Citation: Mengfan Zhang, Lingyan Liu, Peng Wei, Wei Feng, Tao Yi. A proximity tagging strategy utilizing an activated aldehyde group as the active site[J]. Chinese Chemical Letters, ;2025, 36(4): 110127. doi: 10.1016/j.cclet.2024.110127 shu

A proximity tagging strategy utilizing an activated aldehyde group as the active site

Mengfan Zhang ^a ,
Lingyan Liu ^b ,
Peng Wei ^{b, *,} ,
Wei Feng ^{a, *,} ,
Tao Yi ^{b, *,}

a.
Department of Chemistry, Fudan University, Shanghai 200438, China
b.
State Key Laboratory for Modification of Chemical Fibers and Polymer Materials, Shanghai Engineering Research Center of Nano-Biomaterials and Regenerative Medicine, College of Chemistry and Chemical Engineering, Donghua University, Shanghai 201620, China

weipeng@dhu.edu.cn

fengweifd@fudan.edu.cn

yitao@dhu.edu.cn

Received Date: 4 February 2024
Revised Date: 3 June 2024
Accepted Date: 14 June 2024
Available Online: 14 June 2024

Figures(6)

Utilizing small molecules as markers for specific cells or organs within biosystems is a crucial approach for studying and regulating physiological processes. However, current tagging strategies, due to the presence of exposed highly reactive groups, suffer from drawbacks such as low tagging efficiency or insufficient spatial specificity, thereby diminishing their expected effectiveness. Consequently, there is a pressing need to develop a strategy capable of in situ labeling of active groups in response to cellular or in vivo stimuli, ensuring both high tagging efficiency and spatial specificity. In this work, we devised a strategy for releasing aldehyde groups activated by hypochlorous acid (HOCl). Compounds synthesized through this strategy can release the fluorophore methylene blue (MB) and aldehyde-based compounds upon HOCl activation. Given high reactivity of the released aldehyde group, it can effectively interact with macromolecules in biological systems, facilitating tagging and enabling prolonged imaging. To validate this concept, we further incorporated a naphthalimide structure with stable light emission to create SW-110. SW-110 can specifically respond to in vitro and endogenous HOCl, when release MB, it also releases naphthalimide fluorophore with highly reactive aldehyde group for tagging within cells. This strategy provides a simple but efficient strategy for proximity tagging in situ.
- ROS,
- Aldehyde,
- Fluorescence,
- Methylene blue,
- Proximity tagging strategy
1. [1]
  T. Tamura, I. Hamachi, J. Am. Chem. Soc. 141 (2019) 2782–2799. doi: 10.1021/jacs.8b11747
2. [2]
  R.N. Reddi, E. Resnick, A. Rogel, et al, J. Am. Chem. Soc. 143 (2021) 4979–4992. doi: 10.1021/jacs.0c10644
3. [3]
  R.N. Reddi, A. Rogel, E. Resnick, et al, J. Am. Chem. Soc. 143 (2021) 20095–20108. doi: 10.1021/jacs.1c06167
4. [4]
  Y. Zhang, Y. Liang, F. Huang, et al, Biochemistry, 58 (2019) 1010–1018. doi: 10.1021/acs.biochem.8b01223
5. [5]
  C. Cui, H. Zhang, R. Wang, et al, Angew. Chem. Int. Ed. 56 (2017) 11954–11957. doi: 10.1002/anie.201706285
6. [6]
  Y. Tivon, G. Falcone, A. Deiters, Angew. Chem. Int. Ed. 60 (2021) 15899–15904. doi: 10.1002/anie.202101174
7. [7]
  J.L. Vinkenborg, G. Mayer, M. Famulok, Angew. Chem. Int. Ed. 51 (2012) 9176–9180. doi: 10.1002/anie.201204174
8. [8]
  Z. Xiang, H. Ren, Y.S. Hu, et al, Nat. Methods, 10 (2013) 885–888. doi: 10.1038/nmeth.2595
9. [9]
