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Synthesis, crystal structure, and in vitro antitumor activities of copper(II) complexes containing tetradentate pyridine-based ligands

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Abstract

Several new Cu(II) complexes of Schiff bases obtained by condensation of 2-[N-(α-picolyl)-amino]-benzophenone with different chiral amino acids were synthesized and characterized by physico-chemical and spectroscopic methods. The crystal structure of one of the complexes was determined using single crystal X-ray diffraction. The ligands were coordinated to the metal atom in a tetradentate manner with ONNN donor sets using the carboxyl oxygen, azomethine nitrogen, CON−, and pyridine nitrogen. The cytotoxicities of the complexes were evaluated against human cancer cells. The substituents on the aromatic rings strongly influenced the cytotoxicities of the complexes. The complex with bromine substituents on the pyridine rings showed the highest cytotoxicity. The antitumor activities against tumor cell lines were assayed in vitro, and the complexes were found to be highly effective, with six of the nine complexes having inhibition ratios better than that of 5-Fluorouracil. This behavior is indicative of a high ability to circumvent the cellular drug resistance mechanisms.

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Acknowledgments

This work was financially supported by the National Natural Science Foundation of China (Grant No. 20472032 and 2010CB833300, China). We also thank the support of Nankai University State Key Laboratory of Elemento-Organic Chemistry, and Beijing Institute of Materia Medica, Chinese Academy of Medical Sciences which carried out the antitumor activity measurements.

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Authors and Affiliations

  1. Department of Chemistry, The State Key Laboratory of Elemento-Organic Chemistry, Nankai University, 300071, Tianjin, China

    Xin-Tao Yang, Hao Wu, Shi-Jun Ma & Yong-mei Wang

  2. Institute of Materia Medica, Chinese Academy of Medical Sciences, 100050, Beijing, China

    Juan-Juan Hu

Authors
  1. Xin-Tao Yang
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  2. Hao Wu
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  3. Shi-Jun Ma
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  4. Juan-Juan Hu
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Corresponding author

Correspondence to Yong-mei Wang.

Appendix: Supplementary data

Appendix: Supplementary data

CCDC 754970 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via http://www.ccdc.cam.ac.uk/data_request/cif, or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK, e-mail: deposit@ ccdc.cam.ac.uk.

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Yang, XT., Wu, H., Ma, SJ. et al. Synthesis, crystal structure, and in vitro antitumor activities of copper(II) complexes containing tetradentate pyridine-based ligands. Transition Met Chem 36, 403–407 (2011). https://doi.org/10.1007/s11243-011-9483-1

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