Controlling Antimicrobial Activity of Quinolones Using Visible/NIR Light-Activated BODIPY Photocages
Elena Contreras-García,
Carmen Lozano,
Cristina García-Iriepa,
Marco Marazzi,
Arthur H. Winter,
Carmen Torres,
Diego Sampedro
Affiliations
Elena Contreras-García
Departamento de Química, Centro de Investigación en Síntesis Química (CISQ), Universidad de La Rioja, Madre de Dios 53, 26006 Logroño, Spain
Carmen Lozano
Área Bioquímica y Biología Molecular, Universidad de La Rioja, Madre de Dios 53, 26006 Logroño, Spain
Cristina García-Iriepa
Departamento de Química Analítica, Química Física e Ingeniería Química, Grupo de Reactividad y Estructura Molecular (RESMOL), Universidad de Alcalá, 28805 Alcalá de Henares, Spain
Marco Marazzi
Departamento de Química Analítica, Química Física e Ingeniería Química, Grupo de Reactividad y Estructura Molecular (RESMOL), Universidad de Alcalá, 28805 Alcalá de Henares, Spain
Arthur H. Winter
Department of Chemistry, Iowa State University, Ames, IA 50014, USA
Carmen Torres
Área Bioquímica y Biología Molecular, Universidad de La Rioja, Madre de Dios 53, 26006 Logroño, Spain
Diego Sampedro
Departamento de Química, Centro de Investigación en Síntesis Química (CISQ), Universidad de La Rioja, Madre de Dios 53, 26006 Logroño, Spain
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.