Theoretical investigation on monomer and dimers of Inhibitor of cytochrome P450 enzymes: 1-aminobenzotriazole

Autores
Manzur, Maria Eugenia; Cataldo, Pablo Gabriel; Iramain, Maximiliano Alberto; Castillo, María Victoria; Brandan, Silvia Antonia
Año de publicación
2023
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
In this research, structures and properties of monomer and two dimers (1 and 2) of inhibitor of cytochrome P450 enzymes, 1-Aminobenzotriazole (ABT) have been studied by using functional hybrid B3LYP/6-311++G** calculations. The very good correlations observed between theoretical and experimental 1H-, 13C-NMR, FT-IR and FT-Raman spectra suggest that C-H···N interactions of dimeric species should be expected in the solid phase, as was observed in the experimental crystalline structure of a quinolin benzotriazole derivative. NBO and AIM calculations suggest that dimer 2 with inverted positions of its monomers could be present in the solid phase because it evidence higher stabilities in both media. On the other hand, frontier orbitals studies support a higher reactivity of dimer 2 of ABT higher than the monomer and dimer 1, for which, the presence of dimer 2 containing N-NH2 groups in ABT could justify the biological activities observed for this species with gap values between 4.5933 and 4.8164 eV different from antiviral agents containing the C-NH2 moiety, as amantadine and chloroquine whose gap values are around 4.3012-4.1116 eV. Finally, the presence of bands of monomer and of both dimers are predicted in the vibrational spectra and, hence, its completes assignments have been performed. The scaled force constants for the three studied species are also reported.
Fil: Manzur, Maria Eugenia. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica. Cátedra de Química General.; Argentina
Fil: Cataldo, Pablo Gabriel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Centro de Referencia para Lactobacilos; Argentina. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica. Cátedra de Química General.; Argentina
Fil: Iramain, Maximiliano Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica. Cátedra de Química General.; Argentina
Fil: Castillo, María Victoria. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica. Cátedra de Química General.; Argentina
Fil: Brandan, Silvia Antonia. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica. Cátedra de Química General.; Argentina
Materia
1-AMINOBENZOTRIAZOLE
MOLECULAR STRUCTURE
HARMONIC FORCE FIELDS
DFT CALCULATIONS
VIBRATIONAL ANALYS
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/249216
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/249216
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Theoretical investigation on monomer and dimers of Inhibitor of cytochrome P450 enzymes: 1-aminobenzotriazoleManzur, Maria EugeniaCataldo, Pablo GabrielIramain, Maximiliano AlbertoCastillo, María VictoriaBrandan, Silvia Antonia1-AMINOBENZOTRIAZOLEMOLECULAR STRUCTUREHARMONIC FORCE FIELDSDFT CALCULATIONSVIBRATIONAL ANALYShttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1In this research, structures and properties of monomer and two dimers (1 and 2) of inhibitor of cytochrome P450 enzymes, 1-Aminobenzotriazole (ABT) have been studied by using functional hybrid B3LYP/6-311++G** calculations. The very good correlations observed between theoretical and experimental 1H-, 13C-NMR, FT-IR and FT-Raman spectra suggest that C-H···N interactions of dimeric species should be expected in the solid phase, as was observed in the experimental crystalline structure of a quinolin benzotriazole derivative. NBO and AIM calculations suggest that dimer 2 with inverted positions of its monomers could be present in the solid phase because it evidence higher stabilities in both media. On the other hand, frontier orbitals studies support a higher reactivity of dimer 2 of ABT higher than the monomer and dimer 1, for which, the presence of dimer 2 containing N-NH2 groups in ABT could justify the biological activities observed for this species with gap values between 4.5933 and 4.8164 eV different from antiviral agents containing the C-NH2 moiety, as amantadine and chloroquine whose gap values are around 4.3012-4.1116 eV. Finally, the presence of bands of monomer and of both dimers are predicted in the vibrational spectra and, hence, its completes assignments have been performed. The scaled force constants for the three studied species are also reported.Fil: Manzur, Maria Eugenia. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica. Cátedra de Química General.; ArgentinaFil: Cataldo, Pablo Gabriel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Centro de Referencia para Lactobacilos; Argentina. