Get 20M+ Full-Text Papers For Less Than $1.50/day. Start a 14-Day Trial for You or Your Team.

Learn More →

Synthesis and structure—Activity studies of some antitumor congeners of L ‐canaline

Synthesis and structure—Activity studies of some antitumor congeners of L ‐canaline A number of congeners of the antitumor compound L‐canaline, (l‐2‐amino‐4‐(aminooxy)butyric acid), a structural analog of L‐ornithine, have been synthesized and their growth‐inhibitory effects evaluated in cultured MIA‐PaCa‐2 cells, a human pancreatic adenosarcoma, by the 3‐(4,5‐dimethylthiazol‐2‐yl)‐2,5‐diphenyltetrazolium bromide assay. The results indicate that L‐canaline congeners in which the carbon chain length has been increased by one methylene unit exhibit a significant loss in cytotoxicity relative to the parent compound. Congeners in which the carbon chain length is decreased by one methylene unit retain the cytotoxicity of the parent compound against cultured MIA‐PaCa‐2 cells. Loss of the aminooxy or α‐amino group of L‐canaline severely curtails cell growth‐inhibitory activity. With the exception of the n‐octyl ester, esterification of L‐canaline with simple alcohols has little effect on overall growth‐inhibiting activity. It is noteworthy that the unnatural D‐enantiomer of canaline is as deleterious to MIA‐PaCa‐2 cell growth as the naturally occurring L‐enantiomer. Drug Dev. Res. 47:170–177, 1999. © 1999 Wiley‐Liss, Inc. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Drug Development Research Wiley

Synthesis and structure—Activity studies of some antitumor congeners of L ‐canaline

Download PDF
8 pages

Loading next page...
 
/lp/wiley/synthesis-and-structure-activity-studies-of-some-antitumor-congeners-X56ywZ4HmT

References (0)

References for this paper are not available at this time. We will be adding them shortly, thank you for your patience.

Publisher
Wiley
Copyright
Copyright © 1999 Wiley‐Liss, Inc.
ISSN
0272-4391
eISSN
1098-2299
DOI
10.1002/(SICI)1098-2299(199908)47:4<170::AID-DDR3>3.3.CO;2-2
Publisher site
See Article on Publisher Site

Abstract

A number of congeners of the antitumor compound L‐canaline, (l‐2‐amino‐4‐(aminooxy)butyric acid), a structural analog of L‐ornithine, have been synthesized and their growth‐inhibitory effects evaluated in cultured MIA‐PaCa‐2 cells, a human pancreatic adenosarcoma, by the 3‐(4,5‐dimethylthiazol‐2‐yl)‐2,5‐diphenyltetrazolium bromide assay. The results indicate that L‐canaline congeners in which the carbon chain length has been increased by one methylene unit exhibit a significant loss in cytotoxicity relative to the parent compound. Congeners in which the carbon chain length is decreased by one methylene unit retain the cytotoxicity of the parent compound against cultured MIA‐PaCa‐2 cells. Loss of the aminooxy or α‐amino group of L‐canaline severely curtails cell growth‐inhibitory activity. With the exception of the n‐octyl ester, esterification of L‐canaline with simple alcohols has little effect on overall growth‐inhibiting activity. It is noteworthy that the unnatural D‐enantiomer of canaline is as deleterious to MIA‐PaCa‐2 cell growth as the naturally occurring L‐enantiomer. Drug Dev. Res. 47:170–177, 1999. © 1999 Wiley‐Liss, Inc.

Journal

Drug Development Research – Wiley

Published: Aug 1, 1999

Keywords: L ‐canaline; pancreatic carcinoma; pyridoxal phosphate inhibitors; chemotherapeutic agents

There are no references for this article.