Citation: Wu Minghao, Chen Qing, Wang Yingdi, Li Yulei, Zhao Xia, Chang Qi. Structural modification and antitumor activity of antimicrobial peptide HYL[J]. Chinese Chemical Letters, ;2020, 31(5): 1288-1292. doi: 10.1016/j.cclet.2019.10.013 shu

Structural modification and antitumor activity of antimicrobial peptide HYL

Wu Minghao ^a,b ,
Chen Qing ^a ,
Wang Yingdi ^a ,
Li Yulei ^a,b ,
Zhao Xia ^a,b,*, ,
Chang Qi ^a,b

a.
Key Laboratory of Marine Drugs, Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China
b.
Laboratory for Marine Drugs and Bioproducts of Qingdao National Laboratory for Marine Science and Technology, Qingdao 266237, China

1184748799@qq.com

zhaoxia@ouc.edu.cn

Received Date: 7 September 2019
Revised Date: 29 September 2019
Accepted Date: 12 October 2019
Available Online: 14 October 2019

Figures(5)

HYL derived from the venom of the solitary bee Hylaeus signatus (Hymenoptera:Colletidae) is an α-helical antimicrobial peptide with 16 residues. To explore whether HYL can be applied in anti-tumor therapy, we synthesized HYL and further modified its structure by using a solid-phase synthesis method, and then evaluated their antitumor activities. Firstly, we identified the key residues of HYL by alanine scanning strategy, and then a series of stapled peptides were synthesized by hydrocarbon stapling strategy without destroying the key residues. All the stapled peptides of HYL showed significant improvement not only in α-helicity, but also in antitumor activity and protease resistance when compared to the parent peptide HYL. The results showed that hydrophobicity and amphiphilicity are important factors affecting the antitumor activity of HYL, and the stapling strategy can significantly affect the proteolytic stability and helicity of HYL. What's more, we find that the stapled peptides HYL-14, HYL-16 and HYL-18 show a promising prospect for novel anti-tumor drug development.
- HYL,
- α-Helical peptide,
- Stapled peptide,
- Hydrocarbon stapling strategy,
- Antitumor activity,
- Solid-phase synthesis
1. [1]
  F. Bray, J. Ferlay, I. Soerjomataram, et al., CA Cancer J. Clin. 68(2018) 394-424. doi: 10.3322/caac.21492
2. [2]
  C.E. DeSantis, C.C. Lin, A.B. Mariotto, et al., CA Cancer J. Clin. 64(2014) 252-271. doi: 10.3322/caac.21235
3. [3]
  R.L. Siegel, K.D. Miller, A. Jemal, CA Cancer J. Clin. 68(2018) 7-30. doi: 10.3322/caac.21442
4. [4]
  R. Shashidharamurthy, E.N. Bozeman, J. Patel, et al., Med. Res. Rev. 32(2012) 1197-1219. doi: 10.1002/med.20237
5. [5]
  M.M. Wei, Y.S. Wang, X.S. Ye, Med. Res. Rev. 38(2018) 1003-1026. doi: 10.1002/med.21493
6. [6]
  T.K. Sawyer, A.W. Partridge, H.Y.K. Kaan, et al., Bioorg. Med. Chem. 26(2018) 2807-2815. doi: 10.1016/j.bmc.2018.03.008
7. [7]
  O. Nesuta, R. Hexnerova, M. Budesinsky, et al., J. Nat. Prod. 79(2016) 1073-1083. doi: 10.1021/acs.jnatprod.5b01129
8. [8]
  R. Gautier, D. Douguet, B. Antonny, G. Drin, Bioinformatics 24(2008) 2101-2102. doi: 10.1093/bioinformatics/btn392
9. [9]
  B. Villavicencio, R. Ligabue-Braun, H. Verli, J. Chem. Inf. Model. 58(2018) 2015-2023. doi: 10.1021/acs.jcim.8b00404
10. [10]
  A.A. Vinogradov, Y.Z. Yin, H. Suga, J. Am. Chem. Soc. 141(2019) 4167-4181. doi: 10.1021/jacs.8b13178
