双卤代萘甲酰腙的合成、晶体结构及其与BSA和ct-DNA的相互作用  

Synthesis,crystal structure and interaction with BSA and ct-DNA of double halogenated naphthoyl hydrazone

作　　者：宗新杰 刘向荣[1] 赵顺省[1] 杨再文[1] ZONG Xin-jie;LIU Xiang-rong;ZHAO Shun-sheng;YANG Zai-wen(College of Chemistry and Chemical Engineering,Xi’an University of Science and Technology,Xi’an 710054,China)

机构地区：[1]西安科技大学化学与化工学院,陕西西安710054

出　　处：《化学研究与应用》2018年第4期542-549,共8页Chemical Research and Application

基　　金：国家自然科学基金项目(No.21073139;21103135和21301139)

摘　　要：利用6-溴-2-萘甲酸甲酯和水合肼缩合生成6-溴-2-萘甲酰肼,再与卤代苯甲醛反应得到三种新型双卤代萘甲酰腙(C_(18)H_(12)BrXN_2O,X=F、1,Cl、2,Br、3)。X-射线单晶衍射表明三种酰腙化合物均属单斜晶系,P21空间群。三种酰腙化合物最大热分解处的温度均超过330℃,说明它们都具有较高的热稳定性。荧光光谱显示每个酰腙化合物都与牛血清蛋白(BSA)通过静态猝灭的方式形成了复合物,与BSA的结合常数KA均在105L·mol^(-1)左右,表明它们之间的结合能力较强。紫外-可见光谱表明三种酰腙化合物与小牛胸腺DNA(ctDNA)的作用模式均为嵌插互入作用,1、2、3与ct-DNA的结合常数Kb分别为5.94×108L·mol^(-1)、4.29×108L·mol^(-1)和5.96×108L·mol^(-1)。6-bromo-2-naphthoyl hydrazine was synthesized by the condensation reaction of methyl 6-bromo-2-naphthoate and hydrazine hydrate,then reacted with halogenated benzaldehyde to get three novel double halogenated naphthoyl hydrazones(C 18 H 12 BrXN 2O,X=F,1;Cl,2;Br,3).The results of X-ray single crystal diffraction showed that three acylhydrazone compounds all belonged to the monoclinic,P 2 1 space group.The temperatures at the maximum thermal decomposition of three acylhydrazone compounds were all beyond 330℃,which proved that all of them had higher thermal stabilities.The fluorescence spectra showed each aclyhydrazone compound reacted with bovine serum albumin(BSA)to form a complex by static quenching effect,the binding constants K A of three compounds with BSA were all around 10 5 L·mol-1,which indicated that they had strong combining abilities.UV-Vis spectra showed that three acylhydrazone compounds reacted with ct-DNA by the modes of insertion,the binding constants K b for 1,2 and 3 were 5.94×10 8 L·mol-1,4.29×10 8 L·mol-1 and 5.96×10 8 L·mol-1,respectively.

关 键 词：萘甲酰腙 晶体结构 热重分析 BSA CT-DNA 

分 类 号：O641.4[理学—物理化学]