Pyrrole-based hydrazone for fluorescent imaging of Hg2+ in lysosomes
- Corresponding author: Lei ZHANG, leizh2008@163.com Zhong CHEN, chenzhonglzu@hotmail.com
Citation:
Zhen WANG, Si-Yuan LI, Yuan WANG, Wei-Na WU, Lei ZHANG, Zhong CHEN, Ling-Ling YAN. Pyrrole-based hydrazone for fluorescent imaging of Hg2+ in lysosomes[J]. Chinese Journal of Inorganic Chemistry,
;2023, 39(6): 1122-1130.
doi:
10.11862/CJIC.2023.083
CHENG Z, LIANG J, REN X L, CUI Y W, YANG L N.. Research progress in organic small-molecule fluorescent Zn2+ probes and fluo- rescent imaging analysis of biological Zn2+.[J]. Chemical World, 2021,62(12):707-716.
Marumoto M, Sakamoto M, Marumoto K, Tsuruta S, Komohara Y. Mer- cury and selenium localization in the cerebrum, cerebellum, liver, and kidney of a Minamata disease case[J]. Acta Histochem.Cytochem., 2020,53(6):147-155. doi: 10.1267/ahc.20-00009
Kim K H, Kabir E, Jahan S A. A review on the distribution of Hg in the environment and its human health impacts[J]. J. Hazard. Mater., 2016,306:376-385. doi: 10.1016/j.jhazmat.2015.11.031
Erdemir S, Kocyigit O, Malkondu S. Detection of Hg2+ ion in aqueous media by new fluorometric and colorimetric sensor based on triazole- rhodamine[J]. J. Photochem. Photobiol. A, 2015,309:15-21. doi: 10.1016/j.jphotochem.2015.04.017
Sarkar A, Chakraborty S, Lohar S, Ahmmed E, Saha N C, Mandal S K, Dhara K. Chattopadhyay P. A lysosome- targetable fluorescence sen- sor for ultrasensitive detection of Hg2+ in living cells and real sam- ples[J]. Chem. Res. Toxicol., 2019,32(6):1144-1150. doi: 10.1021/acs.chemrestox.9b00005
Yuan X, Leng T H, Guo Z Q, Wang C Y, Li J Z, Yang W W, Zhu W H. A FRET - based dual - channel turn - on fluorescence probe for the detection of Hg2+ in living cells[J]. Dyes Pigm., 2018,161:403-410.
Wang Y S, Ding H C, Wang S, Fan C B, Tu Y Y, Liu G, Pu S Z. A rati- ometric and colorimetric probe for detecting Hg2+ based on naph- thalimide rhodamine and its staining function in cell imaging[J]. RSC Adv., 2019,9(21):11664-11669. doi: 10.1039/C9RA01459D
Lan L X, Niu Q F, Li T D.. A highly selective colorimetric and ratio- metric fluorescent probe for instantaneous sensing of Hg2+ in water, soil and seafood and its application on test strips[J]. Anal. Chim. Acta, 2018,1023:105-114. doi: 10.1016/j.aca.2018.03.023
HOU S H, LI S Q, TANG L J.. Synthesis of a novel water-soluble rho- damine-based fluorescent probe and its selective detection of free tri- valent ions.[J]. Chinese Journal of Applied Chemistry, 2022,39(2):241-246.
Wu C J, Wang J B, Shen J J, Bi C, Zhou H W. Coumarin-based Hg2+ fluorescent probe: Synthesis and turn - on fluorescence detection in neat aqueous solution[J]. Sens. Actuator B-Chem., 2017,243:678-683. doi: 10.1016/j.snb.2016.12.046
Zhang Y F, Chen H Y, Chen D, Wu D, Chen Z, Zhang J, Chen X Q, Liu S H, Yin J. A colorimetric and ratiometric fluorescent probe for mercury in lysosome[J]. Sens. Actuator B-Chem.., 2016,224:907-914. doi: 10.1016/j.snb.2015.11.018
SUN J F, QIAN Y.. A novel naphthalimide- rhodamine fluorescence sensor: synthesis, aggregation - induced emission enhancement and its dual-channel detection property[J]. Chin. J. Org. Chem., 2016,36(1):151-157.
