制备17α-碘乙炔基雄甾烷和17α-(2-碘乙烯基)雄甾-4,6-二烯-17β-醇-3-酮作为雄激素结合蛋白的活性位点定向光亲和配体。
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.
作者信息
Cruz P J, Mason N S, Danzo B J, Smith H E
机构信息
Department of Chemistry, Vanderbilt University, Nashville, Tennessee 37235.
出版信息
Steroids. 1992 Nov;57(11):569-76. doi: 10.1016/0039-128x(92)90027-7.
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.
制备了雄甾-4-烯-17β-醇-3-酮的不饱和类似物，每个类似物都带有17α-碘乙炔基或17α-(2-碘乙烯基)取代基，并将它们与雄激素结合蛋白(ABP)的相对结合亲和力(RBA)与5α-雄甾烷-17β-醇-3-酮、雄甾-4-烯-17β-醇-3-酮、雄甾-4,6-二烯-17β-醇-3-酮和雄甾-1,4,6-三烯-17β-醇-3-酮的相对结合亲和力进行了比较。这些结合研究表明，雄甾-4,6-二烯-17β-醇-3-酮和雄甾-1,4,6-三烯-17β-醇-3-酮的17α-碘乙炔基和17α-[(E)-2-碘乙烯基]衍生物的碘[¹²⁵I]类似物的RBA将至少是5α-雄甾烷-17β-醇-3-酮的两倍。它们可以由17α-乙炔基雄甾-4-烯-17β-醇-3-酮制备，最后一步合成使用N-[¹²⁵I]碘代琥珀酰亚胺，并且是用于ABP和睾酮结合球蛋白的潜在放射性碘化、活性位点导向的光亲和配体。
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