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Synthesis and structure-activity studies of some antitumor congeners of L-canavanine

✍ Scribed by Supinan R. Na Phuket; Latchezar S. Trifonov; Peter A. Crooks; Gerald A. Rosenthal; James W. Freeman; William E. Strodel

Publisher
John Wiley and Sons
Year
1997
Tongue
English
Weight
198 KB
Volume
40
Category
Article
ISSN
0272-4391

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✦ Synopsis

A number of structural analogs of the antitumor compound, L-canavanine, [L-2-amino-4-(guanidinooxy)butyric acid], a δ-oxa analog of L-arginine, have been synthesized and their growth-inhibitory effects evaluated in cultured MIA-PaCa-2 pancreatic carcinoma cells by the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. The results indicate that L-canavanine analogs in which the carbon chain-length and/or terminal guanidinooxy functional group has been modified elicit less growth inhibitory activity against these pancreatic cell lines than L-canavanine. On the other hand, several ester derivatives of L-canavanine have markedly enhanced growth inhibitory activity compared to L-canavanine. Thus, esterification of the carboxylic acid group constitutes an effective structural modification, which significantly amplifies the growth inhibitory properties of the parent compound against MIA-PaCa-2 cells.

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