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica. Cátedra de Química General.; ArgentinaFil: Iramain, Maximiliano Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica. Cátedra de Química General.; ArgentinaFil: Castillo, María Victoria. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica. Cátedra de Química General.; ArgentinaFil: Brandan, Silvia Antonia. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica. Cátedra de Química General.; ArgentinaAMO Publisher2023-06info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/249216Manzur, Maria Eugenia; Cataldo, Pablo Gabriel; Iramain, Maximiliano Alberto; Castillo, María Victoria; Brandan, Silvia Antonia; Theoretical investigation on monomer and dimers of Inhibitor of cytochrome P450 enzymes: 1-aminobenzotriazole; AMO Publisher; European Journal of Theoretical and Applied Sciences; 1; 3; 6-2023; 456-4842786-7447CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://ejtas.com/index.php/journal/article/view/117info:eu-repo/semantics/altIdentifier/doi/10.59324/ejtas.2023.1(3).45info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:57:22Zoai:ri.conicet.gov.ar:11336/249216instacron: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 09:57:22.665CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Theoretical investigation on monomer and dimers of Inhibitor of cytochrome P450 enzymes: 1-aminobenzotriazole
title Theoretical investigation on monomer and dimers of Inhibitor of cytochrome P450 enzymes: 1-aminobenzotriazole
spellingShingle Theoretical investigation on monomer and dimers of Inhibitor of cytochrome P450 enzymes: 1-aminobenzotriazole
Manzur, Maria Eugenia
1-AMINOBENZOTRIAZOLE
MOLECULAR STRUCTURE
HARMONIC FORCE FIELDS
DFT CALCULATIONS
VIBRATIONAL ANALYS
title_short Theoretical investigation on monomer and dimers of Inhibitor of cytochrome P450 enzymes: 1-aminobenzotriazole
title_full Theoretical investigation on monomer and dimers of Inhibitor of cytochrome P450 enzymes: 1-aminobenzotriazole
title_fullStr Theoretical investigation on monomer and dimers of Inhibitor of cytochrome P450 enzymes: 1-aminobenzotriazole
title_full_unstemmed Theoretical investigation on monomer and dimers of Inhibitor of cytochrome P450 enzymes: 1-aminobenzotriazole
title_sort Theoretical investigation on monomer and dimers of Inhibitor of cytochrome P450 enzymes: 1-aminobenzotriazole
dc.creator.none.fl_str_mv Manzur, Maria Eugenia
Cataldo, Pablo Gabriel
Iramain, Maximiliano Alberto
Castillo, María Victoria
Brandan, Silvia Antonia
author Manzur, Maria Eugenia
author_facet Manzur, Maria Eugenia
Cataldo, Pablo Gabriel
Iramain, Maximiliano Alberto
Castillo, María Victoria
Brandan, Silvia Antonia
author_role author
author2 Cataldo, Pablo Gabriel
Iramain, Maximiliano Alberto
Castillo, María Victoria
Brandan, Silvia Antonia
author2_role author
author
author
author
dc.subject.none.fl_str_mv 1-AMINOBENZOTRIAZOLE
MOLECULAR STRUCTURE
HARMONIC FORCE FIELDS
DFT CALCULATIONS
VIBRATIONAL ANALYS
topic 1-AMINOBENZOTRIAZOLE
MOLECULAR STRUCTURE
HARMONIC FORCE FIELDS
DFT CALCULATIONS
VIBRATIONAL ANALYS
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv In this research, structures and properties of monomer and two dimers (1 and 2) of inhibitor of cytochrome P450 enzymes, 1-Aminobenzotriazole (ABT) have been studied by using functional hybrid B3LYP/6-311++G** calculations. The very good correlations observed between theoretical and experimental 1H-, 13C-NMR, FT-IR and FT-Raman spectra suggest that C-H···N interactions of dimeric species should be expected in the solid phase, as was observed in the experimental crystalline structure of a quinolin benzotriazole derivative. NBO and AIM calculations suggest that dimer 2 with inverted positions of its monomers could be present in the solid phase because it evidence higher stabilities in both media. On the other hand, frontier orbitals studies support a higher reactivity of dimer 2 of ABT higher than the monomer and dimer 1, for which, the presence of dimer 2 containing N-NH2 groups in ABT could justify the biological activities observed for this species with gap values between 4.5933 and 4.8164 eV different from antiviral agents containing the C-NH2 moiety, as amantadine and chloroquine whose gap values are around 4.3012-4.1116 eV. Finally, the presence of bands of monomer and of both dimers are predicted in the vibrational spectra and, hence, its completes assignments have been performed. The scaled force constants for the three studied species are also reported.
