L-Serine and glycine based ceramide analogues as transdermal permeation enhancers: polar head size and hydrogen bonding.
Novel transdermal permeation enhancers related to stratum corneum ceramides were investigated. The synthesis of a series of simple compounds based on two selected amino acids, L-serine and glycine, and their enhancement activities are reported. Glycine derivative 3 enhanced the permeation of theophylline through human skin in vitro 12.5+/-0.5 times. The relationships between properties of the polar head of the compounds and their activity are discussed.
Vávrová
Katerina
K
Department of Inorganic & Organic Chemistry, Faculty of Pharmacy, Charles University, Heyrovského 1203, 500 05, Hradec Králové, Czech Republic. vavrovak@faf.cuni.cz
Hrabálek
Alexandr
A
Dolezal
Pavel
P
Holas
Tomás
T
Zbytovská
Jarmila
J
D000279:Administration, Cutaneous; D001381:Azepines / Q000494:pharmacology; D002518:Ceramides / Q000138:chemical synthesis* / Q000494:pharmacology*; D002851:Chromatography, High Pressure Liquid; D015194:Diffusion Chambers, Culture; D005079:Excipients; D005998:Glycine / Q000737:chemistry*; D006801:Humans; D006860:Hydrogen Bonding; D066298:In Vitro Techniques; D007202:Indicators and Reagents; D012694:Serine / Q000737:chemistry*; D012869:Skin Absorption / Q000187:drug effects*; D013329:Structure-Activity Relationship; D013806:Theophylline / Q000008:administration & dosage / Q000493:pharmacokinetics; D014665:Vasodilator Agents / Q000008:administration & dosage / Q000493:pharmacokinetics
D001381:Azepines; D002518:Ceramides; D005079:Excipients; D007202:Indicators and Reagents; D014665:Vasodilator Agents; C035229:laurocapram; D012694:Serine; D013806:Theophylline; D005998:Glycine