Citation: Guangzhong Yin, Jingjing Wei, Yu Shao, Wen-Hao Wu, Lianjie Xu, Wen-Bin Zhang. Native conjugation between proteins and [60]fullerene derivatives using SpyTag as a reactive handle[J]. Chinese Chemical Letters, ;2021, 32(1): 353-356. doi: 10.1016/j.cclet.2020.04.034 shu

Native conjugation between proteins and [60]fullerene derivatives using SpyTag as a reactive handle

Guangzhong Yin ^{a, b, 1} ,
Jingjing Wei ^{a, b, 1} ,
Yu Shao ^a ,
Wen-Hao Wu ^a ,
Lianjie Xu ^a ,
Wen-Bin Zhang ^{a, *,}

a.
Beijing National Laboratory for Molecular Sciences, Key Laboratory of Polymer Chemistry and Physics of the Ministry of Education, College of Chemistry and Molecular Engineering, Center for Soft Matter Science and Engineering, Peking University, Beijing 100871, China
b.
College of Chemical and Environmental Engineering, Anyang Institute of Technology, Anyang 455000, China

wenbin@pku.edu.cn

Received Date: 12 March 2020
Revised Date: 9 April 2020
Accepted Date: 21 April 2020
Available Online: 26 April 2020

Figures(3)

