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 and Karel LACINA

Basic information

Original name

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

Authors

VĚŽNÍK, Jakub (203 Czech Republic, belonging to the institution), Martin KONHEFR (203 Czech Republic, belonging to the institution), Zdenka FOHLEROVÁ (203 Czech Republic, belonging to the institution) and Karel LACINA (203 Czech Republic, guarantor, belonging to the institution)

Edition

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

Other information

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

10608 Biochemistry and molecular biology

Country of publisher

United States of America

Confidentiality degree

není předmětem státního či obchodního tajemství

References:

URL

Impact factor

Impact factor: 4.336

RIV identification code

RIV/00216224:14740/21:00119669

Organization unit

Central European Institute of Technology

DOI

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

UT WoS

000704419600008

Keywords in English

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

Abstract

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.

Links

GJ19-16273Y, research and development project

Name: ROS-indukované uvolňování léčiv založené na interakcích ferocenylboronátů

Investor: Czech Science Foundation, ROS-Induced Drug Release Based on Interactions of Ferrocenylboronates

LQ1601, research and development project

Name: CEITEC 2020 (Acronym: CEITEC2020)

Investor: Ministry of Education, Youth and Sports of the CR

MUNI/A/1424/2019, interní kód MU

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

Investor: Masaryk University, Category A

90043, large research infrastructures

Name: CIISB

Citovat

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

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