A Raman, Sers and UV-Circular dichroism spectroscopic study of N-acetyl-L-Cisteine in aqueous solutions

Autores
Cobos Picot, Rafael Alejandro; Puiatti, Marcelo; Ben Altabef, Aida; Rubira, R. J.; Tuttolomondo, María Eugenia
Año de publicación
2019
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The aim of this work is to evaluate the vibrational and structural properties of N-acetyl-L-cysteine (NAC),and its molecular structure and electronic properties in relation to the action of thiol and amine groupsat different pH. Raman and Surface Enhanced Raman Spectroscopy (SERS) spectra were measured inaqueous solution. The influence of an aqueous environment on the NAC spectra was simulated bymeans of an implicit (polarizable continuum model) method. SERS spectra indicate that the S atom isinteracting with the surface through the sulfur atom. One of the consequences of the interaction withthe surface is the deprotonation of the SH group, as revealed by the disappearance of the n(S?H) band.The calculations performed for the Ag?NAC complex confirm the experimental data obtained by SERS,where the S?Ag interaction is the most important. These results are very interesting when one canformulate the drug feasibility of NAC using silver nanoparticles as a carrier. Raman spectra were measuredto compare the behavior of different functional groups in the molecule, both in the solid phase and inaqueous solution at different pH. Apparent ionization constants (pK0 values) for the S?H group at highionic strengths were calculated from the intensity of the 2580 cm1 frequency as a function of pH. UVand circular dichroism spectra were also measured in aqueous solution at different pH. Finally, the studywas completed with natural bond orbital (NBO) analysis to determine the presence of hyper-conjugativeinteractions. It is important to observe the behavior of the C2?N bond with the delocalization effect; asthe pH increases the hyperconjugative interaction of this bond decreases in the same way as in the caseof nCN. The way in which the LP pO1 - s*C2?N interaction and nCN decrease is an inverse reflectionof the fractional ionization aSH.
Fil: Cobos Picot, Rafael Alejandro. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Química del Noroeste. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química del Noroeste; Argentina
Fil: Puiatti, Marcelo. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
Fil: Ben Altabef, Aida. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Química del Noroeste. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química del Noroeste; Argentina
Fil: Rubira, R. J.. Universidade Estadual Paulista Julio de Mesquita Filho. Faculdade de Engenharia.; Brasil
Fil: Tuttolomondo, María Eugenia. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Química del Noroeste. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química del Noroeste; Argentina
Materia
RAMAN
SERS
UV-CIRCULAR DICHROISM
N-ACETYL
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:11336/119053
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/119053
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling A Raman, Sers and UV-Circular dichroism spectroscopic study of N-acetyl-L-Cisteine in aqueous solutionsCobos Picot, Rafael AlejandroPuiatti, MarceloBen Altabef, AidaRubira, R. J.Tuttolomondo, María EugeniaRAMANSERSUV-CIRCULAR DICHROISMN-ACETYLhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The aim of this work is to evaluate the vibrational and structural properties of N-acetyl-L-cysteine (NAC),and its molecular structure and electronic properties in relation to the action of thiol and amine groupsat different pH. Raman and Surface Enhanced Raman Spectroscopy (SERS) spectra were measured inaqueous solution. The influence of an aqueous environment on the NAC spectra was simulated bymeans of an implicit (polarizable continuum model) method. SERS spectra indicate that the S atom isinteracting with the surface through the sulfur atom. One of the consequences of the interaction withthe surface is the deprotonation of the SH group, as revealed by the disappearance of the n(S?H) band.The calculations performed for the Ag?NAC complex confirm the experimental data obtained by SERS,where the S?Ag interaction is the most important. These results are very interesting when one canformulate the drug feasibility of NAC using silver nanoparticles as a carrier. Raman spectra were measuredto compare the behavior of different functional groups in the molecule, both in the solid phase and inaqueous solution at different pH. Apparent ionization constants (pK0 values) for the S?H group at highionic strengths were calculated from the intensity of the 2580 cm1 frequency as a function of pH. UVand circular dichroism spectra were also measured in aqueous solution at different pH. Finally, the studywas completed with natural bond orbital (NBO) analysis to determine the presence of hyper-conjugativeinteractions. It is important to observe the behavior of the C2?N bond with the delocalization effect; asthe pH increases the hyperconjugative interaction of this bond decreases in the same way as in the caseof nCN. The way in which the LP pO1 - s*C2?N interaction and nCN decrease is an inverse reflectionof the fractional ionization aSH.Fil: Cobos Picot, Rafael Alejandro. