Novel Fluorescence Probe for Fe3+and Application of Imaging in Living Cells

doi:10.6023/cjoc201506017

Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (12): 2629-2635.DOI: 10.6023/cjoc201506017 Previous Articles Next Articles

Notes

新型Fe³⁺荧光探针的合成及活细胞成像中的应用

李波, 孟文斐, 杨美盼, 苏娜, 刘晓静, 杨秉勤

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:2015-06-15 修回日期:2015-07-11 发布日期:2015-08-26
通讯作者: 杨秉勤 E-mail:yangbq@nwu.edu.cn;libo19886@163.com
基金资助:
国家自然科学基金(No. 21172178)资助项目.

Novel Fluorescence Probe for Fe³⁺and Application of Imaging in Living Cells

Li Bo, Meng Wenfei, Yang Meipan, Su Na, Liu Xiaojing, Yang Bingqin

Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of Ministry of Education, College of Chemistry & Materials Science, Northwest University, Xi'an 710069

Received:2015-06-15 Revised:2015-07-11 Published:2015-08-26
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21172178).

1. Novel Fluorescence Probe for Fe³⁺and Application of Imaging in Living Cells.PDF(266KB)

Abstract

A novel rhodamine B derivative R1 was synthesized facilely by the condensation reaction of rhodamine B, 2-aminothiophenol and benzyl chloride, and the structure of R1 was further characterized by IR, HRMS-ESI, ¹H NMR, ¹³C NMR. Then, the recognition properties of compound R1 with metal ions had been investigated in water solution by the fluorescence spectrophotometry. The results showed that probe R1 demonstrated excellent specificity toward Fe³⁺with high speed and sensitivity, and the fluorescence intensity was not affected by the other common metal ions. Furthermore, there was a good linearity between the fluorescence intensity and the concentration of Fe³⁺. Importantly, fluorescence imaging experiments of Fe³⁺ in living cells demonstrated their valuable application.

Key words: fluorescence probe, rhodamine B, Fe³⁺, recognition, PC-12 living cells

Cite this article

Li Bo, Meng Wenfei, Yang Meipan, Su Na, Liu Xiaojing, Yang Bingqin. Novel Fluorescence Probe for Fe³⁺and Application of Imaging in Living Cells[J]. Chin. J. Org. Chem., 2015, 35(12): 2629-2635.

