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

Supinan R. Na Phuket, Latchezar S. Trifonov, Peter A. Crooks, Gerald A. Rosenthal, James W. Freeman, William E. Strodel

Research output: Contribution to journalArticlepeer-review

8 Scopus citations

Abstract

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.

Original languageEnglish (US)
Pages (from-to)325-332
Number of pages8
JournalDrug Development Research
Volume40
Issue number4
DOIs
StatePublished - Apr 1997
Externally publishedYes

Keywords

  • Arginine analogues
  • L-canavanine
  • Pancreatic cancer

ASJC Scopus subject areas

  • Drug Discovery

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