A pH Sensitive Fluorescence Probe Based on Tricarbocyanine

doi:10.1007/s40242-016-6213-4

高等学校化学研究 ›› 2016, Vol. 32 ›› Issue (6): 877-881.doi: 10.1007/s40242-016-6213-4

A pH Sensitive Fluorescence Probe Based on Tricarbocyanine

YAN Luomei^1,2, ZHOU Hua¹, WU Cunqi¹, WANG Lidan¹, YANG Wei¹, JIN Manyu^1,2, ZHAO Yongxia¹, XU Jingwei¹

1. State Key Laboratory of Electroanalytical Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, P. R. China;
2. University of Chinese Academy of Sciences, Beijing 100049, P. R. China

收稿日期:2016-05-20 修回日期:2016-09-18 出版日期:2016-12-01 发布日期:2016-10-24
通讯作者: ZHAO Yongxia, E-mail:zyx@ciac.ac.cn; XU Jingwei, E-mail:jwxu@ciac.ac.cn E-mail:zyx@ciac.ac.cn;jwxu@ciac.ac.cn
基金资助:
Supported by the State Key Laboratory of Electroanalytical Chemistry of China.

A pH Sensitive Fluorescence Probe Based on Tricarbocyanine

YAN Luomei^1,2, ZHOU Hua¹, WU Cunqi¹, WANG Lidan¹, YANG Wei¹, JIN Manyu^1,2, ZHAO Yongxia¹, XU Jingwei¹

1. State Key Laboratory of Electroanalytical Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, P. R. China;
2. University of Chinese Academy of Sciences, Beijing 100049, P. R. China

Received:2016-05-20 Revised:2016-09-18 Online:2016-12-01 Published:2016-10-24
Contact: ZHAO Yongxia, E-mail:zyx@ciac.ac.cn; XU Jingwei, E-mail:jwxu@ciac.ac.cn E-mail:zyx@ciac.ac.cn;jwxu@ciac.ac.cn
Supported by:
Supported by the State Key Laboratory of Electroanalytical Chemistry of China.

摘要/Abstract

摘要： A pH sensitive near-infrared (NIR) fluorescent probe, IR-DO3A, was synthesized. It was based on combination of tricarbocyanine that had typical NIR absorption and fluorescent emission spectrum, and DO3A (1,4,7,10-tetra azacyclododecane -1,4,7-triyl)triacetic acid) that had three side chain of carboxylic acids. Phenyl sulfonamide that was used to maintain the density of electronic cloud of tricarbocyanine backbone and improve the solubility of the whole molecule was selected to connect tricarbocyanine and DO3A by several substitution reactions under some certain conditions. The final product, IR-DO3A was confirmed by NMR and MS spectrums, and had a better solubility in polar solvent than tricarbocyanine. The optical properties of IR-DO3A in two mixture solvents were studied. It had maximum Uv-vis absorption at 750nm and 805nm, fluorescent emission at 808nm, all these wavelengths were in NIR range and there was a 58nm Stokes-Shift. Also its optical properties at different pH in water were studied and it was sensitive in pH 6~9, which related with the protonation and deprotonation processes of IR-DO3A at different pH. These pH sensitive and NIR-fluorescent properties may result in an application for revealing the pH changes of physiological diseases.

关键词: pH sensitive probe, Near-infrared fluorescence emission, Tricarbocyanine

Abstract: A pH sensitive near-infrared (NIR) fluorescent probe, IR-DO3A, was synthesized. It was based on combination of tricarbocyanine that had typical NIR absorption and fluorescent emission spectrum, and DO3A (1,4,7,10-tetra azacyclododecane -1,4,7-triyl)triacetic acid) that had three side chain of carboxylic acids. Phenyl sulfonamide that was used to maintain the density of electronic cloud of tricarbocyanine backbone and improve the solubility of the whole molecule was selected to connect tricarbocyanine and DO3A by several substitution reactions under some certain conditions. The final product, IR-DO3A was confirmed by NMR and MS spectrums, and had a better solubility in polar solvent than tricarbocyanine. The optical properties of IR-DO3A in two mixture solvents were studied. It had maximum Uv-vis absorption at 750nm and 805nm, fluorescent emission at 808nm, all these wavelengths were in NIR range and there was a 58nm Stokes-Shift. Also its optical properties at different pH in water were studied and it was sensitive in pH 6~9, which related with the protonation and deprotonation processes of IR-DO3A at different pH. These pH sensitive and NIR-fluorescent properties may result in an application for revealing the pH changes of physiological diseases.

