Estrogenic properties of 3,9-dihydroxy-7,12-dimethylbenz[a]anthracene in rats

J Natl Cancer Inst. 1979 Jun;62(6):1585-8.

Abstract

Previously, the 3,9-dihydroxy derivative of benz[a]-anthracene was shown to be weakly estrogenic. The availability of the related diol of the mammary carcinogen dimethylbenz[a]-anthracene, i.e., 3,9-dihydroxy-7,12-dimethylbenz[a]anthracene (3,9-diOHDMBA), prompted a similar study of its estrogenic properties. The competitive binding studies of 3,9-diOHDMBA with 17beta-estradiol in the uterine cytosol of immature SD rats gave a Ka of 1.7 x 10(8) M-1. 17beta-Estradiol (10(-9) M) binding to the 8S binding protein was inhibited by 3,9-diOHDMBA at concentrations similar to those of nafoxidine HCl (1 x 10(-5) M). Bioassay demonstrated that the diol possesses 1/4,464 the activity of 17beta-estradiol.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • 9,10-Dimethyl-1,2-benzanthracene* / analogs & derivatives
  • 9,10-Dimethyl-1,2-benzanthracene* / metabolism
  • 9,10-Dimethyl-1,2-benzanthracene* / pharmacology
  • Animals
  • Benz(a)Anthracenes* / analogs & derivatives
  • Binding, Competitive
  • Cytosol / metabolism
  • Estradiol / metabolism
  • Estrogens*
  • Female
  • In Vitro Techniques
  • Rats
  • Receptors, Estrogen / metabolism*
  • Uterus / metabolism

Substances

  • Benz(a)Anthracenes
  • Estrogens
  • Receptors, Estrogen
  • Estradiol
  • 9,10-Dimethyl-1,2-benzanthracene