Structures, Reactivities and Vibrational Study of Species Derived from the Adrenergic Α 2 Receptor Agonist Guanfacine Agent

Autores
Romani, Davide; Ruiz Hidalgo, José; Iramain, Maximiliano Alberto; Brandan, Silvia Antonia
Año de publicación
2019
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
In the present work, eight different species of adrenergic α 2 receptor agonist guanfacine have been theoretically studied in gas phase and in aqueous solution combining hybrid B3LYP/6- 31G* calculations with the Scaled Mechanical Quantum Force Field (SQMFF) methodology and the experimental available infrared and Raman spectra in order to perform their complete vibrational assignments. Hence, the different structures of three tautomeric forms of free base (A, B and C), two cationic (E and G), one anionic (D) and two hydrochloride (F and H) species of that antihypertensive agent were optimized in solution with the Integral Equation F variant Polarised Continuum Method (IEFPCM) and the universal solvation model. The anionic species of guanfacine presents the higher corrected solvation energy with valor of -301,60 kJ/mol, slightly lower than the corresponding to scopolamine alkaloid (-310.34 J/mol) and higher than the corresponding to cocaine alkaloid (-255.24 J/mol). The studies of the frontier orbitals have evidenced that in gas phase, the anionic D species is the most reactive while in solution the hydrochloride H species is the most reactive together with the anionic species. High global nucleophilicity (E) and electrophilicity indexes (ω) values have evidenced both cationic species E and G while the lower values of both indexes are predicted for the anionic D species in both media. In addition, the harmonic force fields, force constants and the complete vibrational assignments for the 63, 66, 69 and 72 vibration normal modes expected for the anionic, free bases, cationic and hydrochloride species of guanfacine are respectively reported for first time.
Fil: Romani, Davide. Servicio Sanitario Della Toscana; Italia
Fil: Ruiz Hidalgo, José. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica. Cátedra de Química General.; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán; Argentina
Fil: Iramain, Maximiliano Alberto. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica. Cátedra de Química General.; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán; 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
REACTIVITY
GUANFACINE
HYPERTENSION
STRUCTURE
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:11336/119321
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/119321
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Structures, Reactivities and Vibrational Study of Species Derived from the Adrenergic Α 2 Receptor Agonist Guanfacine AgentRomani, DavideRuiz Hidalgo, JoséIramain, Maximiliano AlbertoBrandan, Silvia AntoniaREACTIVITYGUANFACINEHYPERTENSIONSTRUCTUREhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1In the present work, eight different species of adrenergic α 2 receptor agonist guanfacine have been theoretically studied in gas phase and in aqueous solution combining hybrid B3LYP/6- 31G* calculations with the Scaled Mechanical Quantum Force Field (SQMFF) methodology and the experimental available infrared and Raman spectra in order to perform their complete vibrational assignments. Hence, the different structures of three tautomeric forms of free base (A, B and C), two cationic (E and G), one anionic (D) and two hydrochloride (F and H) species of that antihypertensive agent were optimized in solution with the Integral Equation F variant Polarised Continuum Method (IEFPCM) and the universal solvation model. The anionic species of guanfacine presents the higher corrected solvation energy with valor of -301,60 kJ/mol, slightly lower than the corresponding to scopolamine alkaloid (-310.34 J/mol) and higher than the corresponding to cocaine alkaloid (-255.24 J/mol). The studies of the frontier orbitals have evidenced that in gas phase, the anionic D species is the most reactive while in solution the hydrochloride H species is the most reactive together with the anionic species. High global nucleophilicity (E) and electrophilicity indexes (ω) values have evidenced both cationic species E and G while the lower values of both indexes are predicted for the anionic D species in both media. In addition, the harmonic force fields, force constants and the complete vibrational assignments for the 63, 66, 69 and 72 vibration normal modes expected for the anionic, free bases, cationic and hydrochloride species of guanfacine are respectively reported for first time.Fil: Romani, Davide. Servicio Sanitario Della Toscana; ItaliaFil: Ruiz Hidalgo, José. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica. Cátedra de Química General.; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán; ArgentinaFil: Iramain, Maximiliano Alberto. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica. Cátedra de Química General.; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán; ArgentinaFil: Brandan, Silvia Antonia. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica. Cátedra de Química General.; ArgentinaIJSRM2019-06info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/119321Romani, Davide; Ruiz Hidalgo, José; Iramain, Maximiliano Alberto; Brandan, Silvia Antonia; Structures, Reactivities and Vibrational Study of Species Derived from the Adrenergic Α 2 Receptor Agonist Guanfacine Agent; IJSRM; International journal of science and research methodology; 12; 4; 6-2019; 1-252454-2008CONICET DigitalCONICETenginfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-10T13:12:44Zoai:ri.conicet.gov.ar:11336/119321instacron: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 13:12:44.341CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Structures, Reactivities and Vibrational Study of Species Derived from the Adrenergic Α 2 Receptor Agonist Guanfacine Agent
title Structures, Reactivities and Vibrational Study of Species Derived from the Adrenergic Α 2 Receptor Agonist Guanfacine Agent
spellingShingle Structures, Reactivities and Vibrational Study of Species Derived from the Adrenergic Α 2 Receptor Agonist Guanfacine Agent
