Behaviour of N-CH3 Group in Tropane Alkaloids and Correlations in their Properties

Autores
Rudyk, Roxana Amelia; Checa, Maria Alejandra; Guzetti, Karina; Iramain, Maximiliano Alberto; Brandan, Silvia Antonia
Año de publicación
2018
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
In this work, the influence of common >N-CH3 group present in the three free base, cationic and hydrochloride/bromide structures of scopolamine, heroin, morphine, cocaine and tropane alkaloids in gas and aqueous solution phases has been investigated theoretically by using B3LYP/6-31G* calculations and the Polarized Continuum model (PCM) in order to find possible correlations in their properties. Hence, the N-C distances, Mulliken and Merz-Kollman (MK) charges, bond orders, stabilization and solvation energies, frontier orbitals, some descriptors and their topological properties were compared and analysed among them. The presence of two fused piperidine and pyrrolidine rings in the three species of scopolamine, cocaine and tropane alkaloids produces changes in the charges, stabilization and solvation energies and densities of their rings linked to that group in these alkaloids, as compared with heroin and morphine. Here, the higher solvation energies observed for the heroin species are supported by the Mulliken and MK charges on C and N atoms of >N-CH3 groups. On the other hand, the higher reactivities of three cocaine species in the two media could be easily justified by the most negative MK charges observed on the N atoms. The presence of only one ring of six members in the heroin and morphine species linked to >N-CH3 groups could justify the low electronic densities of their rings different from scopolamine, cocaine and tropane alkaloids. In addition, the higher N-C distances observed in the three forms of heroin and morphine in both media suggest low electronic densities of their rings and higher stabilities, as compared with scopolamine, cocaine and tropane. The incorporation of additional groups and rings in tropane alkaloid increase their reactivity, as evidenced in the cocaine species. Finally, the Lipinski’s and Veber rules justify broadly the potential pharmacological properties of these alkaloids
Fil: Rudyk, Roxana Amelia. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica. Cátedra de Química General.; Argentina
Fil: Checa, Maria Alejandra. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica. Cátedra de Química General.; Argentina
Fil: Guzetti, Karina. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica. Cátedra de Química General.; 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
ALKALOIDS
STRUCTURAL PROPERTIES
DESCRIPTORS
DFT CALCULATIONS
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:11336/159947
Acceder
id CONICETDig_1c84523b3e72b6071d92c4ad3b9e937f
oai_identifier_str oai:ri.conicet.gov.ar:11336/159947
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Behaviour of N-CH3 Group in Tropane Alkaloids and Correlations in their PropertiesRudyk, Roxana AmeliaCheca, Maria AlejandraGuzetti, KarinaIramain, Maximiliano AlbertoBrandan, Silvia AntoniaALKALOIDSSTRUCTURAL PROPERTIESDESCRIPTORSDFT CALCULATIONShttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1In this work, the influence of common >N-CH3 group present in the three free base, cationic and hydrochloride/bromide structures of scopolamine, heroin, morphine, cocaine and tropane alkaloids in gas and aqueous solution phases has been investigated theoretically by using B3LYP/6-31G* calculations and the Polarized Continuum model (PCM) in order to find possible correlations in their properties. Hence, the N-C distances, Mulliken and Merz-Kollman (MK) charges, bond orders, stabilization and solvation energies, frontier orbitals, some descriptors and their topological properties were compared and analysed among them. The presence of two fused piperidine and pyrrolidine rings in the three species of scopolamine, cocaine and tropane alkaloids produces changes in the charges, stabilization and solvation energies and densities of their rings linked to that group in these alkaloids, as compared with heroin and morphine. Here, the higher solvation energies observed for the heroin species are supported by the Mulliken and MK charges on C and N atoms of >N-CH3 groups. On the other hand, the higher reactivities of three cocaine species in the two media could be easily justified by the most negative MK charges