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Molybdenum(II) complexes with p-substituted BIAN ligands: synthesis, characterization, biological activity and computational study

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Abstract

New complexes [Mo(η3-C3H5)X(CO)2(4-Y-BIAN)] (4-Y-BIAN = bis(4-Y-phenyl)-acenaphthenequinonediimine), with X = Br and Y = H, Me, OMe, COOH and X = Cl, Y = OMe, as well as the cation with X = NCMe and Y = OMe were synthesized, expanding the scope of this family. Two single crystal X-ray structures (X = Br, Y = Me, OMe) display a less symmetric arrangement (axial isomer), where one N donor atom is trans to the allyl group and the second to one CO. DFT studies showed similar energies for the two possible isomers of the complexes, with a very small preference for the observed axial isomer. The HOMO of the complexes is localized in the metal and the HOMO−1 of the oxidized species has a contribution from the BIAN ligand, while the LUMO is fully localized in BIAN. Electrochemical studies showed one process corresponding to the oxidation of Mo(II) to Mo(III) for complexes with X = Br, Y = H, Me, and two oxidation reactions for those with X = Br, Y = Cl, OMe, while the COOH derivative exhibited no oxidation wave. The antitumor effect of the complexes with X = Br was tested in cancer lines, and the H and OMe complexes were particularly active, with EC50 values below 8 μM in HeLa cell lines. The DNA binding constants determined by titration experiments were comparable with those of doxorubicin and ethidium bromide, suggesting a mechanism of action based on intercalation in DNA.

Graphical abstract: Molybdenum(ii) complexes with p-substituted BIAN ligands: synthesis, characterization, biological activity and computational study

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Publication details

The article was received on 31 Jan 2019, accepted on 26 Apr 2019 and first published on 03 May 2019


Article type: Paper
DOI: 10.1039/C9DT00469F
Dalton Trans., 2019, Advance Article

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    Molybdenum(II) complexes with p-substituted BIAN ligands: synthesis, characterization, biological activity and computational study

    S. Quintal, M. J. Pires da Silva, S. R. M. Martins, R. Sales, V. Félix, M. G. B. Drew, M. Meireles, A. C. Mourato, C. D. Nunes, M. S. Saraiva, M. Machuqueiro and M. J. Calhorda, Dalton Trans., 2019, Advance Article , DOI: 10.1039/C9DT00469F

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