pH Sensitive surfactants from lysine: assessment of their cytotoxicity and environmental behavior

The toxicity and environmental behavior of new pH-sensitive surfactants from lysine are presented. Three different chemical structures are studied: surfactants with one amino acid and one alkyl chain, surfactants with two amino acids on the polar head and one alkyl chain, and gemini surfactants. The...

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Autores: Colomer Flores, Aurora, Pinazo Gassol, Aurora, Garcia Ramón, Maria Teresa, Mitjans Arnal, Montserrat, Vinardell Martínez-Hidalgo, Ma. Pilar, Infante Martínez-Pardo, Ma. Rosa, Martínez Ocaña, Verónica, Pérez Muñoz, Lourdes
Tipo de documento: artigo
Estado:Versión aceptada para publicación
Data de publicação:2012
País:España
Recursos:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
Repositório:Recercat. Dipósit de la Recerca de Catalunya
OAI Identifier:oai:recercat.cat:2445/32351
Acesso em linha:https://hdl.handle.net/2445/32351
Access Level:Acceso aberto
Palavra-chave:Toxicologia
Aminoàcids
Agents tensioactius
Concentració dels ions d'hidrogen
Toxicology
Amino acids
Surface active agents
Hydrogen-ion concentration
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spelling pH Sensitive surfactants from lysine: assessment of their cytotoxicity and environmental behaviorColomer Flores, AuroraPinazo Gassol, AuroraGarcia Ramón, Maria TeresaMitjans Arnal, MontserratVinardell Martínez-Hidalgo, Ma. PilarInfante Martínez-Pardo, Ma. RosaMartínez Ocaña, VerónicaPérez Muñoz, LourdesToxicologiaAminoàcidsAgents tensioactiusConcentració dels ions d'hidrogenToxicologyAmino acidsSurface active agentsHydrogen-ion concentrationThe toxicity and environmental behavior of new pH-sensitive surfactants from lysine are presented. Three different chemical structures are studied: surfactants with one amino acid and one alkyl chain, surfactants with two amino acids on the polar head and one alkyl chain, and gemini surfactants. The pH sensitivity of these compounds can be tuned by modifying their chemical structures. Cytotoxicity has been evaluated using erythrocytes and fibroblast cells. The toxic effects against these cells depend on the hydrophobicity of the molecules as well as their cationic charge density. The effect of hydrophobicity and cationic charge density on toxicity is different for each type of cells. For erythrocytes, the toxicity increases as hydrophobicity and charge density increases. Nevertheless, for fibroblasts cationic charge density affects cytotoxicity in the opposite way: the higher charge density, the lower the toxicity. The effect of the pH on hemolysis has been evaluated in detail. The aquatic toxicity was established using Daphnia magna. All surfactants yielded EC50 values considerably higher than that reported for cationic surfactants based on quaternary ammonium groups. Finally, their biodegradability was evaluated using the CO2 headspace test (ISO 14593). These lysine derivatives showed high levels of biodegradation under aerobic conditions and can be classified as"readily biodegradable compounds".American Chemical Society2012201320122012info:eu-repo/semantics/articleinfo:eu-repo/semantics/acceptedVersion13 p.application/pdfhttps://hdl.handle.net/2445/32351Articles publicats en revistes (Bioquímica i Fisiologia)reponame:Recercat. Dipósit de la Recerca de Catalunyainstname:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)InglésVersió postprint del document publicat a: http://dx.doi.org/10.1021/la203974fLangmuir, 2012, vol. 28, num. 14, p. 5900-5912http://dx.doi.org/10.1021/la203974f(c) American Chemical Society , 2012info:eu-repo/semantics/openAccessoai:recercat.cat:2445/323512026-05-29T05:05:01Z
dc.title.none.fl_str_mv pH Sensitive surfactants from lysine: assessment of their cytotoxicity and environmental behavior
title pH Sensitive surfactants from lysine: assessment of their cytotoxicity and environmental behavior
spellingShingle pH Sensitive surfactants from lysine: assessment of their cytotoxicity and environmental behavior
Colomer Flores, Aurora
Toxicologia
Aminoàcids
Agents tensioactius
Concentració dels ions d'hidrogen
Toxicology
Amino acids
Surface active agents
Hydrogen-ion concentration
title_short pH Sensitive surfactants from lysine: assessment of their cytotoxicity and environmental behavior
