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Transition metal complexes of α-aminophosphonates Part I: synthesis, spectroscopic characterization, and in vitro anticancer activity of copper(II) complexes of α-aminophosphonates

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Abstract

New generation of copper(II) complexes with α-aminophosphonate as tridentate ligands has been synthesized. It is characterized by elemental analyses, spectral (IR, UV–Vis, MS, EPR, and 1H NMR) studies, thermal analysis as well as magnetic and molar conductance measurements. On the basis of spectral studies, a distorted square planar geometry has been assigned for all the complexes. Specific rotation measurements for both ligands and copper(II) complexes showed that they are enantiomerically enriched. The metal-free ligands and their Cu(II) complexes were tested for their in vitro anticancer activity against human colon carcinoma HT-29 cell lines. The results showed that the synthesized copper(II) complexes exhibited significantly higher anticancer activity than their free ligands. Among all the tested compounds in the series, the complex 5g demonstrated the highest anticancer activity at low micromolar inhibitory concentrations (IC50 = 14.2 µM) which is about a half of the reference drug activity, cisplatin (IC50 = 7.0 µM) in the same assay.

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Acknowledgments

The authors would like to thank Professor Masaharu Seno research team, Division of Biochemistry, Graduate School of Natural Science and Technology, Okayama University, Japan, for their help with the in vitro anticancer activity. The authors also thank Prof. Dr. Pierre Koch, Pharmazeutisches Institut at the University of Tübingen, Germany for assisting with specific rotation measurements.

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Authors and Affiliations

  1. Chemistry Department, Faculty of Science, El-Menoufia University, Shebin El Koom, Egypt

    Hanaa Abdel Latif El-Boraey, Ahmed Abdel Aleem El-Gokha, Ibrahim El Tantawy El-Sayed & Mariam Ahmed Azzam

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  1. Hanaa Abdel Latif El-Boraey
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  2. Ahmed Abdel Aleem El-Gokha
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  3. Ibrahim El Tantawy El-Sayed
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  4. Mariam Ahmed Azzam
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Correspondence to Ibrahim El Tantawy El-Sayed.

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El-Boraey, H.A.L., El-Gokha, A.A.A., El-Sayed, I.E.T. et al. Transition metal complexes of α-aminophosphonates Part I: synthesis, spectroscopic characterization, and in vitro anticancer activity of copper(II) complexes of α-aminophosphonates. Med Chem Res 24, 2142–2153 (2015). https://doi.org/10.1007/s00044-014-1282-8

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