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

Přehled o publikaci

J 2024

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

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

Basic information

Original name

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

Authors

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

Edition

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

Other information

Language

English

Type of outcome

Article in a journal

Country of publisher

United States of America

Confidentiality degree

is not subject to a state or trade secret

References:

URL

Marked to be transferred to RIV

Yes

RIV identification code

RIV/00216224:14310/24:00135436

Organization

Přírodovědecká fakulta – Repository – Repository

Keywords in English

Flavonoids; Inorganic carbon compounds; Irradiation; Oxides; Pyrroles

Links

EF17_043/0009632, research and development project. GA21-01799S, research and development project. 857560, interní kód Repo. RECETOX RI, large research infrastructures. CIISB II, large research infrastructures. CZ-OPENSCREEN IV, large research infrastructures.

Changed: 21/10/2025 00:50, RNDr. Daniel Jakubík

Abstract

In the original language

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.

Files attached

https://is.muni.cz/publication/2368518/2368518.pdf

Cite

RAMUNDO, Andrea; Jiří JANOŠ; Lucie MUCHOVÁ; Mária ŠRANKOVÁ; Jakub DOSTÁL; Miroslav KLOZ; Libor VÍTEK; Petr SLAVÍČEK and Petr KLÁN. Visible-Light-Activated Carbon Monoxide Release from Porphyrin-Flavonol Hybrids. Journal of the American Chemical Society. Washington: American Chemical Society, 2024, vol. 146, No 1, p. 920-929. ISSN 0002-7863. Available from: https://doi.org/10.1021/jacs.3c11426.

@article{59548,
   author = {Ramundo, Andrea and Janoš, Jiří and Muchová, Lucie and Šranková, Mária and Dostál, Jakub and Kloz, Miroslav and Vítek, Libor and Slavíček, Petr and Klán, Petr},
   article_location = {Washington},
   article_number = {1},
   doi = {https://doi.org/10.1021/jacs.3c11426},
   keywords = {Flavonoids; Inorganic carbon compounds; Irradiation; Oxides; Pyrroles},
   language = {eng},
   issn = {0002-7863},
   journal = {Journal of the American Chemical Society},
   title = {Visible-Light-Activated Carbon Monoxide Release from Porphyrin-Flavonol Hybrids},
   url = {https://pubs.acs.org/doi/10.1021/jacs.3c11426},
   volume = {146},
   year = {2024}
}

TY  - JOUR
ID  - 59548
AU  - Ramundo, Andrea - Janoš, Jiří - Muchová, Lucie - Šranková, Mária - Dostál, Jakub - Kloz, Miroslav - Vítek, Libor - Slavíček, Petr - Klán, Petr
PY  - 2024
TI  - Visible-Light-Activated Carbon Monoxide Release from Porphyrin-Flavonol Hybrids
JF  - Journal of the American Chemical Society
VL  - 146
IS  - 1
SP  - 920-929
EP  - 920-929
PB  - American Chemical Society
SN  - 0002-7863
KW  - Flavonoids
KW  - Inorganic carbon compounds
KW  - Irradiation
KW  - Oxides
KW  - Pyrroles
UR  - https://pubs.acs.org/doi/10.1021/jacs.3c11426
N2  - 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.
ER  -

RAMUNDO, Andrea; Jiří JANOŠ; Lucie MUCHOVÁ; Mária ŠRANKOVÁ; Jakub DOSTÁL; Miroslav KLOZ; Libor VÍTEK; Petr SLAVÍČEK and Petr KLÁN. Visible-Light-Activated Carbon Monoxide Release from Porphyrin-Flavonol Hybrids. \textit{Journal of the American Chemical Society}. Washington: American Chemical Society, 2024, vol.~146, No~1, p.~920-929. ISSN~0002-7863. Available from: https://doi.org/10.1021/jacs.3c11426.

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