Visible light-mediated photodegradation of imidazoline drugs in the presence of Riboflavin: Possible undesired effects on imidazoline-based eye drops

Autores
Challier, Cecilia; Martire, Daniel Osvaldo; Garcia, Norman Andino; Criado, Susana Noemi
Año de publicación
2017
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The imidazoline-based ophthalmic drugs oxymetazoline and xylometazoline are widely used as ocular decongestants in pharmaceutical preparations. In this paper, the degradation of these drugs and the model compound 2-methyl-2-imidazoline, was studied in the presence of the vitamin B2 (Riboflavin) and visible light. The photogenerated Riboflavin electronically excited triplet state interacts with oxymetazoline and xylometazoline and as a result different free radicals and reactive oxygen species are produced. These species interact with the drugs in further steps, producing their degradation. Oxymetazoline is more easily photo-degradable than xylometazoline towards reactive oxygen species. Particularly, oxymetazoline reacts four orders of magnitude faster than xylometazoline with singlet oxygen. This fact is due to the presence of an OH-group in the benzene ring of oxymetazoline, increasing the oxidability of the drug. The degradation of xylometazoline by reactive oxygen species becomes more important as its concentration increases. This finding should warn against long-time treatments with xylometazoline. An eventual local accumulation of the drug may cause adverse effects in the ocular organ in the presence of Riboflavin. In parallel, the present results advise for a moderate precaution in relation to light exposure after topical application of the imidazoline derivatives oxymetazoline and xylometazoline.
Fil: Challier, Cecilia. 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: Martire, Daniel Osvaldo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas; 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
Fil: Criado, Susana Noemi. 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
DEGRADATION
IMIDAZOLINE DERIVATIVES
OPHTHALMIC DRUGS
REACTIVE OXYGEN SPECIES
RIBOFLAVIN
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:11336/97460
Acceder
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network_name_str CONICET Digital (CONICET)
spelling Visible light-mediated photodegradation of imidazoline drugs in the presence of Riboflavin: Possible undesired effects on imidazoline-based eye dropsChallier, CeciliaMartire, Daniel OsvaldoGarcia, Norman AndinoCriado, Susana NoemiDEGRADATIONIMIDAZOLINE DERIVATIVESOPHTHALMIC DRUGSREACTIVE OXYGEN SPECIESRIBOFLAVINhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The imidazoline-based ophthalmic drugs oxymetazoline and xylometazoline are widely used as ocular decongestants in pharmaceutical preparations. In this paper, the degradation of these drugs and the model compound 2-methyl-2-imidazoline, was studied in the presence of the vitamin B2 (Riboflavin) and visible light. The photogenerated Riboflavin electronically excited triplet state interacts with oxymetazoline and xylometazoline and as a result different free radicals and reactive oxygen species are produced. These species interact with the drugs in further steps, producing their degradation. Oxymetazoline is more easily photo-degradable than xylometazoline towards reactive oxygen species. Particularly, oxymetazoline reacts four orders of magnitude faster than xylometazoline with singlet oxygen. This fact is due to the presence of an OH-group in the benzene ring of oxymetazoline, increasing the oxidability of the drug. The degradation of xylometazoline by reactive oxygen species becomes more important as its concentration increases. This finding should warn against long-time treatments with xylometazoline. An eventual local accumulation of the drug may cause adverse effects in the ocular organ in the presence of Riboflavin. In parallel, the present results advise for a moderate precaution in relation to light exposure after topical application of the imidazoline derivatives oxymetazoline and xylometazoline.Fil: Challier, Cecilia. 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: Martire, Daniel Osvaldo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas; 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; ArgentinaFil: Criado, Susana Noemi. 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 Sa2017-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/97460Challier, Cecilia; Martire, Daniel Osvaldo; Garcia, Norman Andino; Criado, Susana Noemi; Visible light-mediated photodegradation of imidazoline drugs in the presence of Riboflavin: Possible undesired effects on imidazoline-based eye drops; Elsevier Science Sa; Journal of Photochemistry and Photobiology A: Chemistry; 332; 1-2017; 399-4051010-6030CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1016/j.jphotochem.2016.09.009info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-15T14:38:39Zoai:ri.conicet.gov.ar:11336/97460instacron: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 14:38:39.831CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Visible light-mediated photodegradation of imidazoline drugs in the presence of Riboflavin: Possible undesired effects on imidazoline-based eye drops
title Visible light-mediated photodegradation of imidazoline drugs in the presence of Riboflavin: Possible undesired effects on imidazoline-based eye drops
spellingShingle Visible light-mediated photodegradation of imidazoline drugs in the presence of Riboflavin: Possible undesired effects on imidazoline-based eye drops
Challier, Cecilia
DEGRADATION
IMIDAZOLINE DERIVATIVES
OPHTHALMIC DRUGS
REACTIVE OXYGEN SPECIES
