A kinetic study on the inhibitory action of sympathomimetic drugs towards photogenerated oxygen active species: The case of phenylephrine

Autores
Massad, Walter Alfredo; Bertolotti, Sonia Graciela; Romero, Mario Raul; Garcia, Norman Andino
Año de publicación
2005
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Kinetics and mechanism of the aerobic Riboflavin (Rf, vitamin B2) sensitized photodegradation of Phenylephrine (Phen), a phenolamine belonging to the sympathomimetic drugs family, has been studied in water, employing continuous photolysis, polarographic detection of oxygen uptake, steady-state and time-resolved fluorescence spectroscopy, time-resolved IR-phosphorescence and laser flash photolysis. Results indicate the formation of a weak dark complex Rf–Phen, with an apparent association constant of 5.5 ± 0.5 M 1 , only detectable at Phen concentrations much higher than those employed in the photochemical experiments. Under irradiation, an intricate mechanism of competitive reactions operates. Phen quenches excited singlet and triplet states of Rf, with rate constants of 3.33 ± 0.08 and 1.60 ± 0.03 · 109 M 1 s 1 , respectively. With the sympathomimetic drug in a concentration similar to that of dissolved molecular oxygen in water, Phen and oxygen competitively quench triplet excited Rf, generating superoxide radical anion and singlet molecular oxygen (O2( 1 Dg)) by processes initiated by electron- and energy-transfer mechanisms respectively. As a global result, the photodegradation of the vitamin, a known process taking place from its excited triplet state, is retarded, whereas the phenolamine, practically unreactive towards these oxidative species, behaves as a highly efficient physical deactivator of O2( 1 Dg). The phenolamine structure in Phen appears as an excellent scavenger of activated oxygen species, comparatively superior, in kinetic terms, to some commercial phenolic antioxidants.
Fil: Massad, Walter Alfredo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; Argentina. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina
Fil: Bertolotti, Sonia Graciela. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; Argentina
Fil: Romero, Mario Raul. Universidad Nacional de Rio Cuarto. Facultad de Cs.exactas Fisicoquímicas y Naturales. Departamento de Física; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; Argentina
Fil: Garcia, Norman Andino. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; Argentina
Materia
Phenylephrine
Photo-oxidation
Riboflavin
Singlet molecular oxygen
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:11336/240769
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/240769
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling A kinetic study on the inhibitory action of sympathomimetic drugs towards photogenerated oxygen active species: The case of phenylephrineMassad, Walter AlfredoBertolotti, Sonia GracielaRomero, Mario RaulGarcia, Norman AndinoPhenylephrinePhoto-oxidationRiboflavinSinglet molecular oxygenhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Kinetics and mechanism of the aerobic Riboflavin (Rf, vitamin B2) sensitized photodegradation of Phenylephrine (Phen), a phenolamine belonging to the sympathomimetic drugs family, has been studied in water, employing continuous photolysis, polarographic detection of oxygen uptake, steady-state and time-resolved fluorescence spectroscopy, time-resolved IR-phosphorescence and laser flash photolysis. Results indicate the formation of a weak dark complex Rf–Phen, with an apparent association constant of 5.5 ± 0.5 M 1 , only detectable at Phen concentrations much higher than those employed in the photochemical experiments. Under irradiation, an intricate mechanism of competitive reactions operates. Phen quenches excited singlet and triplet states of Rf, with rate constants of 3.33 ± 0.08 and 1.60 ± 0.03 · 109 M 1 s 1 , respectively. With the sympathomimetic drug in a concentration similar to that of dissolved molecular oxygen in water, Phen and oxygen competitively quench triplet excited Rf, generating superoxide radical anion and singlet molecular oxygen (O2( 1 Dg)) by processes initiated by electron- and energy-transfer mechanisms respectively. As a global result, the photodegradation of the vitamin, a known process taking place from its excited triplet state, is retarded, whereas the phenolamine, practically unreactive towards these oxidative species, behaves as a highly efficient physical deactivator of O2( 1 Dg). The phenolamine structure in Phen appears as an excellent scavenger of activated oxygen species, comparatively superior, in kinetic terms, to some commercial phenolic antioxidants.Fil: Massad, Walter Alfredo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; Argentina. