Citation: Yanye Fan, Jingjing Chen, Bichun Chen, Jinyu Bai, Bowen Yang, Feng Liang, Lijing Fang. Design, synthesis and biological evaluation of Leu₁₀-teixobactin analogues[J]. Chinese Chemical Letters, ;2025, 36(4): 110075. doi: 10.1016/j.cclet.2024.110075 shu

Design, synthesis and biological evaluation of Leu₁₀-teixobactin analogues

Yanye Fan ^{a, b} ,
Jingjing Chen ^{b, e} ,
Bichun Chen ^b ,
Jinyu Bai ^b ,
Bowen Yang ^b ,
Feng Liang ^{a, *,} ,
Lijing Fang ^{b, c, d, *,}

a.
The State Key Laboratory of Refractories and Metallurgy, School of Chemistry and Chemical Engineering, Wuhan University of Science and Technology, Wuhan 430081, China
b.
Guangdong Key Laboratory of Nanomedicine, CAS-HK Joint Lab of Biomaterials, ACS Key Laboratory of Biomedical Imaging Science and System, Institute of Biomedicine and Biotechnology, Shenzhen Institute of Advanced Technology (SIAT), Chinese Academy of Sciences, Shenzhen 518055, China
c.
University of Chinese Academy of Sciences, Beijing 100049, China
d.
Sino-Euro Center of Biomedicine and Health, Shenzhen 518024, China
e.
School of Pharmacy, Lanzhou University, Lanzhou 730000, China

lj.fang@siat.ac.cn

feng_liang@whu.edu.cn

Received Date: 19 March 2024
Revised Date: 16 May 2024
Accepted Date: 30 May 2024
Available Online: 31 May 2024

Figures(3)

