Synthesis and effects of 3-methylthiopropanoyl thiolesters of lipoic acid, methional metabolite mimics

6 S,8 S-Bis(3-methylthiopropanoyl) thiolesters of lipoic acid were synthesized with the carboxyl moiety of lipoate modified as methyl or water soluble choline esters. Evaluation on different cell lines in culture showed that they possessed modest antiproliferative activity. However, the 6-fold decre...

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Veröffentlicht in:	Bioorganic chemistry 2006-02, Vol.34 (1), p.49-58
Hauptverfasser:	Courvoisier, Celine, Paret, Marie Julie, Chantepie, Jacqueline, Goré, Jacques, Fournet, Guy, Quash, Gerard
Format:	Artikel
Sprache:	eng
Schlagworte:	Aldehydes - chemistry Aldehydes - metabolism Antineoplastic Agents - chemical synthesis Antineoplastic Agents - pharmacology Antiproliferative activity Branched chain oxoacid dehydrogenase complex Cancer Chemical Sciences Choline Esters - chemical synthesis Esters - pharmacology Humans Inhibitory Concentration 50 Lipoic acid Male Methionine - chemistry Methionine metabolism Molecular Mimicry Organic chemistry Propionates - chemistry Prostatic Neoplasms - pathology Sulfhydryl Compounds - chemistry Synthesis Thioctic Acid - chemical synthesis Thioctic Acid - pharmacology Tumor Cells, Cultured
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Beschreibung
Zusammenfassung:	6 S,8 S-Bis(3-methylthiopropanoyl) thiolesters of lipoic acid were synthesized with the carboxyl moiety of lipoate modified as methyl or water soluble choline esters. Evaluation on different cell lines in culture showed that they possessed modest antiproliferative activity. However, the 6-fold decrease in IC 50 (from 270 to 45 μM) observed with the water soluble 6 S,8 S-bis(3-methylthiopropenoyl) thiolester dehydro derivative on a human epithelial prostate cancer cell line (DU145) argues in favor of 3-methylthiopropanoyl metabolites as endogenous growth regulatory (apoptogenic) compounds derived from methionine.
ISSN:	0045-2068 1090-2120
DOI:	10.1016/j.bioorg.2005.11.001