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; ArgentinaFil: Bertolotti, Sonia Graciela. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; ArgentinaFil: Romero, Mario Raul. Universidad Nacional de Rio Cuarto. Facultad de Cs.exactas Fisicoquímicas y Naturales. Departamento de Física; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; ArgentinaFil: Garcia, Norman Andino. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; ArgentinaElsevier Science SA2005-12info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/240769Massad, Walter Alfredo; Bertolotti, Sonia Graciela; Romero, Mario Raul; Garcia, Norman Andino; A kinetic study on the inhibitory action of sympathomimetic drugs towards photogenerated oxygen active species: The case of phenylephrine; Elsevier Science SA; Journal of Photochemistry and Photobiology B: Biology; 80; 2; 12-2005; 130-1381011-1344CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S1011134405000801info:eu-repo/semantics/altIdentifier/doi/10.1016/j.jphotobiol.2005.03.010info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T09:58:07Zoai:ri.conicet.gov.ar:11336/240769instacron: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 09:58:07.439CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv A kinetic study on the inhibitory action of sympathomimetic drugs towards photogenerated oxygen active species: The case of phenylephrine
title A kinetic study on the inhibitory action of sympathomimetic drugs towards photogenerated oxygen active species: The case of phenylephrine
spellingShingle A kinetic study on the inhibitory action of sympathomimetic drugs towards photogenerated oxygen active species: The case of phenylephrine
Massad, Walter Alfredo
Phenylephrine
Photo-oxidation
Riboflavin
Singlet molecular oxygen
title_short A kinetic study on the inhibitory action of sympathomimetic drugs towards photogenerated oxygen active species: The case of phenylephrine
title_full A kinetic study on the inhibitory action of sympathomimetic drugs towards photogenerated oxygen active species: The case of phenylephrine
title_fullStr A kinetic study on the inhibitory action of sympathomimetic drugs towards photogenerated oxygen active species: The case of phenylephrine
title_full_unstemmed A kinetic study on the inhibitory action of sympathomimetic drugs towards photogenerated oxygen active species: The case of phenylephrine
title_sort A kinetic study on the inhibitory action of sympathomimetic drugs towards photogenerated oxygen active species: The case of phenylephrine
dc.creator.none.fl_str_mv Massad, Walter Alfredo
Bertolotti, Sonia Graciela
Romero, Mario Raul
Garcia, Norman Andino
author Massad, Walter Alfredo
author_facet Massad, Walter Alfredo
Bertolotti, Sonia Graciela
Romero, Mario Raul
Garcia, Norman Andino
author_role author
author2 Bertolotti, Sonia Graciela
Romero, Mario Raul
Garcia, Norman Andino
author2_role author
author
author
dc.subject.none.fl_str_mv Phenylephrine
Photo-oxidation
Riboflavin
Singlet molecular oxygen
topic Phenylephrine
Photo-oxidation
Riboflavin
Singlet molecular oxygen
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Kinetics and mechanism of the aerobic Riboflavin (Rf, vitamin B2) sensitized photodegradation of Phenylephrine (Phen), a phenolamine belonging to the sympathomimetic drugs family, has been studied in water, employing continuous photolysis, polarographic detection of oxygen uptake, steady-state and time-resolved fluorescence spectroscopy, time-resolved IR-phosphorescence and laser flash photolysis. Results indicate the formation of a weak dark complex Rf–Phen, with an apparent association constant of 5.5 ± 0.5 M 1 , only detectable at Phen concentrations much higher than those employed in the photochemical experiments. Under irradiation, an intricate mechanism of competitive reactions operates. Phen quenches excited singlet and triplet states of Rf, with rate constants of 3.33 ± 0.08 and 1.60 ± 0.03 · 109 M 1 s 1 , respectively. With the sympathomimetic drug in a concentration similar to that of dissolved molecular oxygen in water, Phen and oxygen competitively quench triplet excited Rf, generating superoxide radical anion and singlet molecular oxygen (O2( 1 Dg)) by processes initiated by electron- and energy-transfer mechanisms respectively. As a global result, the photodegradation of the vitamin, a known process taking place from its excited triplet state, is retarded, whereas the phenolamine, practically unreactive towards these oxidative species, behaves as a highly efficient physical deactivator of O2( 1 Dg). The phenolamine structure in Phen appears as an excellent scavenger of activated oxygen species, comparatively superior, in kinetic terms, to some commercial phenolic antioxidants.
