Improving cytotoxic properties of ferrocenes by incorporation of saturated N-heterocycles
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388955%3A_____%2F17%3A00475666" target="_blank" >RIV/61388955:_____/17:00475666 - isvavai.cz</a>
Alternative codes found
RIV/67985858:_____/17:00475666 RIV/00209805:_____/17:00077849 RIV/00216208:11310/17:10364241
Result on the web
<a href="http://dx.doi.org/10.1016/j.jorganchem.2017.06.005" target="_blank" >http://dx.doi.org/10.1016/j.jorganchem.2017.06.005</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1016/j.jorganchem.2017.06.005" target="_blank" >10.1016/j.jorganchem.2017.06.005</a>
Alternative languages
Result language
angličtina
Original language name
Improving cytotoxic properties of ferrocenes by incorporation of saturated N-heterocycles
Original language description
A family of ferrocene derivatives of the general formula [Fe(eta(5)-C5H4CH2(p-C6H4)CH2(N-het))(2)] bearing saturated six- and five-membered N-heterocycles (N-het) was prepared. Reactions of the selected complexes with acids (HCl, acetic acid) afforded either the corresponding hydrochlorides or led to deprotection of the functionalized pendant N-heterocycles. The reaction of [{Ru(eta(6)-p-cymene)Cl-2}(2)] with the corresponding cyclopentadienide derivatives afforded cationic ruthenium complexes [Ru(eta(6)-p-cymene)( eta(5)-C5H4CH2(p-C6H4)CH2(N-het))] Cl while ruthenocenes [Ru(eta(5)-C5H4CH2(p-C6H4)CH2(N-het))(2)] were formed as minor byproducts. The prepared complexes (20 examples) were characterized by elemental analysis, melting point, NMR and ESI-MS and the molecular structures of selected ferrocene derivatives were determined by X-ray diffraction analysis. The ferrocene derivatives and the ruthenium complexes were tested in vitro for their cytotoxic properties against three cell lines derived from ovarian cancer (A2780, A2780cis, and SK-OV-3) and against non-tumour embryonic cell line HEK293 (human kidney cells). The most active ferrocene derivatives displayed cytotoxicity in submicromolar and low micromolar concentration against both cisplatin (CisPt) sensitive and resistant cells. The results showed a significant effect of the pendant N-heterocycle on the ferrocene derivative toxicity and selectivity against cancer cells. Ultimately, ferrocene derivatives bearing either piperidine or morpholine groups were proposed to be the most promising substitutes for platinum drugs, as they exhibited comparable or even higher activity (in comparison to CisPt) against cancer cells, whereas these compounds were found to exhibit lower toxicity against embryonic HEK293 cells. (C) 2017 Elsevier B.V. All rights reserved.n
Czech name
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Czech description
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Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10402 - Inorganic and nuclear chemistry
Result continuities
Project
Result was created during the realization of more than one project. More information in the Projects tab.
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)
Others
Publication year
2017
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Journal of Organometallic Chemistry
ISSN
0022-328X
e-ISSN
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Volume of the periodical
846
Issue of the periodical within the volume
OCT 2017
Country of publishing house
CH - SWITZERLAND
Number of pages
11
Pages from-to
141-151
UT code for WoS article
000407858700018
EID of the result in the Scopus database
2-s2.0-85020737791