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Article

Controlling Antimicrobial Activity of Quinolones Using Visible/NIR Light-Activated BODIPY Photocages

1
Departamento de Química, Centro de Investigación en Síntesis Química (CISQ), Universidad de La Rioja, Madre de Dios 53, 26006 Logroño, Spain
2
Área Bioquímica y Biología Molecular, Universidad de La Rioja, Madre de Dios 53, 26006 Logroño, Spain
3
Departamento de Química Analítica, Química Física e Ingeniería Química, Grupo de Reactividad y Estructura Molecular (RESMOL), Universidad de Alcalá, 28805 Alcalá de Henares, Spain
4
Instituto de Investigación Química “Andrés M. del Río” (IQAR), Universidad de Alcalá, 28805 Alcalá de Henares, Spain
5
Department of Chemistry, Iowa State University, Ames, IA 50014, USA
*
Author to whom correspondence should be addressed.
Academic Editors: Giuseppina Sandri, Giulia Suarato and Rossella Castagna
Pharmaceutics 2022, 14(5), 1070; https://doi.org/10.3390/pharmaceutics14051070
Received: 28 March 2022 / Revised: 3 May 2022 / Accepted: 13 May 2022 / Published: 17 May 2022
Controlling the activity of a pharmaceutical agent using light offers improved selectivity, reduction of adverse effects, and decreased environmental build-up. These benefits are especially attractive for antibiotics. Herein, we report a series of photoreleasable quinolones, which can be activated using visible/NIR light (520–800 nm). We have used BODIPY photocages with strong absorption in the visible to protect two different quinolone-based compounds and deactivate their antimicrobial properties. This activity could be recovered upon green or red light irradiation. A comprehensive computational study provides new insight into the reaction mechanism, revealing the relevance of considering explicit solvent molecules. The triplet excited state is populated and the photodissociation is assisted by the solvent. The light-controlled activity of these compounds has been assessed on a quinolone-susceptible E. coli strain. Up to a 32-fold change in the antimicrobial activity was measured. View Full-Text
Keywords: photodrugs; quinolones; BODIPYs; antibiotics; photoprotecting groups; photocages photodrugs; quinolones; BODIPYs; antibiotics; photoprotecting groups; photocages
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MDPI and ACS Style

Contreras-García, E.; Lozano, C.; García-Iriepa, C.; Marazzi, M.; Winter, A.H.; Torres, C.; Sampedro, D. Controlling Antimicrobial Activity of Quinolones Using Visible/NIR Light-Activated BODIPY Photocages. Pharmaceutics 2022, 14, 1070. https://doi.org/10.3390/pharmaceutics14051070

AMA Style

Contreras-García E, Lozano C, García-Iriepa C, Marazzi M, Winter AH, Torres C, Sampedro D. Controlling Antimicrobial Activity of Quinolones Using Visible/NIR Light-Activated BODIPY Photocages. Pharmaceutics. 2022; 14(5):1070. https://doi.org/10.3390/pharmaceutics14051070

Chicago/Turabian Style

Contreras-García, Elena, Carmen Lozano, Cristina García-Iriepa, Marco Marazzi, Arthur H. Winter, Carmen Torres, and Diego Sampedro. 2022. "Controlling Antimicrobial Activity of Quinolones Using Visible/NIR Light-Activated BODIPY Photocages" Pharmaceutics 14, no. 5: 1070. https://doi.org/10.3390/pharmaceutics14051070

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