Pyridinium-chalcone-based ClO- fluorescent probe: Preparation and biological imaging applications
- Corresponding author: Xu WANG, 573907861@qq.com Weina WU, wuwn08@hpu.edu.cn
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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Inset in a: fluorescence color changes of probe 1 solution with and without ClO-; In b: 1: probe 1; 2: 1+ClO-; 3: 1+ClO-+ROO-; 4: 1+ClO-+ONOO-; 5: 1+ClO-+NO; 6: 1+ClO-+H2O2; 7: 1+ClO-+·OH; 8: 1+ClO-+Ag+; 9: 1+ClO-+Ca2+; 10: 1+ClO-+Cd2+; 11: 1+ClO-+Co2+; 12: 1+ClO-+Cr3+; 13: 1+ClO-+Cu2+; 14: 1+ClO-+Fe3+; 15: 1+ClO-+K+; 16: 1+ClO-+Mg2+; 17: 1+ClO-+Mn2+; 18: 1+ClO-+Na+; 19: 1+ClO-+Ni2+; 20: 1+ClO-+Pb2+; 21: 1+ClO-+Zn2+; 22: 1+ClO-+Cys; 23: 1+ClO-+Hcy; 24: 1+ClO-+GSH; 25: 1+ClO-+OAc-; 26: 1+ClO-+ClO4-; 27: 1+ClO-+H2PO4-; 28: 1+ClO-+PO43-; 29: 1+ClO-+HPO42-; 30: 1+ClO-+SO42-; 31: 1+ClO-+HSO4-; 32: 1+ClO-+Br-; 33: 1+ClO-+SO32-; 34: 1+ClO-+HSO3-; 35: 1+ClO-+PPi; 36: 1+ClO-+I-.
Inset: possible reaction mechanism between probe 1 and ClO-; C: gray ball; N: blue ball; O: red ball; H: green ball; B: cyan ball.
Scale bar: 10 μm.
Scale bar: 200 μm.