observed on the N atoms. The presence of only one ring of six members in the heroin and morphine species linked to >N-CH3 groups could justify the low electronic densities of their rings different from scopolamine, cocaine and tropane alkaloids. In addition, the higher N-C distances observed in the three forms of heroin and morphine in both media suggest low electronic densities of their rings and higher stabilities, as compared with scopolamine, cocaine and tropane. The incorporation of additional groups and rings in tropane alkaloid increase their reactivity, as evidenced in the cocaine species. Finally, the Lipinski’s and Veber rules justify broadly the potential pharmacological properties of these alkaloidsFil: Rudyk, Roxana Amelia. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica. Cátedra de Química General.; ArgentinaFil: Checa, Maria Alejandra. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica. Cátedra de Química General.; ArgentinaFil: Guzetti, Karina. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica. Cátedra de Química General.; 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.; ArgentinaParipex2018-10info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/159947Rudyk, Roxana Amelia; Checa, Maria Alejandra; Guzetti, Karina; Iramain, Maximiliano Alberto; Brandan, Silvia Antonia; Behaviour of N-CH3 Group in Tropane Alkaloids and Correlations in their Properties; Paripex; Indian Journal of Research; 10; 4; 10-2018; 70-972250-1991CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/http://ijsrm.humanjournals.com/wp-content/uploads/2018/11/6.Roxana-A.-Rudyk-Mar%C3%ADa-A.-Checa-Karina-A.Guzzetti-Maximiliano-A.-Iramain-Silvia-Antonia-Brand%C3%A1n.pdfinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-10T13:17:47Zoai:ri.conicet.gov.ar:11336/159947instacron: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 13:17:47.383CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Behaviour of N-CH3 Group in Tropane Alkaloids and Correlations in their Properties
title Behaviour of N-CH3 Group in Tropane Alkaloids and Correlations in their Properties
spellingShingle Behaviour of N-CH3 Group in Tropane Alkaloids and Correlations in their Properties
Rudyk, Roxana Amelia
ALKALOIDS
STRUCTURAL PROPERTIES
DESCRIPTORS
DFT CALCULATIONS
title_short Behaviour of N-CH3 Group in Tropane Alkaloids and Correlations in their Properties
title_full Behaviour of N-CH3 Group in Tropane Alkaloids and Correlations in their Properties
title_fullStr Behaviour of N-CH3 Group in Tropane Alkaloids and Correlations in their Properties
title_full_unstemmed Behaviour of N-CH3 Group in Tropane Alkaloids and Correlations in their Properties
title_sort Behaviour of N-CH3 Group in Tropane Alkaloids and Correlations in their Properties
dc.creator.none.fl_str_mv Rudyk, Roxana Amelia
Checa, Maria Alejandra
Guzetti, Karina
Iramain, Maximiliano Alberto
Brandan, Silvia Antonia
author Rudyk, Roxana Amelia
author_facet Rudyk, Roxana Amelia
Checa, Maria Alejandra
Guzetti, Karina
Iramain, Maximiliano Alberto
Brandan, Silvia Antonia
author_role author
author2 Checa, Maria Alejandra
Guzetti, Karina
Iramain, Maximiliano Alberto
Brandan, Silvia Antonia
author2_role author
author
author
author
dc.subject.none.fl_str_mv ALKALOIDS
STRUCTURAL PROPERTIES
DESCRIPTORS
DFT CALCULATIONS
topic ALKALOIDS
STRUCTURAL PROPERTIES
DESCRIPTORS
DFT CALCULATIONS
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 work, the influence of common >N-CH3 group present in the three free base, cationic and hydrochloride/bromide structures of scopolamine, heroin, morphine, cocaine and tropane alkaloids in gas and aqueous solution phases has been investigated theoretically by using B3LYP/6-31G* calculations and the Polarized Continuum model (PCM) in order to find possible correlations in their properties. Hence, the N-C distances, Mulliken and Merz-Kollman (MK) charges, bond orders, stabilization and solvation energies, frontier orbitals, some descriptors and their topological properties were compared and analysed among them. The presence of two fused piperidine and pyrrolidine rings in the three species of scopolamine, cocaine and tropane alkaloids produces changes in the charges, stabilization and solvation energies and densities of their rings linked to that group in these alkaloids, as compared with heroin and morphine. Here, the higher solvation energies observed for the heroin species are supported by