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Tritium labeled prostacyclin sodium salt
Author(s) -
Hsi Richard S. P.,
Stolle Wayne T.,
McGrath James P.,
Morton Douglas R.
Publication year - 1981
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.2580181007
Subject(s) - chemistry , prostacyclin , sodium , yield (engineering) , hydrolysis , salt (chemistry) , prostaglandin , tritium , sodium salt , nuclear chemistry , organic chemistry , inorganic chemistry , biochemistry , materials science , physics , nuclear physics , metallurgy
Crystalline [11β‐ 3 H]prostacyclin (PGI 2 ) sodium salt (5) was prepared from prostaglandin D 2 (PGD 2 ) methyl ester ( 1 ). Reduction of PGD 2 methyl ester with sodium borotritide afforded [11β‐ 3 H]prostaglandin F 2 α (PGF 2 α) methyl ester ( 2a ) in 57% radiochemical yield. [11β‐ 3 H]PGF 2 α methyl ester was converted via (5R, 6R)‐ and (5S, 6S)‐5‐iodo‐[11β‐ 3 H]prostaglandin I 1 methyl ester ( 3 ) to [11β‐ 3 H]‐prostacyclin methyl ester ( 4 ). Carefully controlled hydrolysis of 4 produced crystalline [11β‐ 3 H]PGI 2 sodium salt which was shown to be >95% pure by means of high performance liquid chromatographic (HPLC) analysis. The overall yield from [11β‐ 3 H]PGF 2 α methyl ester to [11β‐ 3 H]PGI 2 sodium salt was 53%. [11β‐ 3 H]PGI 2 sodium salt with a specific activity of 502 μCi/mg has only limited radiochemical stability. Its radiochemical purity declined 15% after three weeks of storage at −20°C in the crystalline state.