Symplostatin 3, a new dolastatin 10 analogue from the marine cyanobacterium Symploca sp. VP452.

Abstract

Symplostatin 3 (1), a new analogue of dolastatin 10 (2), has been isolated from a tumor selective extract of a Hawaiian variety of the marine cyanobacterium Symploca sp. VP452. Compound 1 differs from 2 only in the C-terminal unit; the dolaphenine unit is substituted by a 3-phenyllactic acid residue. Symplostatin 3 (1) possesses IC(50) values for in vitro cytotoxicity toward human tumor cell lines ranging from 3.9 to 10.3 nM. It disrupts microtubules, but at a higher concentration than 2, correlating with the weaker in vitro cytotoxicity.

• Authors: Hendrik Luesch, Wesley Y Yoshida, Richard E Moore, Valerie J Paul, Susan L Mooberry, Thomas H Corbett
• Journal: Journal of natural products (J Nat Prod) Vol. 65 Issue 1 Pg. 16-20 (Jan 2002) ISSN: 0163-3864 [Print] United States
• PMID: 11809057 (Publication Type: Comparative Study, Journal Article, Research Support, Non-U.S. Gov't, Research Support, U.S. Gov't, Non-P.H.S., Research Support, U.S. Gov't, P.H.S.)

Chemical References

• Antineoplastic Agents
• Depsipeptides
• Oligopeptides
• Thiazoles
• symplostatin 3
• dolastatin 1

Topics

• Animals
• Antineoplastic Agents (chemistry, isolation & purification, pharmacology)
• Chromatography, High Pressure Liquid
• Cyanobacteria (chemistry)
• Depsipeptides
• Dose-Response Relationship, Drug
• Drug Screening Assays, Antitumor
• Fibroblasts (drug effects)
• Hawaii
• Humans
• Inhibitory Concentration 50
• KB Cells (drug effects)
• Leukemia L1210
• Mass Spectrometry
• Mice
• Microscopy, Fluorescence
• Microtubules (drug effects)
• Molecular Structure
• Neoplasms
• Nuclear Magnetic Resonance, Biomolecular
• Oligopeptides (chemistry, isolation & purification, pharmacology)
• Spectrometry, Mass, Electrospray Ionization
• Structure-Activity Relationship
• Thiazoles (chemistry, pharmacology)
• Tumor Cells, Cultured (drug effects)