Citation: Dake Liu, Shuyan Liu, Fanlei Hu, Zhongtang Li, Zhongjun Li. N-Glycosylated type Ⅱ collagen peptides as therapeutic saccharide vaccines for rheumatoid arthritis[J]. Chinese Chemical Letters, ;2024, 35(5): 108762. doi: 10.1016/j.cclet.2023.108762 shu

N-Glycosylated type Ⅱ collagen peptides as therapeutic saccharide vaccines for rheumatoid arthritis

Dake Liu ^a ,
Shuyan Liu ^b ,
Fanlei Hu ^{b, *,} ,
Zhongtang Li ^{a, *,} ,
Zhongjun Li ^{a, *,}

a.
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing 100191, China
b.
Department of Rheumatology and Immunology, Peking University People's Hospital, Beijing 100044, China

fanleihu@bjmu.edu.cn

lizhongtang@bjmu.edu.cn

zjli@bjmu.edu.cn

Received Date: 11 May 2023
Revised Date: 29 June 2023
Accepted Date: 2 July 2023
Available Online: 4 July 2023

Figures(3)

The interaction among type Ⅱ collagen (CII), human DR4 major histocompatibility complex type Ⅱ molecule (MHC Ⅱ) and T-cell receptor (TCR) is associated with the development of rheumatoid arthritis (RA). The activation of T cells can be reduced through exposure to modified CII(263–272) glycopeptide fragment via competitive inhibition with self-antigen. In this work, 30 peptides based on the sequence of CII(263–272) were prepared and evaluated for their binding to DR4 protein by surface plasmon resonance (SPR) assay. The effect on the secretion of pro-inflammatory factors by the spleen cells in collagen induced rheumatoid arthritis (CIA) mouse was also investigated. Two N-glycosylated CII peptides were identified to have strong binding to the human recombinant DR4 protein and weak proinflammatory effect. These glycopeptides could be developed as therapeutic saccharide vaccines for the treatment of rheumatoid arthritis (RA).
- Rheumatoid arthritis,
- Type Ⅱ collegan,
- Glycosylation,
- N-Glycosylated altered peptides,
- Saccharide vaccines
1. [1]
  J.K. Pedersen, N.K. Kjær, A.J. Svendsen, K. Hørslev-Petersen, Rheumatol. Int. 29 (2009) 411–415. doi: 10.1007/s00296-008-0713-6
2. [2]
  Y.T. Wen, M. Zhang, Y.X. Yao, et al., Chin. Chem. Lett. 34 (2023) 107549. doi: 10.1016/j.cclet.2022.05.063
3. [3]
  D.E. Trentham, A.S. Townes, A.H. Kang, J. Exp. Med. 146 (1977) 857–868. doi: 10.1084/jem.146.3.857
4. [4]
  A. VanderBorght, P. Geusens, J. Raus, P. Stinissen, Semin. Arthritis. Rheum. 1 (2001) 160–175.
5. [5]
  M. Cornelia, M.D. Weyand, C. Kevin, et al., Ann. Intern. Med. 117 (1992) 801–806. doi: 10.7326/0003-4819-117-10-801
6. [6]
  E.F. Rosloniec, K.B. Whittington, D.D. Brand, L.K. Myers, J.M. Stuart, Cell. Immunol. 172 (1996) 21–28. doi: 10.1006/cimm.1996.0210
7. [7]
  E. Michaёlsson, J. Broddefalk, A. Engstrom, J. Kihlberg, R. Holmdahl, Eur. J. Immunol. 26 (1996) 1906–1910. doi: 10.1002/eji.1830260835
8. [8]
  B. Dzhambazov, K. Nandakumar, J. Kihlberg, et al., J. Immunol. 176 (2006) 1525–1533. doi: 10.4049/jimmunol.176.3.1525
9. [9]
  R.G. Spiro, J. Biol. Chem. 242 (1967) 4813–4823. doi: 10.1016/S0021-9258(18)99529-3
10. [10]
  R. Li, X. Li, Z.G. Li, Clin. Immunol. 118 (2006) 317–323. doi: 10.1016/j.clim.2005.09.020
11. [11]
  Y.J. Cheng, Q. Zhou, Z.G. Li, Scand. J. Immunol. 61 (2005) 260–265. doi: 10.1111/j.1365-3083.2005.01553.x
12. [12]
  C. Lindgren, M. Tyagi, J. Viljanen, et al., J. Med. Chem. 61 (2018) 4774–4790. doi: 10.1021/acs.jmedchem.7b01880
13. [13]
  E. Wakamatsu, I. Matsumoto, Y. Yoshiga, et al., Mod. Rheumatol. 19 (2009) 366–371. doi: 10.3109/s10165-009-0174-0
14. [14]
  B. Holm, J. Bäcklund, M.A.F. Recio, R. Holmdahl, J. Kihlberg, ChemBioChem 3 (2002) 1209–1222. doi: 10.1002/1439-7633(20021202)3:12<1209::AID-CBIC1209>3.0.CO;2-0
15. [15]
  B. Holm, S.M. Baquer, L. Holm, R. Holmdahl, J. Kihlberg, Bioorg. Med. Chem. 11 (2003) 3981–3987. doi: 10.1016/S0968-0896(03)00407-3
16. [16]
  E. Michaёlsson, M. Andersson, A. Engström, R. Holmdahl, Eur. J. Immunol. 22 (1992) 1819–1825. doi: 10.1002/eji.1830220722
17. [17]
  R.M. Williams, M.N. Im, J. Am. Chem. Soc. 113 (1991) 9276–9286. doi: 10.1021/ja00024a038
18. [18]
  U. Schöllkopf, U. Groth, C. Deng, Angew. Chem. 93 (1981) 793–795. doi: 10.1002/ange.19810930915
19. [19]
  L. Guo, T.B. Liu, K. Chen, et al., Org. Biomol. Chem. 12 (2014) 7310–7317. doi: 10.1039/C4OB01220H
20. [20]
  U.M. Abdel-Motal, L. Berg, A. Rosén, et al., Eur. J. Immunol. 26 (1996) 544–551. doi: 10.1002/eji.1830260307
21. [21]
  E.F. Rosloniec, K.B. Whittington, D.D. Brand, L.K. Myers, J.M. Stuart, Cell. Immunol. 172 (1996) 21–28. doi: 10.1006/cimm.1996.0210
22. [22]
  M. Johannes, M.A. Brimble, J. Org. Chem. 78 (2013) 12809–12813. doi: 10.1021/jo402220s
23. [23]
  E. Durantie, C. Bucher, R. Gilmour, Chem. Eur. J. 18 (2012) 8208–8215. doi: 10.1002/chem.201200468
24. [24]
  J. Wang, W.J. Qi, G.S. Chen, Chin. Chem. Lett. 30 (2019) 587–591. doi: 10.1016/j.cclet.2018.12.014
25. [25]
  J. Marin, M.A. Blaton, J.P. Briand, et al., ChemBioChem 6 (2005) 1796–1804. doi: 10.1002/cbic.200500075
26. [26]
  J. Ameijde, H.B. Albada, R.M.J. Liskamp, J. Chem. Soc. Perkin Trans. 1 (2002) 1042–1049.
27. [27]
  J. Bäcklund, S. Carlsen, T. Höger, et al., Proc. Natl. Acad. Sci. U. S. A. 99 (2002) 9960–9965. doi: 10.1073/pnas.132254199
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