Structure-Photoreactivity Relationship of
3-Hydroxyflavone-BasedCO-Releasing Molecules

J 2022

Structure-Photoreactivity Relationship of 3-Hydroxyflavone-BasedCO-Releasing Molecules

RUSSO, Marina; Vojtěch OREL; Peter ŠTACKO; Mária ŠRANKOVÁ; Lucie ŠRANKOVÁ et al.

Základní údaje

Originální název

Structure-Photoreactivity Relationship of 3-Hydroxyflavone-BasedCO-Releasing Molecules

Autoři

RUSSO, Marina; Vojtěch OREL; Peter ŠTACKO; Mária ŠRANKOVÁ; Lucie ŠRANKOVÁ; Libor ŠRANKOVÁ a Petr KLÁN

Vydání

Journal of Organic Chemistry, American Chemical Society, 2022, 0022-3263

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

10401 Organic chemistry

Stát vydavatele

Spojené státy

Utajení

není předmětem státního či obchodního tajemství

Odkazy

URL

Impakt faktor

Impact factor: 3.600

Označené pro přenos do RIV

Ano

Kód RIV

RIV/00216224:14310/22:00126179

Organizační jednotka

Přírodovědecká fakulta

Klíčová slova anglicky

INTRAMOLECULAR PROTON-TRANSFER; CARBON-MONOXIDE; SINGLET OXYGEN; CHARGE-TRANSFER; ANTIOXIDANT ACTIVITY; SOLVATION DYNAMICS; RATE CONSTANTS; CO; LIGHT; 3-HYDROXYFLAVONE

Štítky

14313010, 143180, rivok

Příznaky

Mezinárodní význam, Recenzováno

Změněno: 13. 6. 2025 10:44, Mgr. Michaela Hylsová, Ph.D.

Anotace

V originále

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.

Návaznosti

EF17_043/0009632, projekt VaV

Název: CETOCOEN Excellence

EF19_073/0016943, projekt VaV

Název: Interní grantová agentura Masarykovy univerzity

GA21-01799S, projekt VaV

Název: Flavonoidy jako unikátní třída molekul fotochemicky uvolňujících oxid uhelnatý

Investor: Grantová agentura ČR, Flavonoidy jako unikátní třída molekul fotochemicky uvolňujících oxid uhelnatý

90121, velká výzkumná infrastruktura

Název: RECETOX RI

Citovat

RUSSO, Marina; Vojtěch OREL; Peter ŠTACKO; Mária ŠRANKOVÁ; Lucie ŠRANKOVÁ; Libor ŠRANKOVÁ a Petr KLÁN. Structure-Photoreactivity Relationship of 3-Hydroxyflavone-BasedCO-Releasing Molecules. Journal of Organic Chemistry. American Chemical Society, 2022, roč. 87, č. 7, s. 4750-4763. ISSN 0022-3263. Dostupné z: https://doi.org/10.1021/acs.joc.2c00032.

@article{1863614,
   author = {Russo, Marina and Orel, Vojtěch and Štacko, Peter and Šranková, Mária and Šranková, Lucie and Šranková, Libor and Klán, Petr},
   article_number = {7},
   doi = {https://doi.org/10.1021/acs.joc.2c00032},
   keywords = {INTRAMOLECULAR PROTON-TRANSFER; CARBON-MONOXIDE; SINGLET OXYGEN; CHARGE-TRANSFER; ANTIOXIDANT ACTIVITY; SOLVATION DYNAMICS; RATE CONSTANTS; CO; LIGHT; 3-HYDROXYFLAVONE},
   language = {eng},
   issn = {0022-3263},
   journal = {Journal of Organic Chemistry},
   title = {Structure-Photoreactivity Relationship of 3-Hydroxyflavone-BasedCO-Releasing Molecules},
   url = {https://pubs.acs.org/doi/10.1021/acs.joc.2c00032},
   volume = {87},
   year = {2022}
}

TY  - JOUR
ID  - 1863614
AU  - Russo, Marina - Orel, Vojtěch - Štacko, Peter - Šranková, Mária - Šranková, Lucie - Šranková, Libor - Klán, Petr
PY  - 2022
TI  - Structure-Photoreactivity Relationship of 3-Hydroxyflavone-BasedCO-Releasing Molecules
JF  - Journal of Organic Chemistry
VL  - 87
IS  - 7
SP  - 4750-4763
EP  - 4750-4763
PB  - American Chemical Society
SN  - 00223263
KW  - INTRAMOLECULAR PROTON-TRANSFER
KW  - CARBON-MONOXIDE
KW  - SINGLET OXYGEN
KW  - CHARGE-TRANSFER
KW  - ANTIOXIDANT ACTIVITY
KW  - SOLVATION DYNAMICS
KW  - RATE CONSTANTS
KW  - CO
KW  - LIGHT
KW  - 3-HYDROXYFLAVONE
UR  - https://pubs.acs.org/doi/10.1021/acs.joc.2c00032
N2  - 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.
ER  -

RUSSO, Marina; Vojtěch OREL; Peter ŠTACKO; Mária ŠRANKOVÁ; Lucie ŠRANKOVÁ; Libor ŠRANKOVÁ a Petr KLÁN. Structure-Photoreactivity Relationship of 3-Hydroxyflavone-BasedCO-Releasing Molecules. \textit{Journal of Organic Chemistry}. American Chemical Society, 2022, roč.~87, č.~7, s.~4750-4763. ISSN~0022-3263. Dostupné z: https://doi.org/10.1021/acs.joc.2c00032.

Přehled o publikaci