Alkyne-Tagged Analogue of Jaspine B: New Tool for Identifying Jaspine B Mode of Action

Chembiochem. 2018 Dec 4;19(23):2438-2442. doi: 10.1002/cbic.201800496. Epub 2018 Nov 7.

Abstract

The first biologically relevant clickable probe related to the antitumor marine lipid jaspine B is reported. The concise synthetic route to both enantiomers relied on the supercritical fluid chromatography (SFC) enantiomeric resolution of racemic materials. The eutomeric dextrogyre derivative represents the first jaspine B analogue with enhanced cytotoxicity with IC50 down to 30 nm. These enantiomeric probes revealed a chiralitydependent cytoplasmic imaging of U2OS cancer cells by in situ click labeling.

Keywords: Jaspine B; bioorthogonality; click chemistry; fluorescent probes; pachastrissamine.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes / chemical synthesis
  • Alkynes / chemistry*
  • Alkynes / toxicity
  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry*
  • Antineoplastic Agents / toxicity
  • Cell Line, Tumor
  • Click Chemistry
  • Fluorescent Dyes / chemical synthesis
  • Fluorescent Dyes / chemistry*
  • Fluorescent Dyes / toxicity
  • Humans
  • Molecular Probes / chemical synthesis
  • Molecular Probes / chemistry*
  • Molecular Probes / toxicity
  • Sphingosine / analogs & derivatives*
  • Sphingosine / chemical synthesis
  • Sphingosine / toxicity
  • Stereoisomerism

Substances

  • Alkynes
  • Antineoplastic Agents
  • Fluorescent Dyes
  • Molecular Probes
  • pachastrissamine
  • Sphingosine