Citation: Pengli GUAN, Renhu BAI, Xiuling SUN, Bin LIU. Trianiline-derived aggregation-induced emission luminogen probe for lipase detection and cell imaging[J]. Chinese Journal of Inorganic Chemistry, ;2025, 41(9): 1817-1826. doi: 10.11862/CJIC.20250058 shu

Trianiline-derived aggregation-induced emission luminogen probe for lipase detection and cell imaging

Pengli GUAN ¹ ,
Renhu BAI ¹ ,
Xiuling SUN ¹ ,
Bin LIU ^2,,

1.
College of New Energy and Materials Engineering, Shanxi University of Electronic Science and Technology, Linfen, Shanxi 041000, China
2.
Key Laboratory of Chemical Biology and Molecular Engineering of Ministry of Education, Institute of Molecular Science, Shanxi University, Taiyuan 030006, China

Corresponding author: Bin LIU, liubin@sxu.edu.cn
Received Date: 21 February 2025
Revised Date: 19 May 2025

Figures(12)

As a potential biomarker for breast cancer, the highly sensitive detection of lipase is conducive to improving the accuracy of disease diagnosis. Lipase has the property that it can react with the reactant at the contact surface, such as when a solid in solution reacts with lipase. Illuminated by the lipase catalytic property, a lipase-responsive fluorescent probe BTPA with the aggregation-induced emission (AIE) was designed and synthesized. The probe could be hydrolyzed by the lipase enzyme and emit yellow fluorescence, because it self-aggregated into granulums with the external solution, and the granulums provided a surface to activate the activity of the lipase enzyme. The fluorescence emission intensity of BTPA was linearly correlated with the activity of lipase in a range of 5.0×10^-5-4.5×10^-4 U·mL^-1, and the detection limit was 4.94×10^-6 U·mL^-1. Besides, the probe could be applied in a complex biochemical system investigated by a selectivity and interference experiment. The laser-confocal imaging experiment showed that the fluorescent probe could accurately identify breast cancer cells in situ and emit strong fluorescence.
- lipase,
- fluorescent probe,
- cell imaging,
- cancer cell
1. [1]
  BRAY F, LAVERSANNE M, SUNG H, FERLAY J, REBECCA L, SIEGEL R L, SOERJOMATARAM I, SOERJOMATARAM I, JEMAL A. Global cancer statistics 2022: GLOBOCAN estimates of incidence and mortality worldwide for 36 cancers in 185 countries[J]. CA Cancer J. Clin., 2024, 74(3): 229-263
2. [2]
  FRANCESCHINI G. Reevaluating the promise: Is primary tumor surgery really the key to survival or just a misinterpretation in de novo stage Ⅳ breast cancer?[J]. Expert Rev. Anticancer Ther., 2025, 25(2): 189-190 doi: 10.1080/14737140.2025.2454998
3. [3]
  KONDAPALLI K, DONEPUDI M, AMOS S, VENKANTESHAN P. Breast cancer statistics and markers[J]. J. Canc. Res. Ther., 2014, 10(3): 506-511 doi: 10.4103/0973-1482.137927
4. [4]
  SWEEP C G, GEURTS-MOESPOT J, GREBENSCHIKOV N, DE WITTE J H, HEUVEL J J, SCHMITT M, DUFFY M J, JÄNICKE F, KRAMER M D, FOEKENS J A, BRÜNNER N, BRUGAL G, PEDERSEN A N, BENRAAD T J. External quality assessment of trans-European multicentre antigen determinations (enzyme-linked immunosorbent assay) of urokinase-type plasminogen activator (uPA) and its type 1 inhibitor (PAI-1) in human breast cancer tissue extracts[J]. Br. J. Cancer, 1998, 78(11): 1434-1441 doi: 10.1038/bjc.1998.704
