Biocatalytic synthesis, antimicrobial properties and toxicity studies of arginine derivative surfactants

Autores
Fait, María Elisa; Garrote, Graciela Liliana; Clapés, Pere; Tanco, Sebastian; Lorenzo, Julia; Morcelle del Valle, Susana Raquel
Año de publicación
2015
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Abstract Two novel arginine-based cationic surfactants were synthesized using as biocatalyst papain, an endopeptidase from Carica papaya latex, adsorbed onto polyamide. The classical substrate N α-benzoyl-arginine ethyl ester hydrochloride for the determination of cysteine and serine proteases activity was used as the arginine donor, whereas decyl- and dodecylamine were used as nucleophiles for the condensation reaction. Yields higher than 90 and 80 % were achieved for the synthesis of N α-benzoyl-arginine decyl amide (Bz-Arg-NHC10) and N α-benzoyl-arginine dodecyl amide (Bz-Arg-NHC12), respectively. The purification process was developed in order to make it more sustainable, by using water and ethanol as the main separation solvents in a single cationic exchange chromatographic separation step. Bz-Arg-NHC10 and Bz-Arg-NHC12 proved antimicrobial activity against both Gram-positive and Gram-negative bacteria, revealing their potential use as effective disinfectants as they reduced 99 % the initial bacterial population after only 1 h of contact. The cytotoxic effect towards different cell types of both arginine derivatives was also measured. Bz-Arg-NHCn demonstrated lower haemolytic activity and were less eye-irritating than the commercial cationic surfactant cetrimide. A similar trend could also be observed when cytotoxicity was tested on hepatocytes and fibroblast cell lines: both arginine derivatives were less toxic than cetrimide. All these properties would make the two novel arginine compounds a promising alternative to commercial cationic surfactants, especially for their use as additives in topical formulations.
Fil: Fait, María Elisa. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Ciencias Biológicas; Argentina
Fil: Garrote, Graciela Liliana. Provincia de Buenos Aires. Gobernación. Comisión de Investigaciones Científicas. Centro de Investigación y Desarrollo en Criotecnología de Alimentos. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Criotecnología de Alimentos. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Criotecnología de Alimentos; Argentina
Fil: Clapés, Pere. Consejo Superior de Investigaciones Científicas; España
Fil: Tanco, Sebastian. Universitat Autònoma de Barcelona; España. Department of Medical Protein Research; Bélgica. University of Ghent; Bélgica
Fil: Lorenzo, Julia. Universitat Autònoma de Barcelona; España
Fil: Morcelle del Valle, Susana Raquel. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Ciencias Biológicas; Argentina
Materia
Antimicrobial Activity
Arginine-Based Surfactants
Biocatalysis
Cytotoxic Effect
Papain
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/49210
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/49210
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Biocatalytic synthesis, antimicrobial properties and toxicity studies of arginine derivative surfactantsFait, María ElisaGarrote, Graciela LilianaClapés, PereTanco, SebastianLorenzo, JuliaMorcelle del Valle, Susana RaquelAntimicrobial ActivityArginine-Based SurfactantsBiocatalysisCytotoxic EffectPapainhttps://purl.org/becyt/ford/2.9https://purl.org/becyt/ford/2Abstract Two novel arginine-based cationic surfactants were synthesized using as biocatalyst papain, an endopeptidase from Carica papaya latex, adsorbed onto polyamide. The classical substrate N α-benzoyl-arginine ethyl ester hydrochloride for the determination of cysteine and serine proteases activity was used as the arginine donor, whereas decyl- and dodecylamine were used as nucleophiles for the condensation reaction. Yields higher than 90 and 80 % were achieved for the synthesis of N α-benzoyl-arginine decyl amide (Bz-Arg-NHC10) and N α-benzoyl-arginine dodecyl amide (Bz-Arg-NHC12), respectively. The purification process was developed in order to make it more sustainable, by using water and ethanol as the main separation solvents in a single cationic exchange chromatographic separation step. Bz-Arg-NHC10 and Bz-Arg-NHC12 proved antimicrobial activity against both Gram-positive and Gram-negative bacteria, revealing their potential use as effective disinfectants as they reduced 99 % the initial bacterial population after only 1 h of contact. The cytotoxic effect towards different cell types of both arginine derivatives was also measured. Bz-Arg-NHCn demonstrated lower haemolytic activity and were less eye-irritating than the commercial cationic surfactant cetrimide. A similar trend could also be observed when cytotoxicity was tested on hepatocytes and fibroblast cell lines: both arginine derivatives were less toxic than cetrimide. All these properties would make the two novel arginine compounds a promising alternative to commercial cationic surfactants, especially for their use as additives in topical formulations.Fil: Fait, María Elisa. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Ciencias Biológicas; ArgentinaFil: Garrote, Graciela Liliana. Provincia de Buenos Aires. Gobernación. Comisión de Investigaciones Científicas. Centro de Investigación y Desarrollo en Criotecnología de Alimentos. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Criotecnología de Alimentos. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Criotecnología de Alimentos; ArgentinaFil: Clapés, Pere. Consejo Superior de Investigaciones Científicas; EspañaFil: Tanco, Sebastian. Universitat Autònoma de Barcelona; España. Department of Medical Protein Research; Bélgica. University of Ghent; BélgicaFil: Lorenzo, Julia. Universitat Autònoma de Barcelona; EspañaFil: Morcelle del Valle, Susana Raquel. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Ciencias Biológicas; ArgentinaSpringer2015-07info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/49210Fait, María Elisa; Garrote, Graciela Liliana; Clapés, Pere; Tanco, Sebastian; Lorenzo, Julia; et al.; Biocatalytic synthesis, antimicrobial properties and toxicity studies of arginine derivative surfactants; Springer; Amino Acids; 47; 7; 7-2015; 1465-14770939-4451CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1007/s00726-015-1979-0info:eu-repo/semantics/altIdentifier/url/https://link.springer.com/article/10.1007%2Fs00726-015-1979-0info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:34:28Zoai:ri.conicet.gov.ar:11336/49210instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-09-29 10:34:28.431CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Biocatalytic synthesis, antimicrobial properties and toxicity studies of arginine derivative surfactants
title Biocatalytic synthesis, antimicrobial properties and toxicity studies of arginine derivative surfactants
spellingShingle Biocatalytic synthesis, antimicrobial properties and toxicity studies of arginine derivative surfactants
Fait, María Elisa
Antimicrobial Activity
Arginine-Based Surfactants
Biocatalysis
Cytotoxic Effect
Papain
title_short Biocatalytic synthesis, antimicrobial properties and toxicity studies of arginine derivative surfactants
title_full Biocatalytic synthesis, antimicrobial properties and toxicity studies of arginine derivative surfactants
title_fullStr Biocatalytic synthesis, antimicrobial properties and toxicity studies of arginine derivative surfactants
title_full_unstemmed Biocatalytic synthesis, antimicrobial properties and toxicity studies of arginine derivative surfactants
title_sort Biocatalytic synthesis, antimicrobial properties and toxicity studies of arginine derivative surfactants
dc.creator.none.fl_str_mv Fait, María Elisa
Garrote, Graciela Liliana
Clapés, Pere
Tanco, Sebastian
Lorenzo, Julia
Morcelle del Valle, Susana Raquel
author Fait, María Elisa
author_facet Fait, María Elisa
Garrote, Graciela Liliana
Clapés, Pere
Tanco, Sebastian
Lorenzo, Julia
Morcelle del Valle, Susana Raquel
author_role author
author2 Garrote, Graciela Liliana
Clapés, Pere
Tanco, Sebastian
Lorenzo, Julia
Morcelle del Valle, Susana Raquel
author2_role author
author
author
author
author
dc.subject.none.fl_str_mv Antimicrobial Activity
Arginine-Based Surfactants
Biocatalysis
Cytotoxic Effect
Papain
topic Antimicrobial Activity
Arginine-Based Surfactants
Biocatalysis
Cytotoxic Effect
Papain
purl_subject.fl_str_mv https://purl.org/becyt/ford/2.9
https://purl.org/becyt/ford/2
dc.description.none.fl_txt_mv Abstract Two novel arginine-based cationic surfactants were synthesized using as biocatalyst papain, an endopeptidase from Carica papaya latex, adsorbed onto polyamide. The classical substrate N α-benzoyl-arginine ethyl ester hydrochloride for the determination of cysteine and serine proteases activity was used as the arginine donor, whereas decyl- and dodecylamine were used as nucleophiles for the condensation reaction. Yields higher than 90 and 80 % were achieved for the synthesis of N α-benzoyl-arginine decyl amide (Bz-Arg-NHC10) and N α-benzoyl-arginine dodecyl amide (Bz-Arg-NHC12), respectively. The purification process was developed in order to make it more sustainable, by using water and ethanol as the main separation solvents in a single cationic exchange chromatographic separation step. Bz-Arg-NHC10 and Bz-Arg-NHC12 proved antimicrobial activity against both Gram-positive and Gram-negative bacteria, revealing their potential use as effective disinfectants as they reduced 99 % the initial bacterial population after only 1 h of contact. The cytotoxic effect towards different cell types of both arginine derivatives was also measured. Bz-Arg-NHCn demonstrated lower haemolytic activity and were less eye-irritating than the commercial cationic surfactant cetrimide. A similar trend could also be observed when cytotoxicity was tested on hepatocytes and fibroblast cell lines: both arginine derivatives were less toxic than cetrimide. All these properties would make the two novel arginine compounds a promising alternative to commercial cationic surfactants, especially for their use as additives in topical formulations.
