期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 87, 期 7, 页码 4750-4763出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.2c00032
关键词
-
资金
- Czech Science Foundation [GA21-01799S]
- Czech Ministry of Education, Youth and Sports [CZ.02.1.01/0.0/0.0/17_043/0009632]
- RECETOX research infrastructure [LM2018121]
- Ministry of Health, Czech Republic
Carbon monoxide (CO) is an endogenous signaling molecule that regulates physiological processes. Researchers have developed photoactivatable CO-releasing molecules (photoCORMs) to overcome the toxicity of CO and provide precise control over its release. By introducing specific substituents, the efficiency of CO release can be enhanced and side effects can be minimized.
Carbon monoxide (CO) is an endogenous signalingmolecule that regulates diverse physiological processes. The therapeuticpotential of CO is hampered by its intrinsic toxicity, and its administrationposes a significant challenge. Photoactivatable CO-releasing molecules(photoCORMs) are an excellent tool to overcome the side effects ofuntargeted CO administration and provide precise spatial and temporalcontrol over its release. Here, we studied the CO release mechanism of asmall library of derivatives based on 3-hydroxy-2-phenyl-4H-benzo[g]-chromen-4-one (flavonol), previously developed as an efficient photo-CORM, by steady-state and femto/nanosecond transient absorptionspectroscopies. The main objectives of the work were to explore in detailhow to enhance the efficiency of CO photorelease fromflavonols,bathochromically shift their absorption bands, control their acid-baseproperties and solubilities in aqueous solutions, and minimize primary orsecondary photochemical side-reactions, such as self-photooxygenation. The best photoCORM performance was achieved bycombining substituents, which simultaneously bathochromically shift the chromophore absorption spectrum, enhance the formationof the productive triplet state, and suppress the singlet oxygen production by shorteningflavonol triplet-state lifetimes. In addition,the cell toxicity of selectedflavonol compounds was analyzed using in vitro hepatic HepG2 cells.
作者
我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。
推荐
暂无数据