Citation: Wang Jie, Chen Peng. Development and Applications of Bioorthogonal Cleavage Reactions[J]. Acta Chimica Sinica, ;2017, 75(12): 1173-1182. doi: 10.6023/A17090419 shu

Development and Applications of Bioorthogonal Cleavage Reactions

Wang Jie ^a,b ,
Chen Peng ^a,b,,

a.
College of Chemistry and Molecular Engineering, Peking University, Beijing 100871
b.
Academy for Advanced Interdisciplinary Studies, Peking University, Beijing 100871

Corresponding author: Chen Peng, pengchen@pku.edu.cn
Received Date: 14 September 2017
Available Online: 9 December 2017
Fund Project: the National Natural Science Foundation of China 21432002the National Natural Science Foundation of China 21521003Project supported by the National Natural Science Foundation of China (Nos. 21521003, 21432002)

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Bioorthogonal reactions enable us to study and manipulate biological processes under living conditions. As widely used and powerful tools, biorthogonal reactions are largely defined as "ligation reactions" that are used for labeling, tracing and capturing biomolecules. Recently, an emerging collection of biorthogonal "bond-cleavage reactions" have been developed and applied for biological studies, especially in releasing, activating and manipulating biomolecules. In this review, we will first summarize the characteristics and applications of these biorthogonal cleavage reactions. We will then focus on introducing diverse applications of biorthogonal cleavage reactions, including activation of prodrugs, rescue of intracellular protein activity, engineering of cell surface, among other interesting applications. Finally, the outlook of future development and applications of biorthogonal cleavage reactions will be discussed.
- biorthogonal cleavage reaction,
- protein activation,
- pro-drug,
- unnatural amino acids,
- chemical decaging
1. [1]
  Lemieux, G. A.; de Graffenried, C. L.; Bertozzi, C. R. J. Am. Chem. Soc. 2003, 125, 4708. doi: 10.1021/ja029013y
2. [2]
  Prescher, J. A.; Bertozzi, C. R. Nat. Chem. Biol. 2005, 1, 13. doi: 10.1038/nchembio0605-13
3. [3]
  Patterson, D. M.; Nazarova, L. A.; Prescher, J. A. ACS Chem. Biol. 2014, 9, 592. doi: 10.1021/cb400828a
4. [4]
  Li, J.; Wang, J.; Chen, P. Acta Chim. Sinica 2012, 70, 1439. doi: 10.3866/PKU.WHXB201203142
5. [5]
  Yang, M. Y.; Chen, P. Acta Chim. Sinica 2015, 73, 783. doi: 10.3866/PKU.WHXB201502062
6. [6]
  Azagarsamy, M. A.; Anseth, K. S. ACS Macro Lett. 2013, 2, 5. doi: 10.1021/mz300585q
7. [7]
  Rogozhnikov, D.; O'Brien, P. J.; Elahipanah, S.; Yousaf , M. N. 2016, 6, 39806.
8. [8]
  Koo, H.; Lee, S.; Na, J. H.; Kim, S. H.; Hahn, S. K.; Choi, K.; Kwon, I. C.; Jeong, S. Y.; Kim, K. Angew. Chem., Int. Ed. 2012, 51, 11836. doi: 10.1002/anie.201206703
