Dibutyltin(IV) formulations as potential antitubercular scaffold: DFT assisted emerging advances and mechanism of antitubercular action

Abstract

The interplay between N, O-orthometallated, O, O′-chelated and dibutyltin(IV) groups in biopotent hybrid formulations to combat tuberculosis is deciphered. The present study emphasized on the design, generation, spectroscopic as well as DFT assisted structural characterization, understanding structure-antitubercular activity relationship and mode of action of some dibutyltin(IV) formulations against Mycobacterium tuberculosis as possible antituberculosis agents. Dibutyltin(IV) formulations of the general formula Bu2SnLL′ (where LH = heterocyclic/non-fluorinated/fluorinated β-diketones and L′H = aminophenol/substituted aminophenols) have been generated by the reaction of Bu2SnCl2 with sodium salts of the ligands in 1:1:1 molar ratio. The newly generated dibutyltin(IV) formulations have been characterized with the assistance of spectroscopic techniques and mass studies. Computational calculations of some representative complexes (1 and 2) also supported the obtained spectral data. Antituberculosis activity analysis was also performed on some representative dibutyltin(IV) complexes (1, 4 and 8). Out of these, complex 4 demonstrated highest activity against Mycobacterium tuberculosis. The structure-antitubercular activity relationship and mechanism of action of the active complexes against Mycobacterium tuberculosis have also been investigated. Intercluster electron hopping mechanism of mode of action has also been suggested.