Citation: Juan Liu, Tian Wang, Jinghan Yang, Peiyi Wang. A predictable supramolecular strategy overcomes the aggregation-caused quenching (ACQ) problem in sensitive bioimaging of plant signaling species[J]. Chinese Chemical Letters, ;2026, 37(6): 111782. doi: 10.1016/j.cclet.2025.111782 shu

A predictable supramolecular strategy overcomes the aggregation-caused quenching (ACQ) problem in sensitive bioimaging of plant signaling species

Juan Liu ¹ ,
Tian Wang ¹ ,
Jinghan Yang ^*, ,
Peiyi Wang ^*,

State Key Laboratory of Green Pesticide, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Center for Research and Development of Fine Chemicals of Guizhou University, Guiyang 550025, China

jhyang333@163.com

pywang@gzu.edu.cn

Received Date: 2 April 2025
Revised Date: 16 August 2025
Accepted Date: 1 September 2025
Available Online: 2 September 2025

Figures(5)

Conventional aromatic fluorophores in fluorescent probes can easily initiate molecular aggregation via π–π stacking, which drastically quenches fluorescence and hinders cellular permeability. To address this challenge, we developed an ingenious host-guest recognition strategy that converted detrimental π-π stacking into a relaxed molecular aggregation state, enabling the creation of a rhodamine-based supramolecular fluorescent probe called RAO@2CB[8]. This ternary conjugate, assembled by encapsulating adamantyl-modified rhodamine (RAO) with two cucurbit[8]uril (CB[8]), showcased enhanced fluorescence properties for the precise detection of salicylic acid (SA). Intriguingly, in intricate biological systems, RAO@2CB[8] demonstrated exceptional cell permeability, facilitating susceptible detection and imaging of SA in HEK-293 cells, radish roots, and salt-stressed white pea seedlings. This facile supramolecular strategy not only mitigates aggregation-induced quenching, but also provides profound insights for the precise modulation of molecular aggregation behavior.
- Aggregation-caused quenching (ACQ),
- Supramolecular technique,
- Host-guest,
- Fluorescence probe,
- Bioimaging
1. [1]
  L. Wu, A.C. Sedgwick, X. Sun, et al., Acc. Chem. Res. 52 (2019) 2582–2587. doi: 10.1021/acs.accounts.9b00302
2. [2]
  D. Zhang, H. Liu, T. He, et al., Small 17 (2021) 2005113. doi: 10.1002/smll.202005113
3. [3]
  M.K. Goshisht, N. Tripathi, G.K. Patra, et al., Chem. Sci. 14 (2023) 5842–5871. doi: 10.1039/d3sc01036h
4. [4]
  R. Sivakumar, N.Y. Lee, et al., Coord. Chem. Rev. 501 (2024) 215563. doi: 10.1016/j.ccr.2023.215563
5. [5]
  J. Zhao, J. Chen, S. Ma, et al., Acta Pharm. Sin. B 8 (2018) 320–338. doi: 10.1016/j.apsb.2018.03.010
6. [6]
  N.C. Payne, A.S. Kalyakina, K. Singh, et al., Nat. Chem. Biol. 17 (2021) 1168–1177. doi: 10.1038/s41589-021-00877-5
7. [7]
  Y. Zhu, B. Wu, X. Gao, et al., Biosens. Bioelectron. 244 (2024) 115809. doi: 10.1016/j.bios.2023.115809
8. [8]
  Y. Kang, N. Fei, L. Niu, et al., Chin. Chem. Lett. 30 (2019) 1791–1798. doi: 10.1016/j.cclet.2019.08.013
9. [9]
  A.S. Burange, K.G. Gadam, P.S. Tugaonkar, et al., Environ. Chem. Lett. 19 (2021) 3283–3314. doi: 10.1007/s10311-021-01223-w
10. [10]