Key words: pH sensitive probe, Near-infrared fluorescence emission, Tricarbocyanine

YAN Luomei, ZHOU Hua, WU Cunqi, WANG Lidan, YANG Wei, JIN Manyu, ZHAO Yongxia, XU Jingwei. A pH Sensitive Fluorescence Probe Based on Tricarbocyanine[J]. 高等学校化学研究, 2016, 32(6): 877-881.

YAN Luomei, ZHOU Hua, WU Cunqi, WANG Lidan, YANG Wei, JIN Manyu, ZHAO Yongxia, XU Jingwei. A pH Sensitive Fluorescence Probe Based on Tricarbocyanine[J]. Chemical Research in Chinese Universities, 2016, 32(6): 877-881.

参考文献

[1] John V. F., Journal of Clinical Oncology, 2008, 26, 4012
[2] Weissleder R., Pittet M. J., Nature, 2008, 452, 580
[3] Weissleder R., Nat. Biotechnol., 2001, 19(4), 316
[4] Jung H. S., Chen X. Q., Jong S. K., Yoon J., Chem. Soc. Rev., 2013, 42, 6019
[5] Yuan Z., Younes A. H., Allen J. R., Davidson M. W., Zhu L., J. Org. Chem., 2015, 80(11), 5600
[6] Li H., Fan J., Peng X., Chem. Soc. Rev., 2013, 42, 7943
[7] Sreenath K., Yuan Z., Allen J. R., Zhu L., Chem. Eur. J., 2015, 21, 867
[8] Zhu L., Younes A. H., Yuan Z., Clark R. J., Journal of Photochemistry and Photobiology A:Chemistry, 2015, 311, 1
[9] Mishra A., Behera R. K., Behera G. B., Chem. Rev., 2000, 100(6), 1973
[10] Lichtman J. W., Conchello J. A., Nat. Methods, 2005, 2(12), 910
[11] Guo Z., Park S., Yoon J., Shin I., Chem. Soc. Rev., 2014, 43, 16
[12] Schutt F., Fischer J., Kopitz J., Holz F. G., Clin. Exp. Ophthalmol., 2002, 30(2), 110
[13] Sakka S. G., Curr. Opin. Critical Care, 2007, 13, 207
[14] Strekowski L., Lipowska M., Patonay G., J. Org. Chem., 1992, 57(17), 4578
[15] Montcourrier P., Mangeat P. H., Valembois C., Rochefort H., J. Cell Sci., 1994, 107, 2381
[16] Cousin M. A., Nicholls D. G., J. Neuro. Chem., 1997, 69(5), 1927
[17] Chen X. Y., Conti P. S., Moats R. A., Cancer Res., 2004, 64(21), 8009
[18] Cheng Z., Wu Y., Xiong Z. M., Gambhir S. S., Chen X. Y., Bioconjugate Chem., 2005, 16(6), 1433
[19] Kiyose K., Aizawa S., Sasaki E., Kojima H., Hanaoka K., Terai T., Chem. Eur. J., 2009, 15(36), 9191
[20] Myochin T., Kiyose K., Kojima H., Terai T., Nagano T., J. Am. Chem. Soc., 2011, 133(10), 3401
[21] Zhu L., Yuan Z., Simmons J. T. and Sreenath K., RSC Adv., 2014, 4, 20398
[22] Mizukami S., Tonai K., Kaneko M., Kikuchi K., J. Am. Chem. Soc., 2008, 130, 14376
[23] Faulkner S., Carrie M. C., Pope S. J., Squire J., Beeby A., Sammes P. G., Dalton Trans., 2004, 9, 1405
[24] Zhu D. J., Li G. P., Xue L., Hua J., Org. Biomol. Chem., 2013, 11, 4577
[25] Xu J., Niu L., Gao X., Cui M., Spectrum Analysis, Science Press, Beijing, 2013, 285

A pH Sensitive Fluorescence Probe Based on Tricarbocyanine

A pH Sensitive Fluorescence Probe Based on Tricarbocyanine

可视化

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 0

编辑推荐

Metrics

本文评价