Citation: Li Xiang, Zou Yan, Hu Hong-Gang. Different stapling-based peptide drug design: Mimicking α-helix as inhibitors of protein-protein interaction[J]. Chinese Chemical Letters, ;2018, 29(7): 1088-1092. doi: 10.1016/j.cclet.2018.01.018 shu

Different stapling-based peptide drug design: Mimicking α-helix as inhibitors of protein-protein interaction

School of Pharmacy, Second Military Medical University, Shanghai 200433, China

Corresponding author: Hu Hong-Gang, hhu66@smmu.edu.cn
Received Date: 7 December 2017
Revised Date: 5 January 2018
Accepted Date: 8 January 2018
Available Online: 11 July 2018

Figures(7)

Peptide stapling strategy has been proven a promising solution in addressing two major pharmacological hurdles, proteolytic stability and membrane permeability, for small peptides as therapeutics. This stapling peptides feature a covalent cross-link of side chains, thus effectively mimicking α-helix as inhibitors of protein-protein interactions. In this review, we category and analyze key examples of various peptide stapling strategies based on different cross-links aligned on the side chain of peptides mainly in the last three years.
- Stapling,
- Peptide,
- α-Helix,
- Protein-protein interaction
1. [1]
  L.G. Milroy, T.N. Grossmann, S. Hennig, L. Brunsveld, C. Ottmann, Chem. Rev. 114(2014) 4695-4748. doi: 10.1021/cr400698c
2. [2]
  N. London, B. Raveh, D. Movshovitz-Attias, O. Schueler-Furman, Proteins Struct. Funct. Bioinf. 78(2010) 3140-3149. doi: 10.1002/prot.v78:15
3. [3]
  I.S. Moreira, P.A. Fernandes, M.J. Ramos, Proteins Struct. Funct. Bioinf. 68(2007) 803-812. doi: 10.1002/prot.21396
4. [4]
  J.M. Mason, Future Med. Chem. 2(2010) 1813-1822. doi: 10.4155/fmc.10.259
5. [5]
  O. Keskin, A. Gursoy, B. Ma, R. Nussinov, Chem. Rev. 108(2008) 1225-1244. doi: 10.1021/cr040409x
6. [6]
  V. Azzarito, K. Long, N.S. Murphy, A.J. Wilson, Nat. Chem. 5(2013) 161-173. doi: 10.1038/nchem.1568
7. [7]
  D.S. Nielsen, N.E. Shepherd, W. Xu, et al., Chem. Rev. 117(2017) 8094-8128. doi: 10.1021/acs.chemrev.6b00838
8. [8]
  M. Yang, K. Sunderland, C. Mao, Chem. Rev. 117(2017) 10377-10402. doi: 10.1021/acs.chemrev.7b00100
9. [9]
  K.R. Mahendran, A. Niitsu, L. Kong, et al., Nat. Chem. 9(2017) 411-419.
10. [10]
  A.N. Zelikin, C. Ehrhardt, A.M. Healy, Nat. Chem. 8(2016) 997-1007. doi: 10.1038/nchem.2629
11. [11]
  H.M. Berman, J. Westbrook, Z. Feng, et al., Nucleic Acids Res. 28(2000) 235-242. doi: 10.1093/nar/28.1.235
12. [12]
  B.N. Bullock, A.L. Jochim, P.S. Arora, J. Am. Chem. Soc. 133(2011) 14220-14223. doi: 10.1021/ja206074j
13. [13]
  O. Koch, J. Cole, P. Block, G. Klebe, J. Chem. Inf. Model. 49(2009) 2388-2402. doi: 10.1021/ci900202d
14. [14]
  S. Marqusee, R.L. Baldwin, Proc. Natl. Acad. Sci. U. S. A. 84(1987) 8898-8902. doi: 10.1073/pnas.84.24.8898
15. [15]
  M. Chorev, E. Roubini, R.L. McKee, et al., Biochemistry 30(1991) 5968-5974. doi: 10.1021/bi00238a022
16. [16]
  D.Y. Jackson, D.S. King, J. Chmielewski, S. Singh, P.G. Schultz, J. Am. Chem. Soc. 113(1991) 9391-9392. doi: 10.1021/ja00024a067
17. [17]
  A.M. Felix, E.P. Heimer, C.T. Wang, et al., Int. J. Pept. Protein Res. 32(1988) 441-454.
18. [18]
  C.E. Schafmeister, J. Po, G.L. Verdine, J. Am. Chem. Soc. 122(2000) 5891-5892. doi: 10.1021/ja000563a
