A Water-Soluble Rhodamine-Based Fluorescent Probe for Fe3+ and Its Application in Live Cell Imaging

doi:10.6023/cjoc201610014

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (3): 617-623.DOI: 10.6023/cjoc201610014 Previous Articles Next Articles

ARTICLE

水溶性罗丹明基Fe³⁺荧光探针及其在细胞成像中的应用

高勇^a,b, 汪军^a, 付妹^a, 陈宏伟^a, 方明章^a

a 福建师范大学化学与化工学院福州 350007;
b 福建师范大学福建省先进材料化工基础重点实验室福州 350007

收稿日期:2016-10-11 修回日期:2016-12-15 发布日期:2016-12-29
通讯作者: 高勇,E-mail:gaoyong77@126.com E-mail:gaoyong77@126.com
基金资助:
福建省自然科学基金重点（No.2013H0019）资助项目.

A Water-Soluble Rhodamine-Based Fluorescent Probe for Fe³⁺ and Its Application in Live Cell Imaging

Gao Yong^a,b, Wang Jun^a, Fu Mei^a, Chen Hongwei^a, Fang Mingzhang^a

a College of Chemistry and Chemical Engineering, Fujian Normal University, Fuzhou 350007;
b Fujian Provincial Key Laboratory of Advanced Materials Oriented Chemical Engineering, Fujian Normal University, Fuzhou 350007

Received:2016-10-11 Revised:2016-12-15 Published:2016-12-29
Contact: 10.6023/cjoc201610014 E-mail:gaoyong77@126.com
Supported by:
Project supported by the Natural Science Foundation of Fujian Province (No. 2013H0019).

1. A Water-Soluble Rhodamine-Based Fluorescent Probe for Fe³⁺ and Its Application in Live Cell Imaging.PDF(1107KB)

Abstract

A rhodamine-based water-soluble fluorescent probe of Fe³⁺(T1) was designed and synthesized, in which a carboxy was linked to enhance its water solubility. Its structure was characterized by ¹H NMR, ¹³C NMR and HRMS-ESI. The fluorescent probe showed remarkable "turn-on" fluorescent responses to Fe³⁺ with good selectivity over other competitive cations. It has a good water solubility that the recognition properties of the probe with Fe³⁺ ions can be investigated in DMF/Tris-HCl (V:V=1:9, pH=7.4). The fluorescence imaging experiments of Fe³⁺ in MCF-7 living cells demonstrated that the probe had a good cell-membrane permeability and it could be used in biological systems.

Key words: rhodamine, water solubility, Fe³⁺, fluorescent probe, live cell imaging

Cite this article

Gao Yong, Wang Jun, Fu Mei, Chen Hongwei, Fang Mingzhang. A Water-Soluble Rhodamine-Based Fluorescent Probe for Fe³⁺ and Its Application in Live Cell Imaging[J]. Chin. J. Org. Chem., 2017, 37(3): 617-623.

