SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

2018 , Vol. 38 >Issue 3: 612 - 628

DOI: https://doi.org/10.6023/cjoc201709020

Reviews

Review of the Small Molecular Fluorescent Sensors for Intracellular Reactive Oxygen Species

  • Hou Jiting ,
  • Li Kun ,
  • Qin Caiqin ,
  • Yu Xiaoqi
Expand
  • a Hubei Collaboration Innovation Center for Biomass Conversion and Utilization, Hubei Engineering University, Xiaogan 432000;
    b School of Chemistry and Materials Science, Hubei Engineering University, Xiaogan 432000;
    c College of Chemistry, Sichuan University, Chengdu 610064

Received date: 2017-09-13

  Revised date: 2017-10-17

  Online published: 2017-10-31

Supported by

Project supported by the National Natrual Science Foundation of China (No. 31371750).

Fold

Abstract

Among the numerous bio-active species which are involved in the various chemical reactions in our body, reactive oxygen species (ROS) are a class of important biological species, which are oxidative. ROS can maintain the intracellular redox balance and are tightly related with the cell growth and death. Hence, the fluorescence detection of intracellular ROS has attracted wide attention. However, owining to the inherent features of ROS, such as the short lifetime and high reactivity, fluorescence analysis of ROS is always faced with some problems, like low selectivity and side reactions. Herein, the development of small molecular fluorescent probes for intracellular ROS over the past decade is summarized, and the design mechanisms and bio-applications of these probes are emphasized.

Key words： reactive oxygen species (ROS); fluorescent sensor; intracellular imaging

Cite this article

Hou Jiting , Li Kun , Qin Caiqin , Yu Xiaoqi . Review of the Small Molecular Fluorescent Sensors for Intracellular Reactive Oxygen Species[J]. Chinese Journal of Organic Chemistry, 2018 , 38(3) : 612 -628 . DOI: 10.6023/cjoc201709020