Fil: Massad, Walter Alfredo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; Argentina. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina
Fil: Bertolotti, Sonia Graciela. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; Argentina
Fil: Romero, Mario Raul. Universidad Nacional de Rio Cuarto. Facultad de Cs.exactas Fisicoquímicas y Naturales. Departamento de Física; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; Argentina
Fil: Garcia, Norman Andino. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; Argentina
description Kinetics and mechanism of the aerobic Riboflavin (Rf, vitamin B2) sensitized photodegradation of Phenylephrine (Phen), a phenolamine belonging to the sympathomimetic drugs family, has been studied in water, employing continuous photolysis, polarographic detection of oxygen uptake, steady-state and time-resolved fluorescence spectroscopy, time-resolved IR-phosphorescence and laser flash photolysis. Results indicate the formation of a weak dark complex Rf–Phen, with an apparent association constant of 5.5 ± 0.5 M 1 , only detectable at Phen concentrations much higher than those employed in the photochemical experiments. Under irradiation, an intricate mechanism of competitive reactions operates. Phen quenches excited singlet and triplet states of Rf, with rate constants of 3.33 ± 0.08 and 1.60 ± 0.03 · 109 M 1 s 1 , respectively. With the sympathomimetic drug in a concentration similar to that of dissolved molecular oxygen in water, Phen and oxygen competitively quench triplet excited Rf, generating superoxide radical anion and singlet molecular oxygen (O2( 1 Dg)) by processes initiated by electron- and energy-transfer mechanisms respectively. As a global result, the photodegradation of the vitamin, a known process taking place from its excited triplet state, is retarded, whereas the phenolamine, practically unreactive towards these oxidative species, behaves as a highly efficient physical deactivator of O2( 1 Dg). The phenolamine structure in Phen appears as an excellent scavenger of activated oxygen species, comparatively superior, in kinetic terms, to some commercial phenolic antioxidants.
publishDate 2005
dc.date.none.fl_str_mv 2005-12
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/11336/240769
Massad, Walter Alfredo; Bertolotti, Sonia Graciela; Romero, Mario Raul; Garcia, Norman Andino; A kinetic study on the inhibitory action of sympathomimetic drugs towards photogenerated oxygen active species: The case of phenylephrine; Elsevier Science SA; Journal of Photochemistry and Photobiology B: Biology; 80; 2; 12-2005; 130-138
1011-1344
CONICET Digital
CONICET
url http://hdl.handle.net/11336/240769
identifier_str_mv Massad, Walter Alfredo; Bertolotti, Sonia Graciela; Romero, Mario Raul; Garcia, Norman Andino; A kinetic study on the inhibitory action of sympathomimetic drugs towards photogenerated oxygen active species: The case of phenylephrine; Elsevier Science SA; Journal of Photochemistry and Photobiology B: Biology; 80; 2; 12-2005; 130-138
1011-1344
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S1011134405000801
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.jphotobiol.2005.03.010
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
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Elsevier Science SA
publisher.none.fl_str_mv Elsevier Science SA
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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