  S.R. Adusumalli, D.G. Rawale, K. Thakur, et al, Angew. Chem. Int. Ed. 59 (2020) 10332–10336. doi: 10.1002/anie.202000062
10. [10]
  A.K. Hurben, P. Ge, J.L. Bouchard, T.M. Doran, N.Y. Tretyakova, Chem. Commun. 58 (2022) 855–858. doi: 10.1039/d1cc06651j
11. [11]
  Y. Guo, J. Tao, Y. Li, et al, J. Am. Chem. Soc. 142 (2020) 7404–7412. doi: 10.1021/jacs.9b12182
12. [12]
  H. Liu, X. Wei, R. Nie, et al, LWT-Food Sci. Technol. 155 (2022) 112977.
13. [13]
  Y. Zhang, M. Ucuncu, A. Gambardella, et al, J. Am. Chem. Soc. 142 (2020) 21615–21621. doi: 10.1021/jacs.0c07869
14. [14]
  M. Wolter, D. Valenti, P.J. Cossar, et al, Angew. Chem. Int. Ed. 59 (2020) 21520–21524. doi: 10.1002/anie.202008585
15. [15]
  P.J. Cossar, M. Wolter, L. van Dijck, et al, J. Am. Chem. Soc. 143 (2021) 8454–8464. doi: 10.1021/jacs.1c03035
16. [16]
  Y. Liang, Z. Li, Y. Huang, R. Yu, B. Guo, ACS Nano, 15 (2021) 7078–7093. doi: 10.1021/acsnano.1c00204
17. [17]
  W. Zhang, B. Bao, F. Jiang, et al, Adv. Mater. 33 (2021) 2105667. doi: 10.1002/adma.202105667
18. [18]
  M. Wu, J. Chen, W. Huang, et al, Biomacromolecules, 21 (2020) 2409–2420. doi: 10.1021/acs.biomac.0c00347
19. [19]
  R. Heras-Mozos, R. Gavara, P. Hernández-Muñoz, Carbohydr. Polym. 283 (2022) 119137. doi: 10.1016/j.carbpol.2022.119137
20. [20]
  Y. Guo, M. Wang, Q. Liu, et al, Theranostics, 13 (2023) 161–196. doi: 10.7150/thno.79639
21. [21]
  W. Chen, Y. Ming, M. Wang, et al, Macromol. Rapid Comm. 44 (2023) e2300128.
22. [22]
  F.Y. Chung, Y.Z. Lin, C.R. Huang, K.W. Huang, Y.F. Chen, Int. J. Biol. Macromol. 255 (2024) 127947.
23. [23]
  M. Wang, F.A. Dingler, K.J. Patel, Blood, 139 (2022) 2119–2129. doi: 10.1182/blood.2019004316
24. [24]
  J.M. Garlick, S.M. Sturlis, P.A. Bruno, et al, J. Am. Chem. Soc. 143 (2021) 9297–9302. doi: 10.1021/jacs.1c03258
25. [25]
  H.Y. Wang, Y. Zhang, M. Zhang, Y.Q. Zhang, Int. J. Biol. Macromol. 259 (2024) 129099.
26. [26]
  V. Dhayalan, Mini-rev. Org. Chem. 20 (2023) 593–611. doi: 10.2174/2352096516666221101145135
27. [27]
  A.N. Fajer, H.A. Al-Bahrani, A.A.H. Kadhum, M. Kazemi, J. Mol. Struct. 1296 (2024) 136800.
28. [28]
  Y. Liu, Z. Fu, H. Dong, et al, Angew. Chem. Int. Ed. 62 (2023) e202300906.
29. [29]
  E. Uhl, F. Wolff, S. Mangal, H. Dube, E. Zanin, Angew. Chem. Int. Ed. 60 (2021) 1187–1196. doi: 10.1002/anie.202008267
30. [30]
  Y. Chen, Y. Liu, X. Hou, Z. Ye, C. Wang, Chem. Res. Toxicol. 32 (2019) 467–473. doi: 10.1021/acs.chemrestox.8b00343
31. [31]
  S. Ma, W. Song, Y. Xu, et al, Nano Lett. 20 (2020) 2514–2521. doi: 10.1021/acs.nanolett.9b05265
32. [32]
  K. Wang, J. Li, Y. Yi, et al, Nano Today, 42 (2022) 101355.
33. [33]
  H. Gavilan, G.M.R. Rizzo, N. Silvestri, B.T. Mai, T. Pellegrino, Nat. Protoc. 18 (2023) 783–809. doi: 10.1038/s41596-022-00779-3
34. [34]
  R.E. Mohamed, M.A. Islam, Chelonian Research Foundation, 18 (2023) 555–594. doi: 10.1007/978-3-031-21216-1_57
35. [35]
  R.L. Brabham, R.J. Spears, J. Walton, et al, Chem. Commun. 54 (2018) 1501–1504. doi: 10.1039/c7cc07740h
36. [36]
  C. Wang, Y. Liu, C. Bao, et al, Chem. Commun. 56 (2020) 2264–2267.
37. [37]
  A. Trachsel, N. Paret, D.L. Berthier, A. Herrmann, ChemPhotoChem, 6 (2022) e202200045.
38. [38]
  S. Azeez, P. Sureshbabu, S. Sabiah, J. Kandasamy, Org. Biomol. Chem. 20 (2022) 2048–2053. doi: 10.1039/d1ob02414k
39. [39]
  G.Y. Liou, P. Storz, Free Radic Res. 44 (2010) 479–496. doi: 10.3109/10715761003667554
40. [40]
