Synthesis of fluorescent C24-ceramide: evidence for acyl chain length dependent differences in penetration of exogenous NBD-ceramides into human skin

Jakub Novotný; Katerina Pospechová; Alexandr Hrabálek; Robert Cáp; Katerina Vávrová

doi:10.1016/j.bmcl.2009.10.047

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.

Authors

Jakub Novotný¹, Katerina Pospechová, Alexandr Hrabálek, Robert Cáp, Katerina Vávrová

Affiliation

¹ Centre for New Antivirals and Antineoplastics, Department of Inorganic and Organic Chemistry, Charles University in Prague, Faculty of Pharmacy, Hradec Králové, Czech Republic.

PMID: 19879139
DOI: 10.1016/j.bmcl.2009.10.047

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