Citation: Qingyu Huan, Tao Lin, Yong-Hong Fu, Jun-Li Hou. Vesicle fusion induced by zwitterionic amphiphilic channels[J]. Chinese Chemical Letters, ;2024, 35(1): 108566. doi: 10.1016/j.cclet.2023.108566 shu

Vesicle fusion induced by zwitterionic amphiphilic channels

Department of Chemistry, Fudan University, Shanghai 200433, China

^☆

houjl@fudan.edu.cn

Received Date: 10 February 2023
Revised Date: 7 May 2023
Accepted Date: 10 May 2023
Available Online: 12 May 2023

Figures(4)

A new strategy to induce vesicle fusion has been developed by employing pillar[5]arene derivatives that were channel-like and were prepared by appending side chains onto pillar[5]arenes backbones. The channels feature with hydrophilic negatively and positively charged groups at both ends and hydrophobic Trp residues at the outer surface, which endows the channels with amphiphilicity. The zwitterionic amphiphilic channels could spontaneously incorporate into the bilayer membranes of lipid vesicles to induce vesicle fusion driven by the electrostatic interactions between negatively charged and positively charged groups.
- Vesicle fusion,
- Pillar[5]arene,
- Electrostatic interaction,
- Lipid bilayers
1. [1]
  R. Blumenthal, M.J. Clague, S.R. Durell, Chem. Rev. 103 (2003) 53–70. doi: 10.1021/cr000036+
2. [2]
  L.V. Chernomordik, J. Zimmerberg, Curr. Opin. Struct. Biol. 5 (1995) 541–547. doi: 10.1016/0959-440X(95)80041-7
3. [3]
  L.V. Chernomordik, M.M. Kozlov, Cell 123 (2005) 375–382. doi: 10.1016/j.cell.2005.10.015
4. [4]
  D. Fasshauer, Biochim. Biophys. Acta Mol. Cell Res. 1641 (2003) 87–97. doi: 10.1016/S0167-4889(03)00090-9
5. [5]
  W. Hong, Biochim. Biophys. Acta Mol. Cell Res. 1744 (2005) 120–144. doi: 10.1016/j.bbamcr.2005.03.014
6. [6]
  V. Rossi, D.K. Banfield, M. Vacca, et al., Trends Biochem. Sci. 29 (2004) 682–688. doi: 10.1016/j.tibs.2004.10.002
7. [7]
  A.T. Brunger, Q. Rev. Biophys. 38 (2005) 1–47.
8. [8]
  J. Rizo, T.C. Südhof, Nat. Struct. Biol. 5 (1998) 839–842. doi: 10.1038/2280
9. [9]
  B. Gong, B.K. Choi, J.Y. Kim, et al., J. Am. Chem. Soc. 137 (2015) 8908–8911. doi: 10.1021/jacs.5b05385
10. [10]
  L.V. Chernomordik, M.M. Kozlov, Annu. Rev. Biochem. 72 (2003) 175–207. doi: 10.1146/annurev.biochem.72.121801.161504
11. [11]
  D.L. Perrier, L. Rems, P.E. Boukany, Adv. Colloid Interface Sci. 249 (2017) 248–271. doi: 10.1016/j.cis.2017.04.016
12. [12]
  J. Xu, W. Cao, P. Wang, H. Liu, Pharmaceuticals 15 (2022) 876. doi: 10.3390/ph15070876
13. [13]
  B.P. Jena, J. Cell. Mol. Med. 8 (2004) 1–21. doi: 10.1111/j.1582-4934.2004.tb00255.x
14. [14]
  X. Shi, Q. Cheng, Y. Zhang, Methods 177 (2020) 95–102. doi: 10.1016/j.ymeth.2019.09.017
15. [15]
  M.N. Jones, Curr. Opin. Colloid Interface Sci. 1 (1996) 91–100. doi: 10.2307/1163382
16. [16]
