[Dataset] Phenylalanine and Tryptophan-Based Surfactants as New Antibacterial Agents: Characterization, Self-Aggregation Properties, and DPPC/Surfactants Vesicles Formulation

Cationic surfactants based on phenylalanine (CnPC3NH3Cl) and tryptophan (CnTC3NH3Cl) were synthesized using renewable raw materials as starting compounds and a green synthetic procedure. The synthesis, acid-base equilibrium, aggregation properties, and antibacterial activity were investigated. Condu...

Descripción completa

Detalles Bibliográficos
Autores: Hafidi, Zakaria, Pérez, Lourdes, El Achouri, Mohammed, Pons Pons, Ramon
Tipo de recurso: conjunto de datos
Fecha de publicación:2023
País:España
Institución:Consejo Superior de Investigaciones Científicas (CSIC)
Repositorio:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/383943
Acceso en línea:http://hdl.handle.net/10261/383943
https://digital.csic.es/handle/10261/332508
Access Level:acceso abierto
Palabra clave:Surfactants
SAXS
Antimicrobial activity
Phenylalanine tryptophan
Vesicles
http://metadata.un.org/sdg/3
Ensure healthy lives and promote well-being for all at all ages
id ES_3bbb5bbe06ddfd660a95d3f372eeac2d
oai_identifier_str oai:digital.csic.es:10261/383943
network_acronym_str ES
network_name_str España
repository_id_str
spelling [Dataset] Phenylalanine and Tryptophan-Based Surfactants as New Antibacterial Agents: Characterization, Self-Aggregation Properties, and DPPC/Surfactants Vesicles FormulationHafidi, ZakariaPérez, LourdesEl Achouri, MohammedPons Pons, RamonSurfactantsSAXSAntimicrobial activityPhenylalanine tryptophanVesicleshttp://metadata.un.org/sdg/3Ensure healthy lives and promote well-being for all at all agesCationic surfactants based on phenylalanine (CnPC3NH3Cl) and tryptophan (CnTC3NH3Cl) were synthesized using renewable raw materials as starting compounds and a green synthetic procedure. The synthesis, acid-base equilibrium, aggregation properties, and antibacterial activity were investigated. Conductivity and fluorescence were used to establish critical micelle concentrations. Micellization of CnPC3NH3Cl and CnTC3NH3Cl occurred in the ranges of 0.42-16.2 mM and 0.29-4.6 mM, respectively. Since those surfactants have some acidic character, the apparent pKa was determined through titrations, observing increasing acidity with increasing chain length and being slightly more acidic with the phenylalanine than the tryptophan derivatives. Both families showed promising antibacterial efficacy against eight different bacterial strains. Molecular docking studies against the enzyme peptidoglycan glycosyltransferase (PDB ID:2OQO) were used to investigate the potential binding mechanism of target surfactant molecules. According to small angle X-ray scattering (SAXS) results, the surfactants incorporate into DPPC (Dipalmitoyl Phosphatidyl Choline) bilayers without strong perturbation up to high surfactant concentration. Some of the C12TC3NH3Cl/DPPC formulations (40%/60% and 20%/80% molar ratios) exhibited good antibacterial activity, while the others were not effective against the tested bacteria. The strong affinity between DPPC and surfactant molecules, as determined by the DFT (density functional theory) method, could be one of the reasons for the loss of antibacterial activity of these cationic surfactants when they are incorporated in vesicles.Peer reviewedMultidisciplinary Digital Publishing Institute0000-0001-8554-51890000-0002-3696-021X0000-0003-4273-9084Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]202520252023info:eu-repo/semantics/datasethttp://purl.org/coar/resource_type/c_ddb1http://hdl.handle.net/10261/383943https://digital.csic.es/handle/10261/332508reponame:DIGITAL.CSIC. Repositorio Institucional del CSICinstname:Consejo Superior de Investigaciones Científicas (CSIC)InglésPharmaceuticsPhenylalanine and Tryptophan-Based Surfactants as New Antibacterial Agents: Characterization, Self-Aggregation Properties, and DPPC/Surfactants Vesicles FormulationSíinfo:eu-repo/semantics/openAccessoai:digital.csic.es:10261/3839432026-05-22T06:33:51Z
dc.title.none.fl_str_mv [Dataset] Phenylalanine and Tryptophan-Based Surfactants as New Antibacterial Agents: Characterization, Self-Aggregation Properties, and DPPC/Surfactants Vesicles Formulation
title [Dataset] Phenylalanine and Tryptophan-Based Surfactants as New Antibacterial Agents: Characterization, Self-Aggregation Properties, and DPPC/Surfactants Vesicles Formulation
spellingShingle [Dataset] Phenylalanine and Tryptophan-Based Surfactants as New Antibacterial Agents: Characterization, Self-Aggregation Properties, and DPPC/Surfactants Vesicles Formulation
