Synthesis of W-acetylcysteine conjugates of catechol estrogens

Steroids

Volumn 61, Issue 5, 1996, Pages 296-301

  Suzuki, Emako ^a   Iwasaki, Ryo ^a   Goto, Junichi ^b   Matsuki, Yasuhiko ^a   Nambara, Toshio ^a  

^a HATANO RESEARCH INSTITUTE   (Japan)

^b TOHOKU UNIVERSITY   (Japan)

Author keywords

2 hydroxyestrone; 4 hydroxyestrone; Catechol estrogen; Mercapturic acid; N acetylcysteine conjugate

Indexed keywords

2 HYDROXYESTRONE; ACETYLCYSTEINE DERIVATIVE; CATECHOL ESTROGEN; ESTRONE DERIVATIVE; SULFIDE;

ACETYLATION; ARTICLE; CHEMICAL STRUCTURE; CONJUGATE; CONJUGATION; DERIVATIZATION; METHYLATION; NUCLEAR MAGNETIC RESONANCE;

ACETYLCYSTEINE; ESTROGENS, CATECHOL; HYDROXYESTRONES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE;

EID: 0029891514     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/0039-128x(95)00232-f     Document Type: Article

References (19)

1. Lacort M, Leal AM, Liza M, Martin C, Martinez R, Ruiz-Larrea MB (1995). Protective effect of estrogens and catecholestrogens against peroxidative membrane damage in vitro. Lipids 30:141-146.
2. 60Co-irradiation in mice. J Clin Biochem Nutr 18:49-54.
3. Fotsis T, Zhang Y, Pepper MS, Adlercreutz H, Montesano R, Nawroth PP, Schweigerer L (1994). The endogenous oestrogen metabolite 2-methoxyoestradiol inhibits angiogenesis and suppresses tumor growth. Nature 368:237-239.
4. Aizu-Yokota E, Suaki A, Sato Y (1995). Natural estrogens induce modulation of microtubules in Chinese hamster V79 cells in culture. Cancer Res 55:1863-1868.
5. Roy D, Liehr JG (1990). Inhibition of estrogen-induced kidney carcinogenesis in Syrian hamsters by modulators of estrogen metabolism. Carcinogenesis 11:567-570.
6. KUSS E (1971). Mikrosomale Oxidation des Ostradiols-17B. Hoppe-Seyler's Z Physiol Chem 352:817-836.
7. Elce JS (1970). Metabolism of glutathione conjugate of 2-hy-droxyestradiol by rat liver and kidney preparations in vitro. Biochem J 116:913-917.
8. Suzuki E, Osabe M, Okada M, Ishizaka T, Suzuki T (1987). Urinary metabolites of N-nitrosodibutylamine and N-nitrodibutylamine in the rat: identification of N-acetyl-S-alkyl cysteines. Jpn J Cancer Res (Gann) 78:382-385.
9. Vermeulen, NPE (1989). Analysis of mercapturic acids as a tool in biotransformation, biomonitoring and toxicological studies. Trends Pharmacol Sci 10:177-181.
10. Jellinck PH, Elce JS (1969). Synthesis of estrogen glutathione and cysteine derivatives. Steroids 13:711-718.
11. KUSS E (1969). Wasserlosliche Metabolite des Ostradiols-17B, III. Trennung and Identifizierung der 1- und 4-Glutathionthioather von 2,3-Dihydroxy-oetratrienen. Hoppe-Seyler's 2 Physiol Chem 350: 95-97.
12. Stubenrauch G, Knuppen R (1976). Convenient large scale preparation of catechol estrogens. Steroids 28:733-741.
13. Fotsis T, Heikkinen R (1983). Selective Chromatographic fractionation of catechol estrogens on anion exchangers in borate form. J Steroid Biochem 18:357-363.
14. Numazawa M, Kimura K (1983). Novel and regiospecific synthesis of 2-amino estrogens via Zincke nitration. Steroids 41:675-683.
15. Ohkubo T, Tsuchiko F, Nambara T (1988). New synthesis of 2-hydroxyestrogen 2-monoglucuronides. Chem Pharm Bull 36:419-423.
16. Abul-Hajj YJ, Cisek PL (1988). Catechol estrogen adducts. J Steroid Biochem 31:107-110.
17. Jellinck PH (1988). 4-Hydroxyestradiol is conjugated with thiols primally at C-2: evidence from regiospecific displacement of tritium by rat liver microsomes for tyrosinase. Steroids 51:395-409.
18. Abul-Hajj YJ (1984). Synthesis of 3,4-estrogen-o-quinone. J Steroid Biochem 21:621-622.
19. Abul-Hajj YJ, Cisek PL (1986). Regioselective reaction of thiols with catechol estrogens and estrogen-o-quinones. J Steroid Biochem 25:245-247.