A non-ionic gadolinium complex whose relaxometric behavior is sensitive to the variation of pH: An experimental and theoretical study on geometry, bonding nature of polyaminocarbox...

Autores
Rustoy, Eduardo Miguel; Raggio, Norberto
Año de publicación
2018
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Background: In addition, the contribution of cyclic structure to the stability of lanthanide complexes has been evaluated on different ligand platforms and some indications of their relative stability are now available. Additionally, it is well known that one of the most important factors to design smart contrast is pH. Objectives: The main objectives were to optimize the synthesis of the macrocyclic ligand, using micro-waves. Then study the relaxometric behavior in vitro, depending on the pH, of the gadolinium complex and propose a potential structure-activity relationship of the same. Methods: The reactions assisted by microwaves were carried out using a Discover® CoolMate™. Nuclear Magnetic Resonance (NMR) spectra were acquired at 200 and 500 MHz. The Infrared (IR) spectrum of the complex was measured as KBr discs between 400 and 4000cm-1. Electrospray Ionization-High Resolution Mass Spectrometry (ESI-HRMS) was performed on a Bruker microTOF-Q II spectrome-ter. The r1 measurements of the complexes were at 0.2 T, by the inversion recovery method. For the theoretical analysis presented in this work, Hartre- Fock and semiempirical methods were used. Results: In the first place, it was possible to carry out the microwave-assisted synthesis of two intermediaries, with higher yields and in a more environmentally friendly way. Then the variation of r1 was checked as a function of the pH value, obtaining a maximum approximately at pH 6.5. The computer tools allowed to propose the possible structures of the coordination compound obtained. Conclusion: It was found that the variation of the value of r1 as a function of pH is not a product of the decomposition of the complex, but a stage in which at pH values higher than 7 the complex would undergo a displacement of the water molecule located in the ninth coordination position of the Gd+ 3. This behavior could be due to the replacement of the water molecule by the OH group of the ligand.
Fil: Rustoy, Eduardo Miguel. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos en Química Orgánica. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Unidad de Microanálisis y Métodos Físicos en Química Orgánica; Argentina. Universidad Nacional de Luján. Departamento de Ciencias Básicas; Argentina
Fil: Raggio, Norberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos en Química Orgánica. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Unidad de Microanálisis y Métodos Físicos en Química Orgánica; Argentina
Materia
Gadolinium
Magnetic resonance imaging
Macrocyclic ligand
MOPAC/Sparkle
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:11336/162632
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/162632
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling A non-ionic gadolinium complex whose relaxometric behavior is sensitive to the variation of pH: An experimental and theoretical study on geometry, bonding nature of polyaminocarboxylic ligand and their gadolinium complexRustoy, Eduardo MiguelRaggio, NorbertoGadoliniumMagnetic resonance imagingMacrocyclic ligandMOPAC/Sparklehttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Background: In addition, the contribution of cyclic structure to the stability of lanthanide complexes has been evaluated on different ligand platforms and some indications of their relative stability are now available. Additionally, it is well known that one of the most important factors to design smart contrast is pH. Objectives: The main objectives were to optimize the synthesis of the macrocyclic ligand, using micro-waves. Then study the relaxometric behavior in vitro, depending on the pH, of the gadolinium complex and propose a potential structure-activity relationship of the same. Methods: The reactions assisted by microwaves were carried out using a Discover® CoolMate™. Nuclear Magnetic Resonance (NMR) spectra were acquired at 200 and 500 MHz. The Infrared (IR) spectrum of the complex was measured as KBr discs between 400 and 4000cm-1. Electrospray Ionization-High Resolution Mass Spectrometry (ESI-HRMS) was performed on a Bruker microTOF-Q II spectrome-ter. The r1 measurements of the complexes were at 0.2 T, by the inversion recovery method. For the theoretical analysis presented in this work, Hartre- Fock and semiempirical methods were used. Results: In the first place, it was possible to carry out the microwave-assisted synthesis of two intermediaries, with higher yields and in a more environmentally friendly way. Then the variation of r1 was checked as a function of the pH value, obtaining a maximum approximately at pH 6.5. The computer tools allowed to propose the possible structures of the coordination compound obtained. Conclusion: It was found that the variation of the value of r1 as a function of pH is not a product of the decomposition of the complex, but a stage in which at pH values higher than 7 the complex would undergo a displacement of the water molecule located in the ninth coordination position of the Gd+ 3. This behavior could be due to the replacement of the water molecule by the OH group of the ligand.Fil: Rustoy, Eduardo Miguel. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos en Química Orgánica. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Unidad de Microanálisis y Métodos Físicos en Química Orgánica; Argentina. Universidad Nacional de Luján. Departamento de Ciencias Básicas; ArgentinaFil: Raggio, Norberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos en Química Orgánica. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Unidad de Microanálisis y Métodos Físicos en Química Orgánica; ArgentinaBentham Science Publishers2018-10info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/162632Rustoy, Eduardo Miguel; Raggio, Norberto; A non-ionic gadolinium complex whose relaxometric behavior is sensitive to the variation of pH: An experimental and theoretical study on geometry, bonding nature of polyaminocarboxylic ligand and their gadolinium complex; Bentham Science Publishers; Open Chemistry Journal; 5; 1; 10-2018; 102-1181874-8422CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/http://benthamopen.com/FULLTEXT/CHEM-5-102info:eu-repo/semantics/altIdentifier/doi/10.2174/1874842201805010102info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-15T15:44:02Zoai:ri.conicet.gov.ar:11336/162632instacron: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:34982025-10-15 15:44:03.257CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv A non-ionic gadolinium complex whose relaxometric behavior is sensitive to the variation of pH: An experimental and theoretical study on geometry, bonding nature of polyaminocarboxylic ligand and their gadolinium complex
title A non-ionic gadolinium complex whose relaxometric behavior is sensitive to the variation of pH: An experimental and theoretical study on geometry, bonding nature of polyaminocarboxylic ligand and their gadolinium complex
spellingShingle A non-ionic gadolinium complex whose relaxometric behavior is sensitive to the variation of pH: An experimental and theoretical study on geometry, bonding nature of polyaminocarboxylic ligand and their gadolinium complex
Rustoy, Eduardo Miguel
Gadolinium
Magnetic resonance imaging
Macrocyclic ligand
MOPAC/Sparkle
title_short A non-ionic gadolinium complex whose relaxometric behavior is sensitive to the variation of pH: An experimental and theoretical study on geometry, bonding nature of polyaminocarboxylic ligand and their gadolinium complex
title_full A non-ionic gadolinium complex whose relaxometric behavior is sensitive to the variation of pH: An experimental and theoretical study on geometry, bonding nature of polyaminocarboxylic ligand and their gadolinium complex
title_fullStr A non-ionic gadolinium complex whose relaxometric behavior is sensitive to the variation of pH: An experimental and theoretical study on geometry, bonding nature of polyaminocarboxylic ligand and their gadolinium complex
title_full_unstemmed A non-ionic gadolinium complex whose relaxometric behavior is sensitive to the variation of pH: An experimental and theoretical study on geometry, bonding nature of polyaminocarboxylic ligand and their gadolinium complex
title_sort A non-ionic gadolinium complex whose relaxometric behavior is sensitive to the variation of pH: An experimental and theoretical study on geometry, bonding nature of polyaminocarboxylic ligand and their gadolinium complex
dc.creator.none.fl_str_mv Rustoy, Eduardo Miguel
Raggio, Norberto
author Rustoy, Eduardo Miguel
author_facet Rustoy, Eduardo Miguel
Raggio, Norberto
author_role author
author2 Raggio, Norberto
author2_role author
dc.subject.none.fl_str_mv Gadolinium
Magnetic resonance imaging
Macrocyclic ligand
MOPAC/Sparkle
topic Gadolinium
Magnetic resonance imaging
Macrocyclic ligand
MOPAC/Sparkle
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Background: In addition, the contribution of cyclic structure to the stability of lanthanide complexes has been evaluated on different ligand platforms and some indications of their relative stability are now available. Additionally, it is well known that one of the most important factors to design smart contrast is pH. Objectives: The main objectives were to optimize the synthesis of the macrocyclic ligand, using micro-waves. Then study the relaxometric behavior in vitro, depending on the pH, of the gadolinium complex and propose a potential structure-activity relationship of the same. Methods: The reactions assisted by microwaves were carried out using a Discover® CoolMate™. Nuclear Magnetic Resonance (NMR) spectra were acquired at 200 and 500 MHz. The Infrared (IR) spectrum of the complex was measured as KBr discs between 400 and 4000cm-1. Electrospray Ionization-High Resolution Mass Spectrometry (ESI-HRMS) was performed on a Bruker microTOF-Q II spectrome-ter. The r1 measurements of the complexes were at 0.2 T, by the inversion recovery method. For the theoretical analysis presented in this work, Hartre- Fock and semiempirical methods were used. Results: In the first place, it was possible to carry out the microwave-assisted synthesis of two intermediaries, with higher yields and in a more environmentally friendly way. Then the variation of r1 was checked as a function of the pH value, obtaining a maximum approximately at pH 6.5. The computer tools allowed to propose the possible structures of the coordination compound obtained. Conclusion: It was found that the variation of the value of r1 as a function of pH is not a product of the decomposition of the complex, but a stage in which at pH values higher than 7 the complex would undergo a displacement of the water molecule located in the ninth coordination position of the Gd+ 3. This behavior could be due to the replacement of the water molecule by the OH group of the ligand.
