Citation: Yuce Chen, Zhen Li, Yu Yin, Ping Yang, Yijin Kong, Zhong Li, Daijie Chen, Xiaoyong Xu. Identification of 2-aminothiazoyl piperidine derivatives as a new class of adjuvants potentiating the activity of colistin against Acinetobacter baumannii[J]. Chinese Chemical Letters, ;2023, 34(2): 107948. doi: 10.1016/j.cclet.2022.107948 shu

Identification of 2-aminothiazoyl piperidine derivatives as a new class of adjuvants potentiating the activity of colistin against Acinetobacter baumannii

Yuce Chen ^{a, 1} ,
Zhen Li ^{b, 1} ,
Yu Yin ^b ,
Ping Yang ^b ,
Yijin Kong ^a ,
Zhong Li ^{a, *,} ,
Daijie Chen ^{b, *,} ,
Xiaoyong Xu ^{a, *,}

a.
Shanghai Key Laboratory of Chemical Biology, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, China
b.
School of Pharmacy, Shanghai JiaoTong University, Shanghai 200240, China

lizhong@ecust.edu.cn

cdj@sjtu.edu.cn

xyxu@ecust.edu.cn

Received Date: 22 August 2022
Revised Date: 17 October 2022
Accepted Date: 23 October 2022
Available Online: 26 October 2022

Figures(8)