Fil: Fait, María Elisa. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Ciencias Biológicas; Argentina
Fil: Garrote, Graciela Liliana. Provincia de Buenos Aires. Gobernación. Comisión de Investigaciones Científicas. Centro de Investigación y Desarrollo en Criotecnología de Alimentos. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Criotecnología de Alimentos. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Criotecnología de Alimentos; Argentina
Fil: Clapés, Pere. Consejo Superior de Investigaciones Científicas; España
Fil: Tanco, Sebastian. Universitat Autònoma de Barcelona; España. Department of Medical Protein Research; Bélgica. University of Ghent; Bélgica
Fil: Lorenzo, Julia. Universitat Autònoma de Barcelona; España
Fil: Morcelle del Valle, Susana Raquel. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Ciencias Biológicas; Argentina
description Abstract Two novel arginine-based cationic surfactants were synthesized using as biocatalyst papain, an endopeptidase from Carica papaya latex, adsorbed onto polyamide. The classical substrate N α-benzoyl-arginine ethyl ester hydrochloride for the determination of cysteine and serine proteases activity was used as the arginine donor, whereas decyl- and dodecylamine were used as nucleophiles for the condensation reaction. Yields higher than 90 and 80 % were achieved for the synthesis of N α-benzoyl-arginine decyl amide (Bz-Arg-NHC10) and N α-benzoyl-arginine dodecyl amide (Bz-Arg-NHC12), respectively. The purification process was developed in order to make it more sustainable, by using water and ethanol as the main separation solvents in a single cationic exchange chromatographic separation step. Bz-Arg-NHC10 and Bz-Arg-NHC12 proved antimicrobial activity against both Gram-positive and Gram-negative bacteria, revealing their potential use as effective disinfectants as they reduced 99 % the initial bacterial population after only 1 h of contact. The cytotoxic effect towards different cell types of both arginine derivatives was also measured. Bz-Arg-NHCn demonstrated lower haemolytic activity and were less eye-irritating than the commercial cationic surfactant cetrimide. A similar trend could also be observed when cytotoxicity was tested on hepatocytes and fibroblast cell lines: both arginine derivatives were less toxic than cetrimide. All these properties would make the two novel arginine compounds a promising alternative to commercial cationic surfactants, especially for their use as additives in topical formulations.
publishDate 2015
dc.date.none.fl_str_mv 2015-07
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/49210
Fait, María Elisa; Garrote, Graciela Liliana; Clapés, Pere; Tanco, Sebastian; Lorenzo, Julia; et al.; Biocatalytic synthesis, antimicrobial properties and toxicity studies of arginine derivative surfactants; Springer; Amino Acids; 47; 7; 7-2015; 1465-1477
0939-4451
CONICET Digital
CONICET
url http://hdl.handle.net/11336/49210
identifier_str_mv Fait, María Elisa; Garrote, Graciela Liliana; Clapés, Pere; Tanco, Sebastian; Lorenzo, Julia; et al.; Biocatalytic synthesis, antimicrobial properties and toxicity studies of arginine derivative surfactants; Springer; Amino Acids; 47; 7; 7-2015; 1465-1477
0939-4451
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1007/s00726-015-1979-0
info:eu-repo/semantics/altIdentifier/url/https://link.springer.com/article/10.1007%2Fs00726-015-1979-0
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Springer
publisher.none.fl_str_mv Springer
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
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score 13.070432

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