Chloptosin, an apoptosis-inducing dimeric cyclohexapeptide produced by Streptomyces.

In the course of screening for apoptosis-inducing agents, chloptosin (1) was isolated from the culture broth of Streptomyces. The dumbbell-type structure of the dimeric cyclohexapeptide consisting of D-valine, (3S)- and (3R)-piperazic acids, O-methyl-L-serine, D-threonine, and (2S,3aR,8aR)-6-chloro-3a-hydroxy-2,3,3a, 8a-hexahydropyrrolo[2,3-b]indole-2-carboxylic acid was elucidated by spectroscopic and chemical degradation studies. The amino acid components in each cyclohexapeptide domain were presented in alternating R and S configurations. Chloptosin (1) was found to induce apoptotic activity in apoptosis-resistant human pancreatic adenocarcinoma cell line AsPC-1 and showed a strong antimicrobial activity against Gram-positive bacteria including methicillin-resistant Staphylococcus aureus.
AuthorsK Umezawa, Y Ikeda, Y Uchihata, H Naganawa, S Kondo
JournalThe Journal of organic chemistry (J Org Chem) Vol. 65 Issue 2 Pg. 459-63 (Jan 28 2000) ISSN: 0022-3263 [Print] UNITED STATES
PMID10813957 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
Chemical References
  • Anti-Bacterial Agents
  • Antineoplastic Agents
  • Peptides, Cyclic
  • Pyridazines
  • Anti-Bacterial Agents (chemistry, isolation & purification, metabolism)
  • Antineoplastic Agents (chemistry, isolation & purification, metabolism)
  • Apoptosis (drug effects)
  • Cell Line
  • Humans
  • Hydrolysis
  • Methicillin Resistance
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Peptides, Cyclic (biosynthesis, chemistry, isolation & purification)
  • Pyridazines (chemistry, isolation & purification)
  • Spectrum Analysis
  • Staphylococcus aureus (drug effects)
  • Streptomyces (metabolism)

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