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[1] Meneghini, R. Free Radical Biol. Med. 1997, 23, 783.
[2] Aisen, P.; Wessling, R. M.; Leibold, E. A. Curr. Opin. Chem. Biol. 1999, 3, 200.
[3] Eisenstein, R. S. Annu. Rev. Nutr. 2000, 20, 627.
[4] Rouault, T. A. Nat. Chem. Biol. 2006, 2, 406.
[5] Sumner, J. P.; Kopelman, R. Analyst 2005, 130, 528.
[6] Weizman, H.; Ardon, O.; Mester, B.; Libman, J.; Dwir, O.; Hadar, Y.; Chen, Y.; Shanzer, A. J. Am. Chem. Soc. 1996, 118, 12368.
[7] Brugnara, C. Clin. Chem. 2003, 49, 1573.
[8] Eid, C.; Hémadi, M.; Ha-Duong, N.; Chahine, J. E. H. Biochim. Biophys. Acta 2014, 1840, 1771.
[9] Breuer, W.; Epsztejn, S.; Cabantchik, Z. I. J. Biol. Chem. 1995, 270, 24209.
[10] Petrat, F.; Paluch, S.; Dogruöz, E.; Dörfler, P.; Kirsch, M.; Korth, H.-G.; Sustmann, R.; Groot, H. D. J. Biol. Chem. 2003, 278, 46403.
[11] Crichton, R. R.; Dexter, D. T.; Ward, R. J. Coord. Chem. Rev. 2008, 252, 1189.
[12] Dornelles, A. S.; Garcia, V. A.; Lima, M N. M. d.; Vedana, G.; Alcalde, L. A.; Bogo, M. R.; Schröder, N. Neurochem. Res. 2010, 35, 564.
[13] Ohashi, A.; Ito, H.; Kanai, C.; Imura, H.; Ohashi, K. Talanta 2005, 65, 525.
[14] Liang, Z.-Q.; Wang, C.-X.; Yang, J.-X.; Gao, H.-W.; Tang, Y.-P.; Tao, X.-T. Jiang, M.-H. New J. Chem. 2007, 31, 906.
[15] Lunvongsa, S.; Oshima, M.; Motomizu, S. Talanta 2006, 68, 969.
[16] Tesfaldet, Z. O.; Stefan, R. I. Talanta 2004, 64, 1189.
[17] Gomes, D. M.C.; Segundo, M. A.; Limaa, J. L. F. C.; Rangelb, A. O. S. S. Talanta 2005, 66, 703.
[18] Chen, H.; Liang, P.; Hu, B.; Zhao, L.; Sun, D.-H.; Wang, X.-R. Spectrosc. Spectral Anal. 2002, 22, 1019 (in Chinese).(陈浩, 梁沛, 胡斌, 赵丽, 孙大海, 王小如, 光谱学与光谱分析, 2002, 22, 1019.)
[19] (a) Carter, K. P.; Young, A. M.; Palmer, A. E. Chem. Rev. 2014, 114, 4564.
(b) Li, D.-X.; Sun, X.; Huang, J.-M.; Wang, Q.; Feng, Y.; Chen, M.; Meng, X.-M.; Zhu, M.-Z.; Wang, X. Dyes Pigm. 2016, 125, 185.
(c) Feng, Y.; Li, D.-X.; Wang, Q.; Wang, S.-X.; Meng, X.-M.; Shao, Z.-L.; Zhu, M.-Z.; Wang, X. Sens. Actuators, B 2016, 225, 572.
(d) Wang, Q.; Feng, Y.; Jiang, J.; Wang, W.-J.; Chen, J.-Y.; Sheng, H.-T.; Meng, X.-M.; Zhu, M.-Z. Chin. Chem. Lett. 2016, 27, 1563.
[20] Kim, H. N.; Lee, M. H.; Kim, H. J.; Yoon, J. Chem. Soc. Rev. 2008, 37, 1465.
[21] Zhao, M.; Yang, X.-F.; He, S.; Wang, L. Sens. Actuators, B 2009, 135, 625.
[22] Shang, G.-Q.; Gao, X.; Chen, M.-X.; Zheng, H.; Xu, J.-G. J. Fluoresc. 2008, 18, 1187.
[23] Wu, J.-S.; Hwang, I.-C.; Kim, K. S.; Kim, J. S. Org. Lett. 2007, 9, 907.
[24] (a) Li, N.; Liu, M.; 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.)
(b) 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.)
(c) Guo, Z.-Q.; Park, S.; Yoon, J.; Shin, I. Chem. Soc. Rev. 2014, 43, 16.
(d) Zhu, L.; Yuan, Z.; Simmons, J. T.; Sreenath, K. RSC Adv. 2014, 4, 20398.
(e) Carter, K. P.; Young, A. M.; Palmer, A. E. Chem. Rev. 2014, 114, 4564.
(f) Ding, Y.-B.; Tang, Y.-Y.; Zhu, W.-H.; Xie, Y.-S. Chem. Soc. Rev. 2015, 44, 1101.
(g) Sun, J.-F.; Qian, Y. Chin. J. Org. Chem. 2016, 36, 151 (in Chinese).(孙京府, 钱鹰, 有机化学, 2016, 36, 151.)
[25] (a) Eggeling, C.; Volkmer, A.; Claus, A. M. Chem. Phys. Chem. 2005, 6, 791.
(b) Su, N.; Yang, M.-P.; Meng, W.-F.; Yang, B.-Q. Chin. J. Org. Chem. 2015, 35, 175 (in Chinese).(苏娜, 杨美盼, 孟文斐, 杨秉勤, 有机化学, 2015, 35, 175.)
(c) Zhu, L.; Younes, A. H.; Yuan, Z.; Clark, R. J. J. Photochem. Photobiol. A 2015, 311, 1.
(d) Hou, H.-H.; Qu, Z.-G.; Zhong, K.-L.; Bian, Y.-J.; Tang, L.-J. Chin. J. Org. Chem. 2016, 36, 768 (in Chinese).(侯淑华, 曲忠国, 钟克利, 边延江, 汤立军, 有机化学, 2016, 36, 768.)
[26] Chen, X. Q.; Pradhan, T.; Wang, F.; Kim, J. S.; Yoon, J. Chem. Rev. 2012, 112, 1910.
[27] (a) Gao, Y.; Tian, M.; Zhang, B.; Zhang, M.; Li, J.-L.; Shi, Z. Chin. J. Org. Chem. 2007, 27, 269 (in Chinese).(高勇, 田敏, 张斌, 张敏, 李剑利, 史真, 有机化学, 2007, 27, 269.)
(b) Gao, Y.; Tian, M.; Guo, B. Chem. Bull. 2009, 72, 15 (in Chinese).(高勇, 张敏, 郭斌, 化学通报, 2009, 72, 15.)
(c) Gao, Y.; Yang, X.-H.; You, C.-C.; OuYang, H.; Yuan, Y.-F. J. Chem. Ind. Eng. 2011, 62, 374 (in Chinese).(高勇, 杨晓航, 游楚楚, 欧阳翰, 袁耀锋, 化工学报, 2011, 62, 374.)
(d) Fu, Mei.; Zhang, X.-W.; Wang, J.; Chen, H.-W.; Gao, Y. Curr. Org. Chem. 2016, 20, 1584.
[28] Yang, X.-H.; Li, S.; Tang, Z.-S.; Yu, X.-D.; Huang, T.; Gao, Y. Chin. Chem. Lett. 2015, 26, 129.
[29] Wan, X.-J.; Liu, T.-Q.; Liu, H.-Y.; Gu, L.-Q.; Yao, Y.-W. RSC Adv. 2014, 4, 29479.
[30] Yang, H.; Zhou, Z.-G.; Huang, K.-W.; Yu, M.-X.; Li, F.-Y.; Yi, T.; Huang, C.-H. Org. Lett. 2007, 9, 4729.
[31] Zhu, H.; Fan, J.-L.; Lu, J.; Hu, M.-M.; Cao. J.-F.; Wang. J.; Li, H.-L.; Liu, X.-J.; Peng, X.-J. Talanta 2012, 5, 55.
[32] Yang, X.-F., Guo, X.-Q., Zhao, Y.-B. Talanta 2002, 57, 883.

水溶性罗丹明基Fe³⁺荧光探针及其在细胞成像中的应用

A Water-Soluble Rhodamine-Based Fluorescent Probe for Fe³⁺ and Its Application in Live Cell Imaging

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水溶性罗丹明基Fe3+荧光探针及其在细胞成像中的应用