Citation: Sha Li, Fangjun Huo, Yongkang Yue, Kaiqing Ma, Ying Wen, Caixia Yin. Distinguishable multi-substance detection based on three-channel NIR fluorescent probe in physiology and pathology of living cells and zebrafish[J]. Chinese Chemical Letters, ;2021, 32(12): 3870-3875. doi: 10.1016/j.cclet.2021.05.026 shu

Distinguishable multi-substance detection based on three-channel NIR fluorescent probe in physiology and pathology of living cells and zebrafish

Sha Li ^a ,
Fangjun Huo ^b ,
Yongkang Yue ^a ,
Kaiqing Ma ^a ,
Ying Wen ^a ,
Caixia Yin ^{a, *,}

a.
Institute of Molecular Science, Key Laboratory of Chemical Biology and Molecular Engineering of Ministry of Education, Shanxi University, Taiyuan 030006, China
b.
Research Institute of Applied Chemistry, Shanxi University, Taiyuan 030006, China

yincx@sxu.edu.cn

Received Date: 9 March 2021
Revised Date: 8 May 2021
Accepted Date: 13 May 2021
Available Online: 25 May 2021

Figures(6)

Mitochondria is the main organelle for the production of reactive sulfur species (RSS), such as homocysteine (Hcy), cysteine (Cys), glutathione (GSH) and sulfur dioxide (SO₂). These compounds participate in a large number of physiological processes and play an extremely important role in maintaining the balance of life systems. Abnormal concentration and metabolism are closely related to many diseases. Due to their similarities in chemical properties, it is challenging to develop a single fluorescent probe to distinguish them simultaneously. Here, we synthesized the probe PI-CO-NBD with three fluorophores, NBD-Cl and benzopyranate as the reaction sites of GSH/Cys/Hcy and SO₂, respectively. Three biothiols all could cleavage ether bond to release benzopyrylium and coumarin moiety, which emitted red and blue fluorescence, but Cys/Hcy also could do intramolecular rearrangement after nucleophilic substitution, resulting in yellow fluorescence. Thus the probe can distinguish Cys/Hcy and GSH. Subsequently, only SO₂ could quench red fluorescence by adding C=C of benzopyrylium. The probe also could localize well in mitochondria by oxonium ion for all kinds of cells. The probe not only could detect above sulfur-containing active substances of intracellular and extracellular but also monitor the level of them under oxidative stress and apoptosis process in living cells and zebrafish.
- Mitochondrial-targeted,
- Discrimination detection,
- Distinguishable,
- Multi-substance,
- Three channels
1. [1]
  Z. Meng, Z. Yang, J. Li, Q. Zhang, Chemosphere 89(2012) 579-584. doi: 10.1016/j.chemosphere.2012.05.056
2. [2]
  D. Li, X. Han, Z. Yan, Dyes Pigments 151(2018) 95-101. doi: 10.1016/j.dyepig.2017.12.056
3. [3]
  M. Stipanuk, R. Coloso, R. Garcia, M. Banks, J. Nutr. 122(1992) 420-427. doi: 10.1093/jn/122.3.420
4. [4]
  L.Y. Chen, D. Wu, C.S. Lim, Chem. Commun. 53(2017) 4791-4794. doi: 10.1039/C7CC01695F
5. [5]
  W.J. Zhang, F.J. Huo, F.Q. Cheng, C.X. Yin, J. Am. Chem. Soc. 142(2020) 6324-6331. doi: 10.1021/jacs.0c00992
6. [6]
  S. Iwasawa, Y. Kikuchi, Y. Nishiwaki, Health 51(2009) 38-47. doi: 10.1136/oem.2007.033456
7. [7]
