A comparative photochemical study on the behavior of 3,30 -dihydroxyflavone and its complex with La(III) as generators and quenchers of reactive oxygen species

Autores
Ferrari, Gabriela Verónica; Montaña, Maria Paulina; Dimarco Palencia, Frida Claudia Daniela; Debattista, Nora Beatriz; Pappano, Nora Beatriz; Massad, Walter Alfredo; Garcia, Norman Andino
Año de publicación
2013
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
A 1:1 complex between 3,30-dihydroxyflavone (DHF) and La(III) (DHF?La(III)) is formed in methanolic solution with the relatively high apparent stability constant value of 2.3e6 and a calculated standard entropy change of 88.2 J mol-1 K-1, both at 25 C. The photophysical properties of the complex and the free flavonoid are discussed in comparison to the well known related compound 3-hydroxyflavone. The ligand photogenerates O2(1Dg) by energy transfer from its excited triplet state (3DHF) to dissolved ground state oxygen, with a quantum yield of 0.13. 3DHF is quenched by La(III) with a rate constant close to the diffusion-controlled value. The respective abilities of the free flavonoid and DHF?La(III) as quenchers of the riboflavin-photogenerated reactive oxygen species singlet molecular oxygen (O2(1Dg)) and superoxide radical anion (O 2 ) have been investigated. Both individual compounds were photoirradiated with visible light in the presence of the flavin as the only light-absorbing compound. A detailed kinetics and mechanistic study employing polarographic monitoring of oxygen uptake and time resolved detection of O2(1Dg) phosphorescence indicates that DHF and the complex react with O2(1Dg) and O 2 by a non simple mechanism. The former deactivates O2(1Dg) in a predominant physical fashion, a fact that constitutes a desirable property for antioxidants. It was found that metal chelation greatly enhances the ability of DHF as an overall O2(1Dg) quencher.
Fil: Ferrari, Gabriela Verónica. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico San Luis. Instituto de Química de San Luis; Argentina
Fil: Montaña, Maria Paulina. Universidad Nacional de San Luis. Facultad de Quimica, Bioquimica y Farmacia. Departamento de Quimica. Area de Quimica Fisica; Argentina
Fil: Dimarco Palencia, Frida Claudia Daniela. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico San Luis. Instituto de Química de San Luis; Argentina
Fil: Debattista, Nora Beatriz. Universidad Nacional de San Luis. Facultad de Quimica, Bioquimica y Farmacia. Departamento de Quimica. Area de Quimica Fisica; Argentina
Fil: Pappano, Nora Beatriz. Universidad Nacional de San Luis. Facultad de Quimica, Bioquimica y Farmacia. Departamento de Quimica. Area de Quimica Fisica; Argentina
Fil: Massad, Walter Alfredo. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina
Fil: Garcia, Norman Andino. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina
Materia
3,3'-Dihydroxiflavone-La(Iii) Complex
Photodegradation
Photosensitization
Reactive Oxygen Species
Riboflavin
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/5772
Acceder
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repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling A comparative photochemical study on the behavior of 3,30 -dihydroxyflavone and its complex with La(III) as generators and quenchers of reactive oxygen speciesFerrari, Gabriela VerónicaMontaña, Maria PaulinaDimarco Palencia, Frida Claudia DanielaDebattista, Nora BeatrizPappano, Nora BeatrizMassad, Walter AlfredoGarcia, Norman Andino3,3'-Dihydroxiflavone-La(Iii) ComplexPhotodegradationPhotosensitizationReactive Oxygen SpeciesRiboflavinhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1A 1:1 complex between 3,30-dihydroxyflavone (DHF) and La(III) (DHF?La(III)) is formed in methanolic solution with the relatively high apparent stability constant value of 2.3e6 and a calculated standard entropy change of 88.2 J mol-1 K-1, both at 25 C. The photophysical properties of the complex and the free flavonoid are discussed in comparison to the well known related compound 3-hydroxyflavone. The ligand photogenerates O2(1Dg) by energy transfer from its excited triplet state (3DHF) to dissolved ground state oxygen, with a quantum yield of 0.13. 3DHF is quenched by La(III) with a rate constant close to the diffusion-controlled value. The respective abilities of the free flavonoid and DHF?La(III) as quenchers of the riboflavin-photogenerated reactive oxygen species singlet molecular oxygen (O2(1Dg)) and superoxide radical anion (O 2 ) have been investigated. Both individual compounds were photoirradiated with visible light in the presence of the flavin as the only light-absorbing compound. A detailed kinetics and mechanistic study employing polarographic monitoring of oxygen uptake and time resolved detection of O2(1Dg) phosphorescence indicates that DHF and the complex react with O2(1Dg) and O 2 by a non simple mechanism. The former deactivates O2(1Dg) in a predominant physical fashion, a fact that constitutes a desirable property for antioxidants. It was found that metal chelation greatly enhances the ability of DHF as an overall O2(1Dg) quencher.Fil: Ferrari, Gabriela Verónica. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico San Luis. Instituto de Química de San Luis; ArgentinaFil: Montaña, Maria Paulina. Universidad Nacional de San Luis. Facultad de Quimica, Bioquimica y Farmacia. Departamento de Quimica. Area de Quimica Fisica; ArgentinaFil: Dimarco Palencia, Frida Claudia Daniela. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico San Luis. Instituto de Química de San Luis; ArgentinaFil: Debattista, Nora Beatriz. Universidad Nacional de San Luis. Facultad de Quimica, Bioquimica y Farmacia. Departamento de Quimica. Area de Quimica Fisica; ArgentinaFil: Pappano, Nora Beatriz. Universidad Nacional de San Luis. Facultad de Quimica, Bioquimica y Farmacia. Departamento de Quimica. Area de Quimica Fisica; ArgentinaFil: Massad, Walter Alfredo. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; ArgentinaFil: Garcia, Norman Andino. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; ArgentinaElsevier2013-04info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/vnd.openxmlformats-officedocument.wordprocessingml.documenthttp://hdl.handle.net/11336/5772Ferrari, Gabriela Verónica; Montaña, Maria Paulina; Dimarco Palencia, Frida Claudia Daniela; Debattista, Nora Beatriz; Pappano, Nora Beatriz; et al.; A comparative photochemical study on the behavior of 3,30 -dihydroxyflavone and its complex with La(III) as generators and quenchers of reactive oxygen species; Elsevier; Journal of Photochemistry and Photobiology B: Biology; 124; 4-2013; 42-491011-1344enginfo:eu-repo/semantics/altIdentifier/doi/info:eu-repo/semantics/altIdentifier/doi/10.1016/j.jphotobiol.2013.03.011info:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S1011134413000699info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-nd/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T09:58:42Zoai:ri.conicet.gov.ar:11336/5772instacron: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:34982025-09-03 09:58:43.217CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv A comparative photochemical study on the behavior of 3,30 -dihydroxyflavone and its complex with La(III) as generators and quenchers of reactive oxygen species
title A comparative photochemical study on the behavior of 3,30 -dihydroxyflavone and its complex with La(III) as generators and quenchers of reactive oxygen species
spellingShingle A comparative photochemical study on the behavior of 3,30 -dihydroxyflavone and its complex with La(III) as generators and quenchers of reactive oxygen species
Ferrari, Gabriela Verónica
3,3'-Dihydroxiflavone-La(Iii) Complex
Photodegradation
Photosensitization
Reactive Oxygen Species
Riboflavin
title_short A comparative photochemical study on the behavior of 3,30 -dihydroxyflavone and its complex with La(III) as generators and quenchers of reactive oxygen species
title_full A comparative photochemical study on the behavior of 3,30 -dihydroxyflavone and its complex with La(III) as generators and quenchers of reactive oxygen species
title_fullStr A comparative photochemical study on the behavior of 3,30 -dihydroxyflavone and its complex with La(III) as generators and quenchers of reactive oxygen species
title_full_unstemmed A comparative photochemical study on the behavior of 3,30 -dihydroxyflavone and its complex with La(III) as generators and quenchers of reactive oxygen species
title_sort A comparative photochemical study on the behavior of 3,30 -dihydroxyflavone and its complex with La(III) as generators and quenchers of reactive oxygen species
dc.creator.none.fl_str_mv Ferrari, Gabriela Verónica
Montaña, Maria Paulina
Dimarco Palencia, Frida Claudia Daniela
Debattista, Nora Beatriz
Pappano, Nora Beatriz
Massad, Walter Alfredo
Garcia, Norman Andino
author Ferrari, Gabriela Verónica
author_facet Ferrari, Gabriela Verónica
Montaña, Maria Paulina
Dimarco Palencia, Frida Claudia Daniela
Debattista, Nora Beatriz
Pappano, Nora Beatriz
Massad, Walter Alfredo
Garcia, Norman Andino
author_role author
author2 Montaña, Maria Paulina
Dimarco Palencia, Frida Claudia Daniela
Debattista, Nora Beatriz
Pappano, Nora Beatriz
Massad, Walter Alfredo
Garcia, Norman Andino
author2_role author
author
author
author
author
author
dc.subject.none.fl_str_mv 3,3'-Dihydroxiflavone-La(Iii) Complex
Photodegradation
Photosensitization
Reactive Oxygen Species
Riboflavin
topic 3,3'-Dihydroxiflavone-La(Iii) Complex
Photodegradation
Photosensitization
Reactive Oxygen Species
Riboflavin
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv A 1:1 complex between 3,30-dihydroxyflavone (DHF) and La(III) (DHF?La(III)) is formed in methanolic solution with the relatively high apparent stability constant value of 2.3e6 and a calculated standard entropy change of 88.2 J mol-1 K-1, both at 25 C. The photophysical properties of the complex and the free flavonoid are discussed in comparison to the well known related compound 3-hydroxyflavone. The ligand photogenerates O2(1Dg) by energy transfer from its excited triplet state (3DHF) to dissolved ground state oxygen, with a quantum yield of 0.13. 3DHF is quenched by La(III) with a rate constant close to the diffusion-controlled value. The respective abilities of the free flavonoid and DHF?La(III) as quenchers of the riboflavin-photogenerated reactive oxygen species singlet molecular oxygen (O2(1Dg)) and superoxide radical anion (O 2 ) have been investigated. Both individual compounds were photoirradiated with visible light in the presence of the flavin as the only light-absorbing compound. A detailed kinetics and mechanistic study employing polarographic monitoring of oxygen uptake and time resolved detection of O2(1Dg) phosphorescence indicates that DHF and the complex react with O2(1Dg) and O 2 by a non simple mechanism. The former deactivates O2(1Dg) in a predominant physical fashion, a fact that constitutes a desirable property for antioxidants. It was found that metal chelation greatly enhances the ability of DHF as an overall O2(1Dg) quencher.
