J 2024

Visible-Light-Activated Carbon Monoxide Release from Porphyrin-Flavonol Hybrids

RAMUNDO, Andrea; Jiří JANOŠ; Lucie MUCHOVÁ; Mária ŠRANKOVÁ; Jakub DOSTÁL et al.

Základní údaje

Originální název

Visible-Light-Activated Carbon Monoxide Release from Porphyrin-Flavonol Hybrids

Autoři

RAMUNDO, Andrea; Jiří JANOŠ; Lucie MUCHOVÁ; Mária ŠRANKOVÁ; Jakub DOSTÁL; Miroslav KLOZ; Libor VÍTEK; Petr SLAVÍČEK a Petr KLÁN

Vydání

Journal of the American Chemical Society, Washington, American Chemical Society, 2024, 0002-7863

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Stát vydavatele

Spojené státy

Utajení

není předmětem státního či obchodního tajemství

Odkazy

URL

Označené pro přenos do RIV

Ano

Kód RIV

RIV/00216224:14310/24:00135436

Organizace

Přírodovědecká fakulta – Masarykova univerzita – Repozitář

DOI

https://doi.org/10.1021/jacs.3c11426

UT WoS

001140764800001

EID Scopus

2-s2.0-85181574621

Klíčová slova anglicky

Flavonoids; Inorganic carbon compounds; Irradiation; Oxides; Pyrroles

Návaznosti

EF17_043/0009632, projekt VaV. GA21-01799S, projekt VaV. 857560, interní kód Repo. RECETOX RI, velká výzkumná infrastruktura. CIISB II, velká výzkumná infrastruktura. CZ-OPENSCREEN IV, velká výzkumná infrastruktura.
Změněno: 21. 10. 2025 00:50, RNDr. Daniel Jakubík

Anotace

V originále

We report on porphyrin-flavonol hybrids consisting of a porphyrin antenna and four covalently bound 3-hydroxyflavone (flavonol) groups, which act as highly efficient photoactivatable carbon monoxide (CO)-releasing molecules (photoCORMs). These bichromophoric systems enable activation of the UV-absorbing flavonol chromophore by visible light up to 650 nm and offer precise spatial and temporal control of CO administration. The physicochemical properties of the porphyrin antenna system can also be tuned by inserting a metal cation. Our computational study revealed that the process occurs via endergonic triplet-triplet energy transfer from porphyrin to flavonol and may become feasible thanks to flavonol energy stabilization upon intramolecular proton transfer. This mechanism was also indirectly supported by steady-state and transient absorption spectroscopy techniques. Additionally, the porphyrin-flavonol hybrids were found to be biologically benign. With four flavonol CO donors attached to a single porphyrin chromophore, high CO release yields, excellent uncaging cross sections, low toxicity, and CO therapeutic properties, these photoCORMs offer exceptional potential for their further development and future biological and medical applications.
Zobrazeno: 2. 5. 2026 18:13