Vinoth Kumar G G, Kesavan M P, Tamilselvi A, Rajagopal G, Raja J D, Sakthipandi K, Rajesh J, Sivaraman G. A reversible fluorescent chemosensor for the rapid detection of Hg2+ in an aqueous solution: Its logic gates behavior[J]. Sens. Actuator B-Chem., 2018,273:305-315. doi: 10.1016/j.snb.2018.06.067
Wang Y, Mao P D, Wu W N, Mao X J, Fan Y C, Zhao X L, Xu Z Q, Xu Z H. New pyrrole-based single-molecule multianalyte sensor for Cu2+, Zn2+, and Hg2+ and its AIE Activity[J]. Sens. Actuator B -Chem., 2018,255:3085-3092. doi: 10.1016/j.snb.2017.09.133
Zhu J L, Xu Z, Yang Y, Xu L. Small-molecule fluorescent probes for specific detection and imaging of chemical species inside lysosomes[J]. Chem. Commun., 2019,55(47):6629-6671. doi: 10.1039/C9CC03299A
Yuan L L, Shi X J, Tang B Z, Wang W X. Real-time in vitro monitor- ing of the subcellular toxicity of inorganic Hg and methylmercury in zebrafish cells[J]. Aquat. Toxicol., 2021,236105859. doi: 10.1016/j.aquatox.2021.105859
Lauwerys R, Buchet J P. Study on the mechanism of lysosome labili- zation by inorganic mercury in vitro[J]. Eur. J. Biochem., 1972,26(4):535-542. doi: 10.1111/j.1432-1033.1972.tb01796.x
He D D, Liu W, Sun R, Fan C, Xu Y J, Ge J F. N-pyridineium-2 -yl Darrow Red analogue: Unique near-infrared lysosome-biomarker for the detection of cancer cells[J]. Anal. Chem., 2015,87(3):1499-1502. doi: 10.1021/ac5045912
PU T, YANG Y H, WANG K B, YE M, FAN L M, FU L X, SU F W, ZHA Y G. Determination of the nicotinamide compounds by using MTT colorimetric assay against pathogenic bacteria[J]. J. Yunnan Agric. Univ. (Natural Science), 2019,34(1):15-21.
Wu W N, Wu H, Zhong R B, Wang Y, Xu Z H, Zhao X L, Xu Z Q, Fan Y C. Ratiometric fluorescent probe based on pyrrole - modified rhodamine 6G hydrazone for the imaging of Cu2+ in lysosomes[J]. Spectroc. Acta Pt. A-Molec. Biomolec. Spectr., 2018,212:121-127.
Wang Y, Chang H Q, Wu W N, Zhao X L, Yang Y, Xu Z Q, Xu Z H, Jia L. Rhodamine-2 -thioxoquinazolin -4-one conjugate: A highly sen- sitive and selective chemosensor for Fe3+ ions and crystal structures of its Ag and Hg complexes[J]. Sens. Actuator B-Chem., 2017,239:60-68. doi: 10.1016/j.snb.2016.07.170
Wu W N, Mao P D, Wang Y, Zhao X L, Xu Z Q, Xu Z H, Xue Y. Quinoline containing acetyl hydrazone: An easily accessible switch- on optical chemosensor for Zn2+[J]. Spectroc. Acta Pt. A-Molec. Biomolec. Spectr., 2018,188:324-331. doi: 10.1016/j.saa.2017.07.020
Qin J C, Fan L, Yang Z Y. A small - molecule and resumable two- photon fluorescent probe for Zn2+ based on a coumarin Schiff - base[J]. Sens. Actuator B-Chem., 2016,228:156-161.
Jia F Y, Luo J W, Zhang B. Mechanistic insight into palladium- catalyzed enantioselective remote meta-C-H arylation and alkylation by using density functional theory (DFT) calculations[J]. Adv. Synth. Catal., 2020,362(8):1686-1695.
Linfang ZHANG , Wenzhu YIN , Gui YIN . A 2-dicyanomethylene-3-cyano-4,5,5-trimethyl-2,5-dihydrofuran-based near-infrared fluorescence probe for the detection of hydrogen sulfide and imaging of living cells. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 540-548. doi: 10.11862/CJIC.20240405
Yuan ZHU , Xiaoda ZHANG , Shasha WANG , Peng WEI , Tao YI . Conditionally restricted fluorescent probe for Fe3+ and Cu2+ based on the naphthalimide structure. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 183-192. doi: 10.11862/CJIC.20240232
Jie Zhou , Chuanxiang Zhang , Changchun Hu , Shuo Li , Yuan Liu , Zhu Chen , Song Li , Hui Chen , Rokayya Sami , Yan Deng . Electrochemical aptasensor based on black phosphorus-porous graphene nanocomposites for high-performance detection of Hg2+. Chinese Chemical Letters, 2024, 35(11): 109561-. doi: 10.1016/j.cclet.2024.109561
Meirong HAN , Xiaoyang WEI , Sisi FENG , Yuting BAI . A zinc-based metal-organic framework for fluorescence detection of trace Cu2+. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1603-1614. doi: 10.11862/CJIC.20240150
Lixian Fu , Yiyun Tan , Yue Ding , Weixia Qing , Yong Wang . Water–soluble and polarity–sensitive near–infrared fluorescent probe for long–time specific cancer cell membranes imaging and C. Elegans label. Chinese Chemical Letters, 2024, 35(4): 108886-. doi: 10.1016/j.cclet.2023.108886