9. [9]
  Li, J.; Chen, P. R. Nat. Chem. Biol. 2016, 12, 129. doi: 10.1038/nchembio.2024
10. [10]
  Laughlin, S. T.; Baskin, J. M.; Amacher, S. L.; Bertozzi, C. R. Science 2008, 320, 664. doi: 10.1126/science.1155106
11. [11]
  Hao, Z.; Hong, S.; Chen, X.; Chen, P. R. Acc. Chem. Res. 2011, 44, 742. doi: 10.1021/ar200067r
12. [12]
  Pelliccioli, A. P.; Wirz, J. Photochem. Photobiol. Sci. 2002, 1, 441. doi: 10.1039/b200777k
13. [13]
  Cruz, F. G.; Koh, J. T.; Link, K. H. J. Am. Chem. Soc. 2000, 122, 8777. doi: 10.1021/ja001804h
14. [14]
  Lenox, H. J.; McCoy, C. P.; Sheppard, T. L. Org. Lett. 2001, 3, 2415. doi: 10.1021/ol016255e
15. [15]
  Wu, N.; Deiters, A.; Cropp, T. A.; King, D.; Schultz, P. G. J. Am. Chem. Soc. 2004, 126, 14306. doi: 10.1021/ja040175z
16. [16]
  Chen, P. R.; Groff, D.; Guo, J.; Ou, W.; Cellitti, S.; Geierstanger, B. H.; Schultz, P. G. Angew. Chem., Int. Ed. 2009, 48, 4052. doi: 10.1002/anie.v48:22
17. [17]
  Zhao, J.; Lin, S.; Huang, Y.; Zhao, J.; Chen, P. R. J. Am. Chem. Soc. 2013, 135, 7410. doi: 10.1021/ja4013535
18. [18]
  Arbely, E.; Torres-Kolbus, J.; Deiters, A.; Chin, J. W. J. Am. Chem. Soc. 2012, 134, 11912. doi: 10.1021/ja3046958
19. [19]
  Jayakumar, M. K. G.; Idris, N. M.; Zhang, Y. Proc. Natl. Acad. Sci. U. S. A. 2012, 109, 8483. doi: 10.1073/pnas.1114551109
20. [20]
  Liu, J.; Yang, D.; Minemoto, Y.; Leitges, M.; Rosner, M. R.; Lin, A. Mol. Cell 2006, 21, 467. doi: 10.1016/j.molcel.2005.12.020
21. [21]
  Chen, X.; Tang, S.; Zheng, J.; Zhao, R.; Wang, Z.; Shao, W.; Chang, H.; Cheng, J; Zhao, H.; Liu, L.; Qi, H. Nat. Commun. 2015, 6, 7220. doi: 10.1038/ncomms8220
22. [22]
  Virdee, S.; Kapadnis, P. B.; Elliott, T.; Lang, K.; Madrzak, J.; Nguyen, D. P.; Riechmann, L.; Chin, J. W. J. Am. Chem. Soc. 2011, 133, 10708. doi: 10.1021/ja202799r
23. [23]
  Streu, C.; Meggers, E. Angew. Chem., Int. Ed. 2006, 45, 5645. doi: 10.1002/(ISSN)1521-3773
24. [24]
  Sasmal, P. K.; Carregalromero, S.; Parak, W. J.; Meggers, E. Organometallics 2012, 31, 5968. doi: 10.1021/om3001668
25. [25]
  V lker, T.; Meggers, E. ChemBiochem 2017, 18, 1083. doi: 10.1002/cbic.v18.12
26. [26]
  Garner, A. L.; Song, F.; Koide, K. J. Am. Chem. Soc. 2009, 131, 5163. doi: 10.1021/ja808385a
27. [27]
  Yusop, R. M.; Unciti-Broceta, A.; Johansson, E. M. V.; Sánchez-Martín, R. M.; Bradley, M. Nat. Chem. 2011, 3, 239.
28. [28]
  Li, J.; Yu, J.; Zhao, J.; Wang, J.; Zheng, S.; Lin, S.; Chen, L.; Yang, M.; Jia, S.; Zhang, X.; Chen, P. R. Nat. Chem. 2014, 6, 352. doi: 10.1038/nchem.1887
29. [29]
  Weiss, J. T.; Dawson, J. C.; Macleod, K. G.; Rybski, W.; Fraser, C.; Torres-Sánchez, C.; Patton, E. E.; Bradley, M.; Carragher, N. O.; Unciti-Broceta, A. Nat. Commun. 2014, 5, 3277.
