Publication
Novel serine-based gemini surfactants as chemical permeation enhancers of local anesthetics: a comprehensive study on structure–activity relationships, molecular dynamics and dermal delivery
| dc.contributor.author | Teixeira, Raquel S. | |
| dc.contributor.author | Cova, Tânia F.G.G. | |
| dc.contributor.author | Silva, Sérgio M.C. | |
| dc.contributor.author | Oliveira, Rita | |
| dc.contributor.author | do Vale, M. Luísa C. | |
| dc.contributor.author | Marques, Eduardo F. | |
| dc.contributor.author | Pais, Alberto A.C.C. | |
| dc.contributor.author | Veiga, Francisco J.B. | |
| dc.date.accessioned | 2022-01-27T10:55:30Z | |
| dc.date.available | 2022-01-27T10:55:30Z | |
| dc.date.issued | 2015 | |
| dc.description.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 the experimental observations. Overall, this study suggests the viability of these serine-based surfactants as suitable and promising delivery agents in pharmaceutical formulations. | pt_PT |
| dc.description.version | info:eu-repo/semantics/publishedVersion | pt_PT |
| dc.identifier.doi | 10.1016/j.ejpb.2015.02.024 | pt_PT |
| dc.identifier.issn | 0939-6411 | |
| dc.identifier.uri | http://hdl.handle.net/10284/10667 | |
| dc.language.iso | eng | pt_PT |
| dc.peerreviewed | yes | pt_PT |
| dc.publisher | Elsevier | pt_PT |
| dc.subject | Dermal drug delivery | pt_PT |
| dc.subject | Chemical permeation enhancers | pt_PT |
| dc.subject | Tetracaine | pt_PT |
| dc.subject | Ropivacaine | pt_PT |
| dc.subject | Serinebased surfactants | pt_PT |
| dc.subject | Molecular dynamics simulations | pt_PT |
| dc.title | Novel serine-based gemini surfactants as chemical permeation enhancers of local anesthetics: a comprehensive study on structure–activity relationships, molecular dynamics and dermal delivery | pt_PT |
| dc.type | journal article | |
| dspace.entity.type | Publication | |
| oaire.citation.endPage | 213 | pt_PT |
| oaire.citation.startPage | 205 | pt_PT |
| oaire.citation.title | European Journal of Pharmaceutics and Biopharmaceutics | pt_PT |
| oaire.citation.volume | 93 | pt_PT |
| person.familyName | Oliveira | |
| person.givenName | Rita | |
| person.identifier.ciencia-id | 371C-F327-9C9C | |
| person.identifier.orcid | 0000-0003-0258-9472 | |
| person.identifier.scopus-author-id | 55974811800 | |
| rcaap.rights | closedAccess | pt_PT |
| rcaap.type | article | pt_PT |
| relation.isAuthorOfPublication | eec36871-71b7-4563-b864-3595628f7194 | |
| relation.isAuthorOfPublication.latestForDiscovery | eec36871-71b7-4563-b864-3595628f7194 |
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