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[1] Lin, W. Y.; Long, L. L.; Yuan, L.; Cao, Z. M.; Feng, J. B. Anal. Chim. Acta 2009, 634, 262
[2] Rouault, T. A. Nat. Chem. Biol. 2006, 2, 406.
[3] Hu, X. H. J. Pract. Radiol. 2011, 27, 791 (in Chinese). (胡晓华, 实用放射学杂志, 2011, 27, 791.)
[4] Aquino, D.; Bizzi, A.; Grisoli, M. Radiology 2009, 252, 165.
[5] Dornelles, A.S.; Garcia, V. A.; Vedana, G.; Alcalde, L. A.; Bogo, M. C.; Schroder, N. Neurochem. Res. 2010, 35, 564.
[6] Wang, S. X.; Meng, X. M.; Zhu, M. Z. Tetrahedron Lett. 2011, 52, 2840.
[7] Esposito, B. P.; Epsztejn, S.; Breue, W.; Cabantchik, Z. Anal. Biochem. 2002, 304, 18.
[8] Yin, W. T.; Cui, H.; Yang, Z.; Li, C.; She, M. Y.; Yin, B. Sens. Actuators B: Chem. 2011, 157, 675
[9] Mao, J.; He, Q.; Liu, W. S. Talanta 2010, 80, 2093.
[10] Xiang, Y.; Tong, A. J. Org. Lett. 2006, 8, 1549.
[11] Ohashi, A.; Ito, H.; Kanai, C.; Imura, H.; Ohashi, K. Talanta 2005, 65, 525.
[12] Tesfaldet, Z. O.; Van Staden, J. F.; Stefan, R. I. Talanta 2004, 64, 1189.
[13] Bobrowski, A.; Nowak, K.; Zarebski, J. Anal. Bioanal. Chem. 2005, 382, 1691.
[14] Ugo, P.; Moretto, L. M.; Boni, A. D. Anal. Chim. Acta 2002, 427, 147.
[15] Meng, W. F.; Yang, M. P.; Cheng, Z.; Li, S. N.; Yang, B. Q. Chin. J. Org. Chem. 2013, 33, 398 (in Chinese). (孟文斐, 杨美盼, 成昭, 李少妮, 杨秉勤, 有机化学, 2014, 33, 398.)
[16] Yang, M. P.; Xu, C. C.; Li, S. N.; Cheng, Z.; Zhou, J.; Yang, B. Q. RSC Adv. 2014, 4, 14248
[17] Donga, L.; Wua, C.; Zenga, X.; Mua, L.; Xuea, S. F.; Taoa, Z. Sens. Actuators, B: Chem. 2010, 145, 433.
[18] Yang, M. P.; Meng, W. F.; Liu, X. J.; Su, N.; Zhou, J.;Yang, B. Q. RSC Adv. 2014,4, 22288.
[19] Sun, W.; Hu, D. Y.; Wu, Z. B.; Song, B. A.; Yang, S. Chin. J. Org. Chem. 2011, 31, 997 (in Chinese). (孙伟, 胡德禹, 吴志兵, 宋宝安, 杨松, 有机化学, 2011, 31, 997.)
[20] Su, W. Q.; Tong, J.; Yang, B. Q. Chin. J. Org. Chem. 2013, 33, 982 (in Chinese). (苏文崎, 童杰, 杨秉勤, 有机化学, 2013, 33, 982.)
[21] Yuan, Y. H.; Tian, M. Z.; Feng, F.; Meng, S. M.; Bai, Y. F. Prog. Chem. 2010, 22, 1093 (in Chinese). (袁跃华, 田茂忠, 冯锋, 孟双明, 白云峰, 化学进展, 2010, 22, 1093.)
[22] Li, N.; Liu, M. L.; Yin, W. T.; Yang, Z.; Li, J. L.; Shi, Z. Chin. J. Org. Chem. 2011, 31, 39 (in Chinese). (李娜, 刘美玲, 尹文婷, 杨征, 李剑利, 史真, 有机化学, 2011, 31, 39.)
[23] Huang, W.; Wu, W.; Liang, J. Acta Chim. Sinica 2012, 70, 873.
[24] Zheng, Y.; She, M.; Yin, B. J. Org. Chem. 2012, 77, 1143.
[25] Yu, H.; Xiao, Y.; Guo, H. Chem. Eur. J. 2011, 17, 3179.
[26] Zhang, L.; Wang, J.; Fan, J. Bioorg. Med. Chem. Lett. 2011, 21, 5413.
[27] Kumar, M.; Kumar, R.; Bhalla, V. Org. Lett. 2011, 13, 366.
[28] Kim, H. N.; Lee, M. H.; Kim, H. J. Chem. Soc. Rev. 2008, 37, 1465.
[29] Zhang, W. J.; Wang, Z. M.; Qu, F. L. Chem. Sensors 2010, 30, 36 (in Chinese). (张卫军, 王作茂, 渠凤丽, 化学传感器, 2010, 30, 36.)
[30] Yang, Z.; She, M. Y.; Yin, B.; Cui, J. H.; Zhang, Y. Z.; Sun, W.; Li, J. L.; Shi, Z. J. Org. Chem. 2012, 77, 1143.
[31] Du, Y.; Chen, M.; Zhang, Y.; Luo, F.; He, C.; Li, M.; Chen, X. Talanta 2013, 106, 261.
[32] Chereddy, N.R.; Suman, K.; Korrapati, P. S.; Thennarasu, S.; Mandal, A. B. Dyes Pigm. 2012, 95, 606
[33] Zhou, J.; Yang, M. P.; Meng, W. F.; Cheng, Z.; Yang, B. Q. Chin. J. Org. Chem. 2014, 34, 1646 (in Chinese). (周佳, 杨美盼, 孟文斐, 成昭, 杨秉勤, 有机化学, 2014, 34, 1646.)
[34] Lin, X. M.; Wang, J. F.; Jia, G. L.; Mei, L.; Wang, Z. J. Toxicol. 2008, 22, 216 (in Chinese). (林祥梅, 王建峰, 贾广乐, 梅林, 王众, 毒理学杂志, 2008, 22, 216.)

新型Fe³⁺荧光探针的合成及活细胞成像中的应用

Novel Fluorescence Probe for Fe³⁺and Application of Imaging in Living Cells

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新型Fe3+荧光探针的合成及活细胞成像中的应用