  Y. Zhu, L. Lin, H. Lai, et al., Adv. Sci. 11 (2023) 2307659.
11. [11]
  Z. Zhu, D. Zhang, J. Chen, et al., Mater. Horiz. 10 (2023) 4868–4881. doi: 10.1039/d3mh01263h
12. [12]
  X. Kang, L. Zhang, L. Yang, et al., Chem. Eng. J. 476 (2023) 146923. doi: 10.1016/j.cej.2023.146923
13. [13]
  C. Zeng, Y. Tan, L. Sun, et al., ACS Appl. Mater. Interfaces 15 (2023) 17664–17674. doi: 10.1021/acsami.3c00956
14. [14]
  Y. Zhang, Y. Zhao, Z. Han, et al., Angew. Chem. Int. Ed. 59 (2020) 23261–23267. doi: 10.1002/anie.202010216
15. [15]
  H. Lu, Y. Wang, S.K. Hill, et al., Angew. Chem. Int. Ed. 62 (2023) e202311224. doi: 10.1002/anie.202311224
16. [16]
  W. Li, J. Wang, Y. Xie, et al., Prog. Org. Coat. 120 (2018) 1–9.
17. [17]
  J. Qi, X. Hu, X. Dong, et al., Adv. Drug Deliv. Rev. 143 (2019) 206–225. doi: 10.1016/j.addr.2019.05.009
18. [18]
  J. Wang, H. Liu, M. Wu, et al., Talanta 205 (2019) 120095. doi: 10.1016/j.talanta.2019.06.095
19. [19]
  Y. Jin, R. Sun, G. Li, et al., Spectrochim. Acta A: Mol. Biomol. Spectrosc. 294 (2023) 122558. doi: 10.1016/j.saa.2023.122558
20. [20]
  Y. Tang, H. Huang, B. Peng, et al., J. Mater. Chem. A 8 (2020) 16542–16550. doi: 10.1039/c9ta14252e
21. [21]
  R. Guo, S. Ye, Y. Wang, et al., J. Mater. Chem. C 9 (2021) 13392–13401. doi: 10.1039/d1tc02081a
22. [22]
  L. Ren, Y.J. Kim, S.Y. Park, et al., J. Mater. Chem. B 4 (2016) 4832–4838. doi: 10.1039/C6TB00935B
23. [23]
  F. Zhang, X. Zheng, E. Liu, et al., J. Ind. Eng. Chem. 46 (2017) 397–403. doi: 10.1016/j.jiec.2016.11.009
24. [24]
  X. Zhang, S. Shen, D. Liu, et al., Chem. Sci. 14 (2023) 2928–2934. doi: 10.1039/D3SC00355H
25. [25]
  M. Park, Y. Jeong, H.S. Kim, et al., Adv. Funct. Mater. 31 (2021) 2102741. doi: 10.1002/adfm.202102741
26. [26]
  N. Zhang, D. Zhang, J. Zhao, et al., Dalton Trans. 48 (2019) 6794–6799. doi: 10.1039/c9dt01125k
27. [27]
  X. Yuan, Z. Wang, L. Li, et al., Mater. Chem. Front. 3 (2019) 1097–1104. doi: 10.1039/c8qm00672e
28. [28]
  G. Lutzweiler, A.N. Halili, N.E. Vrana, et al., Mater. Chem. Front. 12 (2020) 602. doi: 10.3390/pharmaceutics12070602
29. [29]
  F.J. Maksoud, M.F. Velázquez de la Paz, A.J. Hann, et al., J. Mater. Chem. B 10 (2022) 8111–8165. doi: 10.1039/d1tb02628c
30. [30]
  A. Reisch, A.S. Klymchenko, et al., Small 12 (2016) 1968–1992. doi: 10.1002/smll.201503396
31. [31]
  H.S. Jung, K.J. Cho, Y. Seol, et al., Adv. Funct. Mater. 28 (2018) 1801252. doi: 10.1002/adfm.201801252
32. [32]
  G. Della Pelle, A.D. López, M.S. Fiol, et al., Int. J. Mol. Sci. 22 (2021) 6914. doi: 10.3390/ijms22136914
33. [33]
  C. Jeong, S. Uthaman, B. Bagheri, et al., J. Control. Release 329 (2021) 50–62. doi: 10.1016/j.jconrel.2020.11.046
34. [34]
  J. Xin, S. Han, M. Zheng, et al., Chin. Chem. Lett. 35 (2024) 109165. doi: 10.1016/j.cclet.2023.109165
