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2018 , Vol. 38 >Issue 3: 636 - 641

DOI: https://doi.org/10.6023/cjoc201709017

研究论文

新型Fe3+荧光探针及其生物成像研究

  • 杨美盼 ,
  • 苏娜 ,
  • 李玉香 ,
  • 王莉 ,
  • 马利锋 ,
  • 张媛 ,
  • 李靖 ,
  • 杨秉勤 ,
  • 康龙丽
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  • a 高原相关疾病分子遗传机制与干预研究重点实验室 西藏民族大学 咸阳 712082;
    b 高原环境与疾病相关基因研究重点实验室 西藏民族大学 咸阳 712082;
    c 合成与天然功能分子化学教育部重点实验室 西北大学 西安 710127

收稿日期: 2017-09-11

  修回日期: 2017-11-24

  网络出版日期: 2017-12-01

基金资助

西藏自治区自然科学基金（（No.XZ2017ZGR-61）和西藏民族大学"青年学人培育计划"（No.17MDQP03）资助项目.

收起

A New Fluorescent Probe for Fe3+ and Its Application to Bioimaging

  • Yang Meipan ,
  • Su Na ,
  • Li Yuxiang ,
  • Wang Li ,
  • Ma Lifeng ,
  • Zhang Yuan ,
  • Li Jing ,
  • Yang Bingqin ,
  • Kang Longli
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  • a Key Laboratory for Molecular Genetic Mechanisms and Intervention Research on High Altitude Disease, Xizang Minzu University, Xianyang 712082;
    b Key Laboratory of High Altitude Environment and Gene Related to Disease, Xizang Minzu University, Xianyang 712082;
    c Key Laboratory for Synthetic and Natural Functional Molecule Chemistry of Ministry of Education, Northwest University, Xi'an 710127

Received date: 2017-09-11

  Revised date: 2017-11-24

  Online published: 2017-12-01

Supported by

Project supported by the Natural Science Foundation of Xizang (Tibet) Autonomous Region (No. XZ2017ZGR-61) and "The Training Plan for the Youth" Support Program of Xizang Minzu University (No. 17MDQP03).

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摘要

以罗丹明为基础合成、表征了一种"turn-on"型荧光探针.该探针对Fe3+表现出很高的选择性和灵敏性.将Fe3+加入到探针中，溶液的紫外吸收值和荧光强度都有很明显的变化，同时伴随着肉眼可见的溶液颜色改变.研究发现，探针与Fe3+按照1：1进行络合，引起了探针内酰胺环的打开，进而吸收值和荧光强度值发生变化.研究表明，在有其他共存离子存在下，该探针仍然可以有效检测Fe3+.细胞实验发现，探针可以穿过细胞膜，在细胞内与Fe3+作用，同时也可检测小鼠体内Fe3+，呈现出很好的荧光成像效果.

关键词： 荧光探针; Fe3+; 光谱性质; 机理; 细胞和小鼠

本文引用格式

杨美盼 , 苏娜 , 李玉香 , 王莉 , 马利锋 , 张媛 , 李靖 , 杨秉勤 , 康龙丽 . 新型Fe3+荧光探针及其生物成像研究[J]. 有机化学, 2018 , 38(3) : 636 -641 . DOI: 10.6023/cjoc201709017

Abstract

A turn-on probe, which exhibited highly selective and sensitive signaling behaviors toward Fe3+ over other common metal ions, has been synthesized and confirmed by 1H NMR, 13C NMR, IR and MS. The addition of Fe3+ to the solution of probe induced a remarkable UV-Vis and fluorescence enhancement along with obvious color change detected by the naked eye. The reaction mechanism was also investigated and proposed as that the probe complexed Fe3+ via a 1:1 binding mode, and the subsequent complexation caused the ring-opening of the rhodamine spirolactam and thereby the changes of absorbance and fluorescence. These remarkable properties may allow Fe3+ to be detected directly in the presence of the other examined competing metal ions. Then, cells experiments showed that the probe could permeate through cell membranes and react to Fe3+ within living cells. Additionally, the probe was further used for detecting Fe3+ ions in living mouse which exhibited excellent fluorescence imaging.

