Deciphering the H-Bonding Preference on Nucleoside Molecular Recognition through Model Copper(II) Compounds

Autores
Velo Gala, Inmaculada; Barceló Oliver, Miquel; Gil, Diego Mauricio; González Pérez, Josefa M.; Castiñeiras, Alfonso; Domínguez Martín, Alicia
Año de publicación
2021
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The synthetic nucleoside acyclovir is considered an outstanding model of the natural nucleoside guanosine. With the purpose of deepening on the influence and nature of non-covalent interactions regarding molecular recognition patterns, three novel Cu(II) complexes, involving acyclovir (acv) and the ligand receptor N-(2-hydroxyethyl)ethylenediamine (hen), have been syn-thesized and thoroughly characterized. The three novel compounds introduce none, one or two acyclovir molecules, respectively. Molecular recognition has been evaluated using single crystal X-ray diffraction. Furthermore, theoretical calculations and other physical methods such as ther-mogravimetric analysis, infrared and UV-Vis spectroscopy, electron paramagnetic resonance and magnetic measurements have been used. Theoretical calculations are in line with experimental results, supporting the relevance of the [metal-N7(acv) + H-bond] molecular recognition pattern. It was also shown that (hen)O-H group is used as preferred H-donor when it is found within the basal coordination plane, since the higher polarity of the terminal (hen)O-H versus the N-H group favours its implication. Otherwise, when (hen)O-H occupies the distal coordination site, (hen)N-H groups can take over.
Fil: Velo Gala, Inmaculada. Universidad de Porto; Portugal
Fil: Barceló Oliver, Miquel. Universidad de las Islas Baleares; España
Fil: Gil, Diego Mauricio. Universidad Nacional de Tucumán. Instituto de Biotecnología Farmacéutica y Alimentaria. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Biotecnología Farmacéutica y Alimentaria; Argentina. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Orgánica; Argentina
Fil: González Pérez, Josefa M.. Universidad de Granada; España
Fil: Castiñeiras, Alfonso. Universidad de Santiago de Compostela; España
Fil: Domínguez Martín, Alicia. Universidad de Granada; España
Materia
ACYCLOVIR
DFT
H-BONDS
MOLECULAR RECOGNITION
NON-COVALENT INTERACTIONS
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:11336/148296
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/148296
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Deciphering the H-Bonding Preference on Nucleoside Molecular Recognition through Model Copper(II) CompoundsVelo Gala, InmaculadaBarceló Oliver, MiquelGil, Diego MauricioGonzález Pérez, Josefa M.Castiñeiras, AlfonsoDomínguez Martín, AliciaACYCLOVIRDFTH-BONDSMOLECULAR RECOGNITIONNON-COVALENT INTERACTIONShttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The synthetic nucleoside acyclovir is considered an outstanding model of the natural nucleoside guanosine. With the purpose of deepening on the influence and nature of non-covalent interactions regarding molecular recognition patterns, three novel Cu(II) complexes, involving acyclovir (acv) and the ligand receptor N-(2-hydroxyethyl)ethylenediamine (hen), have been syn-thesized and thoroughly characterized. The three novel compounds introduce none, one or two acyclovir molecules, respectively. Molecular recognition has been evaluated using single crystal X-ray diffraction. Furthermore, theoretical calculations and other physical methods such as ther-mogravimetric analysis, infrared and UV-Vis spectroscopy, electron paramagnetic resonance and magnetic measurements have been used. Theoretical calculations are in line with experimental results, supporting the relevance of the [metal-N7(acv) + H-bond] molecular recognition pattern. It was also shown that (hen)O-H group is used as preferred H-donor when it is found within the basal coordination plane, since the higher polarity of the terminal (hen)O-H versus the N-H group favours its implication. Otherwise, when (hen)O-H occupies the distal coordination site, (hen)N-H groups can take over.Fil: Velo Gala, Inmaculada. Universidad de Porto; PortugalFil: Barceló Oliver, Miquel. Universidad de las Islas Baleares; EspañaFil: Gil, Diego Mauricio. Universidad Nacional de Tucumán. Instituto de Biotecnología Farmacéutica y Alimentaria. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Biotecnología Farmacéutica y Alimentaria; Argentina. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Orgánica; ArgentinaFil: González Pérez, Josefa M.. Universidad de Granada; EspañaFil: Castiñeiras, Alfonso. Universidad de Santiago de Compostela; EspañaFil: Domínguez Martín, Alicia. Universidad de Granada; EspañaMDPI2021-03info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/148296Velo Gala, Inmaculada; Barceló Oliver, Miquel; Gil, Diego Mauricio; González Pérez, Josefa M.; Castiñeiras, Alfonso; et al.; Deciphering the H-Bonding Preference on Nucleoside Molecular Recognition through Model Copper(II) Compounds; MDPI; Pharmaceuticals; 14; 3; 3-2021; 1-161424-82471424-8247CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.3390/ph14030244info:eu-repo/semantics/altIdentifier/url/https://www.mdpi.com/1424-8247/14/3/244info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2026-03-31T15:12:06Zoai:ri.conicet.gov.ar:11336/148296instacron: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:34982026-03-31 15:12:06.881CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Deciphering the H-Bonding Preference on Nucleoside Molecular Recognition through Model Copper(II) Compounds
title Deciphering the H-Bonding Preference on Nucleoside Molecular Recognition through Model Copper(II) Compounds
spellingShingle Deciphering the H-Bonding Preference on Nucleoside Molecular Recognition through Model Copper(II) Compounds
Velo Gala, Inmaculada
ACYCLOVIR
DFT
H-BONDS
MOLECULAR RECOGNITION
NON-COVALENT INTERACTIONS
title_short Deciphering the H-Bonding Preference on Nucleoside Molecular Recognition through Model Copper(II) Compounds
title_full Deciphering the H-Bonding Preference on Nucleoside Molecular Recognition through Model Copper(II) Compounds
title_fullStr Deciphering the H-Bonding Preference on Nucleoside Molecular Recognition through Model Copper(II) Compounds
title_full_unstemmed Deciphering the H-Bonding Preference on Nucleoside Molecular Recognition through Model Copper(II) Compounds
title_sort Deciphering the H-Bonding Preference on Nucleoside Molecular Recognition through Model Copper(II) Compounds
dc.creator.none.fl_str_mv Velo Gala, Inmaculada
Barceló Oliver, Miquel
Gil, Diego Mauricio
González Pérez, Josefa M.