Herein, we report the facile conjugation between proteins and water-soluble [60]fullerene derivatives (DC₆₀) under native conditions using SpyTag as a reactive handle. Water-soluble [60]fullerene derivatives were first prepared via sequential Bingel-Hirsch reaction and pclickedq with SpyTag to give DC₆₀-SpyTag for native conjugation with proteins by the highly efficient SpyTag-SpyCatcher chemistry. The bioconjugation was confirmed by MALDI-TOF MS spectra and SDS-PAGE analysis. The TEM and UV-vis spectroscopic study further revealed that the DC₆₀ could alter the optical performance and induce aggregation of the target proteins. It thus provides a general and robust method for modifying proteins with C₆₀ derivatives and could potentially be adapted for native conjugation between proteins and other nonbiological motifs as well.
- SpyTag,
- SpyCatcher,
- Fullerene,
- Protein,
- Bioconjugate
1. [1]
  S. Massa, N. Devoogdt, Bioconjugation:Methods and Protocols, Humana Press, New York, 2019.
2. [2]
  M.M. Zegota, T. Wang, C. Seidler, et al., Bioconjugate Chem. 29 (2018) 2665-2670. doi: 10.1021/acs.bioconjchem.8b00358
3. [3]
  A.H. St. Amant, D. Lemen, S. Florinas, et al., Bioconjugate Chem. 29 (2018) 2406-2414. doi: 10.1021/acs.bioconjchem.8b00320
4. [4]
  J. Morgenstern, G. Gil Alvaradejo, N. Bluthardt, et al., Biomacromolecules 19 (2018) 4250-4262. doi: 10.1021/acs.biomac.8b01020
5. [5]
  S. Carmali, H. Murata, K. Matyjaszewski, A.J. Russell, Biomacromolecules 19 (2018) 4044-4051. doi: 10.1021/acs.biomac.8b01064
6. [6]
  L. Reguera, Y. Méndez, A.R. Humpierre, O. Valdés, D.G. Rivera, Acc. Chem. Res. 51 (2018) 1475-1486. doi: 10.1021/acs.accounts.8b00126
7. [7]
  D. Terada, S. Sotoma, Y. Harada, R. Igarashi, M. Shirakawa, Bioconjugate Chem. 29 (2018) 2786-2792. doi: 10.1021/acs.bioconjchem.8b00412
8. [8]
  Y. Hu, Y. Hou, H. Wang, H. Lu, Bioconjugate Chem. 29 (2018) 2232-2238. doi: 10.1021/acs.bioconjchem.8b00237
9. [9]
  A.M. Wawro, Y. Aoki, T. Muraoka, K. Tsumoto, K. Kinbara, Chem. Commun. 54 (2018) 1913-1916. doi: 10.1039/C7CC05814D
10. [10]
  M.M. Lino, S. Simoes, S. Pinho, L. Ferreira, Nanoscale 9 (2017) 18668-18680. doi: 10.1039/C7NR02414B
11. [11]
  T. Wu, H. Huang, Y. Sheng, et al., J. Mater. Chem. B 6 (2018) 1011-1017. doi: 10.1039/C7TB03132G
12. [12]
  D. Sabatino, S. Shah, C.N. Cultrara, et al., Bioconjugate Chem. 29 (2018) 3638-3648. doi: 10.1021/acs.bioconjchem.8b00580
13. [13]
  K. Renault, J.W. Fredy, P.Y. Renard, C. Sabot, Bioconjugate Chem. 29 (2018) 2497-2513. doi: 10.1021/acs.bioconjchem.8b00252
14. [14]
  J.C. Grim, T.E. Brown, B.A. Aguado, et al., ACS Cent. Sci. 4 (2018) 909-916. doi: 10.1021/acscentsci.8b00325
15. [15]
  E. Montanari, A. Gennari, M. Pelliccia, et al., Bioconjugate Chem. 29 (2018) 2550-2560. doi: 10.1021/acs.bioconjchem.8b00227
16. [16]
  S. Schoffelen, J. Beekwilder, M.F. Debets, D. Bosch, J.C. M. van Hest, Bioconjugate Chem. 24 (2013) 987-996. doi: 10.1021/bc400021j
17. [17]
  W.B. Zhang, X.L. Wu, G.Z. Yin, Y. Shao, S.Z. D. Cheng, Mater. Horiz. 4 (2017) 117-132. doi: 10.1039/C6MH00448B
18. [18]
  E. Saxon, C.R. Bertozzi, Science 287 (2000) 2007-2010. doi: 10.1126/science.287.5460.2007
19. [19]
  B. Zakeri, J.O. Fierer, E. Celik, et al., Proc. Natl. Acad. Sci. U.S. A. 109 (2012) E690-E697. doi: 10.1073/pnas.1115485109
20. [20]
  F. Sun, W.B. Zhang, Chin. Chem. Lett. 28 (2017) 2078-2084. doi: 10.1016/j.cclet.2017.08.052
21. [21]
  F. Zhang, W.B. Zhang, Chin. J. Chem. 38 (2020) 864-878. doi: 10.1002/cjoc.202000083
22. [22]
  F. Sun, W.B. Zhang, Chin. J. Chem. 38 (2020) 894-896. doi: 10.1002/cjoc.202000101
23. [23]
  D. Liu, W.H. Wu, Y.J. Liu, et al., ACS Cent. Sci. 3 (2017) 473-481. doi: 10.1021/acscentsci.7b00104
24. [24]
  X.W. Wang, W.B. Zhang, Trends Biochem. Sci. 43 (2018) 806-817. doi: 10.1016/j.tibs.2018.07.001
25. [25]
  T.U. J. Bruun, A.M. C. Andersson, S.J. Draper, M. Howarth, ACS Nano 12 (2018) 8855-8866. doi: 10.1021/acsnano.8b02805
26. [26]
  L. Yin, X. Guo, L. Liu, Y. Zhang, Y. Feng, ACS Biomater. Sci. Eng. 4 (2018) 2095-2099. doi: 10.1021/acsbiomaterials.8b00279
27. [27]
  R. Wieduwild, M. Howarth, Biomaterials 180 (2018) 253-264. doi: 10.1016/j.biomaterials.2018.07.020
28. [28]
  W.B. Zhang, Y. Tu, R. Ranjan, et al., Macromolecules 41 (2008) 515-517. doi: 10.1021/ma702345r
29. [29]
  V.M. Torres, M. Posa, B. Srdjenovic, A.L. Simplício, Colloid Surf. B 82 (2011) 46-53. doi: 10.1016/j.colsurfb.2010.08.012
30. [30]
  R. Injac, M. Perse, M. Cerne, et al., Biomaterials 30 (2009) 1184-1196. doi: 10.1016/j.biomaterials.2008.10.060
31. [31]
  J.J. Yin, F. Lao, P.P. Fu, et al., Biomaterials 30 (2009) 611-621. doi: 10.1016/j.biomaterials.2008.09.061
32. [32]
  R. Injac, M. Prijatelj, B. Strukelj, Fullerenol nanoparticles: toxicity and antioxidant activity, in: D. Armstrong, D. Bharali (Eds. ), Oxidative Stress and Nanotechnology. Methods in Molecular Biology (Methods and Protocols), vol. 1028, Humana Press, Totowa, NJ, 2013, pp. 75-100.
33. [33]
  W.B. Zhang, F. Sun, D.A. Tirrell, F.H. Arnold, J. Am. Chem. Soc. 135 (2013) 13988-13997. doi: 10.1021/ja4076452
34. [34]
  X. Wu, W. Huang, W.H. Wu, et al., Nano Res. 11 (2018) 5556-5565. doi: 10.1007/s12274-017-1890-y
35. [35]
  J. Wei, W.H. Wu, R. Wang, et al., ACS Macro Lett. 7 (2018) 514-518. doi: 10.1021/acsmacrolett.8b00147
36. [36]
  A. Higashino, M. Mizuno, Y. Mizutani, J. Phys. Chem. B 120 (2016) 3353-3359.
37. [37]
  S. Zanzoni, A. Ceccon, M. Assfalg, et al., Nanoscale 7 (2015) 7197-7205. doi: 10.1039/C5NR00539F
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