De novo design of chiral organotin cancer drug candidates: Validation of enantiopreferential binding to molecular target DNA and 5′-GMP by UV–visible, fluorescence, 1H and 31P NMR

N,N-bis[(R-/S-)-1-benzyl-2-ethoxyethane] tin (IV) complexes were synthesized by applying de novo design strategy by the condensation reaction of (R-/S-)2-amino-2-phenylethanol and dibromoethane in presence of dimethyltin dichloride and thoroughly characterized by elemental analysis, conductivity measurements, IR, ESI-MS, 1H, 13C and 119Sn, multinuclear NMR spectroscopy and XRD study. Enantioselective and specific binding profile of R-enantiomer 1 in comparison to S-enantiomer 2 with ultimate molecular target CT-DNA was validated by UV–visible, fluorescence, circular dichroism, 1H and 31P NMR techniques. This was further corroborated well by interaction of 1 and 2 with 5′-GMP.

► De novo synthesis of N,N-bis[(R-/S-)-1-benzyl-2-ethoxyethane] tin (IV) complexes. ► Elemental analysis, IR, ESI-MS, 1H, 13C and 119Sn, NMR spectroscopy and XRD study. ► 2J [1H–117/119Sn] coupling constant. ► Chiral discrimination of R- and S-enantiomer with CT DNA by employing biophysical techniques. ► R-enantiomer complex binds more avidly to DNA as compared to S-enantiomer complex.