Castiñeiras, Alfonso
Domínguez Martín, Alicia
author Velo Gala, Inmaculada
author_facet Velo Gala, Inmaculada
Barceló Oliver, Miquel
Gil, Diego Mauricio
González Pérez, Josefa M.
Castiñeiras, Alfonso
Domínguez Martín, Alicia
author_role author
author2 Barceló Oliver, Miquel
Gil, Diego Mauricio
González Pérez, Josefa M.
Castiñeiras, Alfonso
Domínguez Martín, Alicia
author2_role author
author
author
author
author
dc.subject.none.fl_str_mv ACYCLOVIR
DFT
H-BONDS
MOLECULAR RECOGNITION
NON-COVALENT INTERACTIONS
topic ACYCLOVIR
DFT
H-BONDS
MOLECULAR RECOGNITION
NON-COVALENT INTERACTIONS
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 synthetic nucleoside acyclovir is considered an outstanding model of the natural nucleoside guanosine. With the purpose of deepening on the influence and nature of non-covalent interactions regarding molecular recognition patterns, three novel Cu(II) complexes, involving acyclovir (acv) and the ligand receptor N-(2-hydroxyethyl)ethylenediamine (hen), have been syn-thesized and thoroughly characterized. The three novel compounds introduce none, one or two acyclovir molecules, respectively. Molecular recognition has been evaluated using single crystal X-ray diffraction. Furthermore, theoretical calculations and other physical methods such as ther-mogravimetric analysis, infrared and UV-Vis spectroscopy, electron paramagnetic resonance and magnetic measurements have been used. Theoretical calculations are in line with experimental results, supporting the relevance of the [metal-N7(acv) + H-bond] molecular recognition pattern. It was also shown that (hen)O-H group is used as preferred H-donor when it is found within the basal coordination plane, since the higher polarity of the terminal (hen)O-H versus the N-H group favours its implication. Otherwise, when (hen)O-H occupies the distal coordination site, (hen)N-H groups can take over.
Fil: Velo Gala, Inmaculada. Universidad de Porto; Portugal
Fil: Barceló Oliver, Miquel. Universidad de las Islas Baleares; España
Fil: Gil, Diego Mauricio. Universidad Nacional de Tucumán. Instituto de Biotecnología Farmacéutica y Alimentaria. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Biotecnología Farmacéutica y Alimentaria; Argentina. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Orgánica; Argentina
Fil: González Pérez, Josefa M.. Universidad de Granada; España
Fil: Castiñeiras, Alfonso. Universidad de Santiago de Compostela; España
Fil: Domínguez Martín, Alicia. Universidad de Granada; España
description The synthetic nucleoside acyclovir is considered an outstanding model of the natural nucleoside guanosine. With the purpose of deepening on the influence and nature of non-covalent interactions regarding molecular recognition patterns, three novel Cu(II) complexes, involving acyclovir (acv) and the ligand receptor N-(2-hydroxyethyl)ethylenediamine (hen), have been syn-thesized and thoroughly characterized. The three novel compounds introduce none, one or two acyclovir molecules, respectively. Molecular recognition has been evaluated using single crystal X-ray diffraction. Furthermore, theoretical calculations and other physical methods such as ther-mogravimetric analysis, infrared and UV-Vis spectroscopy, electron paramagnetic resonance and magnetic measurements have been used. Theoretical calculations are in line with experimental results, supporting the relevance of the [metal-N7(acv) + H-bond] molecular recognition pattern. It was also shown that (hen)O-H group is used as preferred H-donor when it is found within the basal coordination plane, since the higher polarity of the terminal (hen)O-H versus the N-H group favours its implication. Otherwise, when (hen)O-H occupies the distal coordination site, (hen)N-H groups can take over.
publishDate 2021
dc.date.none.fl_str_mv 2021-03
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/11336/148296
Velo Gala, Inmaculada; Barceló Oliver, Miquel; Gil, Diego Mauricio; González Pérez, Josefa M.; Castiñeiras, Alfonso; et al.; Deciphering the H-Bonding Preference on Nucleoside Molecular Recognition through Model Copper(II) Compounds; MDPI; Pharmaceuticals; 14; 3; 3-2021; 1-16
1424-8247
1424-8247
CONICET Digital
CONICET
url http://hdl.handle.net/11336/148296
identifier_str_mv Velo Gala, Inmaculada; Barceló Oliver, Miquel; Gil, Diego Mauricio; González Pérez, Josefa M.; Castiñeiras, Alfonso; et al.; Deciphering the H-Bonding Preference on Nucleoside Molecular Recognition through Model Copper(II) Compounds; MDPI; Pharmaceuticals; 14; 3; 3-2021; 1-16
1424-8247
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.3390/ph14030244
info:eu-repo/semantics/altIdentifier/url/https://www.mdpi.com/1424-8247/14/3/244
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 MDPI
publisher.none.fl_str_mv MDPI
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_ 1861214357569929216
score 12.822162

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