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Full Paper
Biologically Active Trifluoromethyl-Substituted Metallocene Triazoles: Characterization, Electrochemistry, Lipophilicity, and Cytotoxicity
Article first published online: 30 OCT 2012
DOI: 10.1002/ejic.201200798
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Maschke, M., Lieb, M. and Metzler-Nolte, N. (2012), Biologically Active Trifluoromethyl-Substituted Metallocene Triazoles: Characterization, Electrochemistry, Lipophilicity, and Cytotoxicity. Eur. J. Inorg. Chem., 2012: 5953–5959. doi: 10.1002/ejic.201200798
Publication History
- Issue published online: 10 DEC 2012
- Article first published online: 30 OCT 2012
- Manuscript Received: 14 JUL 2012
Keywords:
- Bioinorganic chemistry;
- Medicinal chemistry;
- Cytotoxicity;
- Click chemistry;
- Fluorinated ligands;
- Metallocenes;
- Sandwich complexes;
- N ligands;
- Cycloaddition
Abstract
We report the facile synthesis of four different trifluoromethylated metallocene triazoles and their biological evaluation (M = Fe and Ru). The cytotoxicity of all compounds was evaluated using MCF-7, HT-29, PT-45 and GM5657 cells and IC50 values as low as 33 μM were found. It was shown that the metallocene moiety is crucial for the cytotoxic effect. The electrochemical behavior of triazoles 3–6 was investigated by cyclic voltammetry. These electrochemical measurements revealed that all triazoles are less prone to oxidation than ferrocene. Moreover, Log P determination by RP-HPLC showed increased lipophilicity for the fluorinated derivatives with Log P values up to 3.8. Furthermore, successful bioconjugation could be achieved by coupling triazole 7 to the amino acid L-leucine.