Novel serine-based gemini surfactants as chemical permeation enhancers of local anesthetics: A comprehensive study on structure-activity relationships, molecular dynamics and dermal delivery

European Journal of Pharmaceutics and Biopharmaceutics : Official Journal of Arbeitsgemeinschaft Für Pharmazeutische Verfahrenstechnik E.V
Raquel S TeixeiraFrancisco J B Veiga

Abstract

This work aims at studying the efficacy of a series of novel biocompatible, serine-based surfactants as chemical permeation enhancers for two different local anesthetics, tetracaine and ropivacaine, combining an experimental and computational approach. The surfactants consist of gemini molecules structurally related, but with variations in headgroup charge (nonionic vs. cationic) and in the hydrocarbon chain lengths (main and spacer chains). In vitro permeation and molecular dynamics studies combined with cytotoxicity profiles were performed to investigate the permeation of both drugs, probe skin integrity, and rationalize the interactions at molecular level. Results show that these enhancers do not have significant deleterious effects on the skin structure and do not cause relevant changes on cell viability. Permeation across the skin is clearly improved using some of the selected serine-based gemini surfactants, namely the cationic ones with long alkyl chains and shorter spacer. This is noteworthy in the case of ropivacaine hydrochloride, which is not easily administered through the stratum corneum. Molecular dynamics results provide a mechanistic view of the surfactant action on lipid membranes that essentially corroborate t...Continue Reading

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Aug 12, 2014·International Journal of Pharmaceutics·Raquel S TeixeiraFrancisco J B Veiga

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Citations

Apr 27, 2017·The Journal of Physical Chemistry. B·Jesse G McDaniel, Arun Yethiraj
Nov 9, 2019·International Journal of Molecular Sciences·Lucia Ya ZakharovaEliana B Souto
Jun 18, 2020·International Journal of Nanomedicine·Yun-Chun ZhaoCai-Hong Zheng
Jan 12, 2021·World Journal of Microbiology & Biotechnology·Ewa ObłąkAnna Wieczyńska
Jul 5, 2021·Chemistry and Physics of Lipids·Sukanya Arul Prakash, Ravi Kanth Kamlekar
Feb 13, 2019·Chemical Reviews·Richard M VenableRichard W Pastor

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