水杨醛衍生物缩2-氨甲基苯并咪唑Schiff碱合成、与DNA相互作用及其生物活性研究

Synthesis,DNA interaction and biological activity of N-( benzimidazol-2-ylmethyl)-salicylideneimine Schiff base

合成了3种水杨醛衍生物缩2-氨甲基苯并咪唑Schiff碱化合物(HL),通过元素分析、红外光谱、紫外光谱和核磁共振氢谱进行了表征,分别为:HL1=水杨醛缩2-氨甲基苯并咪唑,C15H13ON3;HL2=5-氯水杨醛缩2-氨甲基苯并咪唑,C_(15)H_(12)ON_3Cl;HL3=邻香兰素缩2-氨甲基苯并咪唑,C16H15O2N3.通过紫外光谱法、荧光光谱法和黏度法检测了3种Schiff碱与DNA相互作用的情况.结果显示:随着DNA的加入,3种Schiff碱的紫外吸收光谱出现减色效应和红移现象;对溴化乙锭-DNA复合体系的荧光有较强的猝灭作用;随着Schiff碱的加入,DNA的黏度减小.表明3种Schiff碱与DNA之间能以部分插入模式发生较强烈的相互作用,且强度按HL1,HL3和HL2的顺序依次增强.HL2和HL3对人体外结肠癌细胞(COLO205)和人乳腺癌细胞(MCF-7)的增殖均有较强的抑制作用,且HL2的抑制活性高于HL3.同时,3种Schiff碱有较好的抑菌活性,其中HL2对大肠杆菌的抑菌效果最显著.

Three Schiff bases,N-( benzimidazol-2-ylmethyl)-salicylideneimine( HL1,C15H13ON3),N-( benzimidazol-2-ylmethyl)-5-chloro-salicylideneimine( HL2,C15H12ON3Cl) and N-( benzimidazol-2-ylmethyl)-ovallineneimine( HL3,C16H15O2N3) were synthesized and characterized by elemental analysis,IR,UV-spectra and1 H NMR. The interaction between compounds and DNA was studied by ultraviolet absorption spectra,fluorescence spectra and viscosity measurements. As increasing concentration of DNA,the absorption bands of the compounds were affected,resulting in hypochromicity and slight red shift. The compounds to the EB-DNA solutions caused significant reduction in emission intensities. The relative viscosity of DNA steadily decreasedafter adding compounds. The results showed that the compounds could bind to DNA with stronger intensity via partial intercalative mode. The binding ability followed the trend from low to high: L1,L3 and L2. Meanwhile,the antiproliferative activities tests showed that HL2 and HL3 had greater activities against human colon cancer cells( COLO205) and human breast cancer cells( MCF-7) in vitro,in which HL2 had stronger inhibition ratios compared to HL3. The antibacterial activities of title compounds against Staphylococcus aureus,Bacillus subtilis,Escherichia coli,Canidia albicans were tested respectively. The results showed that HL2 had stronger inhibition against E. Coli.