5. [5]
  HAYES D F, TROCK B, HARRIS A L. Assessing the clinical impact of prognostic factors: When is "statistically significant" clinically useful?[J]. Breast Cancer Res. Treat., 1998, 52: 305-319 doi: 10.1023/A:1006197805041
6. [6]
  HAYES D F. Do we need better prognostic factors in node-negative breast cancer? Arbiter[J]. Eur. J. Cancer, 2000, 36(3): 302-306 doi: 10.1016/S0959-8049(99)00303-2
7. [7]
  WEN Y, JING N, ZHANG M, HUO F J, LI Z Y, YIN C X. A space-dependent 'enzyme-substrate' type probe based on 'carboxylesterase-amide group' for ultrafast fluorescent imaging orthotopic hepatocellular carcinoma[J]. Adv. Sci., 2023, 10(8): 2206681 doi: 10.1002/advs.202206681
8. [8]
  CUI Y N, JIAO Y, WANG K, HE M, YANG Z Y. A new prognostic factor of breast cancer: High carboxyl ester lipase expression related to poor survival[J]. Cancer Genet., 2019, 239: 54-61 doi: 10.1016/j.cancergen.2019.09.005
9. [9]
  GAGO DOMINGUEZ M, REDONDO C M, CALAZA M, MATABUENA M, BERMUDEZ M A, PEREZ-FERNANDEZ R, TORRES-ESPAÑOL M, CARRACEDO Á, CASTELAO J E. LIPG endothelial lipase and breast cancer risk by subtypes[J]. Sci. Rep., 2021, 11(1): 10436 doi: 10.1038/s41598-021-89669-4
10. [10]
  ROSSI T, ZAMPONI R, CHIRICO M, PISANU M E, IORIO E, TORRICELLI F, GUGNONI M, CIARROCCHI A, PISTONI M. BETi enhance ATGL expression and its lipase activity to exert their antitumoral effects in triple-negative breast cancer (TNBC) cells[J]. J. Exp. Clin. Cancer Res., 2023, 42(1): 7 doi: 10.1186/s13046-022-02571-3
11. [11]
  REVIGLIO C, VOLPI G, WYART E, CIUBINI B, PRANDI C, BAROLO C, PORPORATO P E, GARINO C. Imidazopyridines as fluorogenic substrates for esterase detection[J]. J. Photochem. Photobiol., A, 2025, 462: 116256 doi: 10.1016/j.jphotochem.2024.116256
12. [12]
  CIUFFREDA P, XYNOMILAKIS O, CASATI S, OTTRIA R. Fluorescence-based enzyme activity assay: Ascertaining the activity and inhibition of endocannabinoid hydrolytic enzymes[J]. 2024, 25(14): 7693
13. [13]
  HAN M R, WEI X Y, FENG S S, BAI Y T. A zinc-based metal-organic framework for fluorescence detection of trace Cu²⁺[J]. Chinese J. Inorg. Chem., 2024, 40(8): 1603-1614 doi: 10.11862/CJIC.20240150
14. [14]
  YANG D D, XUE J H, YANG Y Y, WU M X, BAI Y J, WANG Z X, MA Q. Design and synthesis of two coordination polymers for the rapid detection ofciprofloxacin based on triphenylpolycarboxylic acid ligands[J]. Chinese J. Inorg. Chem., 2024, 40(12): 2466-2474 doi: 10.11862/CJIC.20240266
15. [15]
  GUAN P L, SHI S M, ZHANG T S, CHAI J, YANG B S, LIU B. A strategy to distinguish cancers from normal cells through lysosomal targeted double site fluorescent probe for lipase and hydrogen sulfide[J]. Dyes Pigment., 2022, 205: 110545 doi: 10.1016/j.dyepig.2022.110545
16. [16]
  GUAN P L, YANG B S, CHAI J, WEN G, LIU B. A stable hydrazine clicks fluorescent probe based on photo switch[J]. Dyes Pigment., 2021, 186: 108983 doi: 10.1016/j.dyepig.2020.108983
17. [17]
  GUAN P L, YANG B S, LIU B. Fabricating a fluorescence resonance energy transfer system with AIE molecular for sensitive detection of Cu(Ⅱ) ions[J]. Spectroc. Acta Pt. A‒Molec. Biomolec. Spectr., 2020, 225: 117604 doi: 10.1016/j.saa.2019.117604
18. [18]