  H. Nakamura, K. Takada, Cancer Sci. 112 (2021) 3945–3952. doi: 10.1111/cas.15068
41. [41]
  B. Perillo, M. Di Donato, A. Pezone, et al, Exp. Mol. Med. 52 (2020) 192–203. doi: 10.1038/s12276-020-0384-2
42. [42]
  C.R. Reczek, N.S. Chandel, Annu. Rev. Cancer Bio. 1 (2017) 79–98. doi: 10.1146/annurev-cancerbio-041916-065808
43. [43]
  M.V. Irazabal, V.E. Torres, Cells, 9 (2020) 1342. doi: 10.3390/cells9061342
44. [44]
  N. Xu, S. Jiang, P.B. Persson, et al, Acta Physiol. 229 (2020) e13477. doi: 10.1111/apha.13477
45. [45]
  L. Conde de la Rosa, L. Goicoechea, S. Torres, C. Garcia-Ruiz, J.C. Fernandez-Checa, Livers, 2 (2022) 283–314. doi: 10.3390/livers2040023
46. [46]
  S. He, J. Song, J. Qu, Z. Cheng, Chem. Soc. Rev. 47 (2018) 4258–4278. doi: 10.1039/c8cs00234g
47. [47]
  Kenry, Y. Duan, B. Liu, Adv. Mater. 30 (2018) 1802394. doi: 10.1002/adma.201802394
48. [48]
  V. Sanchez-Valle, N.C. Chavez-Tapia, M. Uribe and N. Mendez-Sanchez, Curr. Med. Chem. 19 (2012) 4850–4860. doi: 10.2174/092986712803341520
49. [49]
  D. Moris, M. Spartalis, E. Spartalis, et al, Ann. Transl. Med. 5 (2017) 326. doi: 10.21037/atm.2017.06.27
50. [50]
  N. Panth, K.R. Paudel, K. Parajuli, Adv. Med. 2016 (2016) 9152732. doi: 10.1155/2016/9152732
51. [51]
  J.N. Peoples, A. Saraf, N. Ghazal, T.T. Pham, J.Q. Kwong, Exp. Mol. Med. 51 (2019) 1–13. doi: 10.1038/s12276-019-0355-7
52. [52]
  G.H. Kim, J.E. Kim, S.J. Rhie, S. Yoon, Exp. Neurobiol. 24 (2015) 325–340. doi: 10.5607/en.2015.24.4.325
53. [53]
  E.O. Olufunmilayo, M.B. Gerke-Duncan, R.M.D. Holsinger, Antioxidants, 12 (2023) 517. doi: 10.3390/antiox12020517
54. [54]
  A. Singh, R. Kukreti, L. Saso, S. Kukreti, Molecules, 24 (2019) 1583. doi: 10.3390/molecules24081583
55. [55]
  Y. Zhou, Y. Zhen, G. Wang, B. Liu, Front. Neuroanat. 16 (2022) 910427.
56. [56]
  X. Chen, F. Wang, J.Y. Hyun, et al, Chem. Soc. Rev. 45 (2016) 2976–3016. doi: 10.1039/C6CS00192K
57. [57]
  C. Nathan, J. Clin. Invest. 111 (2003) 769–778. doi: 10.1172/JCI200318174
58. [58]
  Y. Yang, Q. Zhao, W. Feng, F. Li, Chem. Rev. 113 (2013) 192–270. doi: 10.1021/cr2004103
59. [59]
  D. Liu, L. Liu, F. Liu, et al, Adv. Sci. 8 (2021) 2100074. doi: 10.1002/advs.202100074
60. [60]
  F. Liu, L. Liu, D. Liu, et al, Chem. Sci. 13 (2022) 10815–10823. doi: 10.1039/d2sc03365h
61. [61]
  L. Liu, L. Jiang, W. Yuan, et al, ACS Sensors 5 (2020) 2457–2466. doi: 10.1021/acssensors.0c00640
62. [62]
  L. Liu, F. Liu, D. Liu, et al, Angew. Chem. Int. Ed. 61 (2022) e202116807. doi: 10.1002/anie.202116807
63. [63]
  P. Wei, L. Liu, Y. Wen, et al, Angew. Chem. Int. Ed. 58 (2019) 4547–4551. doi: 10.1002/anie.201813648
64. [64]
  P. Wei, W. Yuan, F. Xue, et al, Chem. Sci. 9 (2018) 495–501. doi: 10.1039/C7SC03784H
65. [65]
  N. Fan, C. Wu, Y. Zhou, et al, Anal. Chem. 93 (2021) 7110–7117. doi: 10.1021/acs.analchem.1c00815
66. [66]
  J. Cheng, D. Li, M. Sun, et al, Chem. Sci. 11 (2020) 281–289. doi: 10.1039/c9sc03798e
67. [67]
  T. Peng, X. Chen, L. Gao, et al, Chem. Sci. 7 (2016) 5407–5413. doi: 10.1039/C6SC00012F
68. [68]
  Q. Sun, J. Xu, C. Ji, et al, Anal. Chem. 92 (2020) 4038–4045. doi: 10.1021/acs.analchem.9b05599
69. [69]
  H. Zhang, J. Liu, Y.Q. Sun, et al, Chem. Commun. 51 (2015) 2721–2724. doi: 10.1039/C4CC09122A
70. [70]
  M. Weber, H.H. Han, B.H. Li, et al, Chem. Sci. 11 (2020) 8567–8571. doi: 10.1039/d0sc02438d
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