RIBOFLAVIN
title_short Visible light-mediated photodegradation of imidazoline drugs in the presence of Riboflavin: Possible undesired effects on imidazoline-based eye drops
title_full Visible light-mediated photodegradation of imidazoline drugs in the presence of Riboflavin: Possible undesired effects on imidazoline-based eye drops
title_fullStr Visible light-mediated photodegradation of imidazoline drugs in the presence of Riboflavin: Possible undesired effects on imidazoline-based eye drops
title_full_unstemmed Visible light-mediated photodegradation of imidazoline drugs in the presence of Riboflavin: Possible undesired effects on imidazoline-based eye drops
title_sort Visible light-mediated photodegradation of imidazoline drugs in the presence of Riboflavin: Possible undesired effects on imidazoline-based eye drops
dc.creator.none.fl_str_mv Challier, Cecilia
Martire, Daniel Osvaldo
Garcia, Norman Andino
Criado, Susana Noemi
author Challier, Cecilia
author_facet Challier, Cecilia
Martire, Daniel Osvaldo
Garcia, Norman Andino
Criado, Susana Noemi
author_role author
author2 Martire, Daniel Osvaldo
Garcia, Norman Andino
Criado, Susana Noemi
author2_role author
author
author
dc.subject.none.fl_str_mv DEGRADATION
IMIDAZOLINE DERIVATIVES
OPHTHALMIC DRUGS
REACTIVE OXYGEN SPECIES
RIBOFLAVIN
topic DEGRADATION
IMIDAZOLINE DERIVATIVES
OPHTHALMIC DRUGS
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 The imidazoline-based ophthalmic drugs oxymetazoline and xylometazoline are widely used as ocular decongestants in pharmaceutical preparations. In this paper, the degradation of these drugs and the model compound 2-methyl-2-imidazoline, was studied in the presence of the vitamin B2 (Riboflavin) and visible light. The photogenerated Riboflavin electronically excited triplet state interacts with oxymetazoline and xylometazoline and as a result different free radicals and reactive oxygen species are produced. These species interact with the drugs in further steps, producing their degradation. Oxymetazoline is more easily photo-degradable than xylometazoline towards reactive oxygen species. Particularly, oxymetazoline reacts four orders of magnitude faster than xylometazoline with singlet oxygen. This fact is due to the presence of an OH-group in the benzene ring of oxymetazoline, increasing the oxidability of the drug. The degradation of xylometazoline by reactive oxygen species becomes more important as its concentration increases. This finding should warn against long-time treatments with xylometazoline. An eventual local accumulation of the drug may cause adverse effects in the ocular organ in the presence of Riboflavin. In parallel, the present results advise for a moderate precaution in relation to light exposure after topical application of the imidazoline derivatives oxymetazoline and xylometazoline.
Fil: Challier, Cecilia. 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: Martire, Daniel Osvaldo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas; 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
Fil: Criado, Susana Noemi. 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 The imidazoline-based ophthalmic drugs oxymetazoline and xylometazoline are widely used as ocular decongestants in pharmaceutical preparations. In this paper, the degradation of these drugs and the model compound 2-methyl-2-imidazoline, was studied in the presence of the vitamin B2 (Riboflavin) and visible light. The photogenerated Riboflavin electronically excited triplet state interacts with oxymetazoline and xylometazoline and as a result different free radicals and reactive oxygen species are produced. These species interact with the drugs in further steps, producing their degradation. Oxymetazoline is more easily photo-degradable than xylometazoline towards reactive oxygen species. Particularly, oxymetazoline reacts four orders of magnitude faster than xylometazoline with singlet oxygen. This fact is due to the presence of an OH-group in the benzene ring of oxymetazoline, increasing the oxidability of the drug. The degradation of xylometazoline by reactive oxygen species becomes more important as its concentration increases. This finding should warn against long-time treatments with xylometazoline. An eventual local accumulation of the drug may cause adverse effects in the ocular organ in the presence of Riboflavin. In parallel, the present results advise for a moderate precaution in relation to light exposure after topical application of the imidazoline derivatives oxymetazoline and xylometazoline.
publishDate 2017
dc.date.none.fl_str_mv 2017-01
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/11336/97460
Challier, Cecilia; Martire, Daniel Osvaldo; Garcia, Norman Andino; Criado, Susana Noemi; Visible light-mediated photodegradation of imidazoline drugs in the presence of Riboflavin: Possible undesired effects on imidazoline-based eye drops; Elsevier Science Sa; Journal of Photochemistry and Photobiology A: Chemistry; 332; 1-2017; 399-405
1010-6030
CONICET Digital
CONICET
url http://hdl.handle.net/11336/97460
identifier_str_mv Challier, Cecilia; Martire, Daniel Osvaldo; Garcia, Norman Andino; Criado, Susana Noemi; Visible light-mediated photodegradation of imidazoline drugs in the presence of Riboflavin: Possible undesired effects on imidazoline-based eye drops; Elsevier Science Sa; Journal of Photochemistry and Photobiology A: Chemistry; 332; 1-2017; 399-405
1010-6030
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1016/j.jphotochem.2016.09.009
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
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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