References

[1] Suh, Y. A.; Arnold, R. S.; Lassegue, B.; Shi, J.; Xu, X.; Sorescu, D.; Chung, A. B.; Griendling, K. K.; Lambeth, J. D. Nature 1999, 401, 79.
[2] Koh, C. H.; Whiteman, M.; Li, Q. X.; Halliwell, B.; Jenner, A. M.; Wong, B. S.; Laughton, K. M.; Wenk, M.; Masters, C. L.; Beart, P. M.; Bernard, O.; Cheung, N. S. J. Neurochem. 2006, 98, 1278.
[3] Rhee, S. G. Science 2006, 312, 1882.
[4] Dickinson, B. C.; Srikun, D.; Chang, C. J. Curr. Opin. Chem. Biol. 2010, 14, 50.
[5] Peteu, S. F.; Boukherroub, R.; Szunerits S. Biosens. Bioelectron. 2014, 58, 359.
[6] Yamato, M.; Egashira, T.; Utsumi, H. Free Radical Biol. Med. 2003, 35, 1619.
[7] de Silva, A. P.; Gunaratne, H. Q. N.; Gunnlaugsson, T.; Huxley, A. J. M.; McCoy, C. P.; Rademacher, J. T.; Rice, T. E. Chem. Rev. 1997, 97, 1515.
[8] Berezin, M. Y.; Achilefu, S. Chem. Rev. 2010, 110, 2641.
[9] Que, E. L.; Domaille, D. W.; Chang, C. J. Chem. Rev. 2008, 108, 1517.
[10] Pradhan, T.; Jung, H. S.; Jang, J. H.; Kim, T. W.; Kang, C.; Kim, J. S. Chem. Soc. Rev. 2014, 43, 4684.
[11] Chen, X.; Tian, X.; Shin, I.; Yoon, J. Chem. Soc. Rev. 2011, 40, 4783.
[12] Chen, X.; Wang, F.; Hyun, J. Y.; Wei, T.; Qiang, J.; Ren, X.; Shin, I.; Yoon, J. Chem. Soc. Rev. 2016, 45, 2976.
[13] Nagano, T. J. Clin. Biochem. Nutr. 2009, 45, 111.
[14] Aratani, Y.; Koyama, H.; Nyui, S.-I.; Suzuki, K.; Kura, F.; Maeda, N. Infect. Immun. 1999, 67, 1828.
[15] Kenmoku, S.; Urano, Y.; Kojima, H.; Nagano, T. J. Am. Chem. Soc. 2007, 129, 7313.
[16] Sun, Z.-N.; Liu, F.-Q.; Chen, Y.; Tam, P. K. H.; Yang, D. Org. Lett. 2008, 10, 2171.
[17] Hu, J. J.; Wong N.-K.; Gu, Q.; Bai, X.; Ye, S.; Yang, D. Org. Lett. 2014, 16, 3544.
[18] Chen, X.; Wang, X.; Wang, S.; Shi, W.; Wang, K.; Ma, H. Chem. Eur. J. 2008, 14, 4719.
[19] Lin, W.; Long, L.; Chen, B.; Tan, W. Chem.-Eur. J. 2009, 15, 2305.
[20] Yuan, L.; Lin, W.; Song, J.; Yang, Y. Chem. Commun. 2011, 47, 12691.
[21] Wang, B.; Li, P.; Yu, F.; Song, P.; Sun, X.; Yang, S.; Lou, Z.; Han, K. Chem. Commun. 2013, 49, 1014.
[22] Zhu, H.; Fan, J.; Wang, J.; Mu, H.; Peng, X. J. Am. Chem. Soc. 2014, 136, 12820.
[23] Hou, J.-T.; Wu, M.-Y.; Li, K.; Yang, J.; Yu, K.-K.; Xie, Y.-M.; Yu, X.-Q. Chem. Commun. 2014, 50, 8640.
[24] Hou, J.-T.; Li, K.; Yang, J.; Yu, K.-K.; Liao, Y.-X.; Ran, Y.-Z.; Liu, Y.-H.; Zhou, X.-D.; Yu, X.-Q. Chem. Commun. 2015, 51, 6781.
[25] Li, K.; Hou, J.-T.; Yang, J.; Yu, X.-Q. Chem. Commun. 2017, 53, 5539.
[26] Hu, J. J.; Wong, N.-K.; Lu, M.-Y.; Chen, X.; Ye, S.; Zhao, A. Q.; Gao, P.; Kao, R. Y.-T.; Shen, J.; Yang, D. Chem. Sci. 2016, 7, 2094.
[27] Yang, D.; Wang, H.-L.; Sun, Z.-N.; Chung, N.-W.; She, J.-G. J. Am. Chem. Soc. 2006, 128, 6004.
[28] Sun, Z.-N.; Wang, H.-L.; Liu, F.-Q.; Chen, Y.; Tam, P. K. H.; Yang, D. Org. Lett. 2009, 11, 1887.
[29] Peng, T.; Yang, D. Org. Lett. 2010, 12, 4932.