  A.J.M. Driessen, H.W. van den Hooven, W. Kuiper, et al., Biochemistry 34 (1995) 1606–1614. doi: 10.1021/bi00005a017
17. [17]
  J. Wilschut, N. Duzgunes, D. Papahadjopoulos, et al., Biochemistry 19 (1980) 6011–6021. doi: 10.1021/bi00567a011
18. [18]
  J.A. Peruzzi, M.L. Jacobs, T.Q. Vu, et al., Angew. Chem. Int. Ed. 58 (2019) 18683–18690. doi: 10.1002/anie.201911544
19. [19]
  S.C. Hsu, C.D. Hazuka, R.H. Scheller, et al., Trends Cell Biol. 9 (1999) 150–153. doi: 10.1016/S0962-8924(99)01516-0
20. [20]
  G.R. Prescott, O.A. Gorleku, L.H. Chamberlain, et al., J. Neurochem. 110 (2009) 1135–1149. doi: 10.1111/j.1471-4159.2009.06205.x
21. [21]
  J. Khadake, B. Meldal, S. Panni, et al., Nat. Commun. 10 (2019) 10. doi: 10.1038/s41467-018-07709-6
22. [22]
  C.K. Haluska, K.A. Riske, V. Marchi-Artzner, et al., Proc. Natl. Acad. Sci. U.S.A. 103 (2006) 15841–15846. doi: 10.1073/pnas.0602766103
23. [23]
  M.R. Cheetham, J.P. Bramble, D.G.G. McMillan, et al., J. Am. Chem. Soc. 133 (2011) 6521–6524. doi: 10.1021/ja2007615
24. [24]
  Y. Suzuki, K.H. Nagai, T. Hamada, et al., Langmuir 33 (2017) 2671–2676. doi: 10.1021/acs.langmuir.7b00448
25. [25]
  R.B. Lira, T. Robinson, K.A. Riske, et al., Biophys. J. 116 (2019) 79–91. doi: 10.1016/j.bpj.2018.11.3128
26. [26]
  J. Voskuhl, B.J. Ravoo, Chem. Soc. Rev. 38 (2009) 495–505. doi: 10.1039/B803782P
27. [27]
  T. Ogoshi, T.A. Yamagishi, Y. Nakamoto, Chem. Rev. 116 (2016) 7937–8002. doi: 10.1021/acs.chemrev.5b00765
28. [28]
  B. Hua, L. Shao, F. Huang, et al., Acc. Chem. Res. 55 (2022) 1025–1034. doi: 10.1021/acs.accounts.2c00011
29. [29]
  D. Xia, P. Wang, F. Huang, et al., Chem. Rev. 120 (2020) 6070–6123. doi: 10.1021/acs.chemrev.9b00839
30. [30]
  Z. Li, Y.W. Yang, Acc. Chem. Res. 2 (2021) 292–305. doi: 10.1021/accountsmr.1c00042
31. [31]
  H. Zheng, L. Fu, L. Wang, et al., Nat. Commun. 14 (2023) 590. doi: 10.54254/2754-1169/3/2022839
32. [32]
  X. Liang, Y. Shen, C. Yang, et al., Chem. Commun. 58 (2022) 13584–13587. doi: 10.1039/d2cc05690a
33. [33]
  X.Q. Wang, W.J. Li, H.B. Yang, et al., J. Am. Chem. Soc. 141 (2019) 13923–13930. doi: 10.1021/jacs.9b06739
34. [34]
  J.R. Wu, G. Wu, Y.W. Yang, et al., Angew. Chem. Int. Ed. 62 (2023) e202218142. doi: 10.1002/anie.202218142
35. [35]
  B. Jiang, W. Wang, H.B. Yang, et al., Angew. Chem. Int. Ed. 56 (2017) 14438–14442. doi: 10.1002/anie.201707209
36. [36]
  T. Ogoshi, S. Kanai, S. Fujinami, et al., J. Am. Chem. Soc. 130 (2008) 5022–5023. doi: 10.1021/ja711260m
37. [37]
  X.Y. Yu, Y. Chen, Chin. Chem. Lett. 34 (2023) 107739. doi: 10.1016/j.cclet.2022.08.019
38. [38]
  X.N. Han, Q.S. Zong, C.F. Chen, et al., CCS Chem. 4 (2021) 318–330. doi: 10.1038/s42255-021-00356-0
39. [39]
  X. Shu, W. Chen, C. Li, et al., Chem. Commun. 50 (2014) 4820–4823. doi: 10.1039/C4CC00800F
40. [40]
  Z. Liu, F. Demontrond, A. Imberty, et al., Chin. Chem. Lett. 34 (2023) 107872. doi: 10.1016/j.cclet.2022.107872
