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dc.contributor.author
Challier, Cecilia
dc.contributor.author
Parramón Jurado, Charis David
dc.contributor.author
Sabini, Maria Carola
dc.contributor.author
Altamirano, Marcela Susana
dc.contributor.author
Criado, Susana Noemi
dc.date.available
2024-09-13T11:09:45Z
dc.date.issued
2024-04
dc.identifier.citation
Challier, Cecilia; Parramón Jurado, Charis David; Sabini, Maria Carola; Altamirano, Marcela Susana; Criado, Susana Noemi; Influence of fluorine atoms on reactive oxygen species-mediated degradation of ophthalmic fluoroquinolones: Kinetic and cytotoxicity studies; Elsevier Science SA; Journal of Photochemistry and Photobiology A: Chemistry; 454; 4-2024; 1-11
dc.identifier.issn
1010-6030
dc.identifier.uri
http://hdl.handle.net/11336/244179
dc.description.abstract
Fluoroquinolones have been attractive broad-spectrum antibiotics for ophthalmic application. However, they have shown phototoxicity as a significant side effect, which is strongly dependent on fluoroquinolone structure and some environment conditions. Beyond their photo-reactivity, an indirect light-induced process deserves to be considered. The photosensitized action of molecules present in the ocular organ, such as Riboflavin, may produce reactive oxygen species (ROS) that could degrade fluoroquinolones. As a consequence, the antibiotics may lose their therapeutic action and/or produce degradation products with harmful effects on health. In this contribution, a kinetic analysis of ROS-mediated degradation processes of ophthalmic quinolones is addressed. Further, considering the evidence towards the structure-modulated phototoxicity, we evaluated theinfluence of structural fluorine atoms on these processes. The non-fluorinated precursor Nalidixic Acid and the fluoroquinolones (Ciprofloxacin, Norfloxacin and Lomefloxacin) were selected for this study. Cytotoxicity experiments in Vero cells were performed in order to investigate the potential toxicity of the ROS-mediated degradation products.Our results suggest that quinolones may be degraded by ROS and these processes are regulated by the ionization state of quinolone and the presence of fluorine atoms in their structure. Both effects increase the electron donor ability of the quinolones, which favor electron transfer processes and increase their reactivity towards species with an electrophilic character. Interestingly, this fluorine-dominated effect has been recently called “fluoromaticity”.Cytotoxicity assays indicated that neither the Qs nor their ROS-mediated degradation products presented injury on Vero cells under the current experimental conditions.
dc.format
application/pdf
dc.language.iso
eng
dc.publisher
Elsevier Science SA
dc.rights
info:eu-repo/semantics/restrictedAccess
dc.rights.uri
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.subject
REACTIVE OXYGEN SPECIES
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FLUOROQUINOLONES
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VITAMIN B2
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DEGRADATION
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CYTOTOXICITY
dc.subject.classification
Medicina Química
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Medicina Básica
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CIENCIAS MÉDICAS Y DE LA SALUD
dc.title
Influence of fluorine atoms on reactive oxygen species-mediated degradation of ophthalmic fluoroquinolones: Kinetic and cytotoxicity studies
dc.type
info:eu-repo/semantics/article
dc.type
info:ar-repo/semantics/artículo
dc.type
info:eu-repo/semantics/publishedVersion
dc.date.updated
2024-09-10T12:56:12Z
dc.journal.volume
454
dc.journal.pagination
1-11
dc.journal.pais
Países Bajos
dc.journal.ciudad
Amsterdam
dc.description.fil
Fil: Challier, Cecilia. Universidad Nacional de Río Cuarto. Instituto para el Desarrollo Agroindustrial y de la Salud. - Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto para el Desarrollo Agroindustrial y de la Salud; Argentina
dc.description.fil
Fil: Parramón Jurado, Charis David. Universidad Nacional de Río Cuarto. Instituto para el Desarrollo Agroindustrial y de la Salud. - Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto para el Desarrollo Agroindustrial y de la Salud; Argentina
dc.description.fil
Fil: Sabini, Maria Carola. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Ciencias de la Salud. Universidad Nacional de Córdoba. Instituto de Investigaciones en Ciencias de la Salud; Argentina
dc.description.fil
Fil: Altamirano, Marcela Susana. Universidad Nacional de Río Cuarto. Instituto para el Desarrollo Agroindustrial y de la Salud. - Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto para el Desarrollo Agroindustrial y de la Salud; Argentina
dc.description.fil
Fil: Criado, Susana Noemi. Universidad Nacional de Río Cuarto. Instituto para el Desarrollo Agroindustrial y de la Salud. - Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto para el Desarrollo Agroindustrial y de la Salud; Argentina
dc.journal.title
Journal of Photochemistry and Photobiology A: Chemistry
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/doi/http://dx.doi.org/10.1016/j.jphotochem.2024.115703
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