[30] Peng, T.; Wong, N.-K.; Chen, X.; Chan, Y.-K.; Ho, D. H.-H.; Sun, Z.; Hu, J. J.; Shen, J.; El-Nezami, H.; Yang, D. J. Am. Chem. Soc. 2014, 136, 11728.
[31] Ueno, T.; Urano, Y.; Kojima, H.; Nagano, T. J. Am. Chem. Soc. 2006, 128, 10640.
[32] Yu, F.; Li, P.; Li, G.; Zhao, G.; Chu, T.; Han, K. J. Am. Chem. Soc. 2011, 133, 11030.
[33] Xu, K.; Chen, H.; Tian, J.; Ding, B.; Xie, Y.; Qiang, M.; Tang, B. Chem. Commun. 2011, 47, 9468.
[34] Yu, F.; Li, P.; Wang, B.; Han, K. J. Am. Chem. Soc. 2013, 135, 7674.
[35] Oushiki, D.; Kojima, H.; Terai, T.; Arita, M.; Hanaoka, K.; Urano, Y.; Nagano, T. J. Am. Chem. Soc. 2010, 132, 2795.
[36] Hou, J.-T.; Yang, J.; Li, K.; Liao, Y.-X.; Yu, K.-K.; Xie, Y.-M.; Yu, X.-Q. Chem. Commun. 2014, 50, 9947.
[37] Cheng, D.; Pan, Y.; Wang, L.; Zeng, Z.; Yuan, L.; Zhang, X.; Chang, Y. T. J. Am. Chem. Soc. 2017, 139, 285.
[38] Li, Y.; Xie, X.; Yang, X.; Li, M.; Jiao, X.; Sun, Y.; Wang, X.; Tang, B. Chem. Sci. 2017, 8, 4006.
[39] Chang, M. C. Y.; Pralle, A.; Isacoff, E. Y.; Chang, C. J. J. Am. Chem. Soc. 2004, 126, 15392.
[40] Albers, A. E.; Okreglak, V. S.; Chang, C. J. J. Am. Chem. Soc. 2006, 128, 9640.
[41] Miller, E. W.; Tulyathan, O.; Isacoff, E. Y.; Chang, C. J. Nat. Chem. Biol. 2007, 3, 263.
[42] Srikun, D.; Miller, E. W.; Domaille, D. W.; Chang, C. J. J. Am. Chem. Soc. 2008, 130, 4596.
[43] Dickinson, B. C.; Chang, C. J. J. Am. Chem. Soc. 2008, 130, 9638.
[44] Albers, A. E.; Dickinson, B. C.; Miller, E. W.; Chang, C. J. Bioorg. Med. Chem. Lett. 2008, 18, 5948.
[45] Chung, C.; Srikun, D.; Lim, C. S.; Chang, C. J.; Cho, B. R. Chem. Commun. 2011, 47, 9618.
[46] Masanta, G.; Heo, C. H.; Lim, C. S.; Bae, S. K.; Cho, B. R.; Kim, H. M. Chem. Commun. 2012, 48, 3518.
[47] Karton-Lifshin, N.; Segal, E.; Omer, L.; Portnoy, M.; Satchi-Fainaro, R.; Shabat, D. J. Am. Chem. Soc. 2011, 133, 10960.
[48] Xu, M.; Han, J.-M.; Zhang, Y.; Yang, X.; Zang, L. Chem. Commun. 2013, 49, 11779.
[49] Xu, M.; Han, J.-M.; Wang, C.; Yang, X.; Pei, J.; Zang, L. ACS Appl. Mater. Interfaces 2014, 6, 8708.
[50] Li, G.; Zhu, D.; Liu, Q.; Xue, L.; Jiang, H. Org. Lett. 2013, 15, 924.
[51] Hu, F.; Huang, Y.; Zhang, G.; Zhao, R.; Zhang, D. Tetrahedron Lett. 2014, 55, 1471.
[52] Xu, J.; Li, Q.; Yue, Y.; Guo, Y.; Shao, S. Biosens. Bioelectron. 2014, 56, 58.
[53] Sawaki, Y.; Foote, C. S. J. Am. Chem. Soc. 1979, 101, 6292.
[54] Abo, M.; Urano, Y.; Hanaoka, K.; Terai, T.; Komatsu, T.; Nagano, T. J. Am. Chem. Soc. 2011, 133, 10629.
[55] Zhang, K.-M.; Dou, W.; Li, P.-X.; Shen, R.; Ru, J.-X.; Liu, W.; Cui, Y.-M.; Chen, C.-Y.; Liu, W.-S.; Bai, D.-C. Biosens. Bioelectron. 2015, 64, 542.
[56] Yu, F.; Li, P.; Song, P.; Wang, B.; Zhao, J.; Han, K. Chem. Commun. 2012, 48, 4980.
[57] Liao, Y.-X.; Li, K.; Wu, M.-Y.; Wu, T.; Yu, X.-Q. Org. Biomol. Chem. 2014, 12, 3004.
