Methode de synthese d'acides gras marques substitues ou non en α et en β
2-Propyn-1-ol and the dibromides Br(CH2)nBr (n = 10-12) have been used as starting materials for the synthesis of α- and β-methyl-branched fatty acids (C16) labeled with 123I at the ω-position.The methyl groups are introduced through the use of the lithium salt of either propanoic or isobutyric acid.The synthesis of *IC6H5(CH2)14COOH and *IC6H5(CH2)12CH(CH3)CH2COOH have been achieved in the same way starting from phenylacetylene.In each case, the radioactive iodine atom is introduced by an I/*I exchange reaction.
Apparu, Marcel,Comet, Michel,Leo, Pierre M.,Mathieu, Jean-Paul,Du Moulinet, Amaury,et al.
p. 118 - 124
(2007/10/02)
Synthesis and Evaluation of Radioiodinated Terminal p-Iodophenyl-Substituted α- and β-Methyl-Branched Fatty Acids
Methods have been developed for the preparation of terminal p-iodophenyl-substituted α- and β-methyl-branched long-chain fatty acids.The syntheses and physical properties of 14-(p-iodophenyl)-2(RS)-methyltetradecanoic acid and 15-(p-iodophenyl)-3(RS)-methylpentadecanoic acid are described.The radioiodinated agents are of interest as a result of the expected pronounced uptake and prolonged myocardial retention that may result from the inhibition of fatty acid metabolism.Tissue distribution studies in rats with 14-(p-iodophenyl)-2(RS)-methyltetradecanoic acidand 15-(p-iodophenyl)-3(RS)-methylpentadecanoic acid show significant heart uptake and prolonged retention accompanied by low in vivo deiodination and high blood levels.A comparison of the heart uptake of the radioiodinated methyl-branched fatty acids and their unbranched analogues has demonstrated a greater myocardial retention of the methyl-branched fatty acids than the unbranched analogues.These results suggest that the mechanism of myocardial retention results from steric or chemical inhibition of the metabolism of these fatty acids by the presence of the methyl group.
Goodman, M. M.,Kirsch, G.,Knapp, F. F.
p. 390 - 397
(2007/10/02)
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