N-取代吡啶酰胺与DNA作用的研究  

Studies on DNA-binding properties of N-substituted pyridinecarboxamide

作　　者：林秋月[1,2] 贺新前[1] 王东航[1] 郑菊芳[2] 

机构地区：[1]浙江师范大学化学与生命科学学院化学系,浙江金华321004 [2]浙江师范大学浙江省固体表面反应化学重点实验室,浙江金华321004

出　　处：《浙江师范大学学报（自然科学版）》2009年第2期189-195,共7页Journal of Zhejiang Normal University:Natural Sciences

基　　金：浙江省自然科学基金资助项目(Y404031);浙江师范大学无机化学重点学科资助项目

摘　　要：合成了由N-芳环、氮杂环和脂肪烃取代的5种吡啶酰胺类化合物:N-苯基-吡啶-2-甲酰胺(L1),N-2-氯苯基-吡啶-2-甲酰胺(L2),N-2-硝基苯基-吡啶-2-甲酰胺(L3),N-2-吡啶基-吡啶-2-甲酰胺(L4)和N,N′-双(2-吡啶甲酰胺)-1,4-二乙烯三胺(L5),应用紫外光谱法、荧光光谱法、黏度法、表面增强拉曼光谱法及琼脂糖凝胶电泳法研究了5种化合物与DNA的相互作用.紫外光谱研究发现,随着DNA的加入,5种化合物的吸收带均出现减色效应,且伴随着微弱的红移现象.5种化合物对DNA与溴化乙锭(EB)复合体系的荧光有猝灭作用,测得线性Stern-Volm er常数Ksq分别为1.73(L1),0.92(L2),2.21(L3),1.32(L4)和0.77(L5),表明与DNA作用的增强顺序为:L5,L2,L4,L1,L3.这5种化合物对DNA黏度的影响呈现了不同的变化趋势.研究结果表明,L1,L2,L3和L4与DNA的作用为插入模式,而L5与DNA的作用可能为沟面结合或者静电作用模式.琼脂糖凝胶电泳实验显示,5种化合物能对pBR322 DNA进行一定程度的切割,随着化合物浓度的增加,开环构型DNA逐渐增多,超螺旋构型DNA逐渐减少;并且L3还能将切口环型DNA进一步切割成线型DNA.Five N-substituted pyridinecarboxamide： N-phenyl-2-pyridinecarboxamide （ L1）, N-2-chlorine phenyl-2-pyridinecarboxamide （ L2 ）, N-2-nitro phenyl-2-pyridinecarboxamide （ L3 ） , N-pyridyl-2-pyridine- carboxamide （ L4 ）, N, N′-bis （ 2-pyridinecarboxamide ） -1,4-diethylenetriamine （ L5 ） had been synthesized. The interaction between the compounds and DNA was studied by means of UV-visible spectra, fluorescence spectra, surface enhanced Raman spectroscopic, viscometric titration and agarose gel electrophoresis. In UV-visible spectra, the faint hypochromism of complexes＇ absorp＇tion spectra, the addition of the compounds to the DNA-bound EB solutions caused obvious reduction in emission intensities, indicated that the compounds com- peted with ethidium bromide in binding to DNA. The linear Stern-Volmer quenching constant, Ksq values for L were 1.73 （L1）, 0.92 （L2）, 2.21 （L3）, 1.32 （L4） and 0.77 （L5） respectively. The binding ability followed the trend from high to low： L3, L1 ,L4, L2 and 1.5. The results of viscometric titration showed that compounds changed the relative viscosity of DNA in different degree. L1, L2, L3 and IA were easy to insert their aromatic ring to the base pairs of DNA and L5 were mainly in groove binding. The compounds could cleave the supereoiled plasmid DNA. An increase in concentration of compounds caused more transformation of the DNA from supercoiled plasmid to nicked circular. In addition, a linear form was generated in present of L3.

关 键 词：N-取代吡啶酰胺 DNA作用 紫外光谱 荧光光谱 凝胶电泳 

分 类 号：O626.32[理学—有机化学]