The preparation of three fluorescence-labeled derivatives of testosterone.
Three fluorescence-labelled derivatives of testosterone were prepared consisting of the steroid separated from the fluorochrome by a hydrocarbon "bridge". "Bridges" of different lengths (C2 to C7) were used as the length required to avoid steric hindrance effects by the fluorochrome in studies on steroid-protein binding was unknown. The three derivatives prepared were: 17 beta-hydroxy--4-androsten-3-one 3-(O-(N-(2'-mercapto)ethyl)carbamoylmethyl)oxime, 17 beta-hydroxy-4-androsten-3-one 3-(O-(N-(3'-amino)propyl)carbamoylmethyl)oxime and 17 beta-hydroxy-4-androsten-3-one 3-(O(N-(7'-amino)heptyl)carbamoylmethyl)oxime. These were then coupled with either a dansyl or a fluorescein molecule. Overall yields were sufficient and the products immunoreactive with anti-testosterone antiserum.
D055598:Chemical Phenomena; D002621:Chemistry; D003543:Cysteamine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D016650:Fluorescein-5-isothiocyanate; D005452:Fluoresceins / Q000138:chemical synthesis*; D005455:Fluorescent Antibody Technique; D007460:Iodoacetamide / Q000031:analogs & derivatives; D009282:Naphthalenesulfonates; D013056:Spectrophotometry, Ultraviolet; D013739:Testosterone / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D013861:Thiocyanates
D005452:Fluoresceins; D009282:Naphthalenesulfonates; D013861:Thiocyanates; D013739:Testosterone; D003543:Cysteamine; C006421:1,5-I-AEDANS; C026351:testosterone-cysteamine-DANS; C026349:testosterone-DAP-fluorescein; C026350:testosterone-DAH-fluorescein; D016650:Fluorescein-5-isothiocyanate; D007460:Iodoacetamide