Light-induced isomerization of apoptolidin a leads to inversion of C2-C3 double bond geometry

Org Lett. 2010 Jul 2;12(13):2944-7. doi: 10.1021/ol1009398.

Abstract

The isolation, characterization, and cytotoxicity against H292 cells of apoptolidin G are reported. Apoptolidin G is shown to be derived by a light-induced isomerization of the C2-C3 carbon-carbon double bond of apoptolidin A.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Cell Line, Tumor
  • Cell Survival / drug effects
  • Dose-Response Relationship, Drug
  • Drug Screening Assays, Antitumor
  • Humans
  • Macrolides / chemistry*
  • Macrolides / isolation & purification
  • Macrolides / pharmacology
  • Molecular Conformation
  • Pyrones / chemistry*
  • Pyrones / isolation & purification
  • Pyrones / pharmacology
  • Stereoisomerism
  • Structure-Activity Relationship
  • Ultraviolet Rays*

Substances

  • Macrolides
  • Pyrones
  • apoptolidin A
  • apoptolidin G