Hafidi, Zakaria
Surfactants
SAXS
Antimicrobial activity
Phenylalanine tryptophan
Vesicles
http://metadata.un.org/sdg/3
Ensure healthy lives and promote well-being for all at all ages
title_short [Dataset] Phenylalanine and Tryptophan-Based Surfactants as New Antibacterial Agents: Characterization, Self-Aggregation Properties, and DPPC/Surfactants Vesicles Formulation
title_full [Dataset] Phenylalanine and Tryptophan-Based Surfactants as New Antibacterial Agents: Characterization, Self-Aggregation Properties, and DPPC/Surfactants Vesicles Formulation
title_fullStr [Dataset] Phenylalanine and Tryptophan-Based Surfactants as New Antibacterial Agents: Characterization, Self-Aggregation Properties, and DPPC/Surfactants Vesicles Formulation
title_full_unstemmed [Dataset] Phenylalanine and Tryptophan-Based Surfactants as New Antibacterial Agents: Characterization, Self-Aggregation Properties, and DPPC/Surfactants Vesicles Formulation
title_sort [Dataset] Phenylalanine and Tryptophan-Based Surfactants as New Antibacterial Agents: Characterization, Self-Aggregation Properties, and DPPC/Surfactants Vesicles Formulation
dc.creator.none.fl_str_mv Hafidi, Zakaria
Pérez, Lourdes
El Achouri, Mohammed
Pons Pons, Ramon
author Hafidi, Zakaria
author_facet Hafidi, Zakaria
Pérez, Lourdes
El Achouri, Mohammed
Pons Pons, Ramon
author_role author
author2 Pérez, Lourdes
El Achouri, Mohammed
Pons Pons, Ramon
author2_role author
author
author
dc.contributor.none.fl_str_mv 0000-0001-8554-5189
0000-0002-3696-021X
0000-0003-4273-9084
Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]
dc.subject.none.fl_str_mv Surfactants
SAXS
Antimicrobial activity
Phenylalanine tryptophan
Vesicles
http://metadata.un.org/sdg/3
Ensure healthy lives and promote well-being for all at all ages
topic Surfactants
SAXS
Antimicrobial activity
Phenylalanine tryptophan
Vesicles
http://metadata.un.org/sdg/3
Ensure healthy lives and promote well-being for all at all ages
description Cationic surfactants based on phenylalanine (CnPC3NH3Cl) and tryptophan (CnTC3NH3Cl) were synthesized using renewable raw materials as starting compounds and a green synthetic procedure. The synthesis, acid-base equilibrium, aggregation properties, and antibacterial activity were investigated. Conductivity and fluorescence were used to establish critical micelle concentrations. Micellization of CnPC3NH3Cl and CnTC3NH3Cl occurred in the ranges of 0.42-16.2 mM and 0.29-4.6 mM, respectively. Since those surfactants have some acidic character, the apparent pKa was determined through titrations, observing increasing acidity with increasing chain length and being slightly more acidic with the phenylalanine than the tryptophan derivatives. Both families showed promising antibacterial efficacy against eight different bacterial strains. Molecular docking studies against the enzyme peptidoglycan glycosyltransferase (PDB ID:2OQO) were used to investigate the potential binding mechanism of target surfactant molecules. According to small angle X-ray scattering (SAXS) results, the surfactants incorporate into DPPC (Dipalmitoyl Phosphatidyl Choline) bilayers without strong perturbation up to high surfactant concentration. Some of the C12TC3NH3Cl/DPPC formulations (40%/60% and 20%/80% molar ratios) exhibited good antibacterial activity, while the others were not effective against the tested bacteria. The strong affinity between DPPC and surfactant molecules, as determined by the DFT (density functional theory) method, could be one of the reasons for the loss of antibacterial activity of these cationic surfactants when they are incorporated in vesicles.
publishDate 2023
dc.date.none.fl_str_mv 2023
2025
2025
dc.type.none.fl_str_mv info:eu-repo/semantics/dataset
http://purl.org/coar/resource_type/c_ddb1
format dataset
dc.identifier.none.fl_str_mv http://hdl.handle.net/10261/383943
https://digital.csic.es/handle/10261/332508
url http://hdl.handle.net/10261/383943
https://digital.csic.es/handle/10261/332508
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv Pharmaceutics
Phenylalanine and Tryptophan-Based Surfactants as New Antibacterial Agents: Characterization, Self-Aggregation Properties, and DPPC/Surfactants Vesicles Formulation
Sí
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.publisher.none.fl_str_mv Multidisciplinary Digital Publishing Institute
publisher.none.fl_str_mv Multidisciplinary Digital Publishing Institute
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
_version_ 1869406324856455168
score 15,811543

Similares en LA Referencia