Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 26, Issue 58, Pages 13184-13190Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202003272
Keywords
CO release; cyanine; near-infrared light; photoCORM; photorelease
Categories
Funding
- European Union's Horizon 2020 Research and Innovation Program under the Marie Skodowska-Curie program
- South Moravian Region [665860, 6SA17811]
- Czech Ministry of Health [RVO-VFN64165]
- Czech Ministry of Education, Youth and Sports [CZ.02.1.01/0.0/0.0/17043/0009632]
- EU H2020 [857560]
- RECETOX research infrastructure [LM2018121]
- MEYS CR [LM2018127]
- Czech Science Foundation [GA18-12477S]
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Carbon monoxide (CO) is an endogenous signaling molecule that controls a number of physiological processes. To circumvent the inherent toxicity of CO, light-activated CO-releasing molecules (photoCORMs) have emerged as an alternative for its administration. However, their wider application requires photoactivation using biologically benign visible and near-infrared (NIR) light. In this work, a strategy to access such photoCORMs by fusing two CO-releasing flavonol moieties with a NIR-absorbing cyanine dye is presented. These hybrids liberate two molecules of CO in high chemical yields upon activation with NIR light up to 820 nm and exhibit excellent uncaging cross-sections, which surpass the state-of-the-art by two orders of magnitude. Furthermore, the biocompatibility and applicability of the system in vitro and in vivo are demonstrated, and a mechanism of CO release is proposed. It is hoped that this strategy will stimulate the discovery of new classes of photoCORMs and accelerate the translation of CO-based phototherapy into practice.
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