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

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...

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Veröffentlicht in:	Bioorganic & medicinal chemistry letters 2009-12, Vol.19 (24), p.6975-6977
Hauptverfasser:	NOVOTNY, Jakub, POSPECHOVA, Kateřina, HRABALEK, Alexandr, CAP, Robert, VAVROVA, Kateřina
Format:	Artikel
Sprache:	eng
Schlagworte:	4-Chloro-7-nitrobenzofurazan - chemical synthesis 4-Chloro-7-nitrobenzofurazan - metabolism Biological and medical sciences Bisbenzimidazole - metabolism Ceramide Ceramides - chemical synthesis Ceramides - metabolism Dermatitis, Atopic - metabolism Fluorescence Fluorescent Dyes - chemical synthesis Fluorescent Dyes - metabolism Fluorescent lipids Fundamental and applied biological sciences. Psychology Humans Permeability Psoriasis - metabolism Skin Skin - metabolism Stratum corneum Vertebrates: skin, associated glands, phaneres, light organs, various exocrine glands (salt gland, uropygial gland...), adipose tissue, connective tissue
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Zusammenfassung:	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.
ISSN:	0960-894X 1464-3405
DOI:	10.1016/j.bmcl.2009.10.047