Citation: Qiang HU, Zhiqi CHEN, Zhong CHEN, Xu WANG, Weina WU. Pyridinium-chalcone-based ClO^- fluorescent probe: Preparation and biological imaging applications[J]. Chinese Journal of Inorganic Chemistry, ;2025, 41(9): 1789-1795. doi: 10.11862/CJIC.20250086 shu

Pyridinium-chalcone-based ClO^- fluorescent probe: Preparation and biological imaging applications

Qiang HU ¹ ,
Zhiqi CHEN ² ,
Zhong CHEN ² ,
Xu WANG ^3,, ,
Weina WU ^4,,

1.
School of Physics and Electronic Information Engineering, Henan Polytechnic University, Jiaozuo, Henan 454000, China
2.
School of Materials and Energy, Jiangxi Science and Technology Normal University, Nanchang 330013, China
3.
Lucky Huaguang Graphics Co., Ltd., Nanyang, Henan 473006, China
4.
College of Chemistry and Chemical Engineering, Henan Polytechnic University, Jiaozuo, Henan 454000, China

Corresponding author: Xu WANG, 573907861@qq.com Weina WU, wuwn08@hpu.edu.cn
Received Date: 15 March 2025
Revised Date: 2 July 2025

Figures(6)

A pyridinium-chalcone-based probe (1) was prepared via a two-step reaction, which was characterized through ¹H NMR and mass spectra. Probe 1 was weakly emissive in water-sufficient solution, while hypochlorite (ClO^-) could remarkably enhance the yellow fluorescence emission of the probe at 550 nm. The detection of probe 1 for ClO^- had the advantages of fast response (< 30 s), high sensitivity (a detection limit of 0.4 μmol·L^-1), and large Stokes shift (130 nm). The ClO^--promoted oxidation-elimination of probe 1 was suggested by mass spectra and theoretical calculation methods. Furthermore, the probe was successfully used to monitor mitochondrial ClO^- in living cells and zebrafish.
- biological imaging,
- chalcone,
- fluorescent probe,
- hypochlorite,
- mitochondria-targeting
1. [1]
  HOU J T, YU K K, SUNWOO K, KIM W Y, KOO S, WANG J, REN W X, WANG S, YU X Q, KIM J S. Fluorescent imaging of reactive oxygen and nitrogen species associated with pathophysiological processes[J]. Chem, 2020, 6(4): 832-866 doi: 10.1016/j.chempr.2019.12.005
2. [2]
  WU D, CHEN L, XU Q L, CHEN X Q, YOON J. Design principles, sensing mechanisms, and applications of highly specific fluorescent probes for HOCl/OCl^-[J]. Acc. Chem. Res., 2019, 52(8): 2158-2168 doi: 10.1021/acs.accounts.9b00307
3. [3]
  KWON N, CHEN Y H, CHEN X Q, KIM M H, YOON J. Recent progress on small molecule-based fluorescent imaging probes for hypochlorous acid (HOCl)/hypochlorite (OCl^-)[J]. Dyes Pigment., 2022, 200: 110132 doi: 10.1016/j.dyepig.2022.110132
4. [4]
  DONG S Q, ZHANG L J, LIN Y J, DING C F, LU C. Luminescent probes for hypochlorous acid in vitro and in vivo[J]. Analyst, 2020, 145(15): 5068-5089 doi: 10.1039/D0AN00645A
5. [5]
  ZHAO B, XU X H, WEN X, LIU Q Q, DONG C, YANG Q K, FAN C H, YOON J, LU Z L. Ratiometric near-infrared fluorescent probe monitors ferroptosis in HCC cells by imaging HClO in mitochondria[J]. Anal. Chem., 2024, 96(15): 5992-6000 doi: 10.1021/acs.analchem.4c00328
6. [6]
  FAN G W, ZHANG B, WANG J M, WANG N N, QIN S C, ZHAO W L, ZHANG J. Accurate construction of NIR probe for visualizing HClO fluctuations in type Ⅰ, type Ⅱ diabetes and diabetic liver disease assisted by theoretical calculation[J]. Talanta, 2024, 268: 125298 doi: 10.1016/j.talanta.2023.125298
7. [7]
  LAI H J, YAN J L, WU M, WU W N, BIE H Y, FAN Y C, WANG Y, XU Z H. A simple Golgi targetable fluorescent probe with aggregation induced emission for the visualization of hypochlorite in living cells, plants and animals[J]. J. Mol. Struct., 2025, 1321: 139746 doi: 10.1016/j.molstruc.2024.139746
8. [8]
  HE S, FANG W L, GUO X F, WANG H. A water-soluble two-photon fluorescent probe for rapid and reversible monitoring of redox state[J]. Talanta, 2023, 253: 124066 doi: 10.1016/j.talanta.2022.124066
9. [9]
