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Synthesis and study of 6-((7-nitrobenzo[c][1,2,5]oxadiazol-4-yl)amino)hexanoic acid derivatives as transdermal permeation enhancers
Kučera, Ondřej ; Vávrová, Kateřina (advisor) ; Nováková, Veronika (referee)
Ondřej Kučera Charles University in Prague, Faculty of Pharmacy in Hradec Králové Synthesis and study of 6-((7-nitrobenzo[c][1,2,5]oxadiazol-4-yl)amino)hexanoic acid derivatives as transdermal permeation enhancers Transdermal permeation enhancers are used to increase absorption of drugs through skin or, more importantly, through the stratum corneum, which is the uppermost layer of the skin. Mechanism of action of enhancers is not fully understood. In general the most active enhancers consist of hydrophilic and hydrophobic parts. In this work, we prepared and studied fluorescent permeation enhancers. Fluorescent dye NBD (7-nitrobenzo[c][1,2,5]oxadiazol) is fairly hydrophilic, so we used it as a hydrophilic head of potential enhancers based on dodecyl 6- (dimethylamino)hexanoate (DDAK). Such fluorescent enhancers could help us understand more about the mechanism of action. It enables determination of this enhancer and imaging of its penetration pathways in the skin. We synthesized three esters of 6-((7-nitrobenzo[c][1,2,5]oxadiazol-4-yl)amino)-hexanoic acid (NBD-acid) with ester-linked C8-C12 alkyls. 6-Aminocaproic acid reacted with 4-chloro- NBD and then with a series of alcohols to give us different lengths of alkyl chains. We applied these enhancers to human skin in Franz diffusion cells using two...
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