吡啶二甲醛双Schiff碱的合成及与鲑鱼精DNA的相互作用  

Synthesis of pyridinedialdehyde bis-Schiff base and its interaction with salmon sperm DNA

作　　者：隆新淑 孟德素 庞艳玲 段升霞 LONG Xin-shu;MENG De-su;PANG Yan-ling;DUAN Sheng-xia(School of Chemistry and Chemical Engineering,Heze University,Heze 274015,China)

机构地区：[1]菏泽学院化学化工学院,山东菏泽274015

出　　处：《化学研究与应用》2023年第8期1879-1885,共7页Chemical Research and Application

基　　金：山东省自然科学基金青年项目(ZR2021QB109)资助;教育部产学合作协同育人项目(220404903245344)资助。

摘　　要：利用Schiff碱与生物活性基团结合设计合成新型抗癌药物吸引众多学者关注,能与DNA结合的小分子化合物是筛选抗癌药物的重要物质。以2,6-吡啶二甲醛和异烟肼为原料,通过加热回流,合成了双Schiff碱2,6-吡啶二甲醛异烟肼(S),分别用红外光谱、质谱、核磁共振氢谱对S进行了结构表征。以光谱法研究了S与鲑鱼精DNA(ss-DNA)的相互作用,结果表明,在溶剂DMSO和H_(2)O(V∶V=5∶5),反应时间为18 min时,随着ss-DNA的加入,S的吸收和发射波长均逐渐蓝移,吸光度和荧光强度均逐渐增强,表明S与ss-DNA发生了沟面作用;离子强度、EB-DNA和热变性DNA实验进一步验证了S与ss-DNA之间的作用方式。热力学实验证明:二者的反应是自发进行的,主要作用力是范德华力和氢键,作用方式为沟面作用。The design and synthesis of novel anticancer drugs using Schiff base combined with bioactive groups attracts many scholars\attention,and small molecule compounds that can bind to DNA are important substances for screening anticancer drugs.The bis-Schiff base 2,6-pyridinedialdehyde isoniazid(S)was successfully synthesized by using 2,6-pyridinedialdehyde and isoniazid through heating and refluxing method.The structure of bis-Schiff base was characterized by IR,MS and 1H-NMR.And the interactions between S and salmon sperm DNA(ss-DNA)were investigated through spectrometry measurements.The experiments results indicated that the absorption and emission wavelengths of S became gradually blue shifted,and the absorbance and fluorescence intensity also gradually increased with the addition of ss-DNA insolution of DMSO and H_(2)O(V∶V=5∶5),in accompany with the reaction time of 18 min,demonstrating that there exited groove binding mode between S and ss-DNA.Moreover,ionic strength,EB-DNA and thermal denatured DNA experiments also verified the groove bingding mode between S and ss-DNA.Furthermore,thermodynamic experiments indicated that the reaction between S and ss-DNA was spontaneous,the main forces were van der Waals force and hydrogen bond,and the mode of action was groove binding.

关 键 词：异烟肼 2 6-吡啶二甲醛 双SCHIFF碱 脱氧核糖核酸 光谱法 沟面作用 

分 类 号：O657.3[理学—分析化学]