A Ratiometric Fluorescent Probe for Imaging Hydrogen Peroxide in Living Cells
- Corresponding author: Ji Min, 101010516@seu.edu.cn Wang Peng, wangpeng@cpu.edu.cn
	            Citation:
	            
		            Yang Min, Xia Lili, Zhou Xiaoqin, Jia Chengli, Ji Min, Wang Peng. A Ratiometric Fluorescent Probe for Imaging Hydrogen Peroxide in Living Cells[J]. Chinese Journal of Organic Chemistry,
							;2020, 40(9): 2888-2894.
						
							doi:
								10.6023/cjoc202002030
						
					
				
					 
				
	        
 
	                
				Wen, X.; Wu, J.; Wang, F.; Liu, B.; Huang, C.; Wei, Y. Free Radic. Biol. Med. 2013, 65, 402.
												 doi: 10.1016/j.freeradbiomed.2013.07.013
											
										
				Lou, Z.; Li, P.; Han, K. Acc. Chem. Res. 2015, 48, 1358.
												 doi: 10.1021/acs.accounts.5b00009
											
										
				Balaban, R. S.; Nemoto, S.; Finkel, T. Cell 2005, 120, 483.
												 doi: 10.1016/j.cell.2005.02.001
											
										
				Houstis, N.; Rosen, E. D.; Lander, E. S. Nature 2006, 440, 944.
												 doi: 10.1038/nature04634
											
										
				Teixeira, J. P.; de Castro, A. A.; Soares, F. V.; da Cunha, E. F. F.; Ramalho, T. C. Molecules 2019, 24, 4410.
												 doi: 10.3390/molecules24234410
											
										
				Ohshima, H.; Tatemichi, M.; Sawa, T. Arch. Biochem. Biophys. 2003, 417, 3.
												 doi: 10.1016/S0003-9861(03)00283-2
											
										
				Zhu, H.; Fan, J. L.; Wang, B. H.; Peng, X. J. Chem. Soc. Rev. 2015, 44, 4337.
												 doi: 10.1039/C4CS00285G
											
										
				Chen, X. Q.; Wang, F.; Hyun, J. Y.; Wei, T. W.; Qiang, J.; Ren, X. T.; Shin, I.; Yoon, J. Chem. Soc. Rev. 2016, 45, 2976.
												 doi: 10.1039/C6CS00192K
											
										
				Tian, Q.; Chen, S.; Chen, J.; Liu, R.; Wang, Y.; Yang, X.; Ye, Y. Chin. J. Org. Chem. 2019, 39, 2089(in Chinese).
										 
				Chen, S.; Pang, C.; Chen, X.; Yan, Z.; Huang, S.; Li, X.; Zhong, Y.; Wang, Z. Chin. J. Org. Chem. 2019, 39, 1846(in Chinese).
										 
				Huang, C.; Chen, H.; Li, F.; An, S. Chin. J. Org. Chem. 2019, 39, 2467(in Chinese).
										 
				Wen, Y.; Huo, F.; Yin, C. Chin. Chem. Lett 2019, 30, 1834.
												 doi: 10.1016/j.cclet.2019.07.006
											
										
				Tang, L.; Tian, M.; Chen, H.; Yan, X.; Zhong, K.; Bian, Y. Dyes Pigm. 2018, 158, 482.
												 doi: 10.1016/j.dyepig.2017.12.028
											
										
				Purdey, M. S.; McLennan, H. J.; Sutton-McDowall, M. L.; Drumm, D. W.; Zhang, X.; Capon, P. K.; Heng, S.; Thompson, J. G.; Abell, A. D. Sens. Actuators. B 2018, 262, 750.
												 doi: 10.1016/j.snb.2018.01.198
											
										
				Shen, Y.; Zhang, X.; Zhang, Y.; Wu, Y.; Zhang, C.; Chen, Y.; Jin, J.; Li, H. Sens. Actuators B. Chem. 2018, 255, 42.
												 doi: 10.1016/j.snb.2017.08.020
											
										
				Qiu, X.; Xin, C.; Qin, W.; Li, Z.; Zhang, D.; Zhang, G.; Peng, B.; Han, X.; Yu, C.; Li, L.; Huang, W. Talanta 2019, 199, 628.
												 doi: 10.1016/j.talanta.2019.03.017
											
										
				Zhang, J.; Shi, L.; Li, Z.; Li, D.; Tian, X.; Zhang, C. Analyst 2019, 144, 36438.
										