19. [19]
  Y.H. Lau, P. de Andrade, Y. Wu, D.R. Spring, Chem. Soc. Rev. 44(2015) 91-102. doi: 10.1039/C4CS00246F
20. [20]
  C.J. White, A.K. Yudin, Nat. Chem. 3(2011) 509-524. doi: 10.1038/nchem.1062
21. [21]
  H.E. Blackwell, R.H. Grubbs, Angew. Chem. Int. Ed. 37(1998) 3281-3284. doi: 10.1002/(ISSN)1521-3773
22. [22]
  R.E. Moellering, M. Cornejo, T.N. Davis, et al., Nature 462(2009) 182-188. doi: 10.1038/nature08543
23. [23]
  L.D. Walensky, A.L. Kung, I. Escher, et al., Science 305(2004) 1466-1470. doi: 10.1126/science.1099191
24. [24]
  S. Baek, P.S. Kutchukian, G.L. Verdine, et al., J. Am. Chem. Soc. 134(2012) 103-106. doi: 10.1021/ja2090367
25. [25]
  F. Bernal, A.F. Tyler, S.J. Korsmeyer, L.D. Walensky, G.L. Verdine, J. Am. Chem. Soc. 129(2007) 2456-2457. doi: 10.1021/ja0693587
26. [26]
  P.S. Kutchukian, J.S. Yang, G.L. Verdine, E.I. Shakhnovich, J. Am. Chem. Soc. 131(2009) 4622-4627. doi: 10.1021/ja805037p
27. [27]
  Y.S. Chang, B. Graves, V. Guerlavais, et al., Proc. Natl. Acad. Sci. U. S. A. 110(2013) E3445-E3454. doi: 10.1073/pnas.1303002110
28. [28]
  M. Wade, Y.C. Li, G.M. Wahl, Nat. Rev. Cancer 13(2013) 83-96. doi: 10.1038/nrc3430
29. [29]
  F. Meric-Bernstam, M.N. Saleh, J.R. Infante, et al., J. Clin. Oncol. 35(2017) 2505.
30. [30]
  T.E. Speltz, S.W. Fanning, C.G. Mayne, et al., Angew. Chem. Int. Ed. 55(2016) 4252-4255. doi: 10.1002/anie.201510557
31. [31]
  J.A. Miles, D.J. Yeo, P. Rowell, et al., Chem. Sci. 7(2016) 3694-3702. doi: 10.1039/C5SC04048E
32. [32]
  D.J. Yeo, S.L. Warriner, A.J. Wilson, Chem. Commun. 49(2013) 9131-9133. doi: 10.1039/c3cc45231j
33. [33]
  C.H. Douse, S.J. Maas, J.C. Thomas, et al., ACS Chem. Biol. 9(2014) 2204-2209. doi: 10.1021/cb500271c
34. [34]
  Y. Wu, Y.H. Li, X. Li, et al., Chem. Sci. 8(2017) 7368-7373. doi: 10.1039/C7SC02420G
35. [35]
  M. Oba, M. Kunitake, T. Kato, A. Ueda, M. Tanaka, Bioconj. Chem. 28(2017) 1801-1806. doi: 10.1021/acs.bioconjchem.7b00190
36. [36]
  S.L. Mangold, R.H. Grubbs, Chem. Sci. 6(2015) 4561-4569. doi: 10.1039/C5SC01507C
37. [37]
  C. Hoppmann, R. Kuhne, M. Beyermann, Beilstein J. Org. Chem. 8(2012) 884-889. doi: 10.3762/bjoc.8.100
38. [38]
  A.A. Aimetti, R.K. Shoemaker, C.C. Lin, K.S. Anseth, Chem. Commun. 46(2010) 4061-4063. doi: 10.1039/c001375g
39. [39]
  Y. Wang, D.H.C. Chou, Angew. Chem. Int. Ed. 54(2015) 10931-10934. doi: 10.1002/anie.201503975
40. [40]
  Y. Wang, B.J. Bruno, S. Cornillie, et al., Chem. Eur. J. 23(2017) 7087-7092. doi: 10.1002/chem.201700572
41. [41]
  K. Hu, H. Geng, Q. Zhang, et al., Angew. Chem. Int. Ed. 55(2016) 8013-8017. doi: 10.1002/anie.201602806
42. [42]
  K. Hu, C. Sun, M. Yu, et al., Bioconj. Chem. 28(2017) 1537-1543. doi: 10.1021/acs.bioconjchem.7b00171
43. [43]
  K. Hu, C. Sun, Z. Li, Bioconj. Chem. 28(2017) 2001-2007. doi: 10.1021/acs.bioconjchem.7b00321
44. [44]
  K. Hu, C. Sun, D. Yang, et al., Chem. Commun. 53(2017) 6728-6731. doi: 10.1039/C7CC03799F
45. [45]
  Y. Tian, J. Li, H. Zhao, et al., Chem. Sci. 7(2016) 3325-3330. doi: 10.1039/C6SC00106H
46. [46]
  A.M. Spokoyny, Y. Zou, J.J. Ling, et al., J. Am. Chem. Soc. 135(2013) 5946-5949. doi: 10.1021/ja400119t
47. [47]
  E.V. Vinogradova, C. Zhang, A.M. Spokoyny, B.L. Pentelute, S.L. Buchwald, Nature 526(2015) 687-691. doi: 10.1038/nature15739
