Citation: Kai Ming, Zhang Wei, Xie Huan, Liu Liwei, Huang Sujie, Li Xiao, Zhang Zhengzheng, Liu Yuyang, Zhang Bangzhi, Song Jingjing, Wang Rui. Effects of linker amino acids on the potency and selectivity of dimeric antimicrobial peptides[J]. Chinese Chemical Letters, ;2018, 29(7): 1163-1166. doi: 10.1016/j.cclet.2018.04.011 shu

Effects of linker amino acids on the potency and selectivity of dimeric antimicrobial peptides

Kai Ming ^a ,
Zhang Wei ^b ,
Xie Huan ^b ,
Liu Liwei ^a ,
Huang Sujie ^a ,
Li Xiao ^a ,
Zhang Zhengzheng ^b ,
Liu Yuyang ^b ,
Zhang Bangzhi ^a ,
Song Jingjing ^b,, ,
Wang Rui ^b,,

1.
School of Life Sciences, Lanzhou University, Lanzhou 730000, China
2.
Laboratory of Preclinical Study for New Drugs of Gansu Province, School of Basic Medical Sciences, Lanzhou University, Lanzhou 730000, China

Corresponding author: Song Jingjing, songjj@lzu.edu.cn Wang Rui, wangrui@lzu.edu.cn
Received Date: 6 March 2018
Revised Date: 25 March 2018
Accepted Date: 8 April 2018
Available Online: 14 July 2018

Figures(3)