11. [11]
  X. Qin, H. Zhao, Y.H. Jiang, et al., Chin. Chem. Lett. 29(2018) 1160-1162. doi: 10.1016/j.cclet.2018.04.004
12. [12]
  Y. Guo, L.L. Fu, X.W. Fan, X.L. Shi, Chin. Chem. Lett. 29(2018) 1167-1170. doi: 10.1016/j.cclet.2018.03.024
13. [13]
  G.L. Verdine, G.J. Hilinski, Methods Enzymol. 503(2012) 3-33. doi: 10.1016/B978-0-12-396962-0.00001-X
14. [14]
  Y.H. Lau, P.D. Andrade, Y.T. Wu, D.R. Spring, Chem. Soc. Rev. 44(2015) 91-102. doi: 10.1039/C4CS00246F
15. [15]
  G. Lautrette, F. Touti, H.G. Lee, P. Dai, B.L. Pentelute, J. Am. Chem. Soc.138(2016) 8340-8343. doi: 10.1021/jacs.6b03757
16. [16]
  Y. Tian, J.X. Li, H. Zhao, et al., Chem. Sci. 7(2016) 3325-3330. doi: 10.1039/C6SC00106H
17. [17]
  Y. Wu, Y.H. Li, W. Li, et al., Chem. Sci. 8(2017) 7368-7373. doi: 10.1039/C7SC02420G
18. [18]
  X.D. Shi, Y.X. Jiang, D. Yang, et al., Chin. Chem. Lett. 29(2018) 485-488. doi: 10.1016/j.cclet.2017.07.003
19. [19]
  P. Diderich, D. Bertoldo, P. Dessen, et al., ACS Chem. Biol.11(2016) 1422-1427. doi: 10.1021/acschembio.5b00963
20. [20]
  X. Li, Y. Zou, H.G. Hu, Chin. Chem. Lett. 29(2018) 1088-1092. doi: 10.1016/j.cclet.2018.01.018
21. [21]
  C.M. Haney, H.M. Werner, J.J. McKay, W.S. Horne, Org. Biomol. Chem.14(2016) 5768-5773. doi: 10.1039/C6OB00475J
22. [22]
  Y.H. Li, K.A. Clark, Z.P. Tan, Chin. Chem. Lett. 29(2018) 1074-1078. doi: 10.1016/j.cclet.2018.05.027
23. [23]
  X. Lu, S.J. He, W.M. Cheng, J. Shi, Chin. Chem. Lett. 29(2018) 1001-1008. doi: 10.1016/j.cclet.2018.05.011
24. [24]
  Y. Jiang, H.Y. Long, Y.J. Zhu, Y. Zeng, Chin. Chem. Lett. 29(2018) 1067-1073. doi: 10.1016/j.cclet.2018.05.028
25. [25]
  F. Bernal, A.F. Tyler, S.J. Korsmeyer, L.D. Walensky, G.L. Verdine, J. Am. Chem. Soc. 129(2007) 2456-2457. doi: 10.1021/ja0693587
26. [26]
  G.J. Hilinski, Y.W. Kim, J. Hong, et al., J. Am. Chem. Soc. 136(2014) 12314-12322. doi: 10.1021/ja505141j
27. [27]
  Y.L. Li, M.H. Wu, Q. Chang, X. Zhao, RSC Adv. 8(2018) 22268-22275. doi: 10.1039/C8RA03446J
28. [28]
  Y.L. Li, Y.H. Zhang, M.H. Wu, et al., ACS Chem. Biol. 14(2019) 516-525. doi: 10.1021/acschembio.9b00046
29. [29]
  B. Li, W. Gu, C. Zhang, et al., Onkologie 29(2006) 367-371. doi: 10.1159/000094711
30. [30]
  L.K. Henchey, A.L. Jochim, P.S. Arora, Curr. Opin. Chem. Biol. 12(2008) 692-697. doi: 10.1016/j.cbpa.2008.08.019
31. [31]
  K. Hojo, M.A. Hossain, J. Tailhades, et al., J. Med. Chem. 59(2016) 7445-7456. doi: 10.1021/acs.jmedchem.6b00265
32. [32]
  H.K. Cui, J. Qing, Y. Guo, et al., Bioorg. Med. Chem. 21(2013) 3547-3554. doi: 10.1016/j.bmc.2013.02.011
33. [33]
  N.E. Shepherd, H.N. Hoang, G. Abbenante, D.P. Fairlie, J. Am. Chem. Soc. 127(2005) 2974-2983. doi: 10.1021/ja0456003
34. [34]
  C. Wang, S. Xia, P. Zhang, et al., J. Med. Chem. 61(2018) 2018-2026. doi: 10.1021/acs.jmedchem.7b01732
35. [35]
  T.E. Speltz, C.G. Mayne, S.W. Fanning, et al., Org. Biomol. Chem.16(2018) 3702-3706. doi: 10.1039/C8OB00790J
36. [36]
  Y. Tal-Gan, M. Ivencic, G. Cornilescu, T. Yang, H.E. Blackwell, Angew. Chem. Int. Ed. 55(2016) 8913-8917. doi: 10.1002/anie.201602974
37. [37]
  Y.S. Chang, B. Graves, V. Guerlavais, et al., Proc. Natl. Acad. Sci. U. S. A.110(2013) E3445-54. doi: 10.1073/pnas.1303002110