[58] Dong, B.; Song, X.; Kong, X.; Wang, C.; Tang, Y.; Liu, Y.; Lin, W. Adv. Mater. 2016, 28, 8755.
[59] Zhou, X.; Lesiak, L.; Lai, R.; Beck, J. R.; Zhao, J.; Elowsky, C. G.; Li, H.; Stains, C. I. Angew. Chem., Int. Ed. 2017, 56, 4197.
[60] Tang, B.; Zhang, L.; Zhang, L. L. Anal. Biochem. 2004, 326, 176.
[61] Gao, J. J.; Xu, K. H.; Tang, B.; Yin, L. L.; Yang, G. W.; An, L. G. FEBS J. 2007, 274, 1725.
[62] Li, P.; Zhang, W.; Li, K.; Liu, X.; Xiao, H.; Zhang, W.; Tang, B. Anal. Chem. 2013, 85, 9877.
[63] Maeda, H.; Yamamoto, K.; Nomura, Y.; Kohno, I.; Hafsi, L.; Ueda, N.; Yoshida, S.; Fukuda, M.; Fukuyasu, Y.; Yamauchi, Y.; Itoh, N. J. Am. Chem. Soc. 2005, 127, 68.
[64] Maeda, H.; Yamamoto, K.; Kohno, I.; Hafsi, L.; Itoh, N.; Nakagawa, S.; Kanagawa, N.; Suzuki, K.; Uno, T. Chem.-Eur. J. 2007, 13, 1946.
[65] Zhang, W.; Li, P.; Yang, F.; Hu, X.; Sun, C.; Zhang, W.; Chen, D.; Tang, B. J. Am. Chem. Soc. 2013, 135, 14956.
[66] Zhang, J. J.; Li, C. W.; Zhang, R.; Zhang, F. Y.; Liu, W.; Liu, X. Y.; Lee, S. M. Y.; Zhang, H. X. Chem. Commun. 2016, 52, 2679.
[67] Xiao, H. B.; Liu, X.; Wu, C. C.; Wu, Y. H.; Li, P.; Guo, X. M.; Tang, B. Biosens. Bioelectron. 2017, 91, 449.
[68] Li, R. Q.; Mao, Z. Q.; Rong, L.; Wu, N.; Lei, Q.; Zhu, J. Y.; Zhuang, L.; Zhang, X. Z.; Liu, Z. H. Biosens. Bioelectron. 2017, 87, 73.
[69] Pou, S.; Huang, Y. I.; Bhan, A.; Bhadti, V. S.; Hosmane, R. S.; Wu, S. Y.; Cao, G. L.; Rosen, G. M. Anal. Biochem. 1993, 212, 85.
[70] Yang, X.-F.; Guo, X.-Q. Anal. Chim. Acta 2001, 434, 169.
[71] Yang, X. F.; Guo, X. Q. Analyst 2001, 126, 1800.
[72] Li, P.; Xie, T.; Duan, X.; Yu, F.; Wang, X.; Tang, B. Chem.-Eur. J. 2010, 16, 1834.
[73] Yuan, L.; Lin, W.; Song, J. Chem. Commun. 2010, 46, 7930.
[74] Wang, J. Y.; Liu, Z. R.; Ren, M. G.; Kong, X. Q.; Liu, K. Y.; Deng, B. B.; Lin, W. Y. Sens. Actuators, B 2016, 236, 60.
[75] Kim, M.; Ko, S.-K.; Kim, H.; Shin, I.; Tae, J. Chem. Commun. 2013, 49, 7959.
[76] Meng, L.; Wu, Y.; Yi, T. Chem. Commun. 2014, 50, 4843.
[77] Liu, F.; Du, J.; Song, D.; Xu, M. Y.; Sun, G. P. Chem. Commun. 2016, 52, 4636.
[78] Steinbeck, M. J.; Khan, A. U.; Karnovsky, M. J. J. Biol. Chem. 1992, 267, 13425.
[79] Umezawa, N.; Tanaka, K.; Urano, Y.; Kikuchi, K.; Higuchi, T.; Nagano, T. Angew. Chem., Int. Ed. 1999, 38, 2899.
[80] Tanaka, K.; Miura, T.; Umezawa, N.; Urano, Y.; Kikuchi, K.; Higuchi, T.; Nagano, T. J. Am. Chem. Soc. 2001, 123, 2530.
[81] Kim, S.; Tachikawa, T.; Fujitsuka, M.; Majima, T. J. Am. Chem. Soc. 2014, 136, 11707.
[82] Xu, K.; Wang, L.; Qiang, M.; Wang, L.; Li, P.; Tang, B. Chem. Commun. 2011, 47, 7386.
[83] Aubry, J.-M.; Pierlot, C.; Rigaudy, J.; Schmidt, R. Acc. Chem. Res. 2003, 36, 668.
[84] Song, D.; Cho, S.; Han, Y.; You, Y.; Nam, W. Org. Lett. 2013, 15, 3582.

Options
Outlines

/

〈 〉