Synthesis, characterization and DNA binding studies of organoantimony(V) ferrocenyl benzoates

Organoantimony(V) ferrocenyl benzoates (OFBs) [p-(C5H5FeC5H4)C6H4COO]2SbR3 (R = C6H5, p-CH3C6H4) (3, 4) and [m-(C5H5FeC5H4)C6H4COO]2SbR3 (R = p-CH3C6H4) (5) were synthesized and characterized by FT-IR, 1H and 13C NMR, single crystal XRD and elemental analysis. The DNA interaction of the complexes (3–5) was investigated by UV–Vis spectroscopy and cyclic voltammetry (CV). The complex-DNA binding constant was found to vary in the sequence: K2 (4.80 × 105) > K1 (2.36 × 104) > K3 (1.87 × 104) > K4 (6.61 × 103) > K5 (6.58 × 103). The shift in peak potential, current and absorption maxima of OFBs in the presence of DNA revealed that CV coupled with UV–Vis spectroscopy could provide a convenient way to characterize complex-DNA interaction mechanism, a prerequisite for the design of new anticancer agents and understanding the molecular basis of their action.

The variation of peak potential and current intensity in cyclic voltammetry (I) and the shift of wavelength changes in UV–Vis (II) were exploited for ferrocene derivatives(1–5)-DNA binding parameters as K2 > K1 > K3 > K4 > K5.Figure optionsDownload as PowerPoint slideHighlights
► Organoantimony ferrocenyl benzoates were found to have robust electrochemical signatures.
► The DNA-binding propensity of (1–5) was investigated by UV–Vis and CV techniques.
► The shift in peak potential, current and absorption maxima evidenced complex-DNA interaction.
► So, they constitute a highly useful reference basis for future investigations.
► The compound (5) was studied by single crystal X-ray diffractometer.