Two thioamino acids and four fluorinated amino acids were employed to substitute either partially or entirely the Ile₂, Ser₃, Ile₆, and Ser₇ residues of Leu₁₀-teixobactin to prepare ten analogues and the bioactivity of them was investigated. The SAR studies revealed that Ile₆ was tolerable for both thioamidation and fluoridation, while Ser₇ was identified as the most tolerable site for thioamidation. Analogue 1a demonstrated comparable or slightly improved antibacterial activity, superior protease stability compared to Leu₁₀-teixobactin, while not exhibiting obvious cytotoxicity against mammalian cells.
- Leu₁₀-teixobactin,
- Thioamidation,
- Fluorination,
- Antibacterial activity,
- Protease stability
1. [1]
  L.L. Ling, T. Schneider, A.J. Peoples, et al., Nature 517 (2015) 455–459. doi: 10.1038/nature14098
2. [2]
  R. Shukla, F. Lavore, S. Maity, et al., Nature 608 (2022) 390–396. doi: 10.1038/s41586-022-05019-y
3. [3]
  K. Jin, I.H. Sam, K.H.L. Po, et al., Nat. Commun. 7 (2016) 12394–12399. doi: 10.1038/ncomms12394
4. [4]
  Y. Zong, F. Fang, K.J. Meyer, et al., Nat. Commun. 10 (2019) 3268–3278. doi: 10.1038/s41467-019-11211-y
5. [5]
  E. Matheson, K. Jin, X. Li, Chin. Chem. Lett. 30 (2019) 1468–1480. doi: 10.1016/j.cclet.2019.07.004
6. [6]
  J.A. Karas, F. Chen, E.K. Schneider-Futschik, et al., Ann. N. Y. Acad. Sci. 1459 (2020) 86–105. doi: 10.1111/nyas.14282
7. [7]
  A. Parmar, A. Iyer, S.H. Prior, et al., Chem. Sci. 8 (2017) 8183–8192. doi: 10.1039/C7SC03241B
8. [8]
  K. Jin, K.H.L. Po, S. Wang, et al., Bioorg. Med. Chem. 26 (2018) 1062–1068. doi: 10.1016/j.bmc.2018.01.016
9. [9]
  C.R. Jones, G. Guaglianone, G.H. Lai, et al., Chem. Sci. 13 (2022) 13110–13116. doi: 10.1039/d2sc02670h
10. [10]
  A. Rozek, J.P.S. Powers, C.L. Friedrich, et al., Biochemistry 42 (2003) 14130–14138. doi: 10.1021/bi035643g
11. [11]
  B. Khatri, S. Raghunathan, S. Chakraborti, et al., Angew. Chem. Int. Ed. 60 (2021) 24870–24874. doi: 10.1002/anie.202110978
12. [12]
  X. Chen, E.G. Mietlicki-Baase, T.M. Barrett, et al., J. Am. Chem. Soc. 139 (2017) 16688–16695. doi: 10.1021/jacs.7b08417
13. [13]
  T. Velkov, J.D. Swarbrick, M.H. Hussein, et al., J. Pept. Sci. 25 (2019) e3206. doi: 10.1002/psc.3206
14. [14]
  W. Zhang, J. Li, L.W. Liu, et al., Peptides 31 (2010) 1832–1838. doi: 10.1016/j.peptides.2010.06.019
15. [15]
  R. Gibadullin, R.K. Morris, J. Niu, et al., J. Am. Chem. Soc. 145 (2023) 25559–25569. doi: 10.1021/jacs.3c05300
16. [16]
  P. Ghosh, N. Raj, H. Verma, et al., Nat. Commun. 14 (2023) 6050–6063. doi: 10.1038/s41467-023-41748-y
17. [17]
  K. Müller, C. Faeh, F. Diederich, Science 317 (2007) 1881–1886. doi: 10.1126/science.1131943
18. [18]
  J. Lv, Y. Cheng, Chem. Soc. Rev. 50 (2021) 5435–5467. doi: 10.1039/d0cs00258e
19. [19]
  N. Sheikhi, M. Bahraminejad, M. Saeedi, et al., Eur. J. Med. Chem. 260 (2023) 115758–115777. doi: 10.1016/j.ejmech.2023.115758
20. [20]
  C.J. White, A.K. Yudin, Nat. Chem. 3 (2011) 509–524. doi: 10.1038/nchem.1062
21. [21]
  B. Khatri, P. Bhat, J. Chatterjee, J. Pept. Sci. 26 (2020) e3248. doi: 10.1002/psc.3248
22. [22]
  Y.E. Jad, G.A. Acosta, T. Naicker, et al., Org. Lett. 17 (2015) 6182–6185. doi: 10.1021/acs.orglett.5b03176
23. [23]
  L. Mouls, G. Subra, C. Enjalbal, et al., Tetrahedron Lett. 45 (2004) 1173–1178. doi: 10.1016/j.tetlet.2003.12.008
24. [24]
  Y. Zong, X. Sun, H. Gao, et al., J. Med. Chem. 61 (2018) 3409–3421. doi: 10.1021/acs.jmedchem.7b01241
25. [25]
  H. Yang, M. Wierzbicki, D.R.D. Bois, et al., J. Am. Chem. Soc. 140 (2018) 14028–14032. doi: 10.1021/jacs.8b07709
26. [26]
  A. Parmar, A. Iyer, C.S. Vincent, et al., Chem. Commun. 52 (2016) 6060–6063. doi: 10.1039/C5CC10249A
27. [27]
  S.A.H.A. Monaim, E.J. Ramchuran, A. El-Faham, et al., J. Med. Chem. 60 (2017) 7476–7482. doi: 10.1021/acs.jmedchem.7b00834
28. [28]
  H. Yang, K.H. Chen, J.S. Nowick, ACS Chem. Biol. 11 (2016) 1823–1826. doi: 10.1021/acschembio.6b00295
29. [29]
  M.J. Martín, R. Rodríguez-Acebes, Y. García-Ramos, et al., J. Am. Chem. Soc. 136 (2014) 6754–6762. doi: 10.1021/ja502744a
30. [30]
  M. Pelay-Gimeno, Y. García-Ramos, M.J. Martin, et al., Nat. Commun. 4 (2013) 2352–2361. doi: 10.1038/ncomms3352
31. [31]
  Y. Zheng, Y. Cong, E.W. Schmidt, et al., Acc. Chem. Res. 55 (2022) 1313–1323. doi: 10.1021/acs.accounts.2c00108
32. [32]
  P.C. Wen, J.M. Vanegas, S.B. Rempe, et al., Chem. Sci. 9 (2018) 6997–7008. doi: 10.1039/c8sc02616e
33. [33]
  R. Shukla, J. Medeiros-Silva, A. Parmar, et al., Nat. Commun. 11 (2020) 2848–2857. doi: 10.1038/s41467-020-16600-2
34. [34]
  F.F. Arhin, I. Sarmiento, A. Belley, et al., Int. J. Antimicrob. Agents 52 (2008) 1597–1603. doi: 10.1128/AAC.01513-07
35. [35]
  M. Salwiczek, E.K. Nyakatura, U.I.M. Gerling, et al., Chem. Soc. Rev. 41 (2012) 2135–2171.
36. [36]
  K. Jin, K.H.L. Po, S. Wang, et al., Bioorg. Med. Chem. 25 (2017) 4990–4995. doi: 10.1016/j.bmc.2017.04.039
37. [37]
  H.E. Elashal, M. Raj, Chem. Commun. 52 (2016) 6304–6307.
38. [38]
  Y. Seki, K. Tanabe, D. Sasaki, et al., Angew. Chem. Int. Ed. 53 (2014) 6501–6505. doi: 10.1002/anie.201402618
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Design, synthesis and biological evaluation of Leu10-teixobactin analogues

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通讯作者: 陈斌, bchen63@163.com

Design, synthesis and biological evaluation of Leu₁₀-teixobactin analogues