Fil: Manzur, Maria Eugenia. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica. Cátedra de Química General.; Argentina
Fil: Cataldo, Pablo Gabriel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Centro de Referencia para Lactobacilos; Argentina. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica. Cátedra de Química General.; Argentina
Fil: Iramain, Maximiliano Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica. Cátedra de Química General.; Argentina
Fil: Castillo, María Victoria. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica. Cátedra de Química General.; Argentina
Fil: Brandan, Silvia Antonia. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica. Cátedra de Química General.; Argentina
description In this research, structures and properties of monomer and two dimers (1 and 2) of inhibitor of cytochrome P450 enzymes, 1-Aminobenzotriazole (ABT) have been studied by using functional hybrid B3LYP/6-311++G** calculations. The very good correlations observed between theoretical and experimental 1H-, 13C-NMR, FT-IR and FT-Raman spectra suggest that C-H···N interactions of dimeric species should be expected in the solid phase, as was observed in the experimental crystalline structure of a quinolin benzotriazole derivative. NBO and AIM calculations suggest that dimer 2 with inverted positions of its monomers could be present in the solid phase because it evidence higher stabilities in both media. On the other hand, frontier orbitals studies support a higher reactivity of dimer 2 of ABT higher than the monomer and dimer 1, for which, the presence of dimer 2 containing N-NH2 groups in ABT could justify the biological activities observed for this species with gap values between 4.5933 and 4.8164 eV different from antiviral agents containing the C-NH2 moiety, as amantadine and chloroquine whose gap values are around 4.3012-4.1116 eV. Finally, the presence of bands of monomer and of both dimers are predicted in the vibrational spectra and, hence, its completes assignments have been performed. The scaled force constants for the three studied species are also reported.
publishDate 2023
dc.date.none.fl_str_mv 2023-06
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/11336/249216
Manzur, Maria Eugenia; Cataldo, Pablo Gabriel; Iramain, Maximiliano Alberto; Castillo, María Victoria; Brandan, Silvia Antonia; Theoretical investigation on monomer and dimers of Inhibitor of cytochrome P450 enzymes: 1-aminobenzotriazole; AMO Publisher; European Journal of Theoretical and Applied Sciences; 1; 3; 6-2023; 456-484
2786-7447
CONICET Digital
CONICET
url http://hdl.handle.net/11336/249216
identifier_str_mv Manzur, Maria Eugenia; Cataldo, Pablo Gabriel; Iramain, Maximiliano Alberto; Castillo, María Victoria; Brandan, Silvia Antonia; Theoretical investigation on monomer and dimers of Inhibitor of cytochrome P450 enzymes: 1-aminobenzotriazole; AMO Publisher; European Journal of Theoretical and Applied Sciences; 1; 3; 6-2023; 456-484
2786-7447
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/https://ejtas.com/index.php/journal/article/view/117
info:eu-repo/semantics/altIdentifier/doi/10.59324/ejtas.2023.1(3).45
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv AMO Publisher
publisher.none.fl_str_mv AMO Publisher
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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