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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Detalhes bibliográficos
Autores: Colomer, Aurora, Pinazo Gassol, Aurora, García Ramón, María Teresa, Mitjans, Montserrat, Vinardell, M. Pilar, Infante, María Rosa, Martínez, Verónica, Pérez, Lourdes
Tipo de documento: artigo
Estado:Versión aceptada para publicación
Data de publicação:2012
País:España
Recursos:Consejo Superior de Investigaciones Científicas (CSIC)
Repositório:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/332741
Acesso em linha:http://hdl.handle.net/10261/332741
https://api.elsevier.com/content/abstract/scopus_id/84859595771
Access Level:Acceso aberto
Palavra-chave:Hydrophobicity
Monomers
Peptides and proteins
Surfactants
Toxicity
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spelling pH-Sensitive surfactants from lysine: assessment of their cytotoxicity and environmental behaviorColomer, AuroraPinazo Gassol, AuroraGarcía Ramón, María TeresaMitjans, MontserratVinardell, M. PilarInfante, María RosaMartínez, VerónicaPérez, LourdesHydrophobicityMonomersPeptides and proteinsSurfactantsToxicityThe 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 EC(50) values considerably higher than that reported for cationic surfactants based on quaternary ammonium groups. Finally, their biodegradability was evaluated using the CO(2) headspace test (ISO 14593). These lysine derivatives showed high levels of biodegradation under aerobic conditions and can be classified as "readily biodegradable compounds".Financial support from Spanish Plan National I+D+I CTQ2009-14151-C02-01, CTQ2009-14151-C02-02, CTQ2010-14897, and AGAUR 2009 SRG 246.Peer reviewedAmerican Chemical SocietyComisión Asesora de Investigación Científica y Técnica, CAICYT (España)Generalitat de CatalunyaConsejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]202320232012info:eu-repo/semantics/articlehttp://purl.org/coar/resource_type/c_6501Postprintinfo:eu-repo/semantics/acceptedVersionapplication/pdfhttp://hdl.handle.net/10261/332741https://api.elsevier.com/content/abstract/scopus_id/84859595771reponame:DIGITAL.CSIC. Repositorio Institucional del CSICinstname:Consejo Superior de Investigaciones Científicas (CSIC)Ingléshttps://doi.org/10.1021/la203974fSíinfo:eu-repo/semantics/openAccessoai:digital.csic.es:10261/3327412026-05-22T06:33:51Z
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, Aurora
Hydrophobicity
Monomers
Peptides and proteins
Surfactants
Toxicity
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, Aurora
Pinazo Gassol, Aurora
García Ramón, María Teresa
Mitjans, Montserrat
Vinardell, M. Pilar
Infante, María Rosa
Martínez, Verónica
Pérez, Lourdes
author Colomer, Aurora
author_facet Colomer, Aurora
Pinazo Gassol, Aurora
García Ramón, María Teresa
Mitjans, Montserrat
Vinardell, M. Pilar
Infante, María Rosa
Martínez, Verónica
Pérez, Lourdes
author_role author
author2 Pinazo Gassol, Aurora
García Ramón, María Teresa
Mitjans, Montserrat
Vinardell, M. Pilar
Infante, María Rosa
Martínez, Verónica
Pérez, Lourdes
author2_role author
author
author
author
author
author
author
dc.contributor.none.fl_str_mv Comisión Asesora de Investigación Científica y Técnica, CAICYT (España)
Generalitat de Catalunya
Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]
dc.subject.none.fl_str_mv Hydrophobicity
Monomers
Peptides and proteins
Surfactants
Toxicity
topic Hydrophobicity
Monomers
Peptides and proteins
Surfactants
Toxicity
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 EC(50) values considerably higher than that reported for cationic surfactants based on quaternary ammonium groups. Finally, their biodegradability was evaluated using the CO(2) 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
2023
2023
dc.type.none.fl_str_mv info:eu-repo/semantics/article
http://purl.org/coar/resource_type/c_6501
Postprint
info:eu-repo/semantics/acceptedVersion
format article
status_str acceptedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/10261/332741
https://api.elsevier.com/content/abstract/scopus_id/84859595771
url http://hdl.handle.net/10261/332741
https://api.elsevier.com/content/abstract/scopus_id/84859595771
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv https://doi.org/10.1021/la203974f
Sí
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv 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 reponame:DIGITAL.CSIC. Repositorio Institucional del CSIC
instname:Consejo Superior de Investigaciones Científicas (CSIC)
instname_str Consejo Superior de Investigaciones Científicas (CSIC)
reponame_str DIGITAL.CSIC. Repositorio Institucional del CSIC
collection DIGITAL.CSIC. Repositorio Institucional del CSIC
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15.811543

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