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Selective cytotoxicity of organotin(IV) compounds with 2,3-dihydroxybenzyldithiocarbazate Schiff bases

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Abstract

A series of tridentate ONS Schiff bases were synthesised via condensation by reacting 2,3-dihydroxybenzaldehyde with S-2-methylbenzyldithiocarbazate (S2MBDTC) (1), S-4-methylbenzyldithiocarbazate (S4MBDTC) (2) and S-benzyldithiocarbazate (SBDTC) (3) in an equimolar ratio (10 mmol). The Schiff bases were then reacted with diphenyltin(IV) and dimethyltin(IV) dichloride in an equimolar ratio (1 mmol) yielding six new organotin(IV) compounds (4–9). All the compounds were successfully characterised by elemental analysis, FT-IR, multinuclear NMR, UV–Vis, mass spectroscopy and molar conductivity. The molecular geometries for five compounds, 3, 5, 6, 8 and 9, have been established by X-ray crystallography. The five-coordinate geometry for each of the diorganotin molecules was defined by two carbon atoms from the tin-bound substituents as well as three donor atoms derived from the dinegative, tridentate dithiocarbazate ligands, namely thiolate-S, phenoxide-O and imine-N atoms. The resultant five-coordinate C2NOS geometries were intermediate between ideal square pyramidal and trigonal bipyramidal geometries. The diphenyltin(IV) compounds (4–6) exhibited particularly promising and selective cytotoxicity against the A2780 (ovarian), BE2-C (neuroblastoma), SJ-G2 (glioblastoma) and MIA (pancreas) cancer cell lines. The interactions of the compounds (4–9) with calf thymus (CT-DNA) were evaluated using an electronic absorption method, and 7, 8, 9 were found to have good DNA binding affinity. The molecular docking studies of compounds (4–9) with DNA revealed that the compounds interacted with duplex DNA via hydrogen bonding, hydrophobic and electrostatic interactions.

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Acknowledgements

We thank the Department of Chemistry, Faculty of Science and the Molecular Genetics Laboratory and the Department of Biomedical Sciences, Faculty of Medicine and Health Sciences at Universiti Putra Malaysia, Malaysia, as well as the Discipline of Chemistry, University of Newcastle and the Calvary Mater Hospital, Australia, for their facilities. E. N. M. Y wishes to thank Ministry of Higher Education Malaysia for the award of MyPhD, MyBrain15 and the University of Newcastle for the award of University of Newcastle International Postgraduate Research Scholarship. We would also like to thank Karen A. Crouse, Abhi Veerakumarasivam, Michela Simone, Robert Burns and Zalikha Ibrahim for helpful discussions.

Funding

This research was funded by Universiti Putra Malaysia under the Geran Putra IPS (9504600) and Geran Putra IPB (9581001) (UPM) and the Malaysian Fundamental Research Grant Scheme (FRGS No. 01-01-16-1833FR). Crystallographic research at Sunway University was supported by Sunway University Sdn Bhd (Grant. No. STR-RCTR-RCCM-001-2019).

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Universiti Putra Malaysia, 43400, UPM Serdang, Selangor, Malaysia

    Enis Nadia Md. Yusof, Nurul N. M. Ishak, Muhammad A. M. Latif, Mohamed I. M. Tahir & Thahira B. S. A. Ravoof

  2. Discipline of Chemistry, School of Environmental and Life Sciences, University of Newcastle, University Drive, Callaghan, NSW, 2308, Australia

    Enis Nadia Md. Yusof & Alister J. Page

  3. Experimental Therapeutics Group, Department of Medical Oncology, Calvary Mater Newcastle Hospital, Edith Street, Waratah, NSW, 2298, Australia

    Jennette A. Sakoff

  4. Research Centre for Crystalline Materials, School of Science and Technology, Sunway University, No. 5 Jalan Universiti, 47500, Bandar Sunway, Selangor Darul Ehsan, Malaysia

    Edward R. T. Tiekink

  5. Foundry of Reticular Materials for Sustainability (FORMS), Materials Synthesis and Characterization Laboratory, Institute of Advanced Technology, Universiti Putra Malaysia, 43400, Serdang, Selangor, Malaysia

    Thahira B. S. A. Ravoof

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  1. Enis Nadia Md. Yusof
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Yusof, E.N.M., Ishak, N.N.M., Latif, M.A.M. et al. Selective cytotoxicity of organotin(IV) compounds with 2,3-dihydroxybenzyldithiocarbazate Schiff bases. Res Chem Intermed 46, 2351–2379 (2020). https://doi.org/10.1007/s11164-020-04095-x

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