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

Abstract

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. Exogenous long-chain ceramides do not penetrate into nucleated epidermis; their mechanism of action should be reconsidered.

Keywords

• skin
• ceramide
• stratum corneum
• fluorescent lipids