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
Typ výsledku
Článek v odborném periodiku
Stát vydavatele
Spojené státy
Utajení
není předmětem státního či obchodního tajemství
Označené pro přenos do RIV
Ano
Kód RIV
RIV/00216224:14310/24:00135436
Organizace
Přírodovědecká fakulta – Masarykova univerzita – Repozitář
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.
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