Andreadou, I., Rooseboom, M., Out, M., de Leur, L. J., Groot, E., and Vermeulen, N. P. E., 2000, Bioactivation of selenocysteine Se-conjugates by a highly purified rat renal cysteine conjugate beta-lyase/glutamine transaminase K. J. Pharmacol. Exp. Ther 294: 753–761.
Commandeur, J.N.M., Stijntjes, G.J. and Vermeulen, N.P.E., 1995, Enzymes and transport systems involved in the formation and disposition of glutathione S-conjugates. Role in bioactivation and detoxication mechanisms of xenobiotics. Pharmacol. Rev 47: 271–330.
Comstock, G.W., Bush, T.L. and Herzlsouer, K., 1992, Serum retinol, beta-carotene, vitamin E and selenium as related to subsequent cancer of specific sites. Am.J.Epidemiol 135: 115–121.
Cooper, A.J.L., 1998, Mechanisms of cysteine S-conjugate beta-lyases. Adv.Enzymol 72: 199–238.
Duescher, R. J., Lawton, M. P., Philpot, R. M., and Elfarra, A. A., 1994, Flavin-containing monooxygenase (FMO)-dependent metabolism of methionine and evidence for FMO3 being the major FMO involved in methionine sulfoxidation in rabbit liver and kidney microsomes. J. Biol. Chem 269: 17525–17530.
Elfarra, A. A., Renee, J. D., Hwang, I. Y., Sicuri, A. R., and Nelson, J.A., 1995, Targeting 6-thioguanine to the kidney with S-(guanin-6-yl)-L-cysteine. J. Pharmacol. Exp. Ther 274: 1298–1304.
Elfarra, A.A. and Hwang, I.Y., 1993, Targeting of 6-mercaptopurine to the kidneys. Metabolism and kidney-selectivity of S-(6-purinyl)-L-cysteine analogs in rats. Drug Metab. Dispos, 21: 841–845.
Ganther, H. E., 1999, Selenium metabolism, selenoproteins and mechanisms of cancer prevention: complexities with thioredoxin reductase Carcinogenesis 20: 1657–1666.
Ip, C., Vadhanavikit, S. and Ganther, H., 1995, Cancer chemoprevention by aliphatic selenocyanates: effect of chain length on inhibition of mammary tumors and DMBA adducts. Carcinogenesis 16: 35–38.
Ip, C., El-Bayoumy, K., Upadhyaya, P., Ganther, H., Vadhanavikit, S. and Thompson, H., 1994, Comparative effect of inorganic and organic selenocyanate derivates in mammary cancer chemoprevention. Carcinogenesis 15: 187–192.
Ip, C., Zhu, Z., Thompson, H. J., Lisk, D., and Ganther, H. E., 1999, Chemoprevention of mammary cancer with Se-allylselenocysteine and other selenoamino acids in the rat. Anticancer Res. 19, 2875–2880.
Ip, C., Thompson, H.J., Zhu, Z. and Ganther, H.E., 2000, In vitro and in vivo studies of methyl seleninic acid: evidence that a monomethylated selenium metabolite is critical for cancer chemoprevention. Cancer Res 60: 2882–2886.
Ip, C. and Ganther, H., 1990, Activity of methylated forms of selenium in cancer prevention. Cancer Res 50: 1206–1211.
Ip, C. and Ganther, H.E., 1992, Comparison of selenium and sulfur analogs in cancer prevention. Carcinogenesis 13: 1167–1170.
Ip, C. and Ganther, H., 1992, Relationship between the chemical form of selenium, critical metabolites, and cancer prevention. In: Cancer Chemoprevention (Wattenberg et al., eds.), pp. 479–488. CRC Press, Boca Raton, FL.
Ip, C., 1998, Lessons from basic research in selenium and cancer prevention. J. Nutr 128:1845–1854.
Jacob, C., Maret, W., and Vallee, B. L., 1999, Selenium redox biochemistry of zinc-sulfur coordination sites in proteins and enzymes. Proc. Natl. Acad. Sci. USA 96: 1910–1914.
Jones, D.N., Mundy, D. and Whitehouse, R.D., 1970, Steroidal selenoxides diastereomeric at selenium: synelimination, absolute configuration, and optial rotary dispersion characteristics. J. Chem.Soc.Chem.Commun 86.
Muller, S., Senn, H., Gsell, B., Vetter, W., Baron, C. and Bock, A., 1994, The formation of diselenide bridges in proteins by incorporation of selenocysteine residues: biosynthesis and characterization of (Se)2thioredoxin. Biochemistry 33: 3404–3412.
Perry, D. K., Smyth, M. J., Stennicke, H. R., Salvesen, G. S., Duriez, P., Poirier, G. G., and Hannun, Y. A., 1997, Zinc is a potent inhibitor of the apoptotic protease, caspase-3. A novel target for zinc in the inhibition of apoptosis. J. Biol. Chem 272: 18530–18533.
Rooseboom, M., Commandeur, J.N.M., Floor, G., Rettie, A and Vermeulen, N.P.E., 2001a, Selenoxidation by flavin-containing monooxygenases as a novel pathway for beta-elimination of selenocysteine Se-conjugates. Chem.Res.Toxicol 14:127–134.
Rooseboom, M., Vermeulen, N.P.E., Van Hemert, N., and Commandeur, J.N.M., 200lb, Bioactivation of chemopreventive selenocysteine Se-conjugates and related amino acids by amino acid oxidases. Novel route of metabolism of selenoamino acids. Chem. Res. Toxicol 14: 996–1005.
Sies, H., Klotz, L.O., Sharov, V.S., Assmann, A., Briviba, K., 1998, Protection against peroxynitrite by selenoproteins. Z.Naturforsch. (C) 53: 228–232.
Walsh, C.T., Schonbrunn, A. and Abeles, R.H., 1971, Studies on the mechanism of action of D-amino acid oxidase. Evidence for removal of substrate a-hydrogen as a proton. J.Biol.Chem 246: 6855–66.
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Commandeur, J.N.M., Rooseboom, M., Vermeulen, N.P.E. (2001). Chemistry and Biological Activity of Novel Selenium-Containing Compounds. In: Dansette, P.M., et al. Biological Reactive Intermediates VI. Advances in Experimental Medicine and Biology, vol 500. Springer, Boston, MA. https://doi.org/10.1007/978-1-4615-0667-6_11
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