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

doi:10.6023/cjoc201709020

Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (3): 612-628.DOI: 10.6023/cjoc201709020 Previous Articles Next Articles

Special Issue: 荧光探针-生物传感合辑；有机超分子化学合辑

Reviews

活性氧簇的小分子荧光探针研究进展

后际挺^a,b, 李坤^c, 覃彩芹^a,b, 余孝其^c

a 湖北工程学院生物质资源转化利用湖北省协同创新中心孝感 432000;
b 湖北工程学院化学与材料科学学院孝感 432000;
c 四川大学化学学院成都 610064

收稿日期:2017-09-13 修回日期:2017-10-17 发布日期:2017-10-31
通讯作者: 覃彩芹,E-mail:qincq@hbeu.edu.cn E-mail:qincq@hbeu.edu.cn
基金资助:
国家自然科学基金（No.31371750）资助项目.

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

Hou Jiting^a,b, Li Kun^c, Qin Caiqin^a,b, Yu Xiaoqi^c

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:2017-09-13 Revised:2017-10-17 Published:2017-10-31
Contact: 10.6023/cjoc201709020 E-mail:qincq@hbeu.edu.cn
Supported by:
Project supported by the National Natrual Science Foundation of China (No. 31371750).

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]. Chin. J. Org. Chem., 2018, 38(3): 612-628.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

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.

活性氧簇的小分子荧光探针研究进展

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

PDF

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Ni Wang, Zijun Zheng, Xiaoping Jia, Mengyuan Zhao, Yalei Wang, Chen Zhou, Zhijia Wang, Zelin Xiao, Hongmin Liu, Yu Ke. Study on Synthesis and Pharmacological Research of Jiyuan Oridonin A Derivatives as Potential Anti-tumor Drugs [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 646-659.
[2]	Lixin Ju, Qi Shao, Linchuan Lu, Hongfei Lu. A New Turn-On Fluorescent Chemosensor for Selective Detection of Al³⁺ Based on a Purine Schiff Base and Its Cell Imaging [J]. Chinese Journal of Organic Chemistry, 2022, 42(6): 1706-1712.
[3]	Zhang Yan, Wang Yunyun, Zhao Yuxun, Zhang Chenglong, Gu Wen, Wang Zhonglong, Zhu Yongqiang, Wang Shifa. Camphor-Based Thiosemicarbazone Analogues Induced G2 Cell Cycle Arrest and Apoptosis via Reactive Oxygen Species (ROS)-Mediated Mitochondrial Pathway in Human Breast Cancer Cells [J]. Chinese Journal of Organic Chemistry, 2020, 40(8): 2374-2386.
[4]	Zhang Jidong, Zhan Yan, Li-Hu Yuewen, Qi Yi, Wang Ruipeng, Meng Li. Recent Progress in Fluorescent Chemosensors for Selenium Compounds [J]. Chinese Journal of Organic Chemistry, 2020, 40(7): 1847-1859.
[5]	Ma Xuelin, Han Limin, Zhang Xiaoyong, Zhang Yuheng, Wang Li, Yang Kun, Ji Jie. Triazine Derivative for Fluorescence Sensing of Zr⁴⁺, Fe³⁺ Ions and Acetone [J]. Chinese Journal of Organic Chemistry, 2020, 40(6): 1745-1751.
[6]	Chang Yongxin, Li Bai, Guo Miao, Cai Yonghong, Xu Kuoxi. A Novel Logic Gate Fluorescent Sensor for the Sequential Detection of Cd²⁺ and Pyrophosphate Anion and Application in Cell Imaging [J]. Chin. J. Org. Chem., 2019, 39(9): 2485-2491.
[7]	Zhu Yangmin, Wang Zhonglong, Yang Jian, Xu Xu, Wang Shifa, Cai Zhengchun, Xu Haijun. N,N-Bis(2-pyridylmethyl)amine-Based Truxene Derivative as a Highly Sensitive Fluorescence Sensor for Cu²⁺ and Ni²⁺ Ion [J]. Chin. J. Org. Chem., 2019, 39(2): 427-433.
[8]	Zhou Jianping, Wu Baogeng, Zhou Zhikuan, Tian Jiangwei, Yuan Aihua. A Novel Naphthalene-Fused Boron Dipyrromethene (BODIPY)-Based Near Infrared Fluorescent Probe for Detecting Fluoride in Living Cells [J]. Chin. J. Org. Chem., 2019, 39(2): 406-411.
[9]	Zhou Chan, Qiu Bo, Zeng Yi, Chen Jinping, Yu Tianjun, Li Yi. A Reaction-Based Chemsensor for Hydrogen Sulfide Detection with Fluorescence Enhancement [J]. Chin. J. Org. Chem., 2017, 37(1): 92-96.
[10]	Yang Taiqun, Dai Shan, Qin Cuifang, Huang Kehan, Chen Yuting, Pan Haifeng, Zhang Sanjun, Zhang Kun, Xu Jianhua. Selective Detection of Homocysteine by Using Poly Methyl Vinyl Ether-alt-Maleic Silver Clusters [J]. Chin. J. Org. Chem., 2016, 36(4): 867-871.
[11]	Zhang Chenglu, Guo Yang, Chen Ying, Sun Lijie, Cheng Anqi, Zhao Na, Zhao Baocheng, Tang Jie, Xi Huan. Synthesis and Properties of Novel Tripod Type Multi-benzimidazole Quaternary Ammonium Compounds [J]. Chin. J. Org. Chem., 2015, 35(8): 1665-1672.
[12]	Zhang Peng, Zhang Youming, Lin Qi, Yao Hong, Wei Taibao. Principle and the Research Progress of Fluorescent Chemosensors for Cations Recognition [J]. Chin. J. Org. Chem., 2014, 34(7): 1300-1321.
[13]	Xu Qinchao, Jin Can, Zhu Xuehui, Xing Guowen. Recent Progress in Fluorescent Probes for Pyrophosphate Based on Small Organic Molecules [J]. Chin. J. Org. Chem., 2014, 34(4): 647-661.
[14]	He Yuan, Feng Ruokun, Yi Yunrui, Liu Zhanxiang. Recent Progress in the Research of Borondipyrromethene-Based Fluorescent Ion Chemosensor [J]. Chin. J. Org. Chem., 2014, 34(11): 2236-2248.
[15]	ZHAO Bang-Tun, CAO Shi-Na, GUO Hai-Ming, QU Gui-Rong. Synthesis of Anthraquinone-Based Thiacalixarene via Click Chemis-try and Its Fluorescence Sensing Towards Al^3＋ [J]. Chin. J. Org. Chem., 2011, 31(12): 2121-2125.