Redox-dependent cytotoxicity of ferrocene derivatives and
ROS-activated prodrugs based on ferrocenyliminoboronates

J 2021

Redox-dependent cytotoxicity of ferrocene derivatives and ROS-activated prodrugs based on ferrocenyliminoboronates

VĚŽNÍK, Jakub, Martin KONHEFR, Zdenka FOHLEROVÁ a Karel LACINA

Základní údaje

Originální název

Redox-dependent cytotoxicity of ferrocene derivatives and ROS-activated prodrugs based on ferrocenyliminoboronates

Autoři

VĚŽNÍK, Jakub (203 Česká republika, domácí), Martin KONHEFR (203 Česká republika, domácí), Zdenka FOHLEROVÁ (203 Česká republika, domácí) a Karel LACINA (203 Česká republika, garant, domácí)

Vydání

Journal of Inorganic Biochemistry, NEW YORK, Elsevier, 2021, 0162-0134

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

10608 Biochemistry and molecular biology

Stát vydavatele

Spojené státy

Utajení

není předmětem státního či obchodního tajemství

Odkazy

URL

Impakt faktor

Impact factor: 4.336

Kód RIV

RIV/00216224:14740/21:00119669

Organizační jednotka

Středoevropský technologický institut

DOI

http://dx.doi.org/10.1016/j.jinorgbio.2021.111561

UT WoS

000704419600008

Klíčová slova anglicky

Aminoferrocene; Redox-dependent cytotoxicity; ROS-activated prodrugs; Ferrocenyliminoboronates; MG-63; Electrochemical characterization

Štítky

14110512, CF NANO, podil, rivok

Příznaky

Mezinárodní význam, Recenzováno

Změněno: 2. 11. 2024 19:15, Mgr. Adéla Pešková

Anotace

V originále

Four ferrocene derivatives - ferrocenecarboxylic acid, ferrocenium salt, ferroceneboronic acid, and amino-ferrocene - were characterized electrochemically, and their cytotoxicity was probed using cancer cells (line MG -63). We related the observed cytotoxicity with the determined redox potentials of these four ferrocenes - ami-noferrocene with its lowest redox potential exhibited the highest cytotoxicity. Thus, we synthesized four de-rivatives consisting of aminoferrocene and phenylboronic acid residue with the intent to employ them as ROS-activated prodrugs (ROS - reactive oxygen species). We characterized them and studied their time-dependent stability in aqueous environments. Then, we performed electrochemical measurements at oxidative conditions to confirm ROS-responsivity of the synthesized molecules. Finally, the cytotoxicity of the synthesized molecules was tested using cancer MG-63 cells and noncancerous NIH-3T3 cells. The experiments revealed sought behaviour, especially for para-regioisomers of synthesized ferrocenyliminoboronates.

Návaznosti

GJ19-16273Y, projekt VaV

Název: ROS-indukované uvolňování léčiv založené na interakcích ferocenylboronátů

Investor: Grantová agentura ČR, ROS-indukované uvolňování léčiv založené na interakcích ferocenylboronátů

LQ1601, projekt VaV

Název: CEITEC 2020 (Akronym: CEITEC2020)

Investor: Ministerstvo školství, mládeže a tělovýchovy ČR, CEITEC 2020

MUNI/A/1424/2019, interní kód MU

Název: Vývoj metod a instrumentace pro analýzu biologicky významných látek 2020

Investor: Masarykova univerzita, Vývoj metod a instrumentace pro analýzu biologicky významných látek 2020, DO R. 2020_Kategorie A - Specifický výzkum - Studentské výzkumné projekty

90043, velká výzkumná infrastruktura

Název: CIISB

Citovat

VĚŽNÍK, Jakub, Martin KONHEFR, Zdenka FOHLEROVÁ a Karel LACINA. Redox-dependent cytotoxicity of ferrocene derivatives and ROS-activated prodrugs based on ferrocenyliminoboronates. Journal of Inorganic Biochemistry. NEW YORK: Elsevier, 2021, roč. 224, November 2021, s. 1-8. ISSN 0162-0134. Dostupné z: https://dx.doi.org/10.1016/j.jinorgbio.2021.111561.

@article{1836825,
   author = {Věžník, Jakub and Konhefr, Martin and Fohlerová, Zdenka and Lacina, Karel},
   article_location = {NEW YORK},
   article_number = {November 2021},
   doi = {http://dx.doi.org/10.1016/j.jinorgbio.2021.111561},
   keywords = {Aminoferrocene; Redox-dependent cytotoxicity; ROS-activated prodrugs; Ferrocenyliminoboronates; MG-63; Electrochemical characterization},
   language = {eng},
   issn = {0162-0134},
   journal = {Journal of Inorganic Biochemistry},
   title = {Redox-dependent cytotoxicity of ferrocene derivatives and ROS-activated prodrugs based on ferrocenyliminoboronates},
   url = {https://www.sciencedirect.com/science/article/pii/S0162013421002087?via%3Dihub},
   volume = {224},
   year = {2021}
}

TY  - JOUR
ID  - 1836825
AU  - Věžník, Jakub - Konhefr, Martin - Fohlerová, Zdenka - Lacina, Karel
PY  - 2021
TI  - Redox-dependent cytotoxicity of ferrocene derivatives and ROS-activated prodrugs based on ferrocenyliminoboronates
JF  - Journal of Inorganic Biochemistry
VL  - 224
IS  - November 2021
SP  - 1-8
EP  - 1-8
PB  - Elsevier
SN  - 01620134
KW  - Aminoferrocene
KW  - Redox-dependent cytotoxicity
KW  - ROS-activated prodrugs
KW  - Ferrocenyliminoboronates
KW  - MG-63
KW  - Electrochemical characterization
UR  - https://www.sciencedirect.com/science/article/pii/S0162013421002087?via%3Dihub
N2  - Four ferrocene derivatives - ferrocenecarboxylic acid, ferrocenium salt, ferroceneboronic acid, and amino-ferrocene - were characterized electrochemically, and their cytotoxicity was probed using cancer cells (line MG -63). We related the observed cytotoxicity with the determined redox potentials of these four ferrocenes - ami-noferrocene with its lowest redox potential exhibited the highest cytotoxicity. Thus, we synthesized four de-rivatives consisting of aminoferrocene and phenylboronic acid residue with the intent to employ them as ROS-activated prodrugs (ROS - reactive oxygen species). We characterized them and studied their time-dependent stability in aqueous environments. Then, we performed electrochemical measurements at oxidative conditions to confirm ROS-responsivity of the synthesized molecules. Finally, the cytotoxicity of the synthesized molecules was tested using cancer MG-63 cells and noncancerous NIH-3T3 cells. The experiments revealed sought behaviour, especially for para-regioisomers of synthesized ferrocenyliminoboronates.
ER  -

VĚŽNÍK, Jakub, Martin KONHEFR, Zdenka FOHLEROVÁ a Karel LACINA. Redox-dependent cytotoxicity of ferrocene derivatives and ROS-activated prodrugs based on ferrocenyliminoboronates. \textit{Journal of Inorganic Biochemistry}. NEW YORK: Elsevier, 2021, roč.~224, November 2021, s.~1-8. ISSN~0162-0134. Dostupné z: https://dx.doi.org/10.1016/j.jinorgbio.2021.111561.

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