Fil: Rustoy, Eduardo Miguel. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos en Química Orgánica. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Unidad de Microanálisis y Métodos Físicos en Química Orgánica; Argentina. Universidad Nacional de Luján. Departamento de Ciencias Básicas; Argentina
Fil: Raggio, Norberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos en Química Orgánica. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Unidad de Microanálisis y Métodos Físicos en Química Orgánica; Argentina
description Background: In addition, the contribution of cyclic structure to the stability of lanthanide complexes has been evaluated on different ligand platforms and some indications of their relative stability are now available. Additionally, it is well known that one of the most important factors to design smart contrast is pH. Objectives: The main objectives were to optimize the synthesis of the macrocyclic ligand, using micro-waves. Then study the relaxometric behavior in vitro, depending on the pH, of the gadolinium complex and propose a potential structure-activity relationship of the same. Methods: The reactions assisted by microwaves were carried out using a Discover® CoolMate™. Nuclear Magnetic Resonance (NMR) spectra were acquired at 200 and 500 MHz. The Infrared (IR) spectrum of the complex was measured as KBr discs between 400 and 4000cm-1. Electrospray Ionization-High Resolution Mass Spectrometry (ESI-HRMS) was performed on a Bruker microTOF-Q II spectrome-ter. The r1 measurements of the complexes were at 0.2 T, by the inversion recovery method. For the theoretical analysis presented in this work, Hartre- Fock and semiempirical methods were used. Results: In the first place, it was possible to carry out the microwave-assisted synthesis of two intermediaries, with higher yields and in a more environmentally friendly way. Then the variation of r1 was checked as a function of the pH value, obtaining a maximum approximately at pH 6.5. The computer tools allowed to propose the possible structures of the coordination compound obtained. Conclusion: It was found that the variation of the value of r1 as a function of pH is not a product of the decomposition of the complex, but a stage in which at pH values higher than 7 the complex would undergo a displacement of the water molecule located in the ninth coordination position of the Gd+ 3. This behavior could be due to the replacement of the water molecule by the OH group of the ligand.
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/11336/162632
Rustoy, Eduardo Miguel; Raggio, Norberto; A non-ionic gadolinium complex whose relaxometric behavior is sensitive to the variation of pH: An experimental and theoretical study on geometry, bonding nature of polyaminocarboxylic ligand and their gadolinium complex; Bentham Science Publishers; Open Chemistry Journal; 5; 1; 10-2018; 102-118
1874-8422
CONICET Digital
CONICET
url http://hdl.handle.net/11336/162632
identifier_str_mv Rustoy, Eduardo Miguel; Raggio, Norberto; A non-ionic gadolinium complex whose relaxometric behavior is sensitive to the variation of pH: An experimental and theoretical study on geometry, bonding nature of polyaminocarboxylic ligand and their gadolinium complex; Bentham Science Publishers; Open Chemistry Journal; 5; 1; 10-2018; 102-118
1874-8422
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://benthamopen.com/FULLTEXT/CHEM-5-102
info:eu-repo/semantics/altIdentifier/doi/10.2174/1874842201805010102
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 Bentham Science Publishers
publisher.none.fl_str_mv Bentham Science Publishers
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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