Romani, Davide
REACTIVITY
GUANFACINE
HYPERTENSION
STRUCTURE
title_short Structures, Reactivities and Vibrational Study of Species Derived from the Adrenergic Α 2 Receptor Agonist Guanfacine Agent
title_full Structures, Reactivities and Vibrational Study of Species Derived from the Adrenergic Α 2 Receptor Agonist Guanfacine Agent
title_fullStr Structures, Reactivities and Vibrational Study of Species Derived from the Adrenergic Α 2 Receptor Agonist Guanfacine Agent
title_full_unstemmed Structures, Reactivities and Vibrational Study of Species Derived from the Adrenergic Α 2 Receptor Agonist Guanfacine Agent
title_sort Structures, Reactivities and Vibrational Study of Species Derived from the Adrenergic Α 2 Receptor Agonist Guanfacine Agent
dc.creator.none.fl_str_mv Romani, Davide
Ruiz Hidalgo, José
Iramain, Maximiliano Alberto
Brandan, Silvia Antonia
author Romani, Davide
author_facet Romani, Davide
Ruiz Hidalgo, José
Iramain, Maximiliano Alberto
Brandan, Silvia Antonia
author_role author
author2 Ruiz Hidalgo, José
Iramain, Maximiliano Alberto
Brandan, Silvia Antonia
author2_role author
author
author
dc.subject.none.fl_str_mv REACTIVITY
GUANFACINE
HYPERTENSION
STRUCTURE
topic REACTIVITY
GUANFACINE
HYPERTENSION
STRUCTURE
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 the present work, eight different species of adrenergic α 2 receptor agonist guanfacine have been theoretically studied in gas phase and in aqueous solution combining hybrid B3LYP/6- 31G* calculations with the Scaled Mechanical Quantum Force Field (SQMFF) methodology and the experimental available infrared and Raman spectra in order to perform their complete vibrational assignments. Hence, the different structures of three tautomeric forms of free base (A, B and C), two cationic (E and G), one anionic (D) and two hydrochloride (F and H) species of that antihypertensive agent were optimized in solution with the Integral Equation F variant Polarised Continuum Method (IEFPCM) and the universal solvation model. The anionic species of guanfacine presents the higher corrected solvation energy with valor of -301,60 kJ/mol, slightly lower than the corresponding to scopolamine alkaloid (-310.34 J/mol) and higher than the corresponding to cocaine alkaloid (-255.24 J/mol). The studies of the frontier orbitals have evidenced that in gas phase, the anionic D species is the most reactive while in solution the hydrochloride H species is the most reactive together with the anionic species. High global nucleophilicity (E) and electrophilicity indexes (ω) values have evidenced both cationic species E and G while the lower values of both indexes are predicted for the anionic D species in both media. In addition, the harmonic force fields, force constants and the complete vibrational assignments for the 63, 66, 69 and 72 vibration normal modes expected for the anionic, free bases, cationic and hydrochloride species of guanfacine are respectively reported for first time.
Fil: Romani, Davide. Servicio Sanitario Della Toscana; Italia
Fil: Ruiz Hidalgo, José. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica. Cátedra de Química General.; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán; Argentina
Fil: Iramain, Maximiliano Alberto. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica. Cátedra de Química General.; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán; 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 the present work, eight different species of adrenergic α 2 receptor agonist guanfacine have been theoretically studied in gas phase and in aqueous solution combining hybrid B3LYP/6- 31G* calculations with the Scaled Mechanical Quantum Force Field (SQMFF) methodology and the experimental available infrared and Raman spectra in order to perform their complete vibrational assignments. Hence, the different structures of three tautomeric forms of free base (A, B and C), two cationic (E and G), one anionic (D) and two hydrochloride (F and H) species of that antihypertensive agent were optimized in solution with the Integral Equation F variant Polarised Continuum Method (IEFPCM) and the universal solvation model. The anionic species of guanfacine presents the higher corrected solvation energy with valor of -301,60 kJ/mol, slightly lower than the corresponding to scopolamine alkaloid (-310.34 J/mol) and higher than the corresponding to cocaine alkaloid (-255.24 J/mol). The studies of the frontier orbitals have evidenced that in gas phase, the anionic D species is the most reactive while in solution the hydrochloride H species is the most reactive together with the anionic species. High global nucleophilicity (E) and electrophilicity indexes (ω) values have evidenced both cationic species E and G while the lower values of both indexes are predicted for the anionic D species in both media. In addition, the harmonic force fields, force constants and the complete vibrational assignments for the 63, 66, 69 and 72 vibration normal modes expected for the anionic, free bases, cationic and hydrochloride species of guanfacine are respectively reported for first time.
publishDate 2019
dc.date.none.fl_str_mv 2019-06
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/11336/119321
Romani, Davide; Ruiz Hidalgo, José; Iramain, Maximiliano Alberto; Brandan, Silvia Antonia; Structures, Reactivities and Vibrational Study of Species Derived from the Adrenergic Α 2 Receptor Agonist Guanfacine Agent; IJSRM; International journal of science and research methodology; 12; 4; 6-2019; 1-25
2454-2008
CONICET Digital
CONICET
url http://hdl.handle.net/11336/119321
identifier_str_mv Romani, Davide; Ruiz Hidalgo, José; Iramain, Maximiliano Alberto; Brandan, Silvia Antonia; Structures, Reactivities and Vibrational Study of Species Derived from the Adrenergic Α 2 Receptor Agonist Guanfacine Agent; IJSRM; International journal of science and research methodology; 12; 4; 6-2019; 1-25
2454-2008
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
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 IJSRM
publisher.none.fl_str_mv IJSRM
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
_version_ 1842980666499661824
score 12.993085

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