1. [1]
  Yihao Zhao , Jitian Rao , Jie Han . Synthesis and Photochromic Properties of 3,3-Diphenyl-3H-Naphthopyran: Design and Teaching Practice of a Comprehensive Organic Experiment. University Chemistry, 2024, 39(10): 149-155. doi: 10.3866/PKU.DXHX202402050
2. [2]
  Weiyu Chen , Zenghui Li , Chenguang Zhao , Lisha Zha , Junfeng Shi , Dan Yuan . Enzyme-modulate conformational changes in amphiphile peptide for selectively cell delivery. Chinese Chemical Letters, 2024, 35(12): 109628-. doi: 10.1016/j.cclet.2024.109628
3. [3]
  Xiaofang Luo , Ye Wu , Xiaokun Zhang , Min Tang , Feiye Ju , Zuodong Qin , Gregory J Duns , Wei-Dong Zhang , Jiang-Jiang Qin , Xin Luan . Peptide-based strategies for overcoming multidrug-resistance in cancer therapy. Chinese Chemical Letters, 2025, 36(1): 109724-. doi: 10.1016/j.cclet.2024.109724
4. [4]
  Rui Wang , He Qi , Haijiao Zheng , Qiong Jia . Light/pH dual-responsive magnetic metal-organic frameworks composites for phosphorylated peptide enrichment. Chinese Chemical Letters, 2024, 35(7): 109215-. doi: 10.1016/j.cclet.2023.109215
5. [5]
  Cheng-Yan Wu , Yi-Nan Gao , Zi-Han Zhang , Rui Liu , Quan Tang , Zhong-Lin Lu . Enhancing self-assembly efficiency of macrocyclic compound into nanotubes by introducing double peptide linkages. Chinese Chemical Letters, 2024, 35(11): 109649-. doi: 10.1016/j.cclet.2024.109649
6. [6]
  Jianhui Yin , Wenjing Huang , Changyong Guo , Chao Liu , Fei Gao , Honggang Hu . Tryptophan-specific peptide modification through metal-free photoinduced N-H alkylation employing N-aryl glycines. Chinese Chemical Letters, 2024, 35(6): 109244-. doi: 10.1016/j.cclet.2023.109244
7. [7]
  Chuanfeng Fan , Jian Gao , Yingkai Gao , Xintong Yang , Gaoning Li , Xiaochun Wang , Fei Li , Jin Zhou , Haifeng Yu , Yi Huang , Jin Chen , Yingying Shan , Li Chen . A non-peptide-based chymotrypsin-targeted long-wavelength emission fluorescent probe with large Stokes shift and its application in bioimaging. Chinese Chemical Letters, 2024, 35(10): 109838-. doi: 10.1016/j.cclet.2024.109838
8. [8]
  Hong-Tao Ji , Yu-Han Lu , Yan-Ting Liu , Yu-Lin Huang , Jiang-Feng Tian , Feng Liu , Yan-Yan Zeng , Hai-Yan Yang , Yong-Hong Zhang , Wei-Min He . Nd@C₃N₄-photoredox/chlorine dual catalyzed synthesis and evaluation of antitumor activities of 4-alkylated sulfonyl ketimines. Chinese Chemical Letters, 2025, 36(2): 110568-. doi: 10.1016/j.cclet.2024.110568
9. [9]
  Anqiu LIU , Long LIN , Dezhi ZHANG , Junyu LEI , Kefeng WANG , Wei ZHANG , Junpeng ZHUANG , Haijun HAO . Synthesis, structures, and catalytic activity of aluminum and zinc complexes chelated by 2-((2,6-dimethylphenyl)amino)ethanolate. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 791-798. doi: 10.11862/CJIC.20230424
10. [10]
  Guoping Yang , Zhoufu Lin , Xize Zhang , Jiawei Cao , Xuejiao Chen , Yufeng Liu , Xiaoling Lin , Ke Li . Assembly of Y(Ⅲ)-containing antimonotungstates induced by malic acid with catalytic activity for the synthesis of imidazoles. Chinese Chemical Letters, 2024, 35(12): 110274-. doi: 10.1016/j.cclet.2024.110274
11. [11]
