Structure-activity relationships among the ortho-, meta- and para- isomers of phenylenebis(methylene)selenocyanate (XSC) as inhibitors of 7,12- dimethylbenz(a)anthracene-DNA binding in mammary glands of female CD rats

Oncology Reports

Volumn 4, Issue 5, 1997, Pages 1067-1071

  Chae, Young Heum ^a   Upadhyaya, Pramod ^a   El Bayoumy, Karam ^a  

^a AMERICAN HEALTH FOUNDATION   (United States)

Author keywords

7,12 dimethylbenz(a)anthracene; Chemoprevention; DNA adducts; Mammary carcinogenesis; Organoselenium

Indexed keywords

CYANIC ACID DERIVATIVE; DIMETHYLBENZ[A]ANTHRACENE; DNA; PHENYLENEBIS(METHYLENE)SELENOCYANIC ACID; SELENIUM DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARTICLE; BREAST CANCER; CANCER CHEMOTHERAPY; CONTROLLED STUDY; DNA ADDUCT; DRUG DNA BINDING; DRUG MECHANISM; FEMALE; ISOMERISM; NONHUMAN; ORAL DRUG ADMINISTRATION; PRIORITY JOURNAL; RAT; STRUCTURE ACTIVITY RELATION;

EID: 0030797489     PISSN: 1021335X     EISSN: None     Source Type: Journal    
DOI: 10.3892/or.4.5.1067     Document Type: Article

References (37)

