Redox-dependent cytotoxicity of ferrocene derivatives and ROS-activated prodrugs based on ferrocenyliminoboronates
Jazyk angličtina Země Spojené státy americké Médium print-electronic
Typ dokumentu časopisecké články, práce podpořená grantem
PubMed
34385077
DOI
10.1016/j.jinorgbio.2021.111561
PII: S0162-0134(21)00208-7
Knihovny.cz E-zdroje
- Klíčová slova
- Aminoferrocene, Electrochemical characterization, Ferrocenyliminoboronates, MG-63, ROS-activated prodrugs, Redox-dependent cytotoxicity,
- MeSH
- kyseliny boronové chemie MeSH
- lidé MeSH
- metaloceny chemie farmakologie MeSH
- molekulární struktura MeSH
- myši MeSH
- nádorové buněčné linie MeSH
- oxidace-redukce MeSH
- prekurzory léčiv chemie farmakologie MeSH
- reaktivní formy kyslíku metabolismus MeSH
- viabilita buněk účinky léků MeSH
- železnaté sloučeniny chemie farmakologie MeSH
- zvířata MeSH
- Check Tag
- lidé MeSH
- myši MeSH
- zvířata MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
- Názvy látek
- benzeneboronic acid MeSH Prohlížeč
- ferrocene MeSH Prohlížeč
- ferrocenecarboxylic acid MeSH Prohlížeč
- ferrocenium MeSH Prohlížeč
- kyseliny boronové MeSH
- metaloceny MeSH
- prekurzory léčiv MeSH
- reaktivní formy kyslíku MeSH
- železnaté sloučeniny MeSH
Four ferrocene derivatives - ferrocenecarboxylic acid, ferrocenium salt, ferroceneboronic acid, and aminoferrocene - 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 - aminoferrocene with its lowest redox potential exhibited the highest cytotoxicity. Thus, we synthesized four derivatives 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.
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