The rapid prevalence of antibiotic resistance has led to a significant global health problem. Although colistin is the last resort antibiotic, it is limited by dose dependent toxicity. A critical approach to solve this problem is to use an antibiotic adjuvant, which is able to potentiate the activity of antibiotic and reduce the dosage of antibiotic. Herein, we reported a novel 2-aminothiazoyl piperidine adjuvant, which enhanced the activity of colistin against Acinetobacter baumannii (A. baumannii). Two pilot libraries of 40 compounds were prepared and their adjuvant activities were evaluated. The most potential compound 11j enabled to cause16-fold reduction in the minimum inhibitory concentration (MIC) of colistin at 8 µg/mL. Besides, time-kill curves exhibited that compound 11j had significant adjuvant activity to kill the bacteria. The predicted ADMET analysis showed that 2-aminothiazoyl piperidine derivatives had good drug-likeness and acceptable physicochemical properties. Furthermore, membrane permeability experiments demonstrated that compound 11j was beneficial for colistin to destroy the outer membrane of bacteria. Also, the comparative molecular similarity indices analysis (CoMSIA) and the density functional theory (DFT) calculations were conducted. The results drawn from these analyses indicated that the novel scaffold provided helpful information for the finding of new adjuvant lead.
- 2-Aminothiazole piperidine,
- Antibiotic adjuvant,
- Acinetobacter baumannii,
- Colistin
1. [1]
  C. Greene, G. Vadlamudi, D. Newton, B. Foxman, C. Xi, Am. J. Infect. Control. 44 (2016) e65-e71. doi: 10.1016/j.ajic.2015.12.012
2. [2]
  T. Demirdal, U.S. Sari, S.A. Nemli, Ann. Clin. Microbiol. Antimicrob. 15 (2016) 11-17. doi: 10.1186/s12941-016-0123-7
3. [3]
  O. Ayobami, N. Willrich, T. Harder, et al. Emerg. Microbes Infect. 8 (2019) 1747-1759. doi: 10.1080/22221751.2019.1698273
4. [4]
  S. Domingues, N. Rosário, Â. Cândido, et al. Microorganisms 7 (2019) 30-37. doi: 10.3390/microorganisms7020030
5. [5]
  V. Manchanda, S. Sanchaita, N. Singh, J. Global Infect. Dis. 2 (2010) 291-304. doi: 10.4103/0974-777X.68538
6. [6]
  S. Siricilla, K. Mitachi, J. Yang, et al. J. Med. Chem. 60 (2017) 2869-2878. doi: 10.1021/acs.jmedchem.6b01805
7. [7]
  Global priority list of antibiotic-resistant bacteria to guide research, discovery and development of new antibiotics, WHO, 2017.
8. [8]
  J. Li, R.L. Nation, Clin. Infect. Dis. 43 (2006) 663-664. doi: 10.1086/506571
9. [9]
  T. Velkov, P.E. Thompson, R.L. Nation, J. Li, J. Med. Chem. 53 (2010) 1898-1916. doi: 10.1021/jm900999h
10. [10]
  H. Spapen, R. Jacobs, V.V. Gorp, J. Troubleyn, P.M. Honoré, Ann. Intensive Care 1 (2011) 14-21. doi: 10.1186/2110-5820-1-14
11. [11]
  J.D. Hartzell, R. Neff, J. Ake, et al. Clin. Infect. Dis. 48 (2009) 1724-1728. doi: 10.1086/599225
12. [12]
  C.J. Kubin, T.M. Ellman, V. Phadke, et al. J. Infect. 65 (2012) 80-87. doi: 10.1016/j.jinf.2012.01.015
13. [13]
  D.S. Akajagbor, S.L. Wilson, K.D. Shere-Wolfe, et al. Clin. Infect. Dis. 57 (2013) 1300-1303. doi: 10.1093/cid/cit453
14. [14]
  M.H. Rigatto, T.F. Behle, D.R. Falci, et al. J. Antimicrob. Chemother. 70 (2015) 1552-1557. doi: 10.1093/jac/dku561
15. [15]
  X.Y. Zheng, Q. Cao, Q. Cao, et al. Chin. Chem. Lett. 31 (2020) 413–417. doi: 10.1016/j.cclet.2019.07.063
16. [16]
  M. Tyers, G.D. Wright, Nat. Rev. Microbiol. 17 (2019) 141-155. doi: 10.1038/s41579-018-0141-x
17. [17]
  A.R. Brochado, A. Telzerow, J. Bobonis, et al. Nature 559 (2018) 259-263. doi: 10.1038/s41586-018-0278-9
18. [18]
  C. Liu, H. Shen, S. Wang, et al. Chin. Chem. Lett. 29 (2018) 1824–1828. doi: 10.1016/j.cclet.2018.10.025
19. [19]
  M.D. Mandler, V. Baidin, J. Lee, et al. J. Am. Chem. Soc. 140 (2018) 6749-6753. doi: 10.1021/jacs.8b02283
20. [20]
  C.R. MacNair, J.M. Stokes, L.A. Carfrae, et al. Nat. Commun. 9 (2018) 458. doi: 10.1038/s41467-018-02875-z
21. [21]
  S. French, M. Farha, M.J. Ellis, et al. ACS Infect. Dis. 6 (2020) 1405-1412. doi: 10.1021/acsinfecdis.9b00159