  ZHAO Y, YU X Q, LIU X, ZHANG D L, LI H, ZHOU H L, KONG W H, QU F L. ClO^- induced dual-excitation fluorescent probes responding to diverse testing modes with ratio methodology[J]. Anal. Chem., 2023, 95(18): 7170-7177 doi: 10.1021/acs.analchem.2c05532
10. [10]
  XU S L, GUO F F, XU Z H, WANG Y, JAMES T D. A hemicyanine-based fluorescent probe for ratiometric detection of ClO^- and turn-on detection of viscosity and its imaging application in mitochondria of living cells and zebrafish[J]. Sens. Actuator B‒Chem., 2023, 383: 133510 doi: 10.1016/j.snb.2023.133510
11. [11]
  SHANG Z Y, MENG Q T, ZHANG R, ZHANG Z Q. Bifunctional near-infrared fluorescent probe for the selective detection of bisulfite and hypochlorous acid in food, water samples and in vivo[J]. Anal. Chim. Acta, 2023, 1279: 341783 doi: 10.1016/j.aca.2023.341783
12. [12]
  WANG R Q, ZHOU T, LI A, QU J, ZHANG X, ZHU X F, JING S. The design of fluorescein-ferrocene derivatives as HOCl-triggered turn‑on fluorescent probes and anticancer prodrugs[J]. Dalton Trans., 2022, 51(40): 15330-15338 doi: 10.1039/D2DT02198F
13. [13]
  SHAN Y M, YU K K, WANG N, YU F Y, LI K, LIU Y H, YU X Q. Assessing ClO^- level during ER stress and cellular senescence through a ratio fluorescent probe with dual organelle targeting ability[J]. Sens. Actuator B‒Chem., 2022, 358: 131383 doi: 10.1016/j.snb.2022.131383
14. [14]
  MAO G J, GAO G Q, LIANG Z Z, WANG Y Y, SU L, WANG Z X, ZHANG H, MA Q J, ZHANG G. A mitochondria-targetable two-photon fluorescent probe with a far-red to near-infrared emission for sensing hypochlorite in biosystems[J]. Anal. Chim. Acta, 2019, 1081: 184-192 doi: 10.1016/j.aca.2019.07.040
15. [15]
  LI S J, WANG P P, YANG K, LIU Y, CHENG D, HE L W. Construction of HClO activated near-infrared fluorescent probe for imaging hepatocellular carcinoma[J]. Anal. Chim. Acta, 2023, 1252: 341009 doi: 10.1016/j.aca.2023.341009
16. [16]
  LI S J, YANG K, LIU Y, WANG P P, CHENG D, HE L W. An endoplasmic reticulum-targeted near-infrared probe for monitoring HClO fluctuation in diabetic mice and human blood[J]. Sens. Actuator B‒Chem., 2023, 379: 133253 doi: 10.1016/j.snb.2022.133253
17. [17]
  CHEN Y, ZHAO Y Q, XIE P, HUANG L, WANG Y, ZHANG J F, WU X H, ZHOU Y. Near-infrared fluorescent probes for detection of exogenous and endogenous hypochlorite in living cells[J]. Dyes Pigment., 2020, 177: 108308 doi: 10.1016/j.dyepig.2020.108308
18. [18]
  YAN J L, ZHANG L, WU W N, WANG Y, XU Z H. A novel AIRE-based fluorescent ratiometric probe with endoplasmic reticulum-targeting ability for detection of hypochlorite and bioimaging[J]. Bioorganic Chem., 2023, 131: 106319 doi: 10.1016/j.bioorg.2022.106319
19. [19]
  ZHANG C L, ZHANG J J, SHEN Y, LU J C, HUANG F, XU L. A fast-responsive mitochondria-targeting fluorescent probe detecting hypochlorite in living cells and zebrafish[J]. Chinese J. Inorg. Chem., 2022, 38(8): 1623-1632 doi: 10.11862/CJIC.2022.168
20. [20]
  ZHANG J J, YAN M, LU W, XU L, WANG X Q. Design, synthesis and fluorescence imaging application of hypochlorite probe based on coumarin-oxime[J]. Chinese J. Inorg. Chem., 2021, 37(6): 1623-1632 doi: 10.11862/CJIC.2021.133
21. [21]
  WU W N, CHEN X, LIU S S, BIE H Y, FAN Y C, WANG Y, XU Z H, JAMES T D. A dual response fluorescent hemicyanine probe for the detection of mitochondrial hypochlorite and viscosity based on ESIPT/AIE and TICT[J]. Sens. Actuator B‒Chem., 2025, 423: 136695 doi: 10.1016/j.snb.2024.136695
22. [22]
  XU Z Y, HAN L, WANG X H, CHEN J R, LI N B, LUO H Q. Rational construction of long-wavelength emissive AIE molecules and their application for sensitive and visual detection of HClO[J]. Sens. Actuator B‒Chem., 2022, 352: 131024 doi: 10.1016/j.snb.2021.131024
23. [23]
  HUANG T H, YAN S R, YU Y B, XUE Y S, YU Y Y, HAN C P. Dual-responsive ratiometric fluorescent probe for hypochlorite and peroxynitrite detection and imaging in vitro and in vivo[J]. Anal. Chem., 2022, 94(2): 1415-1424 doi: 10.1021/acs.analchem.1c04729