				Chen, Z.; Li, H.; Wei, J.; Xiao, Y.; Yu, H. Chin. J. Org. Chem. 2015, 35, 789(in Chinese).
										 
				Gao, C.; Tian, Y.; Zhang, R.; Jing, J.; Zhang, X. Anal. Chem. 2017, 89, 12945.
												 doi: 10.1021/acs.analchem.7b03809
											
										
				Hou, J.; Qian, M.; Zhao, H.; Li, Y.; Liao, Y.; Han, G.; Xu, Z.; Wang, F.; Song, Y.; Liu, Y. Anal. Chim. Acta 2018, 1024, 169.
												 doi: 10.1016/j.aca.2018.03.028
											
										
				Wen, Y.; Liu, K.; Yang, H.; Li, Y.; Lan, H.; Liu, Y.; Zhang, X.; Yi, T. Anal. Chem. 2014, 86, 9970.
												 doi: 10.1021/ac502909c
											
										
				Lee, M. H.; Kim, J. S.; Sessler, J. L. Chem. Soc. Rev. 2015, 44, 4185.
												 doi: 10.1039/C4CS00280F
											
										
				Huang, Y.; Zhou, Q.; Feng, Y.; Zhang, W.; Fang, G.; Fang, M.; Chen, M.; Xu, C.; Meng, X. Chem. Commun. (Cambridge. U. K.) 2018, 54, 10495.
												 doi: 10.1039/C8CC05594G
											
										
				Ning, P.; Hou, L.; Feng, Y.; Xu, G.; Bai, Y.; Yu, H.; Meng, X. Chem. Commun. 2019, 55, 1782.
												 doi: 10.1039/C8CC09517E
											
										
				Ning, P.; Wang, W.; Chen, M.; Feng, Y.; Meng, X. Chin. Chem. Lett. 2017, 28, 1943.
												 doi: 10.1016/j.cclet.2017.09.026
											
										
				Xue, X.; Zhang, Y.; Liu, Z.; Song, M.; Xing, Y.; Xiang, Q.; Wang, Z.; Tu, Z.; Zhou, Y.; Ding, K.; Xu, Y. J. Med. Chem. 2016, 59, 1565.
												 doi: 10.1021/acs.jmedchem.5b01511
											
										
				Li, B.; Lu, L.; Zhao, M.; Lei, Z.; Zhang, F. Angew. Chem.. Int. Ed. Engl. 2018, 57, 7483.
												 doi: 10.1002/anie.201801226
											
										
				Shi, Y.; Yuan, W.; Liu, Q.; Kong, M.; Li, Z.; Feng, W.; Hu, K.; Li, F. ACS Mater. Lett. 2019, 1, 418.
												 doi: 10.1021/acsmaterialslett.9b00265
											
										
				Pilipchuk, N. V.; Piryatinski, Y. P.; Kachkovsky, G. O.; Slominskii, Y. L.; Kachkovsky, O. D. Dyes Pigm. 2007, 73, 353.
												 doi: 10.1016/j.dyepig.2006.01.046
											
										
				Pilipchuk, N.; Piryatinski, Y.; Kachkovsky, G.; Slominskii, Y.; Kachkovsky, O. Dyes Pigm. 2007, 74, 47.
												 doi: 10.1016/j.dyepig.2006.01.010
											
										
				Li, X.; Tao, R. R.; Hong, L. J.; Cheng, J.; Jiang, Q.; Lu, Y. M.; Liao, M. H.; Ye, W. F.; Lu, N. N.; Han, F.; Hu, Y. Z.; Hu, Y. H. J. Am. Chem. Soc. 2015, 137, 12296.
												 doi: 10.1021/jacs.5b06865
											
										
				Li, H.; Yao, Q.; Fan, J.; Du, J.; Wang, J.; Peng, X. Biosens. Bioelectron. 2017, 94, 536.
												 doi: 10.1016/j.bios.2017.03.039
											