  D. Lowinsohn, M. Bertotti, Food Addit. Contam. 18(2001) 773-777. doi: 10.1080/02652030117536
8. [8]
  K.R.B. Silva, I.M. Raimundo, I.F. Gimenez, O.L. Alves, J. Agr. Food Chem. 54(2006) 8697-8701. doi: 10.1021/jf061553h
9. [9]
  N. Sang, Y. Yun, H. Li, Toxicol. Sci. 114(2010) 226-236. doi: 10.1093/toxsci/kfq010
10. [10]
  L.C. Azevedo, M.M. Reis, L.F. Motta, G.O. Rocha, L.A. Silva, J. Agr. Food Chem. 55(2007) 8670-8680. doi: 10.1021/jf0709653
11. [11]
  R.C. Claudia, J.C. Francisco, Food Chem. 112(2009) 487-493. doi: 10.1016/j.foodchem.2008.05.085
12. [12]
  S. Shahrokhian, Anal. Chem. 73(2001) 5972-5978. doi: 10.1021/ac010541m
13. [13]
  Y.F. Huang, F.Q. Cheng, C.X. Yin, J. Am. Chem. Soc. 142(2020) 18706-18714. doi: 10.1021/jacs.0c10210
14. [14]
  J. Kaluzna-Czaplinska, E. Zurawicz, M. Michalska, J. Rynkowski, Acta Biochim. Pol. 60(2013) 137-142.
15. [15]
  H.S. Jung, X. Chen, J.S. Kim, J. Yoon, Chem. Soc. Rev. 42(2013) 6019-6031. doi: 10.1039/c3cs60024f
16. [16]
  A. Meister, M. Anderson, E. Glutathione, Annu. Rev. Biochem. 52(1983) 711-760. doi: 10.1146/annurev.bi.52.070183.003431
17. [17]
  M.E. Anderson, Chem-Biol. Interact. (1998) 1-14111-112.
18. [18]
  L.M. Hyman, K.J. Franz, Coordin. Chem. Rev. 256(2012) 2333-2356. doi: 10.1016/j.ccr.2012.03.009
19. [19]
  Y.F. Huang, Y.B. Zhang, F.J. Huo, C.X. Yin, Dyes Pigments 184(2021) 108869. doi: 10.1016/j.dyepig.2020.108869
20. [20]
  J. Yin, Y. Kwon, D. Kim, J. Am. Chem. Soc. 136(2014) 5351-5358. doi: 10.1021/ja412628z
21. [21]
  M.H. Lee, J.H. Han, P.S. Kwon, J. Am. Chem. Soc. 134(2012) 1316-1322. doi: 10.1021/ja210065g
22. [22]
  L. Liu, A. Wang, G. Wang, J. Li, Y. Zhou, Sens. Actuators B: Chem. 215(2015) 388-395. doi: 10.1016/j.snb.2015.03.093
23. [23]
  S. Whillier, J.E. Raftos, P.W. Kuchel, Redox Rep. 13(2008) 277-282. doi: 10.1179/135100008X309046
24. [24]
  R. Schutte, A.E. Schutte, H.W. Huisman, Am. J. hypertens. 22(2009) 1154-1159. doi: 10.1038/ajh.2009.158
25. [25]
  C. Hwang, A.J. Sinskey, H.F. Lodish, Science 257(1992) 1496-1502. doi: 10.1126/science.1523409
26. [26]
  W. Zhang, Y. Huang, Y. Chen, ACS Appl. Mater. Interfaces 11(2019) 10567-10577. doi: 10.1021/acsami.9b00643
27. [27]
  F. Hu, B. Liu, Org. Biomol. Chem. 14(2016) 9931-9944. doi: 10.1039/C6OB01414C
28. [28]
  L. Peng, S. Xu, X. Zheng, Anal. Chem. 89(2017) 3162-3168. doi: 10.1021/acs.analchem.6b04974
29. [29]
  C.W.T. Leung, Y. Hong, S. Chen, J. Am. Chem. Soc. 135(2013) 62-65. doi: 10.1021/ja310324q
30. [30]
  M. Tian, Y. Ma, W. Lin, Acc. Chem. Res. 52(2019) 2147-2157. doi: 10.1021/acs.accounts.9b00289
31. [31]
  Y.F. Huang, Y.B. Zhang, F.J. Huo, C.X. Yin, Sens. Actuators B: Chem. 301(2019) 127123. doi: 10.1016/j.snb.2019.127123
32. [32]
  M. Tian, J. Sun, B. Dong, W. Lin, Anal. Chem. 91(2019) 10056-10063. doi: 10.1021/acs.analchem.9b01959
33. [33]
  Y.T. Yang, T.T. Zhou, F.J. Huo, W. Li, C.X. Yin, J. Am. Chem. Soc. 142(2020) 1614-1620. doi: 10.1021/jacs.9b12629
34. [34]
  N. Zhao, Y. Li, W. Yang, J. Zhuang, Y. Li, Chem. Sci. 10(2019) 9009-9016. doi: 10.1039/C9SC03111A
35. [35]
  S.J. Park, V. Juvekar, J.H. Jo, H.M. Kim, Chem. Sci. 11(2020) 596-601. doi: 10.1039/C9SC04859F