22. [22]
  M. Vaara, Molecules 24 (2019) 249-256. doi: 10.3390/molecules24020249
23. [23]
  B.M. Minrovic, D. Jung, R.J. Melander, C. Melander, ACS Infect. Dis. 4 (2018) 1368-1376. doi: 10.1021/acsinfecdis.8b00103
24. [24]
  J.M. Stokes, C.R. MacNair, B. Ilyas, et al. Nat. Microbiol. 2 (2017) 17028. doi: 10.1038/nmicrobiol.2017.28
25. [25]
  G.Q. Song, W.M. Wang, Z.S. Li, Y. Wang, J.G. Wang, Chin. Chem. Lett. 29 (2018) 899–902. doi: 10.1016/j.cclet.2017.09.035
26. [26]
  R. Wang, S. Hou, X. Dong, et al. MedChemComm 8 (2017), 2060-2066. doi: 10.1039/C7MD00354D
27. [27]
  P. Liu, H. Shen, X. Shao, Z. Li, X. Xu, Synlett 25 (2014) 2797-2801. doi: 10.1055/s-0034-1379100
28. [28]
  G.B. Elion, S. Singer, G.H. Hitchings, J. Biol. Chem. 208 (1954) 477-488. doi: 10.1016/S0021-9258(18)65573-5
29. [29]
  Y.L. Wang, F. Wang, X.X. Shi, et al. Brief Bioinform. 22 (2021) bbaa276. doi: 10.1093/bib/bbaa276
30. [30]
  F.F. Huang, H. Ling, J. Li, et al. Chin. Chem. Lett. 31 (2020) 141–144. doi: 10.1016/j.cclet.2019.03.054
31. [31]
  C.S. Yu, Q. Wang, J. Bajsa-Hirschel, et al. J. Agri. Food. Chem. 69 (2021) 6423–6430. doi: 10.1021/acs.jafc.0c07538
32. [32]
  J.M. Jin, J.F. Chen, H.F. Wang, P.J. Hua, Chin. Chem. Lett. 30 (2019) 618–623. doi: 10.4163/jnh.2019.52.6.618
33. [33]
  Z.H. Shen, Z.H. Sun, J.J. Becnel, et al. Lett. Drug Des. Discov. 15 (2018) 951–956. doi: 10.2174/1570180815666180102141640
34. [34]
  X.H. Liu, L. Pan, C.X. Tan, et al. Pestic. Biochem. Physiol. 101 (2011) 143–147. doi: 10.1016/j.pestbp.2011.08.006
1. [1]
  Liping Zhao , Xixi Guo , Zhimeng Zhang , Xi Lu , Qingxuan Zeng , Tianyun Fan , Xintong Zhang , Fenbei Chen , Mengyi Xu , Min Yuan , Zhenjun Li , Jiandong Jiang , Jing Pang , Xuefu You , Yanxiang Wang , Danqing Song . Novel berberine derivatives as adjuvants in the battle against Acinetobacter baumannii: A promising strategy for combating multi-drug resistance. Chinese Chemical Letters, 2024, 35(10): 109506-. doi: 10.1016/j.cclet.2024.109506
2. [2]
  Jie Wang , Jijie Zhang , Defang Ma , Zhenxiang Sun , Yan Wang , Qinyan Yue , Yanwei Li , Yue Gao , Baoyu Gao , Xing Xu . Simultaneous removal of tetracycline and antibiotic resistant bacteria/genes in UV-LED/H₂O₂ system: Competitive interactions and wavelength dependence. Chinese Chemical Letters, 2026, 37(2): 111209-. doi: 10.1016/j.cclet.2025.111209
3. [3]
  Meijuan Chen , Liyun Zhao , Xianjin Shi , Wei Wang , Yu Huang , Lijuan Fu , Lijun Ma . Synthesis of carbon quantum dots decorating Bi₂MoO₆ microspherical heterostructure and its efficient photocatalytic degradation of antibiotic norfloxacin. Chinese Chemical Letters, 2024, 35(8): 109336-. doi: 10.1016/j.cclet.2023.109336
4. [4]
  Le Han , Zhou Yuan , Bohan Li , Yuchi Zhang , Lin Yang , Yan Xu . Highly-stable cesium lead halide perovskite CsPbBr₃/CsPb₂Br₅ heteronanocrystals in zeolitic imidazolate framework-8 for antibiotic photodegradation. Chinese Chemical Letters, 2025, 36(6): 110349-. doi: 10.1016/j.cclet.2024.110349
5. [5]
  Hanyong Wang , Weijia Zhang , Chenlu Huang , Xinyu Yang , Qingyu Yu , Hai Wang , Wen Li , Linhua Zhang , Dunwan Zhu . Personalized tumor vaccines based on carrier-free double-adjuvant nanoparticles and tumor-associated antigens for enhancing immune responses. Chinese Chemical Letters, 2025, 36(7): 111092-. doi: 10.1016/j.cclet.2025.111092
6. [6]
  Yuxin Li , Chengbin Liu , Qiuju Li , Shun Mao . Fluorescence analysis of antibiotics and antibiotic-resistance genes in the environment: A mini review. Chinese Chemical Letters, 2024, 35(10): 109541-. doi: 10.1016/j.cclet.2024.109541
7. [7]
  Yun Bai , Shengnan Li , Shih-Hsin Ho . How do nanomaterials influence the spread of antibiotic resistance genes in aquatic environments?. Chinese Chemical Letters, 2026, 37(1): 111183-. doi: 10.1016/j.cclet.2025.111183
8. [8]
