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

Date
2022-05-17
Authors
Contreras-García, Elena
Lozano, Carmen
García-Iriepa, Cristina
Marazzi, Marco
Winter, Arthur
Torres, Carmen
Sampedro, Diego
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Chemistry
Abstract
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.
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This article is published as Contreras-García, Elena, Carmen Lozano, Cristina García-Iriepa, Marco Marazzi, Arthur H. Winter, Carmen Torres, and Diego Sampedro. "Controlling Antimicrobial Activity of Quinolones Using Visible/NIR Light-Activated BODIPY Photocages." Pharmaceutics 14, no. 5 (2022): 1070. DOI: 10.3390/pharmaceutics14051070. Copyright 2022 by the authors. Attribution 4.0 International (CC BY 4.0). Posted with permission.
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