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

doi:10.6023/cjoc201212042

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

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水溶性吲哚菁染料的合成、光谱性质及其与DNA和BSA的作用

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

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 E-mail:wanglany@nwu.edu.cn
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 Xiufu^a, Fu Yile^b, Zuo Zhijun^a, Hou Yuan^a, Li Yuexuan^a, Liu Yanxia^a, Wang Lanying^a

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^-1in 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

Cite this article

Zhang Xiufu, Fu Yile, Zuo Zhijun, Hou Yuan, Li Yuexuan, Liu Yanxia, Wang Lanying. Synthesis and Spectral Properties of Water-Soluble Indocyanine Dyes as Well as the Interaction with DNA and BSA[J]. Chin. J. Org. Chem., 2013, 33(08): 1709-1714.

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水溶性吲哚菁染料的合成、光谱性质及其与DNA和BSA的作用

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

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