1,4-二甲基-6,8-二甲氧基-9,10-蒽醌的合成及其与BSA和ct-DNA的相互作用  

Synthesis of 1,4-Dimethyl-6,8-dimethoxy-9,10-anthraquinone and Its Interaction with BSA and Calf Thymus DNA

作　　者：李玉英[1] 管英英 张立伟[1] 王转花[1] 

机构地区：[1]山西大学生物技术研究所化学生物学与分子工程教育部重点实验室,太原030006

出　　处：《化学通报》2015年第6期525-531,共7页Chemistry

基　　金：国家自然科学基金项目(31171659);山西省高校科技开发项目(2012004)资助

摘　　要：合成了大黄素类蒽醌衍生物1,4-二甲基-6,8-二甲氧基-9,10-蒽醌(1)并应用紫外光谱、荧光光谱、圆二色谱等方法研究了其与牛血清白蛋白(BSA)和小牛胸腺DNA(ct-DNA)的相互作用。荧光光谱结果表明,化合物1与BSA的相互作用主要以静态猝灭方式使BSA的内源性荧光发生猝灭;圆二色谱表明,化合物1通过疏水作用及形成氢键破坏了α-螺旋结构,导致BSA分子中的α-螺旋含量下降。在p H 7.4时固定DNA的浓度,加入化合物1后,紫外光谱的最大吸收峰发生红移且吸光度加大。荧光光谱表明,化合物1与DNA-4S green NC的结合为竞争性抑制,并可使溶液体系荧光猝灭;圆二色谱表明,随着化合物1的加入,DNA碱基间作用能迅速减弱,表明化合物1与DNA之间为嵌插作用。此外,MTT方法的结果表明,化合物1对结肠癌细胞株HCT116增殖有明显的抑制作用。1,4-Dimethyl-6,8-dimethoxy-9,10-anthraquinone( 1) had been synthesized. The mechanisms of the interaction between BSA,ct-DNA and 1 were investigated by UV-Vis spectroscopy,fluorescence spectroscopy and circular dichroism( CD) methods. For the interaction of 1 and BSA,it leads to BSA endogenous fluorescence quenching by a static quenching,and the α-helix structure and content of BSA molecules are destroyed and reduced by hydrophobic effect and hydrogen bonding. For the DNA solution of p H 7. 4,hyperchromic effect of UV spectra was observed as adding of compound 1. Owing to its competitive inhibition against 4S greeu NC binding to DNA,the fluorescence of DNA-4 Sgreen NC system could be quenched by adding compound 1. CD spectra study revealed that the energy of base pair of DNA has been weakened due to the addition of compound 1. So it can be concluded that the binding mode of compound 1 with ct-DNA belongs to intercalation action. In addition,the results of MTT method indicated that compound 1 possesses significantly inhibited cells proliferation for HCT116.

关 键 词：蒽醌类衍生物 牛血清白蛋白 DNA 相互作用 光谱 

分 类 号：O625.463[理学—有机化学]