N,N-dimethylsphingosine-coumarin: synthesis, chemical characterization, and biological evaluation

Bioconjug Chem. 2007 May-Jun;18(3):731-5. doi: 10.1021/bc060285q. Epub 2007 Apr 14.

Abstract

Coumarin derivatives of N,N-dimethylsphingosine (DMSP) were prepared and chemically characterized. They were apparently biologically equivalent to DMSP in terms of tumor cell cytotoxicity and were used to establish the rapid mitochondrial localization of this sphingolipid in tumor cells, followed closely by its marked reduction of mitochondrial membrane potential.

MeSH terms

  • Cell Line, Tumor
  • Coumarins / chemistry
  • Coumarins / metabolism*
  • Coumarins / pharmacology*
  • Humans
  • Membrane Potential, Mitochondrial / drug effects
  • Microscopy, Fluorescence
  • Mitochondria / chemistry
  • Mitochondria / metabolism*
  • Sphingosine / analogs & derivatives*
  • Sphingosine / chemistry
  • Sphingosine / metabolism
  • Sphingosine / pharmacology

Substances

  • Coumarins
  • coumarin
  • N,N-dimethylsphingosine
  • Sphingosine