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苯并吲哚半菁、二次甲基菁染料的微波合成、光谱性能及其与生物分子的相互作用
Microwave-Assisted Synthesis and Spectral Properties of Some Benzoindohemicyanine and Benzoindodimethine Cyanine Dyes as well as the Interaction with Biomolecules
【摘要】 采用微波技术,分别以N-烷基-2,3,3-三甲基-4,5-苯并吲哚六氟合磷酸盐与二甲氨基苯甲醛或3-吲哚甲醛为原料,在哌啶的催化下快速合成了4种苯并吲哚半菁染料H1~H4和4种苯并吲哚二次甲基菁染料F1~F4,并采用UV-Vis,1H NMR,IR,元素分析确证了产物的结构.研究了染料在不同溶剂中的吸收光谱性质,结果显示:两类染料在质子性溶剂中随着溶剂极性的增加最大吸收波长出现蓝移;而在非质子性溶剂中随着溶剂极性的减小最大吸收波长发生红移.同时,研究了染料H3和F2在生理条件下与鲑鱼精DNA、牛血清白蛋白、溶菌酶、淀粉酶和糜蛋白酶的相互作用,发现染料H3的荧光强度随着DNA浓度的增加而增强.
【Abstract】 Two series of benzoindocyanine dyes H1~H4 and F1~F4 were synthesized with the assistance of microwave irradiation under solvent-free condition using N-alkyl-2,3,3-trimethyl-4,5-benzoindole phosphate hexafluoropropylene and dimethylaminobenzaldehyde or indole-3-aldehyde as materials and piperidine as catalyst.All of the compounds were characterized by UV-Vis,1H NMR,IR techniques and elemental analysis.Their absorption spectral properities in different solvents were also investigated.The results showed that the λmaxof the dyes showed hypochromatic shifts with the increase of polarity in protic solvents,and bathochromic shifts with the decrease of polarity in aprotic solvents.The interactions of prepared dyes H3 and F2 with salmon sperm DNA,bovine serum albumin,muramidase,amylase and chymotrypsin were investigated,respectively.The results showed that the fluorescence intensity of H3 increased with the increase of DNA concentration.
【Key words】 benzoindocyanine dye; microwave synthesis; spectral property; DNA; protein;
- 【文献出处】 有机化学 ,Chinese Journal of Organic Chemistry , 编辑部邮箱 ,2012年03期
- 【分类号】TQ613
- 【被引频次】3
- 【下载频次】340