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

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, vol. 224, November 2021, p. 1-8. ISSN 0162-0134. doi:10.1016/j.jinorgbio.2021.111561. 2021.

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

• Original language: English
• Type of outcome: Article in a journal
• Field of Study: 10608 Biochemistry and molecular biology
• Country of publisher: United States of America
• Confidentiality degree: is not subject to a state or trade secret
• WWW: 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
• Tags: 14110512, CF NANO, podil, rivok
• Tags: International impact, Reviewed

Abstract

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

• LM2015043, research and development project: Name: Česká infrastruktura pro integrativní strukturní biologii (Acronym: CIISB)

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

• 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