Z. Iqbal, Z. Ashraf, M. Abas
Dec 15, 2019
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Journal
Journal of Molecular Structure
Abstract
Abstract The present study describes the efficient synthesis, structural characterization and DNA binding interactions of ethyl 2-(2-acetamidothiazol-4-yl)acetate 2. Theoretically and experimentally determined bond lengths, angles and DNA binding interactions are compared. The chemical structure of the synthesized compound 2 was confirmed by spectral data and single crystal X-ray diffraction. The presence of –NH signal at 12.16 ppm in 1HNMR spectrum and carbonyl carbon at 170.5 ppm in 13CNMR spectrum confirmed the formation of ethyl 2-(2-acetamidothiazol-4-yl)acetate 2. The bond lengths and angles calculated theoretically are in good agreement with experimentally determined values. Molecular docking studies of synthesized compound 2 against five different DNA structures were performed to check its binding affinity with these targets. It was found that compound 2 binds well with DNA (PDB 1BPX ) having binding energy value −5.7 kcal/mol. The DNA binding interactions was also determined experimentally by spectrophotometric and electrochemical methods. The results showed that compound 2 binds with DNA through intercalation and groove binding which reflected the mixed binding mode. The binding constants (Kb) calculated from these results are 1.45 × 103 M−1 (UV–Vis spectroscopy), 1.41 × 103 M−1 (Fluorescence spectroscopy) and 1.39 × 103 M-1 (Cyclic voltammetry) also revealed strong binding. Based upon our results it was proposed that the synthesized compound 2 may act as a lead structure to design more potent antitumor agents.