Citation: So Wing Ho, Wong Clarence T. T., Xia Jiang. Peptide photocaging: A brief account of the chemistry and biological applications[J]. Chinese Chemical Letters, ;2018, 29(7): 1058-1062. doi: 10.1016/j.cclet.2018.05.015 shu

Peptide photocaging: A brief account of the chemistry and biological applications

Department of Chemistry, The Chinese University of Hong Kong, Hong Kong Special Administrative Region, China

Corresponding author: Wong Clarence T. T., clarenceTTW@cuhk.edu.hk Xia Jiang, jiangxia@cuhk.edu.hk
Received Date: 5 April 2018
Revised Date: 30 April 2018
Accepted Date: 3 May 2018
Available Online: 8 July 2018

Figures(6)

Light is arguably the most convenient non-invasive stimulant to perturb or control specific chemical reactions in the biological systems. Upon light illumination, photosensitive molecules incur conformational changes or formation/breaking of chemical bonds. Consequently, these molecules can be used to transfer signals from one location to another in the cell, from outside of the cell to the inside, or from a light bulb to the interior of animal tissues. The development of the photochemical reactions of organic compounds has paved the road towards their use in peptides and peptide-based biological applications. In this mini-review, we summarized the state-of-the-art development of photo-protecting groups for peptide photocaging including the un-caging mechanism of different PPGs, the synthesis of photo-caged peptides, and the recent applications of peptide photocaging in chemical biology.
- Photo-protecting groups,
- Photocaged peptides,
- Photocaged proteins,
- Photodecaging
1. [1]
  Q. Shao, B. Xing, Chem. Soc. Rev. 39(2010) 2835-2846. doi: 10.1039/b915574k
2. [2]
  N. Ankenbruk, T. Courtney, Y. Naro, A. Deiters, Angew. Chem. Int. Ed. 57(2018) 2768-2798. doi: 10.1002/anie.201700171
3. [3]
  C. Brieke, F. Rohrbach, A. Gottschalk, G. Mayer, A. Heckel, Angew. Chem. Int. Ed. 51(2012) 8446-8476. doi: 10.1002/anie.201202134
4. [4]
  G. Mayer, A. Heckel, Angew. Chem. Int. Ed. 45(2006) 4900-4921. doi: 10.1002/(ISSN)1521-3773
5. [5]
  S. Kantevari, M. Matsuzaki, Y. Kanemoto, H. Kasai, G.C.R. Ellis-Davies, Nat. Methods 7(2010) 123-125. doi: 10.1038/nmeth.1413
6. [6]
  D.K. Sinha, P. Neveu, N. Gagey, et al., ChemBioChem 11(2010) 653-663. doi: 10.1002/cbic.201000008
7. [7]
  P. Kla'n, T. Solomekm, C.G. Bochet, A. Blanc, R. Givens, M. Rubina, et al., Chem. Rev. 113(2013) 119-191. doi: 10.1021/cr300177k
8. [8]
  A.R. Goldfarb, L.J. Saidel, E. Mosovich, J. Biol. Chem. 193(1951) 397-404.
9. [9]
  A. Patchornik, B. Amit, R.B. Woodward, J. Am. Chem. Soc. 92(1970) 6333-6335. doi: 10.1021/ja00724a041
10. [10]
  J.E.T. Corrie, A. Barth, V. Ranjit, et al., J. Am. Chem. Soc. 125(2003) 8546-8554. doi: 10.1021/ja034354c
11. [11]
  G. Papageorgiou, D.C. Ogden, A. Barth, J.E.T. Corrie, J. Am. Chem. Soc.121(1999) 6503-6504. doi: 10.1021/ja990931e
12. [12]
  B. Schade, V. Hagen, R. Schmidt, et al., J. Org. Chem. 64(1999) 9109-9117. doi: 10.1021/jo9910233
13. [13]
  J. Hoffmann, U. Kazmaier, Synthesis 47(2015) 411-420.
14. [14]
  C.P. O'Banion, L.T. Nguyen, Q. Wang, et al., Angew. Chem. Int. Ed. 55(2016) 950-954. doi: 10.1002/anie.201508767
15. [15]
  S. Tang, J. Cheng, J. Zheng, Tetrahedron Lett. 56(2015) 4582-4585. doi: 10.1016/j.tetlet.2015.06.016
16. [16]
  Y. Shamay, L. Adar, G. Ashkenasy, A. David, Biomaterials 32(2011) 1377-1386. doi: 10.1016/j.biomaterials.2010.10.029
17. [17]
  C. Nadler, A. Nadler, C. Hansen, U. Diederichsen, Eur. J. Org. Chem. 14(2015) 3095-3102.
18. [18]