30. [30]
  Weiss, J. T.; Dawson, J. C.; Fraser, C.; Rybski, W.; Torres-Sánchez, C.; Bradley, M.; Patton, E. E.; Carragher, N. O.; Unciti-Broceta, A. J. Med. Chem. 2014, 57, 5395. doi: 10.1021/jm500531z
31. [31]
  Santra, M.; Ko, S.-K.; Shin, I.; Ahn, K. H. Chem. Commun. 2010, 46, 3964. doi: 10.1039/c001922d
32. [32]
  Kislukhin, A. A.; Hong, V. P.; Breitenkamp, K. E.; Finn, M. G. Bioconjugate Chem. 2013, 24, 684. doi: 10.1021/bc300672b
33. [33]
  Pérez-López, A. M.; Rubio-Ruiz, B.; Sebastián, V.; Hamilton, L.; Adam, C.; Bray, T. L.; Irusta, S.; Brennan, P. M.; Lloyd-Jones, G.; Sieger, D.; Santamaría, J.; Unciti-Broceta, A. Angew. Chem., Int. Ed. 2017, DOI: 10.1002/anie.201705609
34. [34]
  Blackman, M. L.; Royzen, M.; Fox, J. M. J. Am. Chem. Soc. 2008, 130, 13518. doi: 10.1021/ja8053805
35. [35]
  Versteegen, R. M.; Rossin, R.; ten Hoeve, W.; Janssen, H. M.; Robillard, M. S. Angew. Chem., Int. Ed. 2013, 52, 14112. doi: 10.1002/anie.201305969
36. [36]
  Li, J.; Jia, S.; Chen, P. R. Nat. Chem. Biol. 2014, 10, 1003. doi: 10.1038/nchembio.1656
37. [37]
  Kim, J.; Bertozzi, C. R. Angew. Chem., Int. Ed. 2015, 54, 15777. doi: 10.1002/anie.201508861
38. [38]
  Steiger, A. K.; Pardue, S.; Kevil, C. G.; Pluth, M. D. J. Am. Chem. Soc. 2016, 138, 7256. doi: 10.1021/jacs.6b03780
39. [39]
  Matikonda, S. S.; Orsi, D. L.; Staudacher, V.; Jenkins, I. A.; Fiedler, F.; Chen, J.; Gamble, A. B. Chem. Sci. 2015, 6, 1212. doi: 10.1039/C4SC02574A
40. [40]
  Ge, Y.; Fan, X.; Chen, P. R. Chem. Sci. 2016, 7, 7055. doi: 10.1039/C6SC02615J
41. [41]
  Luo, J.; Liu, Q.; Morihiro, K.; Deiters, A. Nat. Chem. 2016, 8, 1027. doi: 10.1038/nchem.2573
42. [42]
  Pawlak, J. B.; Gential, G. P. P.; Ruckwardt, T. J.; Bremmers, J. S.; Meeuwenoord, N. J.; Ossendorp, F. A.; Overkleeft, H. S.; Filippov, D. V.; van Kasteren, S. I. Angew. Chem., Int. Ed. 2015, 54, 5628. doi: 10.1002/anie.201500301
43. [43]
  Wang, J.; Zheng, S.; Liu, Y.; Zhang, Z.; Lin, Z.; Li, J.; Zhang, G.; Wang, X.; Li, J.; Chen, P. R. J. Am. Chem. Soc. 2016, 138, 15118. doi: 10.1021/jacs.6b08933
44. [44]
  Wu, H.; Alexander, S. C.; Jin, S.; Devaraj, N. K. J. Am. Chem. Soc. 2016, 138, 11429. doi: 10.1021/jacs.6b01625
45. [45]
  Jiménez-Moreno, E.; Guo, Z.; Oliveira, B. L.; Albuquerque, I. S.; Kitowski, A.; Guerreiro, A.; Boutureira, O.; Rodrigues, T.; Jiménez-Osés, G.; Bernardes, G. J. L. Angew. Chem., Int. Ed. 2017, 56, 243. doi: 10.1002/anie.v56.1
46. [46]
  Zhang, G.; Li, J.; Xie, R.; Fan, X.; Liu, Y.; Zheng, S.; Ge, Y.; Chen, P. R. ACS Central Science 2016, 2, 325. doi: 10.1021/acscentsci.6b00024
47. [47]
  Miller, M. A.; Askevold, B.; Mikula, H.; Kohler, R. H.; Pirovich, D.; Weissleder, R. Nat. Commun. 2017, 8, 15906. doi: 10.1038/ncomms15906
48. [48]
  Li, B.; Liu, P.; Wu, H.; Xie, X.; Chen, Z.; Zeng, F.; Wu, S. Biomaterials 2017, 138, 57. doi: 10.1016/j.biomaterials.2017.05.036
49. [49]
  Doerr, A. Nat. Meth. 2014, 11, 472.
50. [50]
  Anon. Nat. Meth. 2015, 12, 16.