24. [24]
  FANG L, ZHANG X Y, YUAN Q, LI D D, JIAO Q C, YANG Y S, ZHU H L. A novel indanone-derivated fluorescence sensor for cysteine detection and biological imaging[J]. Dyes Pigment., 2020, 175: 108122 doi: 10.1016/j.dyepig.2019.108122
25. [25]
  CUI J W, TENG J J, XIANG P N, LIU F Y, CAO Z X, LU J, DENG Y, LI Y Z, PENG C, DEHAEN W, FANG Y Y. A potent fluorescent probe for HOCl with dual NIR emissions: Achieving the early diagnosis of polystyrene microplastics-induced liver injury involved in ferroptosis[J]. J. Hazard. Mater., 2025, 492: 138087 doi: 10.1016/j.jhazmat.2025.138087
1. [1]
  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
2. [2]
  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
3. [3]
  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
4. [4]
  Jian Li , Yu Zhang , Rongrong Yan , Kaiyuan Sun , Xiaoqing Liu , Zishang Liang , Yinan Jiao , Hui Bu , Xin Chen , Jinjin Zhao , Jianlin Shi . Highly Efficient, Targeted, and Traceable Perovskite Nanocrystals for Photoelectrocatalytic Oncotherapy. Acta Physico-Chimica Sinica, 2025, 41(5): 100042-0. doi: 10.1016/j.actphy.2024.100042
5. [5]
  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
6. [6]
  Yuting DU , Jing YUAN , Peiyao DENG . Synthesis and application of a fluorescent probe for the detection of reduced glutathione. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1331-1337. doi: 10.11862/CJIC.20240461
7. [7]
  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
8. [8]
  Lina Feng , Guoyu Jiang , Xiaoxia Jian , Jianguo Wang . Application of Organic Radical Materials in Biomedicine. University Chemistry, 2025, 40(4): 253-260. doi: 10.12461/PKU.DXHX202405171
9. [9]
  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
10. [10]
  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
11. [11]
  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
12. [12]
  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
13. [13]
  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
14. [14]
  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
15. [15]
  Zhifeng CAI , Ying WU , Yanan LI , Guiyu MENG , Tianyu MIAO , Yihao ZHANG . Effective detection of malachite green by folic acid stabilized silver nanoclusters. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 983-993. doi: 10.11862/CJIC.20240394
16. [16]
  Wei GAO , Meiqi SONG , Xuan REN , Jianliang BAI , Jing SU , Jianlong MA , Zhijun WANG . A self-calibrating fluorescent probe for the selective detection and bioimaging of HClO. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1173-1182. doi: 10.11862/CJIC.20250112
17. [17]
  Lei ZHANG , Cheng HE , Yang JIAO . An azo-based fluorescent probe for the detection of hypoxic tumor cells. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1162-1172. doi: 10.11862/CJIC.20250081
18. [18]
  Jinghan ZHANG , Guanying CHEN . Progress in the application of rare-earth-doped upconversion nanoprobes in biological detection. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2335-2355. doi: 10.11862/CJIC.20240249
19. [19]
  Wei Li , Jinfan Xu , Yongjun Zhang , Ying Guan . 共价有机框架整体材料的制备及食品安全非靶向筛查应用——推荐一个仪器分析综合化学实验. University Chemistry, 2025, 40(6): 276-285. doi: 10.12461/PKU.DXHX202406013
20. [20]
  Bin SUN , Heyan JIANG . Glucose-modified bis-Schiff bases: Synthesis and bio-activities in Alzheimer′s disease therapy. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1338-1350. doi: 10.11862/CJIC.20240428

Get Citation

PDF

XML

Metrics

PDF Downloads(1)
Abstract views(120)
HTML views(16)

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

Pyridinium-chalcone-based ClO- fluorescent probe: Preparation and biological imaging applications

Metrics

通讯作者: 陈斌, bchen63@163.com

Pyridinium-chalcone-based ClO^- fluorescent probe: Preparation and biological imaging applications