Synthesis and characterization of long-chain tartaric acid diamides as novel ceramide-like compounds

Ceramides play a crucial role in the barrier function of the skin as well as in transmembrane signaling. In this study long aliphatic chain tartaric acid diamides able to replace ceramides in an in vitro model of the stratum corneum lipid matrix due to their similar physico-chemical properties were...

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Veröffentlicht in:	Molecules (Basel, Switzerland) Switzerland), 2010-02, Vol.15 (2), p.824-833
Hauptverfasser:	Sinkó, Bálint, Pálfi, Melinda, Béni, Szabolcs, Kökösi, József, Takács-Novák, Krisztina
Format:	Artikel
Sprache:	eng
Schlagworte:	Animals apoptosis Apoptosis - drug effects ceramide-analogues Ceramides - chemical synthesis Ceramides - chemistry Ceramides - pharmacology Diamide - chemical synthesis Diamide - chemistry Diamide - pharmacology Fibroblasts - cytology Fibroblasts - drug effects Lipids Mice Skin Solvents tartradiamides Tartrates - chemical synthesis Tartrates - chemistry Tartrates - pharmacology Transdermal medication transdermal penetration
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Zusammenfassung:	Ceramides play a crucial role in the barrier function of the skin as well as in transmembrane signaling. In this study long aliphatic chain tartaric acid diamides able to replace ceramides in an in vitro model of the stratum corneum lipid matrix due to their similar physico-chemical properties were synthesized from diacetoxysuccinic anhydride in four steps. Their pro-apoptotic effect on fibroblast cells was also investigated.
ISSN:	1420-3049 1420-3049
DOI:	10.3390/molecules15020824