  GUAN P L, LIU Y M, YANG B S, WU Y B, CHAI J, WEN G M, LIU B. Fluorometric probe for the lipase level: Design, mechanism and biological imaging application[J]. Talanta, 2021, 225: 121948 doi: 10.1016/j.talanta.2020.121948
19. [19]
  BAI J K, XU T, ZHANG L, PENG J, LI Y Q, JIA J H. A red-emitting fluorescent probe with a large Stokes shift for selective detection of hypochlorous acid[J]. Chinese J. Inorg. Chem., 2024, 40(6): 1095-1440 doi: 10.11862/CJIC.20240002
20. [20]
  YAN J L, WU W N, WANG Y. A simple Schiff base probe for the fluorescent turn-on detection of hypochlorite and its biological imaging application[J]. Chinese J. Inorg. Chem., 2024, 40(9): 1653-1660
21. [21]
  ZHANG Y Y, CHEN W, FENG D, SHI W, LI X H, MA H M. A spectroscopic off-on probe for simple and sensitive detection of carboxylesterase activity and its application to cell imaging[J]. Analyst, 2012, 137(3): 716-721 doi: 10.1039/C2AN15952J
22. [22]
  RODRIGUEZ-RIOS M, MEGIA-FERNANDEZ A, NORMAN D J, BRADLEY M. Peptide probes for proteases‒Innovations and applications for monitoring proteolytic activity[J]. Chem. Soc. Rev., 2022, 51(6): 2081-2120
23. [23]
  SONG Y Q, JIN Q, WANG D D, HOU J, ZOU L W, GE G B. Carboxylesterase inhibitors from clinically available medicines and their impact on drug metabolism[J]. Chem. Biol. Interact., 2021, 345: 109566
24. [24]
  FAN H W, FANG N, YANG B B, XIAN H, LI Z. Fluorescence lifetime imaging of human pancreatic lipase activity using a novel probe for early diagnosis of severe acute pancreatitis[J]. Spectroc. Acta Pt. A‒Molec. Biomolec. Spectr., 2025, 326: 125171 doi: 10.1016/j.saa.2024.125171
25. [25]
  LUO J D, XIE Z L, LAM J W Y, CHENG L, TANG B Z, CHEN H Y, QIU C F, KWOK H S, ZHAN X W, LIU Y Q, ZHU D B. Aggregation-induced emission of 1-methyl-1,2,3,4,5-pentaphenylsilole[J]. Chem. Commun., 2001, 18: 1740-1741
26. [26]
  WANG Y L, LI C, QU H Q, FAN C, ZHAO P J, TIAN R, ZHU M Q. Real-time fluorescence in situ visualization of latent fingerprints exceeding level 3 details based on aggregation-induced emission[J]. J. Am. Chem. Soc., 2020, 142(16): 7497-7505
27. [27]
  LUO J D, XIE Z L, LAM J W Y, CHENG L, CHEN H Y, QIU C F, KWOK H S, ZHAN X W, LIU Y Q, ZHU D B, TANG B Z. Aggregation-induced emission of 1-methyl-1,2,3,4,5-pentaphenylsilole[J]. Chem. Commun., 2001, 18: 1740-1741
28. [28]
  WAN H B, XU Q F, GU P Y, LI H, CHEN D Y, LI N J, HE J H, LU J M. AIE-based fluorescent sensors for low concentration toxic ion detection in water[J]. J. Hazard. Mater., 2021, 403: 123656
29. [29]
  WÜRTHNER F. Aggregation-induced emission (AIE): A historical perspective[J]. Angew. Chem.‒Int. Edit., 2020, 59(34): 14192-14196
30. [30]
  CEN P P, HUANG J N, JIN C T, WANG J, WEI Y, ZHANG H, TIAN M. Aggregation-induced emission luminogens for in vivo molecular imaging and theranostics in cancer[J]. Aggregate, 2023, 4(5): e325
31. [31]
  CHEN Y Y, JIANG H, HAO T T, ZHANG N, LI M Y, WANG X Y, WANG X X, WEI W, ZHAO J. Fluorogenic reactions in chemical biology: Seeing chemistry in cells[J]. Chem. Biomed. Imaging, 2023, 1(7): 590-619
32. [32]
  WANG S Y, ZHOU K, LYU X Y, LI H W, QIU Z J, ZHAO Z, TANG B Z. The bioimaging story of AIEgens[J]. Chem. Biomed. Imaging, 2023, 1(6): 509-521
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