Regioselective reaction of thiols with catechol estrogens and estrogen-O-quinones

Yusuf J Abul-Hajj, Paul L. Cisek

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28 Scopus citations

Abstract

Incubations of [3H]estradiol and [3H]2-hydroxyestradiol (2-OHE2) with rat liver microsomes and mushroom tyrosinase were carried out in the presence of glutathione and 2-mercaptoethanol. A ratio of about 3.5:1 for the C-4 and C-I thioether conjugates of 2-OHE2 was observed. Chemical reaction of estradiol-2, 3-O-quinone with various thiols showed that alkyl and phenyl thiols gave about a 1:1 ratio of C-4 to C-I thioethers. However, reaction of the O-quinone with 4-nitrothiophenol gave a C-4/C-I ratio of 0.25 while 4-bromothiophenol gave a C-4/C-1 ratio of 4.0. These studies suggest that the regioselectivity of the reaction of thiols with estrogen catechols and O-quinones may be dependent on the nature of the thiol compounds and less on steric hindrance.

Original languageEnglish (US)
Pages (from-to)245-247
Number of pages3
JournalJournal of Steroid Biochemistry
Volume25
Issue number2
DOIs
StatePublished - Aug 1986

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