Chin. J. Org. Chem. ›› 2013, Vol. 33 ›› Issue (08): 1709-1714.DOI: 10.6023/cjoc201212042 Previous Articles     Next Articles



张秀富a, 付义乐b, 左治钧a, 侯媛a, 李玥萱a, 刘艳霞a, 王兰英a   

  1. a 西北大学合成与天然功能分子化学教育部重点实验室 西安 710069;
    b 西安建筑科技大学 西安 710055
  • 收稿日期:2012-12-24 修回日期:2013-03-25 发布日期:2013-04-24
  • 通讯作者: 王兰英
  • 基金资助:

    陕西省教育厅科学研究基金(No. 11JK0558);陕西省科学技术研究发展计划(No. 2012K07-06)及西北大学研究生创新基金交叉学科(No. 09YJC20)资助项目.

Synthesis and Spectral Properties of Water-Soluble Indocyanine Dyes as Well as the Interaction with DNA and BSA

Zhang Xiufua, Fu Yileb, Zuo Zhijuna, Hou Yuana, Li Yuexuana, Liu Yanxiaa, Wang Lanyinga   

  1. a Key Laboratory of Synthetic and Natural Functional Molecule Chemistry (Ministry of Education), College of Chemistry and Materials Science, Northwest University, Xi'an 710069;
    b School of Science, Xi'an University of Architecture and Technology, Xi'an 710055
  • Received:2012-12-24 Revised:2013-03-25 Published:2013-04-24
  • Supported by:

    Project supported by the Special Science Research Foundation of Shaanxi Education Committee (No. 11JK0558), the Scientific and Technological Research and Development Projects in Shaanxi Province (No. 2012K07-06) and the Graduate Cross-discipline Funds of Northwest University (No. 09YJC20).

Six novel water-soluble indocyanine dyes were synthesized using 1,2,3-trimethyl-3-(4-sulphobutyl)-3H-in-dolium-5-sulphonate salt and corresponding aromatic aldehyde as materials and piperidine as catalyst. All of the compounds were characterized by 1H NMR, HRMS, IR and UV-vis techniques. Their spectral properities in different solvents were also investigated. The results showed that the maximum absorption wavelength of the dyes was in the region of 426.0~562.5 nm, the emission wavelength was located in 508.2~596.0 nm and the molar extinction coefficients was in the region of 0.6×104~6.7×104 L·mol-1·cm-1 in different solvents. The interactions of prepared dyes with salmon sperm DNA and bovine serum albumin (BSA) were also investigated. The results showed that the interaction of five water-soluble dyes with DNA or BSA was weak.

Key words: water-soluble indocyanine dye, spectral properties, DNA, BSA