36. [36]
  K.Z. Huang, L. Yu, P.F. Xu, X.T. Zhang, W.B. Zeng, RSC Adv. 5(2015) 17797-17801. doi: 10.1039/C4RA16578K
37. [37]
  W.J. Cheng, Y.T. Xie, Z.Y. Yang, Anal. Chem. 91(2019) 5817-5823. doi: 10.1021/acs.analchem.9b00132
38. [38]
  Y. Gao, Z. He, X. He, J. Am. Chem. Soc. 141(2019) 20097-20106. doi: 10.1021/jacs.9b09239
39. [39]
  B. Feng, Y. Liu, S. Huang, X.Y. Huang, W.B. Zeng, Sens. Actuators B: Chem. 325(2020) 128786. doi: 10.1016/j.snb.2020.128786
40. [40]
  T. Gao, X.Z. Cao, P. Ge, Org. Biomol. Chem. 15(2017) 4375-4382. doi: 10.1039/C7OB00580F
1. [1]
  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
2. [2]
  Linfang Wang , Jing Liu , Minghao Ren , Wei Guo . A highly sensitive fluorescent HClO probe for discrimination between cancerous and normal cells/tissues. Chinese Chemical Letters, 2024, 35(6): 108945-. doi: 10.1016/j.cclet.2023.108945
3. [3]
  Ying-Yu Zhang , Jia-Qi Luo , Yan Han , Wan-Ying Zhang , Yi Zhang , Hai-Feng Lu , Da-Wei Fu . Bistable switch molecule DPACdCl₄ showing four physical channels and high phase transition temperature. Chinese Chemical Letters, 2025, 36(1): 109530-. doi: 10.1016/j.cclet.2024.109530
4. [4]
  Congyan Liu , Xueyao Zhou , Fei Ye , Bin Jiang , Bo Liu . Confined electric field in nano-sized channels of ionic porous framework towards unique adsorption selectivity. Chinese Chemical Letters, 2025, 36(2): 109969-. doi: 10.1016/j.cclet.2024.109969
5. [5]
  Lili Zhang , Hui Gao , Gong Zhang , Yuning Dong , Kai Huang , Zifan Pang , Tuo Wang , Chunlei Pei , Peng Zhang , Jinlong Gong . Cross-section design of the flow channels in membrane electrode assembly electrolyzer for CO₂ reduction reaction through numerical simulations. Chinese Chemical Letters, 2025, 36(1): 110204-. doi: 10.1016/j.cclet.2024.110204
6. [6]
  Zhengyi Shi , Jie Yin , Yang Xiao , Zhangrong Hou , Fei Song , Jianping Wang , Qingyi Tong , Changxing Qi , Yonghui Zhang . Unprecedented sesquiterpene-polycyclic polyprenylated acylphloroglucinol adduct against acute myeloid leukemia via inhibiting mitochondrial complex Ⅴ. Chinese Chemical Letters, 2024, 35(10): 109458-. doi: 10.1016/j.cclet.2023.109458
7. [7]
  Yuhang Li , Yang Ling , Yanhang Ma . Application of three-dimensional electron diffraction in structure determination of zeolites. Chinese Journal of Structural Chemistry, 2024, 43(4): 100237-100237. doi: 10.1016/j.cjsc.2024.100237
8. [8]
  Zhenzhong MEI , Hongyu WANG , Xiuqi KANG , Yongliang SHAO , Jinzhong GU . Syntheses and catalytic performances of three coordination polymers with tetracarboxylate ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1795-1802. doi: 10.11862/CJIC.20240081
9. [9]
  Rui Wang , Yang Liang , Julius Rebek Jr. , Yang Yu . Stabilization and detection of labile reaction intermediates in supramolecular containers. Chinese Chemical Letters, 2024, 35(6): 109228-. doi: 10.1016/j.cclet.2023.109228
10. [10]
  Zihong Li , Jie Cheng , Ping Huang , Guoliang Wu , Weiying Lin . Activatable photoacoustic bioprobe for visual detection of aging in vivo. Chinese Chemical Letters, 2024, 35(4): 109153-. doi: 10.1016/j.cclet.2023.109153