  Jingyi Yang , Sihan Wang , Xubiao Luo , Zhenyang Yu , Yanbo Zhou . Fenton-like process in antibiotic-containing wastewater treatment: Applications and toxicity evaluation. Chinese Chemical Letters, 2025, 36(12): 110996-. doi: 10.1016/j.cclet.2025.110996
9. [9]
  Wei Sun , Anjing Liao , Li Lei , Xu Tang , Ya Wang , Jian Wu . Research progress on piperidine-containing compounds as agrochemicals. Chinese Chemical Letters, 2025, 36(1): 109855-. doi: 10.1016/j.cclet.2024.109855
10. [10]
  Tiantian Man , Fulin Zhu , Yaqi Huang , Yuhao Piao , Yan Su , Shengyuan Deng , Ying Wan . Mobile mini-fluorimeter for antibiotic aptasensing based on surface-plasmonic effect of burlike nanogolds enhanced by digitized imaging diagnosis. Chinese Chemical Letters, 2024, 35(5): 109036-. doi: 10.1016/j.cclet.2023.109036
11. [11]
  Mimi Wu , Shoufeng Tang , Zhibin Wang , Qingrui Zhang , Deling Yuan . Molybdenum carbide activated calcium sulfite for antibiotic decontamination at near-neutral pH: Dissolved oxygen promoted bisulfite adsorption for singlet oxygen generation. Chinese Chemical Letters, 2025, 36(8): 110613-. doi: 10.1016/j.cclet.2024.110613
12. [12]
  Kun Zhang , Li-Min Zhao , Tianhao Xing , Yueyue Bu , Qingyun Wang , Christophe Pannecouque , Erik De Clercq , Angela Corona , Laura Dettori , Enzo Tramontano , Shuai Wang , Fen-Er Chen . Rational structure-based design and optimization of next-generation biphenyl-piperidine-triazine derivatives as potent non-nucleoside reverse transcriptase inhibitors. Chinese Chemical Letters, 2026, 37(1): 111283-. doi: 10.1016/j.cclet.2025.111283
13. [13]
  Haojie Duan , Hejingying Niu , Lina Gan , Xiaodi Duan , Shuo Shi , Li Li . Reinterpret the heterogeneous reaction of α-Fe₂O₃ and NO₂ with 2D-COS: The role of SDS, UV and SO₂. Chinese Chemical Letters, 2024, 35(6): 109038-. doi: 10.1016/j.cclet.2023.109038
14. [14]
  Renshu Huang , Jinli Chen , Xingfa Chen , Tianqi Yu , Huyi Yu , Kaien Li , Bin Li , Shibin Yin . Synergized oxygen vacancies with Mn2O3@CeO2 heterojunction as high current density catalysts for Li–O2 batteries. Chinese Journal of Structural Chemistry, 2023, 42(11): 100171-100171. doi: 10.1016/j.cjsc.2023.100171
15. [15]
  Shengwen Guan , Zhaotong Wei , Ningxu Han , Yude Wei , Bin Xu , Ming Wang , Junjuan Shi . Construction of metallo-complexes with 2,2′:6′,2″-terpyridine substituted triphenylamine in different modified positions and their photophysical properties. Chinese Chemical Letters, 2024, 35(7): 109348-. doi: 10.1016/j.cclet.2023.109348
16. [16]
  Maomao Liu , Guizeng Liang , Ningce Zhang , Tao Li , Lipeng Diao , Ping Lu , Xiaoliang Zhao , Daohao Li , Dongjiang Yang . Electron-rich Ni2+ in Ni3S2 boosting electrocatalytic CO2 reduction to formate and syngas. Chinese Journal of Structural Chemistry, 2024, 43(8): 100359-100359. doi: 10.1016/j.cjsc.2024.100359
17. [17]
  Yongheng Ren , Yang Chen , Hongwei Chen , Lu Zhang , Jiangfeng Yang , Qi Shi , Lin-Bing Sun , Jinping Li , Libo Li . Electrostatically driven kinetic Inverse CO2/C2H2 separation in LTA-type zeolites. Chinese Journal of Structural Chemistry, 2024, 43(10): 100394-100394. doi: 10.1016/j.cjsc.2024.100394
18. [18]
  Huirong Chen , Yingzhi He , Yan Han , Jianbo Hu , Jiantang Li , Yunjia Jiang , Basem Keshta , Lingyao Wang , Yuanbin Zhang . A new SIFSIX anion pillared cage MOF with crs topological structure for efficient C2H2/CO2 separation. Chinese Journal of Structural Chemistry, 2025, 44(2): 100508-100508. doi: 10.1016/j.cjsc.2024.100508
19. [19]
  Cailiang Yue , Nan Sun , Yixing Qiu , Linlin Zhu , Zhiling Du , Fuqiang Liu . A direct Z-scheme 0D α-Fe₂O₃/TiO₂ heterojunction for enhanced photo-Fenton activity with low H₂O₂ consumption. Chinese Chemical Letters, 2024, 35(12): 109698-. doi: 10.1016/j.cclet.2024.109698
20. [20]
  Liyong Ding , Zhenhua Pan , Qian Wang . 2D photocatalysts for hydrogen peroxide synthesis. Chinese Chemical Letters, 2024, 35(12): 110125-. doi: 10.1016/j.cclet.2024.110125

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(1796)
HTML views(249)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142