Structure and Surface Analysis of Ibuprofen-Organotin Conjugate: Potential Anti-Cancer Drug Candidacy of the Compound is Proven by In-Vitro DNA Binding and Cytotoxicity Studies

An ibuprofen-organotin conjugate (TPTDI) was synthesized by reacting ibuprofen with triphenyltin hydroxide (fentin hydroxide) in dry ethanol under acidic conditions. Characterization data of the compound, obtained by spectroscopic techniques (FTIR, 1 H-NMR and 13 C-NMR), elemental analysis and its X-ray single crystal were found to corroborate the stoichiometry and structure of the title organotin (IV) ester. A detailed Hirshfeld surface analysis for the elucidation of possible intermolecular interactions indicated that the most important contributions to the crystal packing were from H…H (66.7%), H…C/C…H (27.9%) and H…O/O…H (5.3%) interactions. Hydrogen-bonding and van der Waals interactions were the dominant interactions in the crystal packing. TPTDI – DNA binding studies were done by DFT, molecular docking, UV-visible and fluorescence spectroscopies, cyclic voltammetry (CV) and by viscosity measurements at neutral pH (7.0) and at 37 o C. Theoretical and experimental investigations were found compatible and revealed significant reactivity of TPTDI with DNA via mixed mode of interaction. Binding parameters (∆G, K b and n) confirmed the reaction spontaneity and intercalation as prominent mode along with groove binding. In-vitro Huh-7 cancer cell line activity suggested TPTDI to be a potential anti-cancer drug candidate. Molecular, chemical and biological findings showed good correlations.