11. [11]
  Chao Ma , Peng Guo , Zhongmin Liu . DNL-16: A new zeolitic layered silicate unraveled by three-dimensional electron diffraction. Chinese Journal of Structural Chemistry, 2024, 43(4): 100235-100235. doi: 10.1016/j.cjsc.2024.100235
12. [12]
  Zhe Li , Ping-Zhao Liang , Li Xu , Fei-Yu Yang , Tian-Bing Ren , Lin Yuan , Xia Yin , Xiao-Bing Zhang . Three positive charge nonapoptotic-induced photosensitizer with excellent water solubility for tumor therapy. Chinese Chemical Letters, 2024, 35(8): 109190-. doi: 10.1016/j.cclet.2023.109190
13. [13]
  Shiyu Hou , Maolin Sun , Liming Cao , Chaoming Liang , Jiaxin Yang , Xinggui Zhou , Jinxing Ye , Ruihua Cheng . Computational fluid dynamics simulation and experimental study on mixing performance of a three-dimensional circular cyclone-type microreactor. Chinese Chemical Letters, 2024, 35(4): 108761-. doi: 10.1016/j.cclet.2023.108761
14. [14]
  Jiajing Wu , Ru-Ling Tang , Sheng-Ping Guo . Three types of promising functional building units for designing metal halide nonlinear optical crystals. Chinese Journal of Structural Chemistry, 2024, 43(6): 100291-100291. doi: 10.1016/j.cjsc.2024.100291
15. [15]
  Bowen Wang , Longwu Sun , Qianqian Cao , Xinzhi Li , Jianai Chen , Shizhao Wang , Miaolin Ke , Fener Chen . Cu-catalyzed three-component CSP coupling for the synthesis of trisubstituted allenyl phosphorothioates. Chinese Chemical Letters, 2024, 35(12): 109617-. doi: 10.1016/j.cclet.2024.109617
16. [16]
  Du Liu , Yuyan Li , Hankun Zhang , Benhua Wang , Chaoyi Yao , Minhuan Lan , Zhanhong Yang , Xiangzhi Song . Three-in-one erlotinib-modified NIR photosensitizer for fluorescence imaging and synergistic chemo-photodynamic therapy. Chinese Chemical Letters, 2025, 36(2): 109910-. doi: 10.1016/j.cclet.2024.109910
17. [17]
  Chunmao Yuan , Yanrong Zeng , Lei Huang , Yu Mou , Jun Jin , Ping Yi , Yanmei Li , Xiaojiang Hao . Hymoins A–C, three unusual polycyclic polyprenylated acylphloroglucinols with lipid-lowering activity from Hypericum monogynum. Chinese Chemical Letters, 2025, 36(3): 109859-. doi: 10.1016/j.cclet.2024.109859
18. [18]
  Yifan LIU , Zhan ZHANG , Rongmei ZHU , Ziming QIU , Huan PANG . A three-dimensional flower-like Cu-based composite and its low-temperature calcination derivatives for efficient oxygen evolution reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 979-990. doi: 10.11862/CJIC.20240008
19. [19]
  Gaofeng WANG , Shuwen SUN , Yanfei ZHAO , Lixin MENG , Bohui WEI . Structural diversity and luminescence properties of three zinc coordination polymers based on bis(4-(1H-imidazol-1-yl)phenyl)methanone. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 849-856. doi: 10.11862/CJIC.20230479
20. [20]
  Wenhao Chen , Muxuan Wu , Han Chen , Lue Mo , Yirong Zhu . Cu₂Se@C thin film with three-dimensional braided structure as a cathode material for enhanced Cu²⁺ storage. Chinese Chemical Letters, 2024, 35(5): 108698-. doi: 10.1016/j.cclet.2023.108698

Get Citation

PDF

XML

Metrics

PDF Downloads(3)
Abstract views(594)
HTML views(42)

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