Cyanine-Flavonol Hybrids for Near-Infrared Light-Activated
Delivery of Carbon Monoxide

J 2020

Cyanine-Flavonol Hybrids for Near-Infrared Light-Activated Delivery of Carbon Monoxide

ŠTACKOVÁ, Lenka; Marina RUSSO; Lucie MUCHOVA; Vojtěch OREL; Libor VITEK et al.

Základní údaje

Originální název

Cyanine-Flavonol Hybrids for Near-Infrared Light-Activated Delivery of Carbon Monoxide

Autoři

ŠTACKOVÁ, Lenka; Marina RUSSO; Lucie MUCHOVA; Vojtěch OREL; Libor VITEK; Peter ŠTACKO a Petr KLÁN

Vydání

Chemistry - A European Journal, Weinheim, Wiley, 2020, 0947-6539

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

10400 1.4 Chemical sciences

Stát vydavatele

Německo

Utajení

není předmětem státního či obchodního tajemství

Odkazy

URL

Impakt faktor

Impact factor: 5.236

Označené pro přenos do RIV

Ano

Kód RIV

RIV/00216224:14310/20:00114565

Organizační jednotka

Přírodovědecká fakulta

Klíčová slova anglicky

CO release; cyanine; near-infrared light; photoCORM; photorelease

Štítky

14313010, 143180, CF NMR, rivok

Příznaky

Mezinárodní význam, Recenzováno

Změněno: 2. 6. 2025 21:38, Mgr. Michaela Hylsová, Ph.D.

Anotace

V originále

Carbon monoxide (CO) is an endogenous signaling molecule that controls a number of physiological processes. To circumvent the inherent toxicity of CO, light-activated CO-releasing molecules (photoCORMs) have emerged as an alternative for its administration. However, their wider application requires photoactivation using biologically benign visible and near-infrared (NIR) light. In this work, a strategy to access such photoCORMs by fusing two CO-releasing flavonol moieties with a NIR-absorbing cyanine dye is presented. These hybrids liberate two molecules of CO in high chemical yields upon activation with NIR light up to 820 nm and exhibit excellent uncaging cross-sections, which surpass the state-of-the-art by two orders of magnitude. Furthermore, the biocompatibility and applicability of the system in vitro and in vivo are demonstrated, and a mechanism of CO release is proposed. It is hoped that this strategy will stimulate the discovery of new classes of photoCORMs and accelerate the translation of CO-based phototherapy into practice.

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

6SA17811, interní kód MU

Název: Visible light-activated photocaged molecules for biological applications (Akronym: VLAMBA)

Investor: Jihomoravský kraj, Visible light-activated photocaged molecules for biological applications, Reintegrační granty

857560, interní kód MU
(Kód CEP: EF17_043/0009632)

Název: CETOCOEN Excellence (Akronym: CETOCOEN Excellence)

Investor: Evropská unie, CETOCOEN Excellence, Spreading excellence and widening participation

90121, velká výzkumná infrastruktura

Název: RECETOX RI

90127, velká výzkumná infrastruktura

Název: CIISB II

Přiložené soubory

1707845.pdf

Citovat

ŠTACKOVÁ, Lenka; Marina RUSSO; Lucie MUCHOVA; Vojtěch OREL; Libor VITEK; Peter ŠTACKO a Petr KLÁN. Cyanine-Flavonol Hybrids for Near-Infrared Light-Activated Delivery of Carbon Monoxide. Chemistry - A European Journal. Weinheim: Wiley, 2020, roč. 26, č. 58, s. 13184-13190. ISSN 0947-6539. Dostupné z: https://doi.org/10.1002/chem.202003272.

@article{1707845,
   author = {Štacková, Lenka and Russo, Marina and Muchova, Lucie and Orel, Vojtěch and Vitek, Libor and Štacko, Peter and Klán, Petr},
   article_location = {Weinheim},
   article_number = {58},
   doi = {https://doi.org/10.1002/chem.202003272},
   keywords = {CO release; cyanine; near-infrared light; photoCORM; photorelease},
   language = {eng},
   issn = {0947-6539},
   journal = {Chemistry - A European Journal},
   title = {Cyanine-Flavonol Hybrids for Near-Infrared Light-Activated Delivery of Carbon Monoxide},
   url = {https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/chem.202003272},
   volume = {26},
   year = {2020}
}

TY  - JOUR
ID  - 1707845
AU  - Štacková, Lenka - Russo, Marina - Muchova, Lucie - Orel, Vojtěch - Vitek, Libor - Štacko, Peter - Klán, Petr
PY  - 2020
TI  - Cyanine-Flavonol Hybrids for Near-Infrared Light-Activated Delivery of Carbon Monoxide
JF  - Chemistry - A European Journal
VL  - 26
IS  - 58
SP  - 13184-13190
EP  - 13184-13190
PB  - Wiley
SN  - 09476539
KW  - CO release
KW  - cyanine
KW  - near-infrared light
KW  - photoCORM
KW  - photorelease
UR  - https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/chem.202003272
L2  - https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/chem.202003272
N2  - Carbon monoxide (CO) is an endogenous signaling molecule that controls a number of physiological processes. To circumvent the inherent toxicity of CO, light-activated CO-releasing molecules (photoCORMs) have emerged as an alternative for its administration. However, their wider application requires photoactivation using biologically benign visible and near-infrared (NIR) light. In this work, a strategy to access such photoCORMs by fusing two CO-releasing flavonol moieties with a NIR-absorbing cyanine dye is presented. These hybrids liberate two molecules of CO in high chemical yields upon activation with NIR light up to 820 nm and exhibit excellent uncaging cross-sections, which surpass the state-of-the-art by two orders of magnitude. Furthermore, the biocompatibility and applicability of the system in vitro and in vivo are demonstrated, and a mechanism of CO release is proposed. It is hoped that this strategy will stimulate the discovery of new classes of photoCORMs and accelerate the translation of CO-based phototherapy into practice.
ER  -

ŠTACKOVÁ, Lenka; Marina RUSSO; Lucie MUCHOVA; Vojtěch OREL; Libor VITEK; Peter ŠTACKO a Petr KLÁN. Cyanine-Flavonol Hybrids for Near-Infrared Light-Activated Delivery of Carbon Monoxide. \textit{Chemistry - A European Journal}. Weinheim: Wiley, 2020, roč.~26, č.~58, s.~13184-13190. ISSN~0947-6539. Dostupné z: https://doi.org/10.1002/chem.202003272.

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