35. [35]
  T. Matsuno, S. Sato, A. Yokoyama, et al., Angew. Chem. Int. Ed. 55 (2016) 15339–15343. doi: 10.1002/anie.201609444
36. [36]
  W.T. Gallonde, C. Poidevin, F. Houard, et al., Angew. Chem. Int. Ed. 62 (2023) e202313696. doi: 10.1002/anie.202313696
37. [37]
  H. Ju, Z. Yin, Z. Demchuk, et al., Adv. Funct. Mater. 34 (2024) 2402165. doi: 10.1002/adfm.202402165
38. [38]
  N. Zhang, W.Y. Lo, Z. Cai, et al., Nano Lett. 17 (2017) 308–312. doi: 10.1021/acs.nanolett.6b04110
39. [39]
  R.M. Veedu, N. Niemeyer, N. Bäumer, et al., Angew. Chem. Int. Ed. 62 (2023) e202314211. doi: 10.1002/anie.202314211
40. [40]
  A.C. Bhasikuttan, H. Pal, J. Mohanty, et al., Chem. Commun. 47 (2011) 9959–9971. doi: 10.1039/c1cc12091c
41. [41]
  S.R. Shariati Pour, S. Oddis, M. Barbalinardo, et al., Molecules 28 (2023) 2528. doi: 10.3390/molecules28062528
42. [42]
  K. Jalani, A.D. Das, R. Sasmal, et al., Nat. Commun. 11 (2020) 3967. doi: 10.1038/s41467-020-17799-w
43. [43]
  A. Sarkar, R. Sasmal, A. Das, et al., Chem. Commun. 57 (2021) 3937–3940. doi: 10.1039/d1cc00332a
44. [44]
  M. Ponce-Vargas, C. Lefebvre, J.C. Boisson, E. Hénon, J. Chem. Inf. Model. 60 (2020) 268–278. doi: 10.1021/acs.jcim.9b01016
45. [45]
  C. Stoffelen, J. Huskens, Small 12 (2016) 96–119. doi: 10.1002/smll.201501348
46. [46]
  Y. Chen, S. Sun, D. Lu, et al., Chin. Chem. Lett. 30 (2019) 37–43. doi: 10.1080/09593330.2017.1377769
47. [47]
  W. Liu, W. Xu, H.H. Luan, et al., Biosens. Bioelectron. 241 (2023) 115678. doi: 10.1016/j.bios.2023.115678
48. [48]
  B.V.K.J. Schmidt, K. Barner, C. Christopher, et al., Angew. Chem. Int. Ed. 56 (2017) 8350–8369. doi: 10.1002/anie.201612150
49. [49]
  X. Zhou, X. Su, P. Pathak, et al., J. Am. Chem. Soc. 139 (2017) 13916–13921. doi: 10.1021/jacs.7b07977
50. [50]
  Y. Zhao, M. Wei, L. Tan, et al., Small 20 (2024) 2308164. doi: 10.1002/smll.202308164
51. [51]
  X.L. Ni, S. Chen, Y. Yang, et al., J. Am. Chem. Soc. 138 (2016) 6177–6183. doi: 10.1021/jacs.6b01223
52. [52]
  J. Barrio, J. Liu, R.A. Brady, et al., J. Am. Chem. Soc. 141 (2019) 14021–14025. doi: 10.1021/jacs.9b07506
53. [53]
  D. Wu, J. Wang, X. Du, et al., J. Nanobiotechnol. 22 (2024) 235. doi: 10.1007/978-981-97-2417-8_21
54. [54]
  C. Wang, Y. Liu, Y. Liu, et al., Small 18 (2022) 2201821. doi: 10.1002/smll.202201821
55. [55]
  L. Yang, Y. Li, H. Zhang, et al., Chin. Chem. Lett. 34 (2023) 108108. doi: 10.1016/j.cclet.2022.108108
56. [56]
  H. Ma, W. Xu, X. Tang, et al., CCS Chem. 7 (2025) 832–842. doi: 10.31635/ccschem.024.202405042
57. [57]
  D. Wu, Y. Wang, N. Wu, et al., J. Hazard. Mater. 479 (2024) 135751. doi: 10.1016/j.jhazmat.2024.135751
58. [58]
  J. Zhou, S. Hou, J. Zhang, et al., Chin. Chem. Lett. 32 (2021) 725–728. doi: 10.1016/j.cclet.2020.07.039
59. [59]