										
				Xiao, H.; Li, P.; Zhang, S.; Zhang, W.; Zhang, W.; Tang, B. Chem. Commun. (Cambridge. U. K.) 2016, 52, 12741.
												 doi: 10.1039/C6CC07182A
											
										
 
						
						
						
	                Liu Lin , Zemin Sun , Huatian Chen , Lian Zhao , Mingyue Sun , Yitao Yang , Zhensheng Liao , Xinyu Wu , Xinxin Li , Cheng Tang . Recent Advances in Electrocatalytic Two-Electron Water Oxidation for Green H2O2 Production. Acta Physico-Chimica Sinica, 2024, 40(4): 2305019-0. doi: 10.3866/PKU.WHXB202305019
Zhaoyu Wen , Na Han , Yanguang Li . Recent Progress towards the Production of H2O2 by Electrochemical Two-Electron Oxygen Reduction Reaction. Acta Physico-Chimica Sinica, 2024, 40(2): 2304001-0. doi: 10.3866/PKU.WHXB202304001
Jiaxi Xu , Yuan Ma . Influence of Hyperconjugation on the Stability and Stable Conformation of Ethane, Hydrazine, and Hydrogen Peroxide. University Chemistry, 2024, 39(11): 374-377. doi: 10.3866/PKU.DXHX202402049
Yanxi LIU , Mengjia XU , Haonan CHEN , Quan LIU , Yuming ZHANG . A fluorescent-colorimetric probe for peroxynitrite-anion-imaging in living cells. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1112-1122. doi: 10.11862/CJIC.20240423
Mahmoud Sayed , Han Li , Chuanbiao Bie . Challenges and prospects of photocatalytic H2O2 production. Acta Physico-Chimica Sinica, 2025, 41(9): 100117-0. doi: 10.1016/j.actphy.2025.100117
Yanyan Zhao , Zhen Wu , Yong Zhang , Bicheng Zhu , Jianjun Zhang . Enhancing photocatalytic H2O2 production via dual optimization of charge separation and O2 adsorption in Au-decorated S-vacancy-rich CdIn2S4. Acta Physico-Chimica Sinica, 2025, 41(11): 100142-0. doi: 10.1016/j.actphy.2025.100142
Jingping Li , Suding Yan , Jiaxi Wu , Qiang Cheng , Kai Wang . Improving hydrogen peroxide photosynthesis over inorganic/organic S-scheme photocatalyst with LiFePO4. Acta Physico-Chimica Sinica, 2025, 41(9): 100104-0. doi: 10.1016/j.actphy.2025.100104
Ke Li , Chuang Liu , Jingping Li , Guohong Wang , Kai Wang . Architecting Inorganic/Organic S-Scheme Heterojunction of Bi4Ti3O12 Coupling with g-C3N4 for Photocatalytic H2O2 Production from Pure Water. Acta Physico-Chimica Sinica, 2024, 40(11): 2403009-0. doi: 10.3866/PKU.WHXB202403009
Zhuoya WANG , Le HE , Zhiquan LIN , Yingxi WANG , Ling LI . Multifunctional nanozyme Prussian blue modified copper peroxide: Synthesis and photothermal enhanced catalytic therapy of self-provided hydrogen peroxide. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2445-2454. doi: 10.11862/CJIC.20240194
Yu Dai , Xueting Sun , Haoyu Wu , Naizhu Li , Guoe Cheng , Xiaojin Zhang , Fan Xia . Determination of the Michaelis Constant for Gold Nanozyme-Catalyzed Decomposition of Hydrogen Peroxide. University Chemistry, 2025, 40(5): 351-356. doi: 10.12461/PKU.DXHX202407052
Xiaofeng Zhu , Bingbing Xiao , Jiaxin Su , Shuai Wang , Qingran Zhang , Jun Wang . Transition Metal Oxides/Chalcogenides for Electrochemical Oxygen Reduction into Hydrogen Peroxides. Acta Physico-Chimica Sinica, 2024, 40(12): 2407005-0. doi: 10.3866/PKU.WHXB202407005
