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Flubendazole Pd(II) complexes: structural studies, cytotoxicity, and quantum chemical calculations

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Abstract

[Pd(FLU)2X2]·yH2O·zCH3OH (FLU = flubendazole; X = Cl (1), y = 0, z = 0; X = Br (2), NO3 (3), y = 2, z = 0; X = SCN (4), y = 2, z = 3) were synthesized as potential anticancer complexes, and their structures were elucidated using elemental analysis, TG/DTA, IR, 1H NMR, UV–vis., and conductivity measurements. FLU interacts with Pd(II) ions as a neutral unidentate ligand via the pyridine-type nitrogen of the benzimidazole ring. Geometry optimization, molecular electrostatic potential maps and natural bond orbital analysis were performed by DFT/B3LYP method. FLU, in comparison to its complexes, was screened for its antibacterial and cytotoxic activity. Complexes 1–4 possess strong anticancer activity with IC50 values (4.13–3.68 μg ml−1) compared with 3.57 μg ml−1 reported for cis-platin. The cytotoxicity was shown to be affected by the nature of the anion, where the sequence is 3 > 2 > 4 > 1 in case of MCF7 cell line. Structural-activity relationships suggested that E HOMO, energy gap and dipole moment were the most significant descriptors for the correlation with the antitumor activity.

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  1. Chemistry Department, Faculty of Science, Cairo University, Gamaa Street, Giza, 12613, Egypt

    Ahmed M. Mansour, Eslam M. El Bakry & Nour T. Abdel-Ghani

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  1. Ahmed M. Mansour
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Correspondence to Ahmed M. Mansour or Nour T. Abdel-Ghani.

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Mansour, A.M., Bakry, E.M.E. & Abdel-Ghani, N.T. Flubendazole Pd(II) complexes: structural studies, cytotoxicity, and quantum chemical calculations. J IRAN CHEM SOC 13, 1429–1437 (2016). https://doi.org/10.1007/s13738-016-0858-2

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