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Generation of [ 75 Se]dimethyl selenide and the synthesis of [ 75 Se]dimethyleselenonium compounds
Author(s) -
Foster Stephen J.,
Kraus Richard J.,
Ganther Howard E.
Publication year - 1985
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.2580220402
Subject(s) - chemistry , nitromethane , selenide , iodide , methyl iodide , selenium , halide , medicinal chemistry , nuclear chemistry , inorganic chemistry , organic chemistry
The synthesis of various [ 75 Se]selenonium compounds of biological interest is described. [ 75 Se]Trimethylselenonium iodide (sp. Ac. 32 mCi/mmol), prepared from commercially available [ 75 Se]selenocystine (Foster S. J. and Ganther H. E. ‐ Anal. Biochem. 137 : 205–9, 1984.) was decomposed thermally, in a stream of nitrogen, to give [ 75 Se]dimethyl selenide, which was trapped in nitromethane at −18°C. [ 75 Se]Dimethyl selenide was reacted, in nitromethane solution, with various alkyl halides to give dimethylselenonium compounds of the type (CH 3 ) 2 Se + ‐R, where R = CH 2 CO 2 H, CH 2 H, CH 2 CO 2 C 2 H 5 , ‐(CH 2 ) 2 CO 2 H and ‐(CH 2 ) 2 CO 2 C 2 H 5 . [ 75 Se]Methyl‐selenomethionine‐selenonium iodide was synthesized from [ 75 Se]selenomethionine and methyl iodide in a mixture of formic and acetic acids at 25°C. [ 75 Se]Selenocystine was reduced and methylated to give [ 75 Se]‐methylselenocysteine, which was slowly converted to [ 75 Se]dimethyl‐selenocysteineselenonium iodide by the same reaction.