  Yao HUANG , Yingshu WU , Zhichun BAO , Yue HUANG , Shangfeng TANG , Ruixue LIU , Yancheng LIU , Hong LIANG . Copper complexes of anthrahydrazone bearing pyridyl side chain: Synthesis, crystal structure, anticancer activity, and DNA binding. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 213-224. doi: 10.11862/CJIC.20240359
12. [12]
  Maosen Xu , Pengfei Zhu , Qinghong Cai , Meichun Bu , Chenghua Zhang , Hong Wu , Youzhou He , Min Fu , Siqi Li , Xingyan Liu . In-situ fabrication of TiO₂/NH₂−MIL-125(Ti) via MOF-driven strategy to promote efficient interfacial effects for enhancing photocatalytic NO removal activity. Chinese Chemical Letters, 2024, 35(10): 109524-. doi: 10.1016/j.cclet.2024.109524
13. [13]
  Maitri Bhattacharjee , Rekha Boruah Smriti , R. N. Dutta Purkayastha , Waldemar Maniukiewicz , Shubhamoy Chowdhury , Debasish Maiti , Tamanna Akhtar . Synthesis, structural characterization, bio-activity, and density functional theory calculation on Cu(Ⅱ) complexes with hydrazone-based Schiff base ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1409-1422. doi: 10.11862/CJIC.20240007
14. [14]
  Xiaomeng Hu , Jie Yu , Lijie Sun , Linfeng Zhang , Wei Zhou , Dongpeng Yan , Xinrui Wang . Synthesis of an AVB@ZnTi-LDH composite with synergistically enhance UV blocking activity and high stability for potential application in sunscreen formulations. Chinese Chemical Letters, 2024, 35(11): 109466-. doi: 10.1016/j.cclet.2023.109466
15. [15]
  Yunjia Jiang , Lingyao Wang , Yuanbin Zhang . Anion pillared MOFs for challenging hydrocarbon separations. Chinese Journal of Structural Chemistry, 2024, 43(11): 100374-100374. doi: 10.1016/j.cjsc.2024.100374
16. [16]
  Jing Zhang , Charles Wang , Yaoyao Zhang , Haining Xia , Yujuan Wang , Kun Ma , Junfeng Wang . Application of magnetotactic bacteria as engineering microrobots: Higher delivery efficiency of antitumor medicine. Chinese Chemical Letters, 2024, 35(10): 109420-. doi: 10.1016/j.cclet.2023.109420
17. [17]
  Shuangying Li , Qingxiang Zhou , Zhi Li , Menghua Liu , Yanhui Li . Sensitive measurement of silver ions in environmental water samples integrating magnetic ion-imprinted solid phase extraction and carbon dot fluorescent sensor. Chinese Chemical Letters, 2024, 35(5): 108693-. doi: 10.1016/j.cclet.2023.108693
18. [18]
  Jin Wang , Xiaoyan Pan , Junyu Zhang , Qingqing Zhang , Yanchen Li , Weiwei Guo , Jie Zhang . Active molecule-based theranostic agents for tumor vasculature normalization and antitumor efficacy. Chinese Chemical Letters, 2024, 35(8): 109187-. doi: 10.1016/j.cclet.2023.109187
19. [19]
  Zhaomin Tang , Qian He , Jianren Zhou , Shuang Yan , Li Jiang , Yudong Wang , Chenxing Yao , Huangzhao Wei , Keda Yang , Jiajia Wang . Active-transporting of charge-reversal Cu(Ⅱ)-doped mesoporous silica nanoagents for antitumor chemo/chemodynamic therapy. Chinese Chemical Letters, 2024, 35(7): 109742-. doi: 10.1016/j.cclet.2024.109742
20. [20]
  Guangyao Wang , Zhitong Xu , Ye Qi , Yueguang Fang , Guiling Ning , Junwei Ye . Electrospun nanofibrous membranes with antimicrobial activity for air filtration. Chinese Chemical Letters, 2024, 35(10): 109503-. doi: 10.1016/j.cclet.2024.109503

Get Citation

PDF

XML

Metrics

PDF Downloads(4)
Abstract views(778)
HTML views(69)

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