Jun LUO , Baoshu LIU , Yunchang ZHANG , Bingkai WANG , Beibei GUO , Lan SHE , Tianheng CHEN . Europium(Ⅲ) metal-organic framework as a fluorescent probe for selectively and sensitively sensing Pb2+ in aqueous solution. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2438-2444. doi: 10.11862/CJIC.20240240
Hui-Juan Wang , Wen-Wen Xing , Zhen-Hai Yu , Yong-Xue Li , Heng-Yi Zhang , Qilin Yu , Hongjie Zhu , Yao-Yao Wang , Yu Liu . Cucurbit[7]uril confined phenothiazine bridged bis(bromophenyl pyridine) activated NIR luminescence for lysosome imaging. Chinese Chemical Letters, 2024, 35(6): 109183-. doi: 10.1016/j.cclet.2023.109183
Huamei Zhang , Jingjing Liu , Mingyue Li , Shida Ma , Xucong Zhou , Aixia Meng , Weina Han , Jin Zhou . Imaging polarity changes in pneumonia and lung cancer using a lipid droplet-targeted near-infrared fluorescent probe. Chinese Chemical Letters, 2024, 35(12): 110020-. doi: 10.1016/j.cclet.2024.110020
Han-Min Wang , Yan-Chen Li , Lu-Lu Sun , Ming-Ye Tang , Jia Liu , Jiahao Cai , Lei Dong , Jia Li , Yi Zang , Hai-Hao Han , Xiao-Peng He . Protein-encapsulated long-wavelength fluorescent probe hybrid for imaging lipid droplets in living cells and mice with non-alcoholic fatty liver. Chinese Chemical Letters, 2024, 35(11): 109603-. doi: 10.1016/j.cclet.2024.109603
Shuwen SUN , Gaofeng WANG . Design and synthesis of a Zn(Ⅱ)-based coordination polymer as a fluorescent probe for trace monitoring 2, 4, 6-trinitrophenol. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 753-760. doi: 10.11862/CJIC.20240399
Jiakun BAI , Ting XU , Lu ZHANG , Jiang PENG , Yuqiang LI , Junhui JIA . A red-emitting fluorescent probe with a large Stokes shift for selective detection of hypochlorous acid. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1095-1104. doi: 10.11862/CJIC.20240002
Yudi Cheng , Xiao Wang , Jiao Chen , Zihan Zhang , Jiadong Ou , Mengyao She , Fulin Chen , Jianli Li . A near-infrared fluorescent probe for visualizing transformation pathway of Cys/Hcy and H2S and its applications in living system. Chinese Chemical Letters, 2024, 35(5): 109156-. doi: 10.1016/j.cclet.2023.109156
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
Yu SU , Xinlian FAN , Yao YIN , Lin WANG . From synthesis to application: Development and prospects of InP quantum dots. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2105-2123. doi: 10.11862/CJIC.20240126
Anjing Liao , Wei Sun , Yaming Liu , Han Yan , Zhi Xia , Jian Wu . Pyrrole and pyrrolidine analogs: The promising scaffold in discovery of pesticides. Chinese Chemical Letters, 2025, 36(3): 110094-. doi: 10.1016/j.cclet.2024.110094
Zhuwen Wei , Jiayan Chen , Congzhen Xie , Yang Chen , Shifa Zhu . Divergent de novo construction of α-functionalized pyrrole derivatives via coarctate reaction. Chinese Chemical Letters, 2024, 35(12): 109677-. doi: 10.1016/j.cclet.2024.109677
Chuan-Zhi Ni , Ruo-Ming Li , Fang-Qi Zhang , Qu-Ao-Wei Li , Yuan-Yuan Zhu , Jie Zeng , Shuang-Xi Gu . A chiral fluorescent probe for molecular recognition of basic amino acids in solutions and cells. Chinese Chemical Letters, 2024, 35(10): 109862-. doi: 10.1016/j.cclet.2024.109862
Tao Liu , Xuwei Han , Xueyi Sun , Weijie Zhang , Ke Gao , Runan Min , Yuting Tian , Caixia Yin . An activated fluorescent probe to monitor NO fluctuation in Parkinson’s disease. Chinese Chemical Letters, 2025, 36(3): 110170-. doi: 10.1016/j.cclet.2024.110170
Gongcheng Ma , Qihang Ding , Yuding Zhang , Yue Wang , Jingjing Xiang , Mingle Li , Qi Zhao , Saipeng Huang , Ping Gong , Jong Seung Kim . Palladium-free chemoselective probe for in vivo fluorescence imaging of carbon monoxide. Chinese Chemical Letters, 2024, 35(9): 109293-. doi: 10.1016/j.cclet.2023.109293
Zhihui Zhang , Ru Sun , Chong Bian , Hongbo Wang , Zhen Zhao , Panpan Lv , Jianzhong Lu , Haixin Zhang , Hulie Zeng , Yuanyuan Chen , Zhijuan Cao . A dual-protease-triggered chemiluminescent probe for precise tumor imaging. Chinese Chemical Letters, 2025, 36(2): 109784-. doi: 10.1016/j.cclet.2024.109784
Inset in a: the color change of 1 solution in the presence of Hg2+; Inset in b: the absorbance ratio of A440/A380 as a function of Hg2+ concentration (4.5-16.5 µmol·L-1)
Inset in a: the color change of 1 solution in the presence of Hg2+ under 365 nm UV lamp; Inset in b: the fluorescence intensity at 475 nm as a function of Hg2+ concentration (6.0-18.0 µ mol·L-1); λex=410 nm