41. [41]
  Q. Wang, J. Fan, X. Bian, et al., Chin. Chem. Lett. 33 (2022) 1979–1982. doi: 10.1016/j.cclet.2021.10.040
42. [42]
  S. Liu, T. Yan, Q. Wu, et al., Chin. Chem. Lett. 33 (2022) 239–242. doi: 10.3390/land11020239
43. [43]
  Y. Chen, B. Sun, L. Wang, et al., Org. Lett. 23 (2021) 7423–7427. doi: 10.1021/acs.orglett.1c02620
44. [44]
  Y. Zhou, H. Tang, D. Cao, et al., Chem. Commun. 57 (2021) 13114–13117. doi: 10.1039/d1cc05153a
45. [45]
  X. Ji, F. Wang, F. Huang, et al., Chin. J. Chem. 38 (2020) 1473–1479. doi: 10.1002/cjoc.202000314
46. [46]
  S. Fa, T. Kakuta, T.A. Yamagishi, T. Ogoshi, CCS Chem. 1 (2019) 50–63. doi: 10.31635/ccschem.019.20180014
47. [47]
  S. Lan, L. Ling, D. Ma, ACS Appl. Mater. Interfaces 14 (2022) 4197–4203. doi: 10.1021/acsami.1c21575
48. [48]
  M. Cheng, W. Gong, H. Li, et al., Chin. J. Chem. 40 (2022) 925–930. doi: 10.1002/cjoc.202100714
49. [49]
  J. Liu, X.W. Sun, Q. Lin, et al., Chin. J. Chem. 39 (2021) 3421–3428. doi: 10.1002/cjoc.202100583
50. [50]
  J.R. Wu, Y.W. Yang, CCS Chem. 3 (2020) 836–843.
51. [51]
  J. Wang, M. Cen, Y. Yao, et al., Chin. Chem. Lett. 33 (2022) 1475–1478. doi: 10.3390/sym14071475
52. [52]
  Y. Zhang, J. Chen, Q. Meng, et al., Chin. Chem. Lett. 34 (2023) 107697. doi: 10.1016/j.cclet.2022.07.040
53. [53]
  T. Ogoshi, K. Kitajima, Y. Nakamoto, et al., Org. Lett. 12 (2010) 636–638. doi: 10.1021/ol902877w
54. [54]
  T. Ogoshi, M. Hashizume, Y. Nakamoto, et al., Chem. Commun. 46 (2010) 3708–3710. doi: 10.1039/c0cc00348d
55. [55]
  K. Kato, S. Fa, T. Ogoshi, et al., Chem. Soc. Rev. 51 (2022) 3648–3687. doi: 10.1039/d2cs00169a
56. [56]
  S. Ohtani, K. Kato, T. Ogoshi, et al., Coord. Chem. Rev. 462 (2022) 214503. doi: 10.1016/j.ccr.2022.214503
57. [57]
  Y.W. Li, Y.H. Fu, J.L. Hou, Chin. J. Chem. 40 (2022) 1293–1297. doi: 10.1002/cjoc.202100836
58. [58]
  W. Si, Z.T. Li, J.L. Hou, et al., Acc. Chem. Res. 48 (2015) 1612–1619. doi: 10.1021/acs.accounts.5b00143
59. [59]
  J.Y. Chen, Z.T. Li, J.L. Hou, et al., Faraday Discuss. 209 (2018) 149–159. doi: 10.1039/C8FD00009C
60. [60]
  W. Si, Z.T. Li, J.L. Hou, et al., Angew. Chem. Int. Ed. 50 (2011) 12564–12568. doi: 10.1002/anie.201106857
61. [61]
  Z.J. Yan, D. Wang, J.L. Hou, et al., J. Am. Chem. Soc. 142 (2020) 15638–15643. doi: 10.1021/jacs.0c00601
62. [62]
  Z.J. Yan, Y. Zhang, J.L. Hou, et al., J. Am. Chem. Soc. 143 (2021) 11332–11336. doi: 10.1021/jacs.1c06000
63. [63]
  V. Fonseca, P. Daumas, L.O.S. Andersen, et al., Biochemistry 31 (1992) 5340–5350. doi: 10.1021/bi00138a014
64. [64]
  S.A. Seoh, D. Busath, Biophys. J. 68 (1995) 2271–2279. doi: 10.1016/S0006-3495(95)80409-1
65. [65]
  Q. Xiao, W.W. Haoyang, J.L. Hou, et al., Chem. Commun. 57 (2021) 863–866. doi: 10.1039/d0cc06974d
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