  B. Hua, L. Shao, Z. Zhang, et al., Sens. Actuators B: Chem. 255 (2018) 1430–1435.
60. [60]
  P. Ding, Y. Ding, et al., Trends Plant Sci. 25 (2020) 549–565. doi: 10.1016/j.tplants.2020.01.004
61. [61]
  Y. Peng, J. Yang, X. Li, et al., Annu. Rev. Plant Biol. 72 (2021) 761–791. doi: 10.1146/annurev-arplant-081320-092855
62. [62]
  M. Iqbal, M. Ashraf, et al., J. Integr. Plant Biol. 49 (2007) 1003–1015. doi: 10.1111/j.1672-9072.2007.00488.x
63. [63]
  V. Kovács, O.K. Gondor, G. Szalai, et al., J. Hazard. Mater. 280 (2014) 12–19. doi: 10.1016/j.jhazmat.2014.07.048
64. [64]
  A.B. Wani, H. Chadar, A.H. Wani, et al., Environ. Chem. Lett. 15 (2017) 101–123. doi: 10.1007/s10311-016-0584-0
65. [65]
  C. Kaya, M. Ashraf, M.N. Alyemeni, et al., J. Hazard. Mater. 399 (2020) 123020. doi: 10.1016/j.jhazmat.2020.123020
66. [66]
  X. Jia, L. Wang, H. Zhao, et al., Mol. Plant 16 (2023) 245–259. doi: 10.1016/j.molp.2022.12.002
67. [67]
  M. Sivakumar, M. Sakthivel, S.M. Chen, et al., J. Colloid Interface Sci. 501 (2017) 350–356. doi: 10.1016/j.jcis.2017.04.074
68. [68]
  X.B. Zhang, B.H. Feng, H.M. Wang, et al., J. Integr. Plant Biol. 60 (2018) 160–172. doi: 10.1111/jipb.12613
69. [69]
  Y. Shi, W. Li, X. Hu, et al., Food Chem. 434 (2024) 137260. doi: 10.1016/j.foodchem.2023.137260
70. [70]
  Z.M. Fang, L.L. Zhang, J.J. Wang, et al., Arabian J. Chem. 16 (2023) 104476. doi: 10.1016/j.arabjc.2022.104476
71. [71]
  A. Kumar, A. Pandith, H.S. Kim, J. Luminesc. 172 (2016) 309–316.
72. [72]
  M.W. Ahmad, B.Y. Kim, H.S. Kim, New J. Chem. 38 (2014) 1711–1716. doi: 10.1039/c3nj01339a
73. [73]
  A. Kumar, M.K. Ghosh, C.H. Choi, et al., RSC Adv. 5 (2015) 23613–23621. doi: 10.1039/C5RA00565E
74. [74]
  A. Pandith, G. Hazra, H.S. Kim, Spectrochim. Acta A: Mol. Biomol. Spectrosc. 178 (2017) 151–159. doi: 10.1016/j.saa.2017.01.053
75. [75]
  C. Chen, L.L. Yang, A.L. Tang, et al., J. Agric. Food Chem. 68 (2020) 4844–4850. doi: 10.1021/acs.jafc.0c01283
76. [76]
  Z.M. Fang, L.L. Zhang, J.J. Wang, et al., Arab. J. Chem. 16 (2023) 104476. doi: 10.1016/j.arabjc.2022.104476
77. [77]
  G.K. Hogendoorn, S.C. Bruggink, M.N.C. de Koning, et al., Br. J. Dermatol. 178 (2018) 253–260. doi: 10.1111/bjd.15758
78. [78]
  D.P. Davis, G.P. Daston, M.R. Odio, et al., Toxicol. Lett. 84 (1996) 135–141.
