Structure-Photoreactivity Relationship of 3-Hydroxyflavone-Based CO-Releasing Molecules
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11110%2F22%3A10444112" target="_blank" >RIV/00216208:11110/22:10444112 - isvavai.cz</a>
Alternative codes found
RIV/00064165:_____/22:10444112
Result on the web
<a href="https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=KEqkoATunH" target="_blank" >https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=KEqkoATunH</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1021/acs.joc.2c00032" target="_blank" >10.1021/acs.joc.2c00032</a>
Alternative languages
Result language
angličtina
Original language name
Structure-Photoreactivity Relationship of 3-Hydroxyflavone-Based CO-Releasing Molecules
Original language description
Carbon monoxide (CO) is an endogenous signaling molecule that regulates diverse physiological processes. The therapeutic potential of CO is hampered by its intrinsic toxicity, and its administration poses a significant challenge. Photoactivatable CO-releasing molecules (photoCORMs) are an excellent tool to overcome the side effects of untargeted CO administration and provide precise spatial and temporal control over its release. Here, we studied the CO release mechanism of a small library of derivatives based on 3-hydroxy-2-phenyl-4H-benzo[g]chromen-4-one (flavonol), previously developed as an efficient photoCORM, by steady-state and femto/nanosecond transient absorption spectroscopies. The main objectives of the work were to explore in detail how to enhance the efficiency of CO photorelease from flavonols, bathochromically shift their absorption bands, control their acid-base properties and solubilities in aqueous solutions, and minimize primary or secondary photochemical side-reactions, such as self-photooxygenation. The best photoCORM performance was achieved by combining substituents, which simultaneously bathochromically shift the chromophore absorption spectrum, enhance the formation of the productive triplet state, and suppress the singlet oxygen production by shortening flavonol triplet-state lifetimes. In addition, the cell toxicity of selected flavonol compounds was analyzed using in vitro hepatic HepG2 cells.
Czech name
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Czech description
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Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10401 - Organic chemistry
Result continuities
Project
<a href="/en/project/GA21-01799S" target="_blank" >GA21-01799S: Flavonoids as a unique class of carbon monoxide photoreleasable molecules</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)
Others
Publication year
2022
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Journal of Organic Chemistry
ISSN
0022-3263
e-ISSN
1520-6904
Volume of the periodical
87
Issue of the periodical within the volume
7
Country of publishing house
US - UNITED STATES
Number of pages
14
Pages from-to
4750-4763
UT code for WoS article
000784116400025
EID of the result in the Scopus database
2-s2.0-85127114706