Synthesis of Fluorescent C24-ceramide: Evidence for Acyl Chain Length Dependent Differences in Penetration of Exogenous NBD-ceramides Into Human Skin

Bioorg Med Chem Lett. 2009 Dec 15;19(24):6975-7. doi: 10.1016/j.bmcl.2009.10.047. Epub 2009 Oct 15.

Abstract

Topical skin lipid supplementation may provide opportunities for controlling ceramide (Cer) deficiency in skin diseases such as atopic dermatitis or psoriasis. Here we describe the synthesis of a long-chain 7-nitrobenzo[c][1,2,5]oxadiazol-4-yl (NBD)-labeled Cer and its different penetration through human skin compared to widely used short-chain fluorescent Cer tools.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 4-Chloro-7-nitrobenzofurazan / chemical synthesis
  • 4-Chloro-7-nitrobenzofurazan / metabolism*
  • Bisbenzimidazole / metabolism
  • Ceramides / chemical synthesis
  • Ceramides / metabolism*
  • Dermatitis, Atopic / metabolism
  • Fluorescence
  • Fluorescent Dyes / chemical synthesis
  • Fluorescent Dyes / metabolism*
  • Humans
  • Permeability
  • Psoriasis / metabolism
  • Skin / metabolism*

Substances

  • Ceramides
  • Fluorescent Dyes
  • 4-Chloro-7-nitrobenzofurazan
  • Bisbenzimidazole