单氟类黄酮的合成及其与牛血清蛋白相互作用的光谱学、热力学和分子动力学模拟研究  

Spectroscopic,thermodynamic and molecular dynamics simulations of the synthesis of monofluorinated flavonoids and their interactions with bovine serum proteins

作　　者：安超娜 姚甜 吴睿[1] 刘存芳[1] 刘波[1] 田光辉[1] AN Chao-Na;YAO Tian;WU Rui;LIU Cun-Fang;LIU Bo;TIAN Guang-Hui(Shaanxi Key Laboratory of Catalysis,School of Chemical and Environmental Science,Shaanxi University of Technology,Hanzhong 723000,China)

机构地区：[1]陕西理工大学陕西省催化基础与应用重点实验室,汉中723000

出　　处：《四川大学学报（自然科学版）》2023年第6期180-192,共13页Journal of Sichuan University(Natural Science Edition)

基　　金：陕西省科技厅社会发展科技攻关(2022SF-356,2021SF-382);陕西省科技厅青年项目(2021JQ-750);陕西省教育厅重点实验室(21JS1004);国家级大学生创新创业训练计划(202210720017);陕西理工大学研究生创新基金(SLGYCX2227)。

摘　　要：本研究通过荧光光谱、热力学和分子动力学模拟研究了六种不同的黄酮类化合物(Ⅳ_(a~c)和V_(a~c))与牛血清蛋白(BSA)的相互作用.Ⅳ_(a~c)和Ⅴ_(a~c)与BSA的荧光行为有定量关系,用Stern-Volmer方程计算的结果表明,Ⅳ_(a~c)和Ⅴ_(a~c)与BSA有明显的荧光猝灭,均为静态猝灭.当单氟黄酮的氟原子处于对位时,与BSA的结合能力最好,当单氟黄酮醇的氟原子处于间位时,与BSA的结合能力最好,当单氟黄酮Ⅳ_(a~c)的C(3)具有羟基时,单氟黄酮醇与BSA的结合能力强于单氟黄酮.计算出的Ⅳ_(a~c)和Ⅴ_(a)~Vc的热力学参数结果为ΔG<0、ΔH<0和ΔS<0,表明Ⅳ_(a~c)和Ⅴ_(a)~Vc与BSA的相互作用是一个自发的放热过程,其相互作用主要依靠氢键和范德华力结合.In this study,the interactions of six different flavonoids(IV_(a~c)and V_(a~c))with bovine serum proteins(BSA)were investigated by fluorescence spectroscopy,thermodynamic and molecular dynamics simulations.The fluorescence behaviors of IV_(a~c)and V_(a~c)were quantitatively related to BSA,and the results calculated using the Stern-Volmer equation showed that IV_(a~c)and V_(a~c)had significant fluorescence quenching with BSA,both of which were static quenching.The binding ability of monofluoroflavone with BSA was best when its fluorine atom was at para position,while the binding ability of monofluoroflavonol with BSA was best when its fluorine atom was at meta position.The binding ability of monofluoroflavonol with BSA was stronger than that of monofluoroflavone when hydroxyl group was attached to the C(3)of monofluoroflavone IV_(a~c).The calculated thermodynamic parameters ofⅣ_(a~c)and Va~Vc wereΔG<0,ΔH<0 andΔS<0,indicating that the interaction ofⅣ_(a~c)and V_(a)~V_(c)with BSA was a spontaneous exothermic process,which mainly relies on hydrogen bonding and van der Waals force.

关 键 词：丹皮酚 黄酮 合成 牛血清蛋白 荧光光谱 

分 类 号：O629.9[理学—有机化学]