Abstract
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.
Highlights
Intersystem crossing efficiency and singlet oxygen production: As the photochemical release of Carbon monoxide (CO) from meso-carboxy BODIPYs was reported to occur from the triplet-excited state [36], we evaluated the intersystem crossing (ISC) efficiency (ΦISC ) by quantitative analysis of the transient optical density [50,51] using nanosecond transient absorption (TA) spectroscopy
High-resolution mass spectra (HRMS) were recorded on an Agilent 6224 Accurate-Mass obtained in CDCl3, CD2Cl2, DMSO-d5, or CD3OD on 75, 125, 30 eters (Bruker AVANCE III (300 MHz) and AVANCE III HD (50 chemical shifts are reported in ppm relative to the tetramethyls ppm) using the residual solvent signal as an internal reference are reported in ppm relative to the solvent signal as 246 an internal mass spectra (HRMS) were recorded on an Agilent 6224 Accu strument using ESI or APCl techniques
We report the synthesis and photophysical and photochemical properties of a series of 2,6-substituted meso-carboxy BODIPY derivatives designed as photoactivatable
Summary
Synthetic methods are available to fine-tune the dye structure to achieve the required spectroscopic and photophysical characteristics [9,10,11,12]. The intersystem crossing (ISC) efficiency in most BODIPY fluorophores is usually small, which precludes their use as triplet photosensitizers [13]. Specific structural modifications, such as the introduction of iodine or bromine atoms as core substituents [8,14,15], can enhance
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