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Química del Noroeste. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química del Noroeste; ArgentinaFil: Puiatti, Marcelo. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; ArgentinaFil: Ben Altabef, Aida. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Química del Noroeste. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química del Noroeste; ArgentinaFil: Rubira, R. J.. Universidade Estadual Paulista Julio de Mesquita Filho. Faculdade de Engenharia.; BrasilFil: Tuttolomondo, María Eugenia. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Química del Noroeste. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química del Noroeste; ArgentinaRoyal Society of Chemistry2019-08info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/119053Cobos Picot, Rafael Alejandro; Puiatti, Marcelo; Ben Altabef, Aida; Rubira, R. J.; Tuttolomondo, María Eugenia; A Raman, Sers and UV-Circular dichroism spectroscopic study of N-acetyl-L-Cisteine in aqueous solutions; Royal Society of Chemistry; New Journal of Chemistry; 43; 38; 8-2019; 15201-152121144-0546CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1039/c9nj02427ainfo:eu-repo/semantics/altIdentifier/url/https://pubs.rsc.org/en/content/articlelanding/2019/NJ/C9NJ02427A#!divAbstractinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-10T13:09:15Zoai:ri.conicet.gov.ar:11336/119053instacron: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:34982025-09-10 13:09:15.389CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv A Raman, Sers and UV-Circular dichroism spectroscopic study of N-acetyl-L-Cisteine in aqueous solutions
title A Raman, Sers and UV-Circular dichroism spectroscopic study of N-acetyl-L-Cisteine in aqueous solutions
spellingShingle A Raman, Sers and UV-Circular dichroism spectroscopic study of N-acetyl-L-Cisteine in aqueous solutions
Cobos Picot, Rafael Alejandro
RAMAN
SERS
UV-CIRCULAR DICHROISM
N-ACETYL
title_short A Raman, Sers and UV-Circular dichroism spectroscopic study of N-acetyl-L-Cisteine in aqueous solutions
title_full A Raman, Sers and UV-Circular dichroism spectroscopic study of N-acetyl-L-Cisteine in aqueous solutions
title_fullStr A Raman, Sers and UV-Circular dichroism spectroscopic study of N-acetyl-L-Cisteine in aqueous solutions
title_full_unstemmed A Raman, Sers and UV-Circular dichroism spectroscopic study of N-acetyl-L-Cisteine in aqueous solutions
title_sort A Raman, Sers and UV-Circular dichroism spectroscopic study of N-acetyl-L-Cisteine in aqueous solutions
dc.creator.none.fl_str_mv Cobos Picot, Rafael Alejandro
Puiatti, Marcelo
Ben Altabef, Aida
Rubira, R. J.
Tuttolomondo, María Eugenia
author Cobos Picot, Rafael Alejandro
author_facet Cobos Picot, Rafael Alejandro
Puiatti, Marcelo
Ben Altabef, Aida
Rubira, R. J.
Tuttolomondo, María Eugenia
author_role author
author2 Puiatti, Marcelo
Ben Altabef, Aida
Rubira, R. J.
Tuttolomondo, María Eugenia
author2_role author
author
author
author
dc.subject.none.fl_str_mv RAMAN
SERS
UV-CIRCULAR DICHROISM
N-ACETYL
topic RAMAN
SERS
UV-CIRCULAR DICHROISM
N-ACETYL
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv The aim of this work is to evaluate the vibrational and structural properties of N-acetyl-L-cysteine (NAC),and its molecular structure and electronic properties in relation to the action of thiol and amine groupsat different pH. Raman and Surface Enhanced Raman Spectroscopy (SERS) spectra were measured inaqueous solution. The influence of an aqueous environment on the NAC spectra was simulated bymeans of an implicit (polarizable continuum model) method. SERS spectra indicate that the S atom isinteracting with the surface through the sulfur atom. One of the consequences of the interaction withthe surface is the deprotonation of the SH group, as revealed by the disappearance of the n(S?H) band.The calculations performed for the Ag?NAC complex confirm the experimental data obtained by SERS,where the S?Ag interaction is the most important. These results are very interesting when one canformulate the drug feasibility of NAC using silver nanoparticles as a carrier. Raman spectra were measuredto compare the behavior of different functional groups in the molecule, both in the solid phase and inaqueous solution at different pH. Apparent ionization constants (pK0 values) for the S?H group at highionic strengths were calculated from the intensity of the 2580 cm1 frequency as a function of pH. UVand circular dichroism spectra were also measured in aqueous solution at different pH. Finally, the studywas completed with natural bond orbital (NBO) analysis to determine the presence of hyper-conjugativeinteractions. It is important to observe the behavior of the C2?N bond with the delocalization effect; asthe pH increases the hyperconjugative interaction of this bond decreases in the same way as in the caseof nCN. The way in which the LP pO1 - s*C2?N interaction and nCN decrease is an inverse reflectionof the fractional ionization aSH.
