The use of 6alpha-and 6beta-carboxymethyl testosterone-bovine serum albumin conjugates in radioimmunoassay for testosterone.
The synthesis of 6alpha- and 6beta-testosterone-bovine serum albumin (BSA) conjugates is described. 6beta-Carboxymethyl-4-androstene-3,17-dione was prepared by a route analogous to that described earlier for 6beta-carboxymethyl progesterone. Sodium borohydride reduction of the 3 and 17 keto groups and subsequent selective oxidation of the resulting 3beta, 17beta-diol using MnO2 provided 6 -carboxymethyl testosterone. Further acid catalyzed epimerization of the C-6 center gave the isomeric 6alpha-carboxymethyl testosterone. The 6alpha- and 6beta-testosterone derivatives were attached to BSA via a mixed anhydride coupling employing tributylamine and i minus-butylchlorocarbonate. For each molecule of BSA, the 6alpha- and 6beta-conjugates contained an average of 23 and 20 steroid residues, respectively. Antisera to the conjugates exhibited similar high specificities toward various steroids, the only incidence of serious cross-reaction being the expected case of dihydrotestosterone.
D000735:Androstenedione / Q000138:chemical synthesis; D000818:Animals; D003429:Cross Reactions; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008722:Methods; D011817:Rabbits / Q000276:immunology; D011863:Radioimmunoassay; D012710:Serum Albumin, Bovine; D013739:Testosterone / Q000031:analogs & derivatives / Q000032:analysis*; D014316:Tritium
D014316:Tritium; D012710:Serum Albumin, Bovine; D013739:Testosterone; D000735:Androstenedione