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 shu

Pyrrole-based hydrazone for fluorescent imaging of Hg²⁺ in lysosomes

Zhen WANG ¹ ,
Si-Yuan LI ² ,
Yuan WANG ¹ ,
Wei-Na WU ¹ ,
Lei ZHANG ^1,, ,
Zhong CHEN ^2,, ,
Ling-Ling YAN ³

1.
College of Chemistry and Chemical Engineering, Henan Polytechnic University, Jiaozuo, Henan 454000 China
2.
School of Materials and Mechanical and Electrical Engineering, Jiangxi Science and Technology Normal University, Nanchang 330013 China
3.
School of Physics and Electronic Information Engineering, Henan Polytechnic University, Jiaozuo, Henan 454000 China

Corresponding author: Lei ZHANG, leizh2008@163.com Zhong CHEN, chenzhonglzu@hotmail.com
Received Date: 3 April 2022
Revised Date: 27 April 2023

Figures(9)

A novel pyrrole-based hydrazone has been synthesized for colorimetric and fluorescent turn-on detection of Hg²⁺ ions. A 1:1 binding ratio of the Hg²⁺ complex has been obtained from Job's plots and MS data. The coordination mode was systematically investigated by ¹H NMR, time-resolved fluorescence spectroscopy, and density functional theory (DFT) calculations. The limit of detection of 1 for Hg²⁺ was as low as 45 nmol·L^-1 with an association constant of 5.78×10⁸ L·mol^-1. It is worth noting that the response of 1 to Hg²⁺ was good in a pH range of 4.0 to 10.0. In addition, owing to the existence of the morpholine group, the probe can detect lysosomal Hg²⁺ in HeLa cells.
- cell imaging,
- fluorescent probe,
- Hg²⁺,
- hydrazone,
- lysosome,
- pyrrole
1. [1]
  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.
2. [2]
  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
3. [3]
  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
4. [4]
  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
5. [5]
  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
6. [6]
  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.
7. [7]
  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
8. [8]
  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
9. [9]
  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.
10. [10]
  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
11. [11]
  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
12. [12]
  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.
13. [13]
  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
14. [14]
  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
15. [15]
  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
16. [16]
  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
17. [17]
  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
18. [18]
  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
19. [19]
  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.
20. [20]
  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.
21. [21]
  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
22. [22]
  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
23. [23]
  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.
24. [24]
  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.
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通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

Pyrrole-based hydrazone for fluorescent imaging of Hg2+ in lysosomes

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通讯作者: 陈斌, bchen63@163.com

Pyrrole-based hydrazone for fluorescent imaging of Hg²⁺ in lysosomes