51. [51]
  He, C. Nat. Sci. Rev. 2015, 2, 250. doi: 10.1093/nsr/nwv030
52. [52]
  Dumas, A.; Couvreur, P. Chem. Sci. 2015, 6, 2153. doi: 10.1039/C5SC00070J
53. [53]
  Rossin, R.; van Duijnhoven, S. M. J.; ten Hoeve, W.; Janssen, H. M.; Kleijn, L. H. J.; Hoeben, F. J. M.; Versteegen, R. M.; Robillard, M. S. Bioconjugate Chem. 2016, 27, 1697. doi: 10.1021/acs.bioconjchem.6b00231
54. [54]
  Khan, I.; Agris, P. F.; Yigit, M. V.; Royzen, M. Chem. Commun. 2016, 52, 6174. doi: 10.1039/C6CC01024E
55. [55]
  Mejia Oneto, J. M.; Khan, I.; Seebald, L.; Royzen, M. ACS Central Science 2016, 2, 476. doi: 10.1021/acscentsci.6b00150
56. [56]
  Heffern, M. C.; Park, H. M.; Au-Yeung, H. Y.; Van de Bittner, G. C.; Ackerman, C. M.; Stahl, A.; Chang, C. J. Proc. Natl. Acad. Sci. U. S. A. 2016, 113, 14219. doi: 10.1073/pnas.1613628113
57. [57]
  Zorn, J. A.; Wells, J. A. Nat. Chem. Biol. 2010, 6, 179. doi: 10.1038/nchembio.318
58. [58]
  Qiao, Y.; Molina, H.; Pandey, A.; Zhang, J.; Cole, P. A. Science 2006, 311, 1293. doi: 10.1126/science.1122224
59. [59]
  Schwartz, E. C.; Saez, L.; Young, M. W.; Muir, T. W. Nat. Chem. Biol. 2007, 3, 50. doi: 10.1038/nchembio832
60. [60]
  Tsai, Y.-H.; Essig, S.; James, J. R.; Lang, K.; Chin, J. W. Nat. Chem. 2015, 7, 554. doi: 10.1038/nchem.2253
61. [61]
  Tian, T.; Song, Y.; Wang, J.; Fu, B.; He, Z.; Xu, X.; Li, A.; Zhou, X.; Wang, S.; Zhou, X. J. Am. Chem. Soc. 2016, 138, 955. doi: 10.1021/jacs.5b11532
62. [62]
  Qian, K.; Zheng, Y. G. Nat. Chem. Biol. 2014, 10, 328. doi: 10.1038/nchembio.1507
63. [63]
  Fan, X.; Ge, Y.; Lin, F.; Yang, Y.; Zhang, G.; Ngai, W. S. C.; Lin, Z.; Zheng, S.; Wang, J.; Zhao, J.; Li, J.; Chen, P. R. Angew. Chem., Int. Ed. 2016, 55, 14046. doi: 10.1002/anie.v55.45
64. [64]
  Wang, J.; Cheng, B.; Li, J.; Zhang, Z.; Hong, W.; Chen, X.; Chen, P. R. Angew. Chem., Int. Ed. 2015, 54, 5364. doi: 10.1002/anie.201409145
65. [65]
  Hoppmann, C.; Wong, A.; Yang, B.; Li, S.; Hunter, T.; Shokat, K. M.; Wang, L. Nat. Chem. Biol. 2017, 13, 842. doi: 10.1038/nchembio.2406
66. [66]
  Xie, X.; Li, X.-M.; Qin, F.; Lin, J.; Zhang, G.; Zhao, J.; Bao, X.; Zhu, R.; Song, H.; Li, X. D.; Chen, P. R. J. Am. Chem. Soc. 2017, 139, 6522. doi: 10.1021/jacs.7b01431
67. [67]
  Lin, S.; He, D.; Long, T.; Zhang, S.; Meng, R.; Chen, P. R. J. Am. Chem. Soc. 2014, 136, 11860. doi: 10.1021/ja504371w
68. [68]
  Yang, Y.; Song, H.; He, D.; Zhang, S.; Dai, S.; Lin, S.; Meng, R.; Wang, C.; Chen, P. R. Nat. Commun. 2016, 7, 12299. doi: 10.1038/ncomms12299
69. [69]
  Zhang, S.; He, D.; Lin, Z.; Yang, Y.; Song, H.; Chen, P. R. Acc. Chem. Res. 2017, 50, 1184. doi: 10.1021/acs.accounts.6b00647
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