79. [79]
  R. Freitas, S. Silvestro, F. Coppola, et al., Aquat. Toxicol. 214 (2019) 105258.
1. [1]
  Haixian Ren , Yuting Du , Xiaojing Yang , Fangjun Huo , Le Zhang , Caixia Yin . Development of ESIPT-based specific fluorescent probes for bioactive species based on the protection-deprotection of the hydroxyl. Chinese Chemical Letters, 2025, 36(2): 109867-. doi: 10.1016/j.cclet.2024.109867
2. [2]
  Chuanfeng Fan , Jian Gao , Yingkai Gao , Xintong Yang , Gaoning Li , Xiaochun Wang , Fei Li , Jin Zhou , Haifeng Yu , Yi Huang , Jin Chen , Yingying Shan , Li Chen . A non-peptide-based chymotrypsin-targeted long-wavelength emission fluorescent probe with large Stokes shift and its application in bioimaging. Chinese Chemical Letters, 2024, 35(10): 109838-. doi: 10.1016/j.cclet.2024.109838
3. [3]
  Zhongyong Xu , Jun Peng , Wenxing Zhang , Lei Wang , Xiongzhi Xiang , Bin Liu . Albumin-based fluorescent sensor array for differentiating of tetracyclines through host-guest recognitions. Chinese Chemical Letters, 2026, 37(6): 111525-. doi: 10.1016/j.cclet.2025.111525
4. [4]
  Longhao Hu , Lingshan Gong , Wenlong Ye , Hao Chen , Xiao-Li Lai , Yingxiang Ye . Luminescent hydrogen-bonded organic frameworks: From design to applications. Chinese Journal of Structural Chemistry, 2025, 44(11): 100703-100703. doi: 10.1016/j.cjsc.2025.100703
5. [5]
  Quan Lu , Lulu Zhang , Zihan Chen , Jiajia Lv , Jie Gao , Xinmin Li , Hongyu Li , Wen Shi , Xiaohua Li , Huimin Ma , Zeli Yuan . A lipid droplet-targeting fluorescence probe for monitoring of lipid peroxidation in ferroptosis and non-alcoholic fatty liver disease. Chinese Chemical Letters, 2025, 36(8): 110620-. doi: 10.1016/j.cclet.2024.110620
6. [6]
  Sem Bleus , Sergio Ribone , Renny Maria Losus , Liliana Dobrzańska , Luc Van Meervelt , Wim Dehaen . Imination enables efficient formation of a pillararene-inspired host with endo-cavity hydrogen-bonding capability. Chinese Chemical Letters, 2026, 37(6): 111792-. doi: 10.1016/j.cclet.2025.111792
7. [7]
  Bin Fang , Jiaqi Yang , Limin Wang , Haoqin Li , Jiaying Guo , Jiaxin Zhang , Qingyuan Guo , Bo Peng , Kedi Liu , Miaomiao Xi , Hua Bai , Li Fu , Lin Li . A mitochondria-targeted H₂S-activatable fluorogenic probe for tracking hepatic ischemia-reperfusion injury. Chinese Chemical Letters, 2024, 35(6): 108913-. doi: 10.1016/j.cclet.2023.108913
8. [8]
  Fan Zheng , Runsha Xiao , Shuai Huang , Zhikang Chen , Chen Lai , Anyao Bi , Heying Yao , Xueping Feng , Zihua Chen , Wenbin Zeng . Accurate visualization colorectal cancer by monitoring viscosity variations with a novel mitochondria-targeted fluorescent probe. Chinese Chemical Letters, 2025, 36(2): 109876-. doi: 10.1016/j.cclet.2024.109876
9. [9]
  Meiling Zhao , Yao Lu , Yutao Zhang , Haoyun Xue , Zhiqian Guo . Ultra-high signal-to-noise ratio near-infrared chemiluminescent probe for in vivo sensing singlet oxygen. Chinese Chemical Letters, 2025, 36(5): 110105-. doi: 10.1016/j.cclet.2024.110105
10. [10]
  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
11. [11]
