高等学校化学学报 ›› 2015, Vol. 36 ›› Issue (10): 1924-1932.doi: 10.7503/cjcu20150128

• 有机化学 • 上一篇    下一篇

吲哚二甲川菁的合成、 晶体结构、光谱性质及生物应用

张江华, 吕英, 贾红亮, 宋银银, 孙晓霞, 柴敦宵, 王兰英()   

  1. 西北大学化学与材料科学学院, 合成与天然功能分子化学教育部重点实验室, 西安 710127
  • 收稿日期:2015-02-04 出版日期:2015-10-10 发布日期:2015-09-14
  • 作者简介:联系人简介: 王兰英, 女, 博士, 教授, 博士生导师, 主要从事功能分子合成及应用研究. E-mail:wanglany@nwu.edu.cn
  • 基金资助:
    国家自然科学基金(批准号: 21272184)和陕西省科学技术研究发展计划(批准号: 2012K07-06)资助

Synthesis, Crystal Structure and Spectral Properties of Six Indole Dimethine Cyanines as Well as Their Biological Application

ZHANG Jianghua, LÜ Ying, JIA Hongliang, SONG Yinyin, SUN Xiaoxia, CHAI Dunxiao, WANG Lanying*()   

  1. Key Laboratory of Synthetic and Natural Functional Molecule Chemistry, Ministry of Education, College of Chemistry and Materials Science, Northwest University, Xi’an 710127, China
  • Received:2015-02-04 Online:2015-10-10 Published:2015-09-14
  • Contact: WANG Lanying E-mail:wanglany@nwu.edu.cn
  • Supported by:
    † Supported by the National Natural Science Foundation of China(No.21272184) and the Development Project of Science and Technology Research of Shaanxi Province, China(No.2012K07-06)

摘要:

以含有活性甲基的杂环季铵盐和N-甲基-3-吲哚甲醛为原料, 在哌啶催化下合成了6种新型的双N-烷基化吲哚二甲川菁染料C1~C6; 采用紫外-可见光谱(UV-Vis)、 氢核磁共振谱(1H NMR)、 红外光谱(IR)和高分辨率质谱(HRMS)对6种染料进行了结构表征; 利用X射线单晶衍射法测定了染料C1和C5的晶体结构. 研究了6种染料在不同溶剂中的光谱性质, 结果表明, 染料C1~C6在不同溶剂中的最大吸收波长处在370.0~521.0 nm之间, 发射波长处在466.4~600.8 nm之间, 摩尔消光系数在0.80×104~3.92×104 L·mol-1·cm-1范围内; 研究了6种染料在近生理条件下分别与DNA、 牛血清蛋白(BSA)、 溶菌酶、 淀粉酶、 牛血红蛋白和糜蛋白酶的相互作用, 结果表明, 染料C3~C5的荧光量子产率随着DNA浓度的增加而增大; 探究了染料C5和C6的细胞毒性和细胞染色性能, 结果显示, 在实验应用的剂量及时间下, 染料C5和C6对人类神经胶质瘤细胞(A172)几乎没有毒性, 且主要对细胞核染色, 可以作为潜在的观察细胞的荧光试剂.

关键词: 吲哚二甲川菁, 晶体结构, 光谱性质, 生物分子, 细胞毒性和染色

Abstract:

Six novel bis(N-alkyl) indole dimethine cyanine dyes(C1—C6) were synthesized using heterocyclic quaternary ammonium salts with active methyl and N-methyl-3-indole formaldehyde as starting materials and piperidine as catalyst. The dyes were identified by UV-Vis, 1H NMR, IR and HRMS and the crystal structures of dyes C1 and C5 were determined by X-ray single crystal diffraction analyzer. The investigation of the spectral properties of dyes C1—C6 in different solvents showed that the maximum absorption wavelength of the dyes was in the range of 370.0—521.0 nm, the emission wavelength was located in 466.4—600.8 nm and the molar extinction coefficients was in the range of 0.80×104—3.92×104 L·mol-1·cm-1 in different solvents. The interactions of dyes C1—C6 with DNA, bovine serum albumin(BSA), muramidase, amylase, bovine hemoglobin and chymotrypsin were investigated, respectively. The results showed that the spectral properties of dyes C3, C4 and C5 were significantly changed with the addition of DNA and the quantum yields of the dyes were increased with the increase of DNA concentration. The investigation of the cytotoxicity and cell staining of the selected dyes C5 and C6 showed that the two dyes had virtually no toxicity at applications dose and time and could stain cell nucleus, suggesting that the dyes C5 and C6 could be used as potential fluorescent reagents to observe living cells.

Key words: Indole dimethine cyanine, Crystal structure, Spectral property, Biomolcule, Cytotoxicity and cell staining

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