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Article

Effects of Substituents on Photophysical and CO-Photoreleasing Properties of 2,6-Substituted meso-Carboxy BODIPY Derivatives

1
Department of Chemistry and RECETOX, Faculty of Science, Masaryk University, Kamenice 5, 625 00 Brno, Czech Republic
2
Institute of Medical Biochemistry and Laboratory Diagnostics, General University Hospital and 1st Faculty of Medicine, Charles University, Kateřinská 32, 121 08 Praha 2, Czech Republic
3
4th Department of Internal Medicine, General University Hospital, and 1st Faculty of Medicine, Charles University, Kateřinská 32, 121 08 Praha 2, Czech Republic
*
Author to whom correspondence should be addressed.
Dedicated to Prof. Josef Michl on the occasion of his 80th birthday.
These authors contributed equally to this work.
Chemistry 2021, 3(1), 238-255; https://doi.org/10.3390/chemistry3010018
Received: 10 December 2020 / Revised: 20 January 2021 / Accepted: 4 February 2021 / Published: 9 February 2021
(This article belongs to the Special Issue A Special Issue in Honor of Professor Josef Michl)
Carbon monoxide (CO) is an endogenously produced signaling molecule involved in the control of a vast array of physiological processes. One of the strategies to administer therapeutic amounts of CO is the precise spatial and temporal control over its release from photoactivatable CO-releasing molecules (photoCORMs). Here we present the synthesis and photophysical and photochemical properties of a small library of meso-carboxy BODIPY derivatives bearing different substituents at positions 2 and 6. We show that the nature of substituents has a major impact on both their photophysics and the efficiency of CO photorelease. CO was found to be efficiently released from π-extended 2,6-arylethynyl BODIPY derivatives possessing absorption spectra shifted to a more biologically desirable wavelength range. Selected photoCORMs were subjected to in vitro experiments that did not reveal any serious toxic effects, suggesting their potential for further biological research. View Full-Text
Keywords: BODIPY; photochemistry; carbon monoxide; photorelease; carbon monoxide-releasing molecules BODIPY; photochemistry; carbon monoxide; photorelease; carbon monoxide-releasing molecules
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MDPI and ACS Style

Sánchez-Carnerero, E.M.; Russo, M.; Jakob, A.; Muchová, L.; Vítek, L.; Klán, P. Effects of Substituents on Photophysical and CO-Photoreleasing Properties of 2,6-Substituted meso-Carboxy BODIPY Derivatives. Chemistry 2021, 3, 238-255. https://doi.org/10.3390/chemistry3010018

AMA Style

Sánchez-Carnerero EM, Russo M, Jakob A, Muchová L, Vítek L, Klán P. Effects of Substituents on Photophysical and CO-Photoreleasing Properties of 2,6-Substituted meso-Carboxy BODIPY Derivatives. Chemistry. 2021; 3(1):238-255. https://doi.org/10.3390/chemistry3010018

Chicago/Turabian Style

Sánchez-Carnerero, Esther M.; Russo, Marina; Jakob, Andreas; Muchová, Lucie; Vítek, Libor; Klán, Petr. 2021. "Effects of Substituents on Photophysical and CO-Photoreleasing Properties of 2,6-Substituted meso-Carboxy BODIPY Derivatives" Chemistry 3, no. 1: 238-255. https://doi.org/10.3390/chemistry3010018

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