48. [48]
  A.J. Rojas, C. Zhang, E.V. Vinogradova, et al., Chem. Sci. 8(2017) 4257-4263. doi: 10.1039/C6SC05454D
49. [49]
  H. Jo, N. Meinhardt, Y. Wu, et al., J. Am. Chem. Soc. 134(2012) 17704-17713. doi: 10.1021/ja307599z
50. [50]
  P. Diderich, D. Bertoldo, P. Dessen, et al., ACS Chem. Biol. 11(2016) 1422-1427. doi: 10.1021/acschembio.5b00963
51. [51]
  L. Peraro, Z. Zou, K.M. Makwana, et al., J. Am. Chem. Soc. 139(2017) 7792-7802. doi: 10.1021/jacs.7b01698
52. [52]
  C.M. Grison, G.M. Burslem, J.A. Miles, et al., Chem. Sci. 8(2017) 5166-5171. doi: 10.1039/C7SC01342F
53. [53]
  S.P. Brown, A.B. Smith, J. Am. Chem. Soc. 137(2015) 4034-4037. doi: 10.1021/ja512880g
54. [54]
  G. Lautrette, F. Touti, H.G. Lee, P. Dai, B.L. Pentelute, J. Am. Chem. Soc. 138(2016) 8340-8343. doi: 10.1021/jacs.6b03757
55. [55]
  C.M.B.K. Kourra, N. Cramer, Chem. Sci. 7(2016) 7007-7012. doi: 10.1039/C6SC02285E
56. [56]
  M. Scrima, A. Le Chevalier-Isaad, P. Rovero, et al., Eur. J. Org. Chem. 2010(2010) 446-457. doi: 10.1002/ejoc.v2010:3
57. [57]
  Y.H. Lau, P. de Andrade, N. Skold, et al., Org. Biomol. Chem. 12(2014) 4074-4077. doi: 10.1039/C4OB00742E
58. [58]
  Y.H. Lau, P. de Andrade, S.T. Quah, et al., Chem. Sci. 5(2014) 1804-1809. doi: 10.1039/C4SC00045E
59. [59]
  Y.H. Lau, Y. Wu, P. de Andrade, W.R.J.D. Galloway, D.R. Spring, Nat. Protoc. 10(2015) 585-594. doi: 10.1038/nprot.2015.033
60. [60]
  M.M. Wiedmann, Y.S. Tan, Y. Wu, et al., Angew. Chem. Int. Ed. 56(2017) 524-529. doi: 10.1002/anie.201609427
61. [61]
  Y. Wu, F. Villa, J. Maman, et al., Angew. Chem. Int. Ed. 56(2017) 12866-12872. doi: 10.1002/anie.201705611
62. [62]
  Y.H. Lau, Y. Wu, M. Rossmann, et al., Angew. Chem. Int. Ed. 54(2015) 15410-15413. doi: 10.1002/anie.201508416
63. [63]
  W. Xu, Y.H. Lau, G. Fischer, et al., J. Am. Chem. Soc. 139(2017) 2245-2256. doi: 10.1021/jacs.6b10234
64. [64]
  S. Das, A. Nag, J. Liang, et al., Angew. Chem. Int. Ed. 54(2015) 13219-13224. doi: 10.1002/anie.201505243
65. [65]
  J. Yamaguchi, A.D. Yamaguchi, K. Itami, Angew. Chem. Int. Ed. 51(2012) 8960-9009. doi: 10.1002/anie.201201666
66. [66]
  A.F.M. Noisier, M.A. Brimble, Chem. Rev. 114(2014) 8775-8806. doi: 10.1021/cr500200x
67. [67]
  L. Mendive-Tapia, S. Preciado, J. García, et al., Nat. Commun. 6(2015) 7160. doi: 10.1038/ncomms8160
68. [68]
  Y. Zhu, M. Bauer, L. Ackermann, Chem. Eur. J. 21(2015) 9980-9983. doi: 10.1002/chem.201501831
69. [69]
  T.J. Osberger, D.C. Rogness, J.T. Kohrt, A.F. Stepan, M.C. White, Nature 537(2016) 214-219. doi: 10.1038/nature18941
70. [70]
  A.F.M. Noisier, J. García, I.A. Ionuţ, F. Albericio, Angew. Chem. Int. Ed. 56(2017) 314-318. doi: 10.1002/anie.201608648
71. [71]
  J. Tang, Y. He, H. Chen, W. Sheng, H. Wang, Chem. Sci. 8(2017) 4565-4570. doi: 10.1039/C6SC05530C
72. [72]
  H.K. Cui, Y. Guo, Y. He, et al., Angew. Chem. Int. Ed. 52(2013) 9558-9562. doi: 10.1002/anie.v52.36
73. [73]
  Y. Guo, D.M. Sun, F.L. Wang, et al., Angew. Chem. Int. Ed. 54(2015) 14276-14281. doi: 10.1002/anie.201500699
74. [74]
  F.L. Wang, Y. Guo, S.J. Li, et al., Org. Biomol. Chem. 13(2015) 6286-6290. doi: 10.1039/C5OB00741K
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