Key words： fluorescent probe; Fe3+; spectral properties; mechanism; cells and mouse

参考文献

[1] Cao, Y. D.; Zheng, Q. Y.; Chen, C. F.; Huang, Z. T. Tetrahedron Lett. 2003, 44, 4751.
[2] Zhang, L. F.; Zhao, J. L.; Zeng, X.; Mu, L.; Jiang, X. K.; Deng, M.; Zhang, J. X.; Wei, G. Sens. Actuators B 2011, 160, 662.
[3] Kim, J. S.; Quang, D. T. Chem. Rev. 2007, 107, 3780.
[4] Haim, W.; Orly, A.; Brenda, M.; Jacqueline, L.; Oren, D.; Yitzhak, H.; Yona, C.; Shanzer, A. J. Am. Chem. Soc. 1996, 118, 12368.
[5] Meneghini, R. Free Radical Biol. Med. 1997, 23, 783.
[6] Rouault, T. A. Nat. Chem. Biol. 2006, 2, 406.
[7] Eisenstein, R. S. Annu. Rev. Nutr. 2000, 20, 627.
[8] James, P. S.; Raoul, K. Analyst 2005, 130, 528.
[9] Aisen, P.; Wessling, R. M.; Leibold, E. A. Curr. Opin. Chem. Biol. 1999, 3, 200.
[10] Hentze, M. W.; Muckenthaler, M. U.; Andrews, N. C. Cell 2004, 117, 285.
[11] Wessling-Resnick, M. Crit. Rev. Biochem. Mol. Biol. 1999, 34, 285.
[12] Toyokuni, S. Cancer Sci. 2009, 100, 9.
[13] Fleming, R. E.; Ponka, P. N. Engl. J. Med. 2012, 366, 348.
[14] Nadadur, S. S.; Srirama, K.; Mudipalli, A. Indian J. Med. Res. 2008, 128, 533.
[15] Martin, R. B.; Savory, J.; Brown, S.; Bertholf, R. L.; Wills, W. R.; Clin. Chem. 1987, 33, 405.
[16] Braun, V.; Killmann, H. Trends Biochem. Sci. 1999, 24, 104.
[17] Pithadia A. S.; Lim, M. H. Curr. Opin. Chem. Biol. 2012, 16, 67.
[18] Burdo, J. R.; Connor, J. R. BioMetals 2003, 16, 63.
[19] Bonda, D. J.; Lee, H.; Blair, J. A.; Zhu, X.; Perry G.; Smith, M. A. Metallomics 2011, 3, 267.
[20] Yang, X. H.; Li, S.; Tang, Z. S.; Yu, X. D.; Huang, T.; Gao, Y. Chin. Chem. Lett. 2015, 26, 129
[21] Bai, Z.; Ren, X.; Gong, Z.; Hao, C.; Chen, Y.; Wan, P.; Meng, X. Chin. Chem. Lett. 2017, 28, 1901
[22] Gao, Y.; Wang, J.; Fu, M.; Chen, H.; Fang, M. Chin. J. Org. Chem. 2017, 37, 617.
[23] Song, F. L.; Garner, A. L.; Koide, K. J. Am. Chem. Soc. 2007, 129, 12354.
[24] Duan, L. P.; Xu, Y. F.; Qian, X. H. Chem. Commun. 2008, 47, 6339.
[25] Mukherjee, S.; Chowdhury, S.; Paul, A. K.; Banerjee, R. J. Lu-min. 2011, 131, 2342.
[26] Jiang, J.; Jiang, H.; Liu, W.; Tang, X. L.; Zhou, X.; Liu, W. S. Org. Lett. 2011, 13, 4922.
[27] Li, H. L.; Fan, J. L.; Du, J. J.; Guo, K. X.; Sun, S. G.; Liu, X. J.; Peng, X. J. Chem. Commun. 2010, 46, 1079.
[28] Liu, B.; Bao, Y. Y.; Du, F. F.; Wang, H.; Tian, J.; Bai, R. Chem. Commun. 2011, 47, 1731.
[29] Li, H.; Cao, J.; Zhu, H.; Fan, J.; Peng, X. Tetrahedron Lett. 2013, 54, 4357.
[30] Dujols, V.; Ford, F.; Czamik, A. W. J. Am. Chem. Soc. 1997, 119, 7386.
[31] Wei, D.; Sun, Y.; Yin, J.; Wei, G.; Du. Y. Sens. Actuators, B 2011, 160, 1316.
[32] Chen, W.; Gong, W.; Ye, Z.; Lin, Y.; Ning, G. L. Dalton Trans., 2013, 42, 10093.
[33] Yang, Z.; She, M.; Yin, B.; Cui, J.; Zhang, Y.; Sun, W.; Li, J.; Shi, Z. J. Org. Chem. 2012, 77, 1143.
[34] Xiang, Y.; Tong, A. Org. Lett. 2006, 8, 1549.
[35] Yin, W.; Cui, H.; Yang, Z.; Li, C.; She, M.; Yin, B.; Li, J.; Zhao, G.; Shi, Z. Sens. Actuators, B 2011, 157, 675.
[36] Dong, L.; Wu, C.; Zeng, X.; Mu, L.; Xue, S. F.; Tao, Z.; Zhang, J. X. Sens. Actuators, B 2010, 145, 433.
[37] 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.)
[38] Xiang, Y.; Tong, A.; Jin, P.; Ju, Y. Org. Lett. 2006, 8, 2863.

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