title: Synthesis of medroxyprogesterone bromoacetate for affinity labeling.
abstract: Medroxyprogesterone bromoacetate (17alpha-hydroxy-6alpha-methyl-4-pregnene-3,20-dione 17-bromoacetate) was synthesized by reaction of 17alpha-hydroxy-6alpha-methyl-4-pregnene-3,20-dione with bromoacetic acid--trifluoroacetic anhydride followed by treatment of the intermediate with dilute ethanolic HBr. The product forms conjugates with L-cysteine, L-histidine, and L-methionine and inactivates 20beta-hydroxy steroid dehydrogenase (E.C. 1.1.1.53.) from Streptomyces hydrogenans in a time-dependent and irreversible manner. The title compound possesses a long-acting progestational effect in day 9 pregnant bilaterally ovariectomized rats. The affinity labeling analogue of the oral contraceptive medroxyprogesterone acetate is proposed for use in reproductive biological experiments.
mesh_terms: D000345:Affinity Labels / Q000138:chemical synthesis* / Q000494:pharmacology; D000596:Amino Acids; D000818:Animals; D002369:Castration; D055598:Chemical Phenomena; D002621:Chemistry; D003349:Cortisone Reductase / Q000037:antagonists & inhibitors; D005260:Female; D005327:Fetal Resorption / Q000139:chemically induced; D066298:In Vitro Techniques; D008525:Medroxyprogesterone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D011247:Pregnancy; D045167:Progesterone Congeners; D051381:Rats; D013302:Streptomyces / Q000201:enzymology
chemical_list: D000345:Affinity Labels; D000596:Amino Acids; D045167:Progesterone Congeners; D003349:Cortisone Reductase; D008525:Medroxyprogesterone