Jichao XU , Ming HU , Xichang CHEN , Chunhui WANG , Leichen WANG , Lingyi ZHOU , Xing HE , Xiamin CHENG , Su JING . Construction and hydrogen peroxide-activated chemodynamic activity of ferrocene?benzoselenadiazole conjugate. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1495-1504. doi: 10.11862/CJIC.20250144
Kangjuan Cheng , Chunxiao Liu , Youpeng Wang , Qiu Jiang , Tingting Zheng , Xu Li , Chuan Xia . Design of noble metal catalysts and reactors for the electrosynthesis of hydrogen peroxide. Acta Physico-Chimica Sinica, 2025, 41(10): 100112-0. doi: 10.1016/j.actphy.2025.100112
Siyi ZHONG , Xiaowen LIN , Jiaxin LIU , Ruyi WANG , Tao LIANG , Zhengfeng DENG , Ao ZHONG , Cuiping HAN . Targeting imaging and detection of ovarian cancer cells based on fluorescent magnetic carbon dots. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1483-1490. doi: 10.11862/CJIC.20240093
Pengli GUAN , Renhu BAI , Xiuling SUN , Bin LIU . Trianiline-derived aggregation-induced emission luminogen probe for lipase detection and cell imaging. Chinese Journal of Inorganic Chemistry, 2025, 41(9): 1817-1826. doi: 10.11862/CJIC.20250058
Qiang HU , Zhiqi CHEN , Zhong CHEN , Xu WANG , Weina WU . Pyridinium-chalcone-based ClO- fluorescent probe: Preparation and biological imaging applications. Chinese Journal of Inorganic Chemistry, 2025, 41(9): 1789-1795. doi: 10.11862/CJIC.20250086
Jinlong YAN , Weina WU , Yuan WANG . A simple Schiff base probe for the fluorescent turn-on detection of hypochlorite and its biological imaging application. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1653-1660. doi: 10.11862/CJIC.20240154
Yingpeng ZHANG , Xingxing LI , Yunshang YANG , Zhidong TENG . A pyrazole-based turn-off fluorescent probe for visual detection of hydrazine. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1301-1308. doi: 10.11862/CJIC.20250064
Chunmei GUO , Weihan YIN , Jingyi SHI , Jianhang ZHAO , Ying CHEN , Quli FAN . Facile construction and peroxidase-like activity of single-atom platinum nanozyme. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1633-1639. doi: 10.11862/CJIC.20240162
Lanjun Cheng , Xinyuan Wang , Jie An , Xiang Wu , Chengfeng Zhu , Yanming Fu , Yougui Li . Improvement of the Resolution Experiment of Racemic Tartaric Acid. University Chemistry, 2025, 40(7): 277-285. doi: 10.12461/PKU.DXHX202408010
Insert: the color changes of the systems after adding H2O2 (500 μmol/L) to the probe HDP-1 (10 μmol/L) under visible light. "—" represents HDP-1 (10 μmol/L) without H2O2; "+" represents HDP-1 (10 μmol/L) with H2O2 (500 μmol/L)
(1) Blank, (2) H2O2 (200 μmol/L), (3) Cu2+ (1 mmol/L), (4) Na+(1 mmol/L), (5) Zn2+ (1 mmol/L), (6) ClO- (500 μmol/L), (7) •OH (500 μmol/L), (8) •O2- (500 μmol/L), (9) •OtBu (500 μmol/L), (10) TBHP (500 μmol/L), (11) CN- (500 μmol/L), (12) HSO3- (500 μmol/L), (13) Cys (1 mmol/L), (14) Hcy (1 mmol/L), (15) GSH (1 mmol/L). λex=420 nm
(a~d) Cells were co-cultured with probe HDP-1 (10 μmol/L), (e~h) cells were co-cultured with probe HDP-1 (10 μmol/L) for 30 min after pre-treatment with LPS (10 μg/mL), and (i~l) cells co-cultured with probe HDP-1 (10 μmol/L) for 30 min after pre-treatment with H2O2 (100 μmol/L). Green channel: λem=497~557 nm. Red channel: λem=570~625 nm.λex=420 nm. Scale bar: 10 μm