  Hui Guo , Wen-Wen Li , Mei-Yin Wu , Jian-Bo Hu , Jun Wang , Yun Liu , Yang Zou , Chu-Luo Yang , Kai-Lu Zheng . Indolizine-benzophenone hybrid acceptors enable TADF materials for bioimaging and photodynamic therapy in living cells. Chinese Chemical Letters, 2026, 37(1): 111721-. doi: 10.1016/j.cclet.2025.111721
12. [12]
  Jialiang Liu , Chengtao Gong , Jinchen Qian , Sen Wang , Yi Liang , Chenglong Guo , Yongwu Peng , Jun Pan . Fluorophore integration strategy endowing 3D covalent organic frameworks with dual-mode white light emission. Chinese Chemical Letters, 2026, 37(4): 111522-. doi: 10.1016/j.cclet.2025.111522
13. [13]
  Zengchao Guo , Weiwei Liu , Tengfei Liu , Jinpeng Wang , Hui Jiang , Xiaohui Liu , Yossi Weizmann , Xuemei Wang . Engineered exosome hybrid copper nanoscale antibiotics facilitate simultaneous self-assembly imaging and elimination of intracellular multidrug-resistant superbugs. Chinese Chemical Letters, 2024, 35(7): 109060-. doi: 10.1016/j.cclet.2023.109060
14. [14]
  Yunlong Li , Xinyu Zhang , Shuang Liu , Chunsheng Li , Qiang Wang , Jin Ye , Yong Lu , Jiating Xu . Engineered iron-based metal-organic frameworks nanoplatforms for cancer theranostics: A mini review. Chinese Chemical Letters, 2025, 36(2): 110501-. doi: 10.1016/j.cclet.2024.110501
15. [15]
  Wenchao Chen , Xiaoting Niu , Xinyu Liang , Guanghao Zhu , Xue Zhang , Qing Gong , Cen Xie , Guangbo Ge , Ping Wang , Yuqi He . Rationally engineered a universal far-red fluorogenic substrate of bile salt hydrolase for functional imaging and inhibitor screening. Chinese Chemical Letters, 2026, 37(4): 111320-. doi: 10.1016/j.cclet.2025.111320
16. [16]
  Lei Wang , Jianing Zhang , Jin Xiong , Wenbo Dai , Miaochang Liu , Xiaobo Huang , Yuye Chai , Yunxiang Lei , Zhengxu Cai , Minyu Zhu . Enhancing the phosphorescence performance of organic doped system by carbonylation of guests. Chinese Chemical Letters, 2026, 37(5): 111706-. doi: 10.1016/j.cclet.2025.111706
17. [17]
  Huihui Wei , Yiming Niu , Mingli Xie , Weining He , Min Chen , Tenghui Wang , Qinhong Jiang , Panfei Xing , Chunming Wang . Photo-bioactivated azido fluorophores for passive and active cell imaging. Chinese Chemical Letters, 2026, 37(6): 111409-. doi: 10.1016/j.cclet.2025.111409
18. [18]
  Cheng He , Renlan Huang , Lingling Wei , Qiuhui He , Jinbo Liu , Jiao Chen , Ge Gao , Cheng Yang , Wanhua Wu . Uncovering the mask of sensitizers to switch on the TTA-UC emission by supramolecular host-guest complexation. Chinese Chemical Letters, 2025, 36(4): 110103-. doi: 10.1016/j.cclet.2024.110103
19. [19]
  Shengyong Liu , Hui Li , Wei Zhang , Yan Zhang , Yan Dong , Wei Tian . Multiple host-guest and metal coordination interactions induce supramolecular assembly and structural transition. Chinese Chemical Letters, 2025, 36(6): 110465-. doi: 10.1016/j.cclet.2024.110465
20. [20]
  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

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(14)
HTML views(2)

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