51101-80-5Relevant articles and documents
Thiol-Containing Androgens as Suicide Substrates of Aromatase
Bednarski, Patrick J.,Porubek, David J.,Nelson, Sidney D.
, p. 775 - 779 (2007/10/02)
The thiol-containing androgens 17β-hydroxy-10β-mercaptoestr-4-en-3-one (1) and 19-mercaptoandrost-4-ene-3,17-dione (2) were synthesized and tested in human placental microsomes for their ability to suicide inhibit aromatase.Both compounds showed time-dependent, pseudo-first-order rates of inactivation of aromatase with Ki's of 106 and 34 nM and kcat's of 3.2E-3 and 1.2E-3 s-1 respectively for 1 and 2 at 30 deg C.Diffusion dialysis failed to reactivate aromatase previously inactivated by either compound, and both compounds required that NaDPH and O2 be present for time -dependent inactivation of the enzyme.The presence of the substrate, androst-4-ene-3,17-dione (5.0 μM), protected the enzyme from inactivation while cysteine (1.0 mM) failed to protect aromatase from inactivation by either compound.The above evidence demonstrates that both compounds are potent suicide inhibitors of aromatase.