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      Dicationic Alkylammonium Bromide Gemini Surfactants. Membrane Perturbation and Skin Irritation

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          Abstract

          Dicationic alkylammonium bromide gemini surfactants represent a class of amphiphiles potentially effective as skin permeation enhancers. However, only a limited number of studies has been dedicated to the evaluation of the respective cytotoxicity, and none directed to skin irritation endpoints. Supported on a cell viability study, the cytotoxicity of gemini surfactants of variable tail and spacer length was assessed. For this purpose, keratinocyte cells from human skin (NCTC 2544 cell line), frequently used as a model for skin irritation, were employed. The impact of the different gemini surfactants on the permeability and morphology of model vesicles was additionally investigated by measuring the leakage of calcein fluorescent dye and analyzing the NMR spectra of 31P, respectively. Detail on the interaction of gemini molecules with model membranes was also provided by a systematic differential scanning calorimetry (DSC) and molecular dynamics (MD) simulation. An irreversible impact on the viability of the NCTC 2544 cell line was observed for gemini concentrations higher than 25 mM, while no cytotoxicity was found for any of the surfactants in a concentration range up to 10 mM. A higher cytotoxicity was also found for gemini surfactants presenting longer spacer and shorter tails. The same trend was obtained in the calorimetric and permeability studies, with the gemini of longest spacer promoting the highest degree of membrane destabilization. Additional structural and dynamical characterization of the various systems, obtained by 31P NMR and MD, provide some insight on the relationship between the architecture of gemini surfactants and the respective perturbation mechanism.

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          VMD: Visual molecular dynamics

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            Ordering effects of cholesterol and its analogues.

            Without any exaggeration, cholesterol is one of the most important lipid species in eukaryotic cells. Its effects on cellular membranes and functions range from purely mechanistic to complex metabolic ones, besides which it is also a precursor of the sex hormones (steroids) and several vitamins. In this review, we discuss the biophysical effects of cholesterol on the lipid bilayer, in particular the ordering and condensing effects, concentrating on the molecular level or inter-atomic interactions perspective, starting from two-component systems and proceeding to many-component ones e.g., modeling lipid rafts. Particular attention is paid to the roles of the methyl groups in the cholesterol ring system, and their possible biological function. Although our main research methodology is computer modeling, in this review we make extensive comparisons between experiments and different modeling approaches.
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              Gemini surfactants: a new class of self-assembling molecules

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                Author and article information

                Contributors
                Role: Editor
                Journal
                PLoS One
                plos
                plosone
                PLoS ONE
                Public Library of Science (San Francisco, USA )
                1932-6203
                2011
                10 November 2011
                : 6
                : 11
                : e26965
                Affiliations
                [1 ]Chemistry Department, University of Coimbra, Coimbra, Portugal
                [2 ]Department of Life Sciences, Centre for Neurosciences and Cellular Biology, University of Coimbra, Coimbra, Portugal
                [3 ]Department of Chemistry and Biochemistry, Centro de Investigação em Química, University of Porto, Porto, Portugal
                King's College, London, United Kingdom
                Author notes

                Conceived and designed the experiments: JASA AACCP. Performed the experiments: JASA HF RAC. Analyzed the data: JASA HF RAC EFM AACCP. Contributed reagents/materials/analysis tools: EFM HF RAC. Wrote the paper: JASA HF RAC EFM AACCP.

                Article
                PONE-D-11-11563
                10.1371/journal.pone.0026965
                3213113
                22102870
                090fab91-5d00-4422-b8bd-7ecc1e0701c4
                Almeida et al. This is an open-access article distributed under the terms of the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are credited.
                History
                : 23 June 2011
                : 6 October 2011
                Page count
                Pages: 12
                Categories
                Research Article
                Biology
                Anatomy and Physiology
                Skin
                Skin Physiology
                Biophysics
                Toxicology
                Predictive Toxicology
                Toxic Agents
                Chemistry
                Computational Chemistry
                Molecular Dynamics
                Medicine
                Anatomy and Physiology
                Skin
                Skin Physiology
                Toxicology
                Predictive Toxicology
                Toxic Agents

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                Uncategorized

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