Mechanisms of Orthogonal Photodecarbonylation Reactions of
3-Hydroxyflavone-Based Acid-Base Forms

J 2020

Mechanisms of Orthogonal Photodecarbonylation Reactions of 3-Hydroxyflavone-Based Acid-Base Forms

RUSSO, Marina, Peter ŠTACKO, Dana NACHTIGALLOVÁ a Petr KLÁN

Základní údaje

Originální název

Mechanisms of Orthogonal Photodecarbonylation Reactions of 3-Hydroxyflavone-Based Acid-Base Forms

Autoři

RUSSO, Marina (380 Itálie, domácí), Peter ŠTACKO (703 Slovensko, domácí), Dana NACHTIGALLOVÁ (203 Česká republika) a Petr KLÁN (203 Česká republika, garant, domácí)

Vydání

Journal of Organic Chemistry, Washington, D.C. American Chemical Society, 2020, 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: 4.354

Kód RIV

RIV/00216224:14310/20:00114240

Organizační jednotka

Přírodovědecká fakulta

DOI

http://dx.doi.org/10.1021/acs.joc.9b03248

UT WoS

000518875700060

Klíčová slova anglicky

Quantum yield; Alcohols; Oxygen; Inorganic carbon compounds; Irradiation

Štítky

rivok

Příznaky

Mezinárodní význam, Recenzováno

Změněno: 17. 2. 2023 21:07, Mgr. Michaela Hylsová, Ph.D.

Anotace

V originále

Carbon monoxide is a naturally occurring gasotransmitter combining inherent toxicity with a remarkable therapeutic potential and arduous administration. Photoactivatable carbon monoxide-releasing molecules (photoCORMs) are chemical agents that allow for precise spatial and temporal control over the CO release. In this work, we present a comprehensive mechanistic study of the photochemical CO release from 3-hydroxy-2-phenyl-4H-chromen-4-one, a pi-extended 3-hydroxyflavone photoCORM, in methanol using steady-state and transient absorption spectroscopies and quantum chemical calculations. The multiplicity of the productive excited states and the role of oxygen (O-2) in the CO production are emphasized, revealing a photoreaction dichotomy of the 3-hydroxyflavone acid and base forms. The utilization of three major orthogonal mechanistic pathways, all of which lead to the CO release, can fuel future endeavors to improve the CO release efficacy of 3-hydroxyflavone-based derivatives and refine their potential medical applications as photoCORMs.

Návaznosti

EF17_043/0009632, projekt VaV

Název: CETOCOEN Excellence

GA18-12477S, projekt VaV

Název: Fotoaktivace CO a H2S jako plynných signálních molekul pro biologické a medicinální aplikace

Investor: Grantová agentura ČR, Fotoaktivace CO a H2S jako plynných signálních molekul pro biologické a medicinální aplikace

LM2018121, projekt VaV

Název: Výzkumná infrastruktura RECETOX (Akronym: RECETOX RI)

Investor: Ministerstvo školství, mládeže a tělovýchovy ČR, RECETOX RI

Citovat

RUSSO, Marina, Peter ŠTACKO, Dana NACHTIGALLOVÁ a Petr KLÁN. Mechanisms of Orthogonal Photodecarbonylation Reactions of 3-Hydroxyflavone-Based Acid-Base Forms. Journal of Organic Chemistry. Washington, D.C.: American Chemical Society, 2020, roč. 85, č. 5, s. 3527-3537. ISSN 0022-3263. Dostupné z: https://dx.doi.org/10.1021/acs.joc.9b03248.

@article{1671638,
   author = {Russo, Marina and Štacko, Peter and Nachtigallová, Dana and Klán, Petr},
   article_location = {Washington, D.C.},
   article_number = {5},
   doi = {http://dx.doi.org/10.1021/acs.joc.9b03248},
   keywords = {Quantum yield; Alcohols; Oxygen; Inorganic carbon compounds; Irradiation},
   language = {eng},
   issn = {0022-3263},
   journal = {Journal of Organic Chemistry},
   note = {CZ.02.1.01/0.0/0.0/18_046/0015975 neuplatňovat. Místo toho uplatnit EF17_043/0009632.},
   title = {Mechanisms of Orthogonal Photodecarbonylation Reactions of 3-Hydroxyflavone-Based Acid-Base Forms},
   url = {https://pubs.acs.org/doi/10.1021/acs.joc.9b03248},
   volume = {85},
   year = {2020}
}

TY  - JOUR
ID  - 1671638
AU  - Russo, Marina - Štacko, Peter - Nachtigallová, Dana - Klán, Petr
PY  - 2020
TI  - Mechanisms of Orthogonal Photodecarbonylation Reactions of 3-Hydroxyflavone-Based Acid-Base Forms
JF  - Journal of Organic Chemistry
VL  - 85
IS  - 5
SP  - 3527-3537
EP  - 3527-3537
PB  - American Chemical Society
SN  - 00223263
N1  - CZ.02.1.01/0.0/0.0/18_046/0015975 neuplatňovat. Místo toho uplatnit EF17_043/0009632.
KW  - Quantum yield
KW  - Alcohols
KW  - Oxygen
KW  - Inorganic carbon compounds
KW  - Irradiation
UR  - https://pubs.acs.org/doi/10.1021/acs.joc.9b03248
L2  - https://pubs.acs.org/doi/10.1021/acs.joc.9b03248
N2  - Carbon monoxide is a naturally occurring gasotransmitter combining inherent toxicity with a remarkable therapeutic potential and arduous administration. Photoactivatable carbon monoxide-releasing molecules (photoCORMs) are chemical agents that allow for precise spatial and temporal control over the CO release. In this work, we present a comprehensive mechanistic study of the photochemical CO release from 3-hydroxy-2-phenyl-4H-chromen-4-one, a pi-extended 3-hydroxyflavone photoCORM, in methanol using steady-state and transient absorption spectroscopies and quantum chemical calculations. The multiplicity of the productive excited states and the role of oxygen (O-2) in the CO production are emphasized, revealing a photoreaction dichotomy of the 3-hydroxyflavone acid and base forms. The utilization of three major orthogonal mechanistic pathways, all of which lead to the CO release, can fuel future endeavors to improve the CO release efficacy of 3-hydroxyflavone-based derivatives and refine their potential medical applications as photoCORMs.
ER  -

RUSSO, Marina, Peter ŠTACKO, Dana NACHTIGALLOVÁ a Petr KLÁN. Mechanisms of Orthogonal Photodecarbonylation Reactions of 3-Hydroxyflavone-Based Acid-Base Forms. \textit{Journal of Organic Chemistry}. Washington, D.C.: American Chemical Society, 2020, roč.~85, č.~5, s.~3527-3537. ISSN~0022-3263. Dostupné z: https://dx.doi.org/10.1021/acs.joc.9b03248.

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