  M. Mohsen Mahmoodi, D. Abate-Pella, T. Pundsack, et al., J. Am. Chem. Soc.128(2016) 5848-8559.
19. [19]
  E. Janett, Y. Bernardinelli, D. Müller, C.G. Bochet, Bioconjugate Chem. 26(2015) 2408-2418. doi: 10.1021/acs.bioconjchem.5b00473
20. [20]
  J.S. Wood, Koszelak M, J. Liu, D.S. Lawrence, J. Am. Chem. Soc. 120(1998) 7145-7146. doi: 10.1021/ja980960+
21. [21]
  Q. Wang, Z. Dai, S.M. Cahill, M. Blumenstein, D.S. Lawrence, J. Am. Chem. Soc. 128(2006) 14016-14017. doi: 10.1021/ja065852z
22. [22]
  S. Tang, Z. Wan, Y. Gao, et al., Chem. Sci. 7(2016) 1891-1895. doi: 10.1039/C5SC03404C
23. [23]
  X. Chen, S. Tang, J. Zheng, et al., Nat. Commun. 6(2015) 7220. doi: 10.1038/ncomms8220
24. [24]
  A. Shigenaga, J. Yamamoto, T. Kohiki, T. Inokuma, A. Otaka, J. Pept. Sci. 23(2017) 505-513. doi: 10.1002/psc.v23.7-8
25. [25]
  A. Zorzi, K. Devie, C. Heinis, Curr. Opin. Chem. Biol. 38(2017) 24. doi: 10.1016/j.cbpa.2017.02.006
26. [26]
  C.J. Whit, A.K. Yudin, Nat. Chem. 3(2011) 509-524. doi: 10.1038/nchem.1062
27. [27]
  G.K.T. Nguyen, C.T.T. Wong, J. Biochem. Chem. Sci. 1(2017) 1-13.
28. [28]
  J.P. Tam, C.T.T. Wong, J. Biol. Chem. 287(2012) 27020-27025. doi: 10.1074/jbc.R111.323568
29. [29]
  S.B.H. Kent, Chem. Soc. Rev. 38(2009) 338-351. doi: 10.1039/B700141J
30. [30]
  G.M. Fang, Y.M. Li, Y.C. Huang, et al., Angew. Chem. Int. Ed. 50(2011) 7645-7649. doi: 10.1002/anie.201100996
31. [31]
  J.S. Zheng, S. Tang, Y.K. Qi, Z.P. Wang, L. Lei, Nat. Protoc. 8(2013) 2483-2495. doi: 10.1038/nprot.2013.152
32. [32]
  L.Z. Yan, P.E. Dawson, J. Am. Chem. Soc. 12(2001) 526-533.
33. [33]
  C.T.T.Wong C.L. Tung, X. Li, Mol. Biosyst. 9(2013) 826-833. doi: 10.1039/c2mb25437a
34. [34]
  K. Jin, T. Li, H.Y. Chow, H. Liu, X. Li, Angew. Chem. Int. Ed. 56(2017) 14607-14611. doi: 10.1002/anie.201709097
35. [35]
  H. Li, S. Dong, Sci. Chin. Chem. 60(2017) 201-213.
36. [36]
  J. Ma, J. Zeng, Q. Wan, Top. Curr. Chem. 363(2015) 57-101.
37. [37]
  H. Rohde, O. Seiz, Biopolymers 94(2010) 551-559. doi: 10.1002/bip.21442
38. [38]
  J. Yang, J. Zhao, Sci. Chin. Chem. 61(2018) 97-112. doi: 10.1007/s11426-017-9056-5
39. [39]
  X. Li, H.Y. Lam, Y. Zhang, C.K. Chan, Org. Lett. 12(2010) 1724-1727. doi: 10.1021/ol1003109
40. [40]
  C.L. Lee, X. Li, Sci. Chin. Chem. 59(2016) 1061-1064.
41. [41]
  Y. Zhang, C. Xi, H.Y. Lam, C.H. Lee, X. Li, Proc. Natl. Acad. Sci. U. S. A. 110(2013) 6657-6662. doi: 10.1073/pnas.1221012110
42. [42]
  C.L. Lee, H. Liu, C.T.T. Wong, H.Y. Chow, X. Li, J. Am. Chem. Soc. 138(2016) 10477-10484. doi: 10.1021/jacs.6b04238
43. [43]
  T. Kawakami, S. Aimoto, Tetrahedron Lett. 44(2003) 6059-6061. doi: 10.1016/S0040-4039(03)01463-1
44. [44]
  R. He, S.H. Chao, Y.J. Tsai, et al., ACS Nano 11(2017) 6795-6807. doi: 10.1021/acsnano.7b01645
45. [45]
  M.A. Priestman, D.S. Lawrence, Biochim. Biophys. Acta 1804(2010) 547-558. doi: 10.1016/j.bbapap.2009.09.005
46. [46]
  A. Gandioso, M. Cano, A. Massaguer, V. Marchan, J. Org. Chem. 81(2016) 11556-11564. doi: 10.1021/acs.joc.6b02415
47. [47]
  Y. Ohmuro-Matsuyama, Y. Tatsu, Angew. Chem. Int. Ed. 47(2008) 7527-7529. doi: 10.1002/anie.v47:39
48. [48]
  X. Xie, Y. Yang, Y. Yang, et al., Drug Deliv. 23(2016) 2445-2456.
49. [49]
  L.T. Nguyen, N.P. Oien, N.L. Allbritton, D.S. Lawrence, Angew. Chem. Int. Ed. 52(2013) 9936-9939. doi: 10.1002/anie.201305510
50. [50]
  D.L. Pettit, S.S.H. Wang, K.R. Gee, G.J. Augustine, Neuron 19(1997) 465-471. doi: 10.1016/S0896-6273(00)80361-X
51. [51]
  K.J. König, J. Microsc. 200(2000) 83-104. doi: 10.1046/j.1365-2818.2000.00738.x
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