Esters of 6-aminohexanoic acid as skin permeation enhancers: The effect of branching in the alkanol moiety

Journal of Pharmaceutical Sciences
Alexandr HrabálekMilos Machácek

Abstract

In order to investigate the effect of branching and cyclization in the hydrophobic part of skin permeation enhancers, 17 novel branched-chain and cyclic 6-aminohexanoic acid esters were prepared. Their permeation enhancing activity was evaluated in vitro using human skin and theophylline as a model drug, and compared to that of the corresponding linear-chain analogues. The results showed that chain branching and cyclization has a negative influence on the enhancing activity of 6-aminohexanoates. For example, the enhancement ratios (ERs) of dodecan-1-yl, dodecan-2-yl, dodecan-4-yl, and cyclododecyl ester were 39.7, 29.3, 3.1, and 2.2, respectively. No significant change in the optimum length of the chain was observed. Dodecan-2-yl 6-aminohexanoate, the most active branched derivative, still maintains a remarkable enhancing activity (ER 29.3). Presumably, the relatively small degree of branching of these molecules does not prevent them from interacting with the lipid components of the stratum corneum. However, a higher degree of branching, cyclization of the chain, and presence of an aromatic ring resulted in a loss of activity.

References

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Citations

Sep 30, 2008·Drug Development and Industrial Pharmacy·Gamal M El MaghrabyIbrahim A Alsarra
Dec 23, 2009·International Journal of Pharmaceutics·K M YerramsettyK A M Gasem
Mar 12, 2016·European Journal of Pharmaceutical Sciences : Official Journal of the European Federation for Pharmaceutical Sciences·Koji KubotaToshikazu Yamaguchi
Dec 7, 2007·International Journal of Pharmaceutics·Ligang ZhaoZhonggui He
Aug 14, 2012·Medicinal Research Reviews·Josef Jampilek, Katerina Brychtova
Nov 26, 2010·Journal of Controlled Release : Official Journal of the Controlled Release Society·Michal NovotnýKateřina Vávrová
Sep 12, 2006·Bioorganic & Medicinal Chemistry·Jana KlimentováAlexandr Hrabálek

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