1. El-Bayoumy K: The role of selenium in cancer prevention. In: Cancer Prevention. DeVita JVT, Hellman S and Rosenberg SA (eds). JB Lippincott Company, Philadelphia, PA, pp1-15, 1991.
2. El-Bayoumy K, Chae Y-H, Upadhyaya P, Meschter C, Cohen LA and Reddy BS: (Selenium in chemoprevention of carcinogenesis 11) 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, 1992.
3. Ip C, El-Bayoumy K, Upadhyaya P, Ganther H, Vadhanavikit S and Thompson H: Comparative effect of inorganic and organic selenocyanate derivatives in mammary cancer chemoprevention. Carcinogenesis 15: 187-192, 1994.
4. El-Bayoumy K, Upadhyaya P, Desai DH, Amin S and Hecht SS: Inhibition of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone tumorigenicity in mouse lung by the synthetic organoselenium compound, 1,4-phenylenebis(methylene)selenocyanate. Carcinogenesis 14: 1111-1113, 1993.
5. Reddy BS, Rivenson A, Kulkarni N, Upadhyaya P and El-Bayoumy K: (Selenium in chemoprevention of Carcinogenesis 14) Chemoprevention of colon carcinogenesis by the synthetic organoselenium compound, 1,4-phenylenebis(methylene)selenocyanate. Cancer Res 52: 5635-5640, 1992.
6. El-Bayoumy K, Upadhyaya P, Chae Y-H, Sohn O-S, Rao CV, Fiala E and Reddy BS: Chemoprevention of cancer by organoselenium compounds. J Cell Biochem Suppl 22: 92-100, 1995.
7. Reddy BS, Rivenson A, El-Bayoumy K, Upadhyaya P, Pittman B and Rao CV: Chemoprevention of colon cancer by organoselenium compounds and impact of high- and low-fat diets. J Natl Cancer Inst 89: 506-512, 1997.
8. Daniel FB and Joyce NJ: DNA adduct formation by 7,12-dimethylbenz[a]anthracene and its noncarcinogenic 2-fluoro analogue in female Sprague-Dawley rats. J Natl Cancer Inst 70: 111-118, 1983.
9. Singletary KW: Effect of dietary butylated hydroxytoluene on the in vivo distribution, metabolism and DNA-binding of 7,12-dimethylbenz[a]anthracene. Cancer Lett 49: 187-193, 1990.
10. Thompson HJ, Wilson A, Lu J, Singh M, Jiang C, Upadhyaya P, El-Bayoumy K and Ip C: Comparison of the effects of an organic and an inorganic form of selenium on a mammary carcinoma cell line. Carcinogenesis 15: 183-186, 1994.
11. Tillotson J, Upadhyaya P and Ronai Z: Inhibition of thymidine kinase in cultured mammary tumor cells by the chemopreventive organoselenium compound, 1,4-phenylenebis(methylene)-selenocyanate. Carcinogenesis 15: 607-610, 1994.
12. Foiles PG, Fujiki H, Suganuma M, Okabe S, Yatsunami J, Miglietta LM, Upadhyaya P, El-Bayoumy K and Ronai Z: Inhibition of PKC and PKA by chemopreventive organoselenium compounds. Int J Oncol 7: 685-690, 1995.
13. Ronai Z, Tillotson JK, Traganos F, Darzynkiewicz Z, Conaway CC, Upadhyaya P and El-Bayoumy K: Effects of organic and inorganic selenium compounds on rat mammary tumor cells. Int J Cancer 63: 428-434, 1996.
14. Adler V, Pincus MR, Posner S, Upadhyaya P, El-Bayoumy K and Ronai Z: Effects of chemopreventive selenium compounds oh Jun N-kinase activities. Carcinogenesis 17: 1849-1854, 1996.
15. Hojjatie M, Muralidharan S and Freiser H: Synthesis of multinuclear NMR characterizations of some [3,3]diselena- and [4,4]tetraselenacyclophanes. Tetrahedron 65: 1611-1622, 1989.
16. Nayini J, El-Bayoumy K, Sugie S, Cohen LA and Reddy BS: Chemoprevention of experimental mammary carcinogenesis by the synthetic organoselenium compound, benzyl selenocyanate, in rats. Carcinogenesis 10: 509-512, 1989.
17. Reddy BS and Maruyama H: Effect of dietary fish oil on azoxymethane-induced colon carcinogenesis in male F344 rats. Cancer Res 46: 3367-3370, 1986.
18. Reddy BS and Maeura Y: Tumor promotion by dietary fat in azoxymethane-induced colon carcinogenesis in female F344 rats: influence of amount and source of dietary fat. J Natl Cancer Inst 72: 745-750, 1984.
19. El-Bayoumy K: (Selenium in Chemoprevention of carcinogenesis 1) Effects of organoselenium compounds on induction of mouse forestomach tumors by benzo[a]pyrene. Cancer Res 45: 3631-3635, 1985.
20. Milner JA, Pigott MA and Dipple A: Selective effects of sodium selenite on 7,12-dimethylbenz(a)anthracene-DNA binding in fetal mouse cell cultures. Cancer Res 45: 6347-6354, 1985.
21. Sawicki JT, Moschel RC and Dipple A: Involvement of both syn- and anti-dihydrodiol-epoxides in the binding of 7,12-dimethylbenz[a]anthracene to DNA in mouse embryo cell cultures. Cancer Res 43: 3212-3218, 1983.
22. Ip C, Vadhanavikit S and Ganther H: Cancer chemoprevention by aliphatic selenocyanates: effect of chain length on inhibition of mammary tumors and DMBA adducts. Carcinogenesis 16: 35-38, 1995.
23. Reddy BS, Sugie S, Maruyama H, El-Bayoumy K and Marra P: Chemoprevention of colon carcinogenesis by dietary organoselenium, benzylselenocyanate, in F344 rats. Cancer Res 47: 5901-5904, 1987.
24. El-Bayoumy K, Chae Y-H, Upadhyaya P and Ip C: Chemoprevention of mammary cancer by diallyl selenide, a novel organoselenium compound. Anticancer Res 16: 2911-2916, 1996.
25. Ip C and Ganther HE: Activity of methylated forms of selenium in cancer prevention. Cancer Res 50: 1206-1211, 1990.
26. Ip C, Lisk DJ and Stoewsand GS: Mammary cancer prevention by regular garlic and selenium-enriched garlic. Nutr Cancer 17: 279-286, 1992.
27. Ip C and Lisk DJ: Enrichment of selenium in allium vegetables for cancer prevention. Carcinogenesis 15: 1881-1885, 1994.
28. Ip C and Lisk DJ: Efficacy of cancer prevention by high-selenium garlic is primarily dependent on the action of selenium. Carcinogenesis 16: 2649-2652, 1995.
29. Liu J and Milner JA: Age, dietary selenium and quantity of 7,12-dimethylbenz(a)anthracene influence the in vivo occurrence of rat mammary DNA adducts. J Nutr 122: 1361-1368, 1992.
30. Ejadi S, Bhattacharya ID, Voss K, Singletary K and Milner JA: In vitro and in vivo effects of sodium selenite on 7,12-dimethylbenz[a]anthracene-DNA adduct formation in isolated rat mammary epithelial cells. Carcinogenesis 10: 823-826, 1989.
31. Liu J, Gilbert K, Parker HM, Haschek WM and Milner JA: Inhibition of 7,12-dimethylbenz(a)anthracene-induced mammary tumors and DNA adducts by dietary selenite. Cancer Res 51: 4613-4617, 1991.
32. Ip C and Daniel FB: Effects of selenium on 7,12-dimethylbenz-(a)anthracene-induced mammary carcinogenesis and DNA adduct formation. Cancer Res 45: 61-65, 1985.
33. Hecht SS: Chemoprevention by isothiocyanates. J Cell Biochem Suppl 22: 195-209, 1995.
34. Stoner GD and Morse MA: Isothiocyanates as inhibitors of esophageal cancer. Adv Exp Med Biol 401: 13-23, 1996.
35. Rao CV, Rivenson A, Simi B, Zang E, Hamid R, Kelloff GJ, Steele V and Reddy BS: Enhancement of experimental colon carcinogenesis by dietary 6-phenylhexyl isothiocyanate. Cancer Res 55: 4311-4318, 1995.
36. Stoner GD, Siglin JC, Morse MA, Desai DH, Amin SG, Kresty LA, Toburen AL, Heffner EM and Francis DJ: Enhancement of esophageal carcinogenesis in male F344 rats by dietary phenylhexyl isothiocyanate. Carcinogenesis 16: 2473-2476, 1995.
37. Sohn OS, Li H, Surace A, El-Bayoumy K, Upadhyaya P and Fiala ES: Contrasting patterns of selenium excretion by female CD rats treated with chemically related chemopreventive organic selenocyanate compounds. Anticancer Res 15: 1849-1856, 1995.