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Deciphering the binding mode of dinitramine herbicide to ct-DNA, a thermodynamic discussion

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Dinitramine is a herbicide that has been used to control annual grasses and broadleaf weeds in cotton and soybeans in Iran. In this study, the electrochemical behavior of dinitramine was studied by cyclic voltammetry (CV) and differential pulse voltammetry (DPV) methods. The interaction of dinitramine with ct-DNA was evaluated by CV, competitive fluorescence, UV-Vis spectroscopy, FT-IR spectroscopy, and viscosity titration. In addition, the thermodynamic parameters of DIN–DNA complex were calculated by spectrophotometric titration. The values of ΔHbin., ΔSbin., and ΔGbin. (T = 290.65 K) of the DIN–DNA complex were +39.25 kJ mol−1, +215.71 J mol−1, and −23.45 KJ mol−1, respectively. These data revealed that the endothermic binding has its origin in the hydrophobic interactions. Also the high positive ΔSbin was explained according to the DIN structure that optimized by mechanical quantum calculations. However, all data showed that the major groove binding between DIN and ct-DNA is more predominant than other binding modes.
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Keywords: DNA binding; dinitramine herbicide; major groove; thermodynamic parameters

Document Type: Research Article

Affiliations: 1: Department of Medicinal Chemistry, Faculty of Pharmacy – International Campus, Iran University of Medical Sciences, Tehran, Iran 2: Department of Toxicology (Pharmacy), Shahreza Branch Islamic Azad University, Isfahan, Iran 3: Department of Clinical Biochemistry, Kermanshah University of Medical Sciences, Kermanshah, Iran

Publication date: January 2, 2016

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