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Radioiododestannylation. Convenient synthesis of a high affinity thromboxane A 2 /prostaglandin H 2 receptor antagonist
Author(s) -
Mais Dale E.,
Halushka Perry V.,
Naka Masao,
Morinelli Thomas A.,
Oatis John E.,
Hamanaka Nobuyuki
Publication year - 1991
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580290110
Subject(s) - chemistry , bicyclic molecule , ligand (biochemistry) , prostaglandin , chloramine t , stereochemistry , receptor , high performance liquid chromatography , antagonist , hydrolysis , chromatography , biochemistry , organic chemistry
Radioiodination of methyl‐7‐[(2R, 2S, 3S, 5R)‐6,6‐dimethyl‐3‐(4‐trimethylstannylbenzenesulfonylamino) bicyclo[3.1.1]hept‐2‐yl]‐5(Z)‐heptenoate with [ 125 I] Na using a modification of the chloramine‐T method in organic solvent is simple with high yields and site specific. The product, following hydrolysis of the ester, 7‐[(2R, 2S, 3S, 5R)‐6,6‐dimethyl‐3‐(4‐[ 125 I]‐iodobenzenesulfonylamino) bicyclo[3.1.1]hept‐2‐yl]‐5(Z)‐heptenoic acid ([ 125 I]‐ISAP), was purified by HPLC. The high specific activity and specific binding will make the ligand a useful tool for the characterization of thromboxane A 2 /prostaglandin H 2 receptors.