Preparation of 17 alpha-iodoethynylandrosta- and 17 alpha-(2-iodoethenyl)androsta-4,6-dien-17 beta-ol-3-ones as active site-directed photoaffinity ligands for androgen-binding proteins

Steroids. 1992 Nov;57(11):569-76. doi: 10.1016/0039-128x(92)90027-7.

Abstract

Unsaturated analogues of androst-4-en-17 beta-ol-3-one, each with a 17 alpha-iodoethynyl or 17 alpha-(2-iodoethenyl) substituent, were prepared, and their relative binding affinities (RBAs) for androgen-binding protein (ABP) were compared with those of 5 alpha-androstan-17 beta-ol-3-one, androst-4-en-17 beta-ol-3-one, androsta-4,6-dien-17 beta-ol-3-one, and androsta-1,4,6-trien-17 beta-ol-3-one. These binding studies indicate that the iodine[125I] analogues of 17 alpha-iodoethynyl and 17 alpha-[(E)-2-iodoethenyl] derivatives of androsta-4,6-dien-17 beta-ol-3-one and androsta-1,4,6-trien-17 beta-ol-3-one will have RBAs at least twice as great as that of 5 alpha-androstan-17 beta-ol-3-one. They can be prepared from 17 alpha-ethynylandrosta-4-en-17 beta-ol-3-one, the final synthetic step using N-[125I]iodosuccinimide, and are potential radioiodinated, active site-directed photoaffinity ligands for ABP and testosterone-binding globulin.

Publication types

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

MeSH terms

  • Affinity Labels / chemical synthesis*
  • Androgen-Binding Protein / metabolism*
  • Animals
  • Binding Sites
  • Dihydrotestosterone / analogs & derivatives*
  • Dihydrotestosterone / chemical synthesis
  • Dihydrotestosterone / metabolism
  • Epididymis / metabolism
  • Iodine Radioisotopes
  • Isotope Labeling
  • Male
  • Molecular Structure
  • Photochemistry
  • Rats

Substances

  • Affinity Labels
  • Androgen-Binding Protein
  • Iodine Radioisotopes
  • Dihydrotestosterone
  • 17-(2-iodoethynyl)androsta-4,6-dien-17-ol-3-one
  • 17-(2-iodoethenyl)androsta-4,6-dien-17-ol-3-one