title_full pH Sensitive surfactants from lysine: assessment of their cytotoxicity and environmental behavior
title_fullStr pH Sensitive surfactants from lysine: assessment of their cytotoxicity and environmental behavior
title_full_unstemmed pH Sensitive surfactants from lysine: assessment of their cytotoxicity and environmental behavior
title_sort pH Sensitive surfactants from lysine: assessment of their cytotoxicity and environmental behavior
dc.creator.none.fl_str_mv Colomer Flores, Aurora
Pinazo Gassol, Aurora
Garcia Ramón, Maria Teresa
Mitjans Arnal, Montserrat
Vinardell Martínez-Hidalgo, Ma. Pilar
Infante Martínez-Pardo, Ma. Rosa
Martínez Ocaña, Verónica
Pérez Muñoz, Lourdes
author Colomer Flores, Aurora
author_facet Colomer Flores, Aurora
Pinazo Gassol, Aurora
Garcia Ramón, Maria Teresa
Mitjans Arnal, Montserrat
Vinardell Martínez-Hidalgo, Ma. Pilar
Infante Martínez-Pardo, Ma. Rosa
Martínez Ocaña, Verónica
Pérez Muñoz, Lourdes
author_role author
author2 Pinazo Gassol, Aurora
Garcia Ramón, Maria Teresa
Mitjans Arnal, Montserrat
Vinardell Martínez-Hidalgo, Ma. Pilar
Infante Martínez-Pardo, Ma. Rosa
Martínez Ocaña, Verónica
Pérez Muñoz, Lourdes
author2_role author
author
author
author
author
author
author
dc.subject.none.fl_str_mv Toxicologia
Aminoàcids
Agents tensioactius
Concentració dels ions d'hidrogen
Toxicology
Amino acids
Surface active agents
Hydrogen-ion concentration
topic Toxicologia
Aminoàcids
Agents tensioactius
Concentració dels ions d'hidrogen
Toxicology
Amino acids
Surface active agents
Hydrogen-ion concentration
description The toxicity and environmental behavior of new pH-sensitive surfactants from lysine are presented. Three different chemical structures are studied: surfactants with one amino acid and one alkyl chain, surfactants with two amino acids on the polar head and one alkyl chain, and gemini surfactants. The pH sensitivity of these compounds can be tuned by modifying their chemical structures. Cytotoxicity has been evaluated using erythrocytes and fibroblast cells. The toxic effects against these cells depend on the hydrophobicity of the molecules as well as their cationic charge density. The effect of hydrophobicity and cationic charge density on toxicity is different for each type of cells. For erythrocytes, the toxicity increases as hydrophobicity and charge density increases. Nevertheless, for fibroblasts cationic charge density affects cytotoxicity in the opposite way: the higher charge density, the lower the toxicity. The effect of the pH on hemolysis has been evaluated in detail. The aquatic toxicity was established using Daphnia magna. All surfactants yielded EC50 values considerably higher than that reported for cationic surfactants based on quaternary ammonium groups. Finally, their biodegradability was evaluated using the CO2 headspace test (ISO 14593). These lysine derivatives showed high levels of biodegradation under aerobic conditions and can be classified as"readily biodegradable compounds".
publishDate 2012
dc.date.none.fl_str_mv 2012
2012
2012
2013
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/acceptedVersion
format article
status_str acceptedVersion
dc.identifier.none.fl_str_mv https://hdl.handle.net/2445/32351
url https://hdl.handle.net/2445/32351
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv Versió postprint del document publicat a: http://dx.doi.org/10.1021/la203974f
Langmuir, 2012, vol. 28, num. 14, p. 5900-5912
http://dx.doi.org/10.1021/la203974f
dc.rights.none.fl_str_mv (c) American Chemical Society , 2012
info:eu-repo/semantics/openAccess
rights_invalid_str_mv (c) American Chemical Society , 2012
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv 13 p.
application/pdf
dc.publisher.none.fl_str_mv American Chemical Society
publisher.none.fl_str_mv American Chemical Society
dc.source.none.fl_str_mv Articles publicats en revistes (Bioquímica i Fisiologia)
reponame:Recercat. Dipósit de la Recerca de Catalunya
instname:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
instname_str Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
reponame_str Recercat. Dipósit de la Recerca de Catalunya
collection Recercat. Dipósit de la Recerca de Catalunya
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15,811543

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