Fil: Cobos Picot, Rafael Alejandro. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Química del Noroeste. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química del Noroeste; Argentina
Fil: Puiatti, Marcelo. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
Fil: Ben Altabef, Aida. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Química del Noroeste. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química del Noroeste; Argentina
Fil: Rubira, R. J.. Universidade Estadual Paulista Julio de Mesquita Filho. Faculdade de Engenharia.; Brasil
Fil: Tuttolomondo, María Eugenia. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Química del Noroeste. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química del Noroeste; Argentina
description The aim of this work is to evaluate the vibrational and structural properties of N-acetyl-L-cysteine (NAC),and its molecular structure and electronic properties in relation to the action of thiol and amine groupsat different pH. Raman and Surface Enhanced Raman Spectroscopy (SERS) spectra were measured inaqueous solution. The influence of an aqueous environment on the NAC spectra was simulated bymeans of an implicit (polarizable continuum model) method. SERS spectra indicate that the S atom isinteracting with the surface through the sulfur atom. One of the consequences of the interaction withthe surface is the deprotonation of the SH group, as revealed by the disappearance of the n(S?H) band.The calculations performed for the Ag?NAC complex confirm the experimental data obtained by SERS,where the S?Ag interaction is the most important. These results are very interesting when one canformulate the drug feasibility of NAC using silver nanoparticles as a carrier. Raman spectra were measuredto compare the behavior of different functional groups in the molecule, both in the solid phase and inaqueous solution at different pH. Apparent ionization constants (pK0 values) for the S?H group at highionic strengths were calculated from the intensity of the 2580 cm1 frequency as a function of pH. UVand circular dichroism spectra were also measured in aqueous solution at different pH. Finally, the studywas completed with natural bond orbital (NBO) analysis to determine the presence of hyper-conjugativeinteractions. It is important to observe the behavior of the C2?N bond with the delocalization effect; asthe pH increases the hyperconjugative interaction of this bond decreases in the same way as in the caseof nCN. The way in which the LP pO1 - s*C2?N interaction and nCN decrease is an inverse reflectionof the fractional ionization aSH.
publishDate 2019
dc.date.none.fl_str_mv 2019-08
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/11336/119053
Cobos Picot, Rafael Alejandro; Puiatti, Marcelo; Ben Altabef, Aida; Rubira, R. J.; Tuttolomondo, María Eugenia; A Raman, Sers and UV-Circular dichroism spectroscopic study of N-acetyl-L-Cisteine in aqueous solutions; Royal Society of Chemistry; New Journal of Chemistry; 43; 38; 8-2019; 15201-15212
1144-0546
CONICET Digital
CONICET
url http://hdl.handle.net/11336/119053
identifier_str_mv Cobos Picot, Rafael Alejandro; Puiatti, Marcelo; Ben Altabef, Aida; Rubira, R. J.; Tuttolomondo, María Eugenia; A Raman, Sers and UV-Circular dichroism spectroscopic study of N-acetyl-L-Cisteine in aqueous solutions; Royal Society of Chemistry; New Journal of Chemistry; 43; 38; 8-2019; 15201-15212
1144-0546
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1039/c9nj02427a
info:eu-repo/semantics/altIdentifier/url/https://pubs.rsc.org/en/content/articlelanding/2019/NJ/C9NJ02427A#!divAbstract
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
dc.publisher.none.fl_str_mv Royal Society of Chemistry
publisher.none.fl_str_mv Royal Society of Chemistry
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 12.993085

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