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

• Main Authors: Esther M. Sánchez-Carnerero, Marina Russo, Andreas Jakob, Lucie Muchová, Libor Vítek, Petr Klán
• Format: Article
• Language: English
• Published: MDPI AG 2021-02-01
• Series: Chemistry
• Subjects: BODIPY; photochemistry; carbon monoxide; photorelease; carbon monoxide-releasing molecules
• Online Access: https://www.mdpi.com/2624-8549/3/1/18
• ISSN: 2624-8549

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 <i>meso</i>-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.