Computational, Experimental Structural Characterization and Molecular Docking Studies of 5,7-Dihydroxy-4-methoxyflavone against Cytochrome P450 Enzymes

A. Harikrishnan, R. Madivanane
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Abstract

In this work, the geometry optimization and harmonic vibrational wavenumbers of kaempferide (5,7-dihydroxy-4-methoxyflavone) were computed by density functional theory (DFT) method. Theoretically computed vibrational wavenumbers were compared with experimental values and the interpretation of the vibrational spectra has been studied. Frontier molecular orbitals (FMO) and molecular electrostatic potential (MEP) analysis of the title compound have been carried out. The 1H & 13C NMR, UV visible and electronic properties of the compound were investigated theoretically and compared with the experimental values. Molecular docking study of the compound against cytochrome P450 family enzymes (CYPs 1A1, 1A2, 3A4, 2C8, 2C9 and 2D6) were also studied and the results revealed that the title compound interact with human CYP2C8 enzymes with minimum binding energy of -9.43 kcal/mol. The compound forms hydrogen bond with the residues of Thr302, Thr305, Leu361, Val362, Cys435, Gln356 and Ala297. Thus, these studies assist to understand the inhibitory mechanism of kaempferide with CYP450 enzymes and may facilitate significant clinical implications in the prevention and treatment of various therapeutic diseases.
5,7-二羟基-4-甲氧基黄酮抗细胞色素P450酶的计算、实验结构表征及分子对接研究
本文利用密度泛函理论(DFT)计算了山奈素(5,7-二羟基-4-甲氧基黄酮)的几何优化和谐波振动波数。将理论计算的振动波数与实验值进行了比较,并对振动谱的解释进行了研究。对该化合物进行了前沿分子轨道(FMO)和分子静电势(MEP)分析。对化合物的1H& 13C核磁共振、紫外可见性和电子性能进行了理论研究,并与实验值进行了比较。对该化合物与细胞色素p450家族酶(CYPs 1A1、1A2、3A4、2C8、2C9和2D6)的分子对接研究表明,该化合物与人CYP2C8酶的相互作用最小结合能为9.43 kcal/mol。该化合物与Thr302、Thr305、Leu361、Val362、Cys435、Gln356和Ala297残基形成氢键。因此,这些研究有助于了解山奈哌啶对CYP450酶的抑制机制,并可能在预防和治疗各种治疗性疾病方面具有重要的临床意义。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
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