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

J 2022

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

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

Basic information

Original name

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

Authors

RUSSO, Marina (380 Italy, belonging to the institution), Vojtěch OREL (203 Czech Republic, belonging to the institution), Peter ŠTACKO (703 Slovakia, belonging to the institution), Mária ŠRANKOVÁ, Lucie ŠRANKOVÁ, Libor ŠRANKOVÁ and Petr KLÁN (203 Czech Republic, guarantor, belonging to the institution)

Edition

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

Other information

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

10401 Organic chemistry

Country of publisher

United States of America

Confidentiality degree

není předmětem státního či obchodního tajemství

References:

URL

Impact factor

Impact factor: 3.600

RIV identification code

RIV/00216224:14310/22:00126179

Organization unit

Faculty of Science

DOI

http://dx.doi.org/10.1021/acs.joc.2c00032

UT WoS

000784116400025

Keywords in English

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

Abstract

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.

Links

EF17_043/0009632, research and development project

Name: CETOCOEN Excellence

EF19_073/0016943, research and development project

Name: Interní grantová agentura Masarykovy univerzity

GA21-01799S, research and development project

Name: Flavonoidy jako unikátní třída molekul fotochemicky uvolňujících oxid uhelnatý

Investor: Czech Science Foundation

LM2018121, research and development project

Name: Výzkumná infrastruktura RECETOX (Acronym: RECETOX RI)

Investor: Ministry of Education, Youth and Sports of the CR, RECETOX RI

Citovat

RUSSO, Marina, Vojtěch OREL, Peter ŠTACKO, Mária ŠRANKOVÁ, Lucie ŠRANKOVÁ, Libor ŠRANKOVÁ and Petr KLÁN. Structure-Photoreactivity Relationship of 3-Hydroxyflavone-BasedCO-Releasing Molecules br. Journal of Organic Chemistry. American Chemical Society, 2022, vol. 87, No 7, p. 4750-4763. ISSN 0022-3263. Available from: https://dx.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 = {http://dx.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 br},
   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 br
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 and Petr KLÁN. Structure-Photoreactivity Relationship of 3-Hydroxyflavone-BasedCO-Releasing Molecules br. \textit{Journal of Organic Chemistry}. American Chemical Society, 2022, vol.~87, No~7, p.~4750-4763. ISSN~0022-3263. Available from: https://dx.doi.org/10.1021/acs.joc.2c00032.

Detailed Information on Publication Record