Notes

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

  • Li Bo ,
  • Meng Wenfei ,
  • Yang Meipan ,
  • Su Na ,
  • Liu Xiaojing ,
  • Yang Bingqin
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  • Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of Ministry of Education, College of Chemistry & Materials Science, Northwest University, Xi'an 710069

Received date: 2015-06-15

  Revised date: 2015-07-11

  Online published: 2015-08-26

Supported by

Project supported by the National Natural Science Foundation of China (No. 21172178).

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.

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]. Chinese Journal of Organic Chemistry, 2015 , 35(12) : 2629 -2635 . DOI: 10.6023/cjoc201506017

References

[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.)

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