the Mulliken and MK charges on C and N atoms of >N-CH3 groups. On the other hand, the higher reactivities of three cocaine species in the two media could be easily justified by the most negative MK charges observed on the N atoms. The presence of only one ring of six members in the heroin and morphine species linked to >N-CH3 groups could justify the low electronic densities of their rings different from scopolamine, cocaine and tropane alkaloids. In addition, the higher N-C distances observed in the three forms of heroin and morphine in both media suggest low electronic densities of their rings and higher stabilities, as compared with scopolamine, cocaine and tropane. The incorporation of additional groups and rings in tropane alkaloid increase their reactivity, as evidenced in the cocaine species. Finally, the Lipinski’s and Veber rules justify broadly the potential pharmacological properties of these alkaloids
Fil: Rudyk, Roxana Amelia. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica. Cátedra de Química General.; Argentina
Fil: Checa, Maria Alejandra. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica. Cátedra de Química General.; Argentina
Fil: Guzetti, Karina. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica. Cátedra de Química General.; 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 this work, the influence of common >N-CH3 group present in the three free base, cationic and hydrochloride/bromide structures of scopolamine, heroin, morphine, cocaine and tropane alkaloids in gas and aqueous solution phases has been investigated theoretically by using B3LYP/6-31G* calculations and the Polarized Continuum model (PCM) in order to find possible correlations in their properties. Hence, the N-C distances, Mulliken and Merz-Kollman (MK) charges, bond orders, stabilization and solvation energies, frontier orbitals, some descriptors and their topological properties were compared and analysed among them. The presence of two fused piperidine and pyrrolidine rings in the three species of scopolamine, cocaine and tropane alkaloids produces changes in the charges, stabilization and solvation energies and densities of their rings linked to that group in these alkaloids, as compared with heroin and morphine. Here, the higher solvation energies observed for the heroin species are supported by the Mulliken and MK charges on C and N atoms of >N-CH3 groups. On the other hand, the higher reactivities of three cocaine species in the two media could be easily justified by the most negative MK charges observed on the N atoms. The presence of only one ring of six members in the heroin and morphine species linked to >N-CH3 groups could justify the low electronic densities of their rings different from scopolamine, cocaine and tropane alkaloids. In addition, the higher N-C distances observed in the three forms of heroin and morphine in both media suggest low electronic densities of their rings and higher stabilities, as compared with scopolamine, cocaine and tropane. The incorporation of additional groups and rings in tropane alkaloid increase their reactivity, as evidenced in the cocaine species. Finally, the Lipinski’s and Veber rules justify broadly the potential pharmacological properties of these alkaloids
publishDate 2018
dc.date.none.fl_str_mv 2018-10
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/11336/159947
Rudyk, Roxana Amelia; Checa, Maria Alejandra; Guzetti, Karina; Iramain, Maximiliano Alberto; Brandan, Silvia Antonia; Behaviour of N-CH3 Group in Tropane Alkaloids and Correlations in their Properties; Paripex; Indian Journal of Research; 10; 4; 10-2018; 70-97
2250-1991
CONICET Digital
CONICET
url http://hdl.handle.net/11336/159947
identifier_str_mv Rudyk, Roxana Amelia; Checa, Maria Alejandra; Guzetti, Karina; Iramain, Maximiliano Alberto; Brandan, Silvia Antonia; Behaviour of N-CH3 Group in Tropane Alkaloids and Correlations in their Properties; Paripex; Indian Journal of Research; 10; 4; 10-2018; 70-97
2250-1991
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/http://ijsrm.humanjournals.com/wp-content/uploads/2018/11/6.Roxana-A.-Rudyk-Mar%C3%ADa-A.-Checa-Karina-A.Guzzetti-Maximiliano-A.-Iramain-Silvia-Antonia-Brand%C3%A1n.pdf
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 Paripex
publisher.none.fl_str_mv Paripex
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_ 1842980971787321344
score 12.993085

Publicaciones similares