Fil: Ferrari, Gabriela Verónica. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico San Luis. Instituto de Química de San Luis; Argentina
Fil: Montaña, Maria Paulina. Universidad Nacional de San Luis. Facultad de Quimica, Bioquimica y Farmacia. Departamento de Quimica. Area de Quimica Fisica; Argentina
Fil: Dimarco Palencia, Frida Claudia Daniela. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico San Luis. Instituto de Química de San Luis; Argentina
Fil: Debattista, Nora Beatriz. Universidad Nacional de San Luis. Facultad de Quimica, Bioquimica y Farmacia. Departamento de Quimica. Area de Quimica Fisica; Argentina
Fil: Pappano, Nora Beatriz. Universidad Nacional de San Luis. Facultad de Quimica, Bioquimica y Farmacia. Departamento de Quimica. Area de Quimica Fisica; Argentina
Fil: Massad, Walter Alfredo. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina
Fil: Garcia, Norman Andino. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina
description A 1:1 complex between 3,30-dihydroxyflavone (DHF) and La(III) (DHF?La(III)) is formed in methanolic solution with the relatively high apparent stability constant value of 2.3e6 and a calculated standard entropy change of 88.2 J mol-1 K-1, both at 25 C. The photophysical properties of the complex and the free flavonoid are discussed in comparison to the well known related compound 3-hydroxyflavone. The ligand photogenerates O2(1Dg) by energy transfer from its excited triplet state (3DHF) to dissolved ground state oxygen, with a quantum yield of 0.13. 3DHF is quenched by La(III) with a rate constant close to the diffusion-controlled value. The respective abilities of the free flavonoid and DHF?La(III) as quenchers of the riboflavin-photogenerated reactive oxygen species singlet molecular oxygen (O2(1Dg)) and superoxide radical anion (O 2 ) have been investigated. Both individual compounds were photoirradiated with visible light in the presence of the flavin as the only light-absorbing compound. A detailed kinetics and mechanistic study employing polarographic monitoring of oxygen uptake and time resolved detection of O2(1Dg) phosphorescence indicates that DHF and the complex react with O2(1Dg) and O 2 by a non simple mechanism. The former deactivates O2(1Dg) in a predominant physical fashion, a fact that constitutes a desirable property for antioxidants. It was found that metal chelation greatly enhances the ability of DHF as an overall O2(1Dg) quencher.
publishDate 2013
dc.date.none.fl_str_mv 2013-04
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/11336/5772
Ferrari, Gabriela Verónica; Montaña, Maria Paulina; Dimarco Palencia, Frida Claudia Daniela; Debattista, Nora Beatriz; Pappano, Nora Beatriz; et al.; A comparative photochemical study on the behavior of 3,30 -dihydroxyflavone and its complex with La(III) as generators and quenchers of reactive oxygen species; Elsevier; Journal of Photochemistry and Photobiology B: Biology; 124; 4-2013; 42-49
1011-1344
url http://hdl.handle.net/11336/5772
identifier_str_mv Ferrari, Gabriela Verónica; Montaña, Maria Paulina; Dimarco Palencia, Frida Claudia Daniela; Debattista, Nora Beatriz; Pappano, Nora Beatriz; et al.; A comparative photochemical study on the behavior of 3,30 -dihydroxyflavone and its complex with La(III) as generators and quenchers of reactive oxygen species; Elsevier; Journal of Photochemistry and Photobiology B: Biology; 124; 4-2013; 42-49
1011-1344
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.jphotobiol.2013.03.011
info:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S1011134413000699
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
application/pdf
application/pdf
application/pdf
application/vnd.openxmlformats-officedocument.wordprocessingml.document
dc.publisher.none.fl_str_mv Elsevier
publisher.none.fl_str_mv Elsevier
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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score 13.13397

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