Diorganotin(IV) carboxylates of 3-methylphenyl ethanoic acid: Synthesis, crystal structure, antibacterial, anticancer and molecular docking studies

Abstract

Di-n-butyl- (1) and diethyltin(IV) (2) derivatives of 3-methylphenylethanoic acid were synthesized and characterized by elemental analysis, atomic absorption, IR, ¹H and 13C NMR spectroscopy and mass spectrometry. The spectroscopic data and single crystal X-ray diffraction studies for complex 2 have confirmed a bidentate coordination mode of the carboxylate ligand and the presence of hexacoordinated tin atoms in the complexes. The complexes were screened for their in vitro antibacterial activity against selected gram positive and gram negative bacterial strains. The anticancer potential was assessed against prostate cancer cell lines. Both complexes have shown higher activities than the ligand acid. Complex 1 with an IC₅₀ value of 4.97 ± 0.27 μg/mL was found to be better anti prostate cancer agent than complex 2 (IC₅₀ = 11.26 ± 2.18 μg/mL). Molecular docking study has suggested antibacterial action of the complexes in terms of their ability to develop hydrogen bonding and hydrophobic interactions with vital residues of the target proteins like tyrosyl-tRNA synthase from Staphylococcus aureus (gram-positive bacteria) and undecaprenyl diphosphate synthase from Escherichia coli (gram-negative bacteria).

Graphical Abstract

Keywords:

• Organotin
• antibacterial
• anticancer
• crystal structure
• molecular docking

Additional information

Funding

We are thankful to the Higher Education Commission, Islamabad, Pakistan for the financial support.