Dimerization is an effective strategy for designing antimicrobial peptides that combine the advantages of different native peptides. In this study, we explored the effects of different linker amino acids, including leucine, proline and aminocaproic acid, on the anticancer, antimicrobial and hemolytic activities of the heteromeric antimicrobial peptides AM-1, AM-2, and AM-3. Proline and aminocaproic acid are ideal linkers for increasing the potency and selectivity of heteromeric antimicrobial peptides. The results of MD simulations provided a rationalization for this observation. Both AM-2, which had a proline linker, and AM-3, which had an aminocaproic acid linker, adopted a compact conformation in water and a bent conformation in membranes. This change in the flexible structures of AM-2 and AM-3 could have resulted in decreased binding of these peptides to zwitterionic lipid bilayers and increased damage to mixed lipid bilayers containing acidic phospholipids. In short, these findings obtained via assessing the effects of linker amino acids will contribute to the design of ideal heteromeric antimicrobial peptides with high selectivity and potency.
- Linker amino acid,
- Flexibility,
- Heteromeric antimicrobial peptides,
- Potency and selectivity
1. [1]
  M.R. Yeaman, N.Y. Yount, Pharmacol. Rev. 55(2003) 27-55. doi: 10.1124/pr.55.1.2
2. [2]
  L.T. Nguyen, E.F. Haney, H.J. Vogel, Trends Biotechnol. 29(2011) 464-472. doi: 10.1016/j.tibtech.2011.05.001
3. [3]
  M. Zasloff, Nature 415(2002) 389-395. doi: 10.1038/415389a
4. [4]
  G. Gabernet, A.T. Muller, J.A. Hiss, et al., MedChemComm 7(2016) 2232-2245. doi: 10.1039/C6MD00376A
5. [5]
  C.D. Fjell, J.A. Hiss, R.E. Hancock, et al., Nat. Rev. Drug Discovery 11(2011) 37-51.
6. [6]
  Z.Y. Ong, N. Wiradharma, Y.Y. Yang, Adv. Drug Delivery Rev. 78(2014) 28-45. doi: 10.1016/j.addr.2014.10.013
7. [7]
  N.K. Brogden, K.A. Brogden, Int. J. Antimicrob. Agents 38(2011) 217-225.
8. [8]
  S.P. Liu, L. Zhou, R. Lakshminarayanan, R.W. Beuerman, Int. J. Pept. Res. Ther. 16(2010) 199-213. doi: 10.1007/s10989-010-9230-z
9. [9]
  C.E. Dempsey, S. Ueno, M.B. Avison, Biochem. 42(2003) 402-409. doi: 10.1021/bi026328h
10. [10]
  S.T. Yang, J.I. Kim, S.Y. Shin, Biotechnol. Lett. 31(2009) 233-237. doi: 10.1007/s10529-008-9848-5
11. [11]
  E.N. Lorenzon, G.F. Cespedes, E.F. Vicente, et al., Antimicrob. Agents Chemother. 56(2012) 3004-3010. doi: 10.1128/AAC.06262-11
12. [12]
  M. Nishida, Y. Imura, M. Yamamoto, et al., Biochemical 46(2007) 14284-14290. doi: 10.1021/bi701850m
13. [13]
  J. Zerweck, E. Strandberg, J. Burck, et al., Eur. Biophys. J. Biophy. 45(2016) 535-547. doi: 10.1007/s00249-016-1120-7
14. [14]
  W.Y. Li, N.M. O'Brien-Simpson, J. Tailhades, et al., Chem. Biol. 22(2015) 1250-1258. doi: 10.1016/j.chembiol.2015.08.011
15. [15]
  K. Konno, M. Hisada, R. Fontana, et al., BBA-Protein Struct. M 1550(2001) 70-80. doi: 10.1016/S0167-4838(01)00271-0
16. [16]
  Y. Hirai, Y. Ueno, T. Yasuhara, et al., Biomed. Res.-Tokyo 1(1980) 185-187. doi: 10.2220/biomedres.1.185
17. [17]
  M. Moreno, E. Giralt, Toxins 7(2015) 1126-1150. doi: 10.3390/toxins7041126
18. [18]
  U. Soomets, M. Lindgren, X. Gallet, et al., BBA-Biomembr. 1467(2000) 165-176. doi: 10.1016/S0005-2736(00)00216-9
19. [19]
  S. El-Andaloussi, P. Jarver, H.J. Johansson, et al., Biochem. J. 407(2007) 285-292. doi: 10.1042/BJ20070507
20. [20]
  J.J. Song, M. Kai, W. Zhang, et al., Peptides 32(2011) 1934-1941. doi: 10.1016/j.peptides.2011.07.018
21. [21]
  J.Q. Xie, Y.M. Gou, Q. Zhao, et al., J. Pept. Sci. 21(2015) 599-607. doi: 10.1002/psc.v21.7
22. [22]
  Y.X. Chen, C.T. Mant, S.W. Farmer, et al., J. Biol. Chem. 280(2005) 12316-12329. doi: 10.1074/jbc.M413406200
23. [23]
  Y.M. Song, Y. Park, S.S. Lim, et al., Biochem.-US 44(2005) 12094-12106. doi: 10.1021/bi050765p
24. [24]
  L.S. Vermeer, Y. Lan, V. Abbate, et al., J. Biol. Chem. 287(2012) 34120-34133. doi: 10.1074/jbc.M112.359067
25. [25]
  S.T. Yang, J.Y. Lee, H.J. Kim, et al., FEBS J. 273(2006) 4040-4054. doi: 10.1111/j.1742-4658.2006.05407.x
26. [26]
  L.J. Zhang, R. Benz, R.E.W. Hancock, Biochemistry 38(1999) 8102-8111. doi: 10.1021/bi9904104
27. [27]
  S. Bobone, G. Bocchinfuso, Y. Park, et al., J. Pept. Sci. 19(2013) 758-769. doi: 10.1002/psc.v19.12
28. [28]
  A. Hollmanna, M. Martinez, M.E. Noguera, et al., Colloid Surf. B 141(2016) 528-536. doi: 10.1016/j.colsurfb.2016.02.003
29. [29]
  L.H. Kondejewski, M. Jelokhani-Niaraki, S.W. Farmer, et al., J. Biol. Chem. 274(1999) 13181-13192. doi: 10.1074/jbc.274.19.13181
30. [30]
  K. Matsuzaki, BBA-Biomembr. 1788(2009) 1687-1692. doi: 10.1016/j.bbamem.2008.09.013
31. [31]
  Y.X. Chen, M.T. Guarnieri, A.I. Vasil, et al., Antimicrob. Agents Chemother. 51(2007) 1398-1406. doi: 10.1128/AAC.00925-06
32. [32]
  Y.B. Huang, J.F. Huang, Y.X. Chen, Protein Cell 1(2010) 143-152. doi: 10.1007/s13238-010-0004-3
33. [33]
  S. Kim, S.S. Kim, B.J. Lee, Peptides 26(2005) 2050-2056. doi: 10.1016/j.peptides.2005.04.007
34. [34]
  C.W. Tsai, N.Y. Hsu, C.H. Wang, et al., J. Mol. Biol. 392(2009) 837-854. doi: 10.1016/j.jmb.2009.06.071
35. [35]
  J.J. Song, W. Zhang, M. Kai, et al., Mol. Pharm. 10(2013) 2934-2941. doi: 10.1021/mp400052s
36. [36]
  D.W. Hoskin, A. Ramamoorthy, BBA-Biomembr. 1778(2008) 357-375. doi: 10.1016/j.bbamem.2007.11.008
1. [1]
  Yiyue Ding , Qiuxiang Zhang , Lei Zhang , Qilu Yao , Gang Feng , Zhang-Hui Lu . Exceptional activity of amino-modified rGO-immobilized PdAu nanoclusters for visible light-promoted dehydrogenation of formic acid. Chinese Chemical Letters, 2024, 35(7): 109593-. doi: 10.1016/j.cclet.2024.109593
2. [2]
  Zixu Xie , Pengfei Zhang , Ziyao Zhang , Chen Chen , Xing Wang . The choice of antimicrobial polymers: Hydrophilic or hydrophobic?. Chinese Chemical Letters, 2024, 35(9): 109768-. doi: 10.1016/j.cclet.2024.109768
3. [3]
  Qijun Tang , Wenguang Tu , Yong Zhou , Zhigang Zou . High efficiency and selectivity catalyst for photocatalytic oxidative coupling of methane. Chinese Journal of Structural Chemistry, 2023, 42(12): 100170-100170. doi: 10.1016/j.cjsc.2023.100170
4. [4]
  Rui HUANG , Shengjie LIU , Qingyuan WU , Nanfeng ZHENG . Enhanced selectivity of catalytic hydrogenation of halogenated nitroaromatics by interfacial effects. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 201-212. doi: 10.11862/CJIC.20240356
5. [5]
  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
6. [6]
  Chen Li , Ziyuan Zhao , Shouyun Yu . Photoredox-catalyzed C-glycosylation of peptides with glycosyl bromides. Chinese Chemical Letters, 2024, 35(6): 109128-. doi: 10.1016/j.cclet.2023.109128
7. [7]
  Yan-Kai Zhang , Yong-Zheng Zhang , Chun-Xiao Jia , Fang Wang , Xiuling Zhang , Yuhang Wu , Zhongmin Liu , Hui Hu , Da-Shuai Zhang , Longlong Geng , Jing Xu , Hongliang Huang . A stable Zn-MOF with anthracene-based linker for Cr(VI) photocatalytic reduction under sunlight irradiation. Chinese Chemical Letters, 2024, 35(12): 109756-. doi: 10.1016/j.cclet.2024.109756
8. [8]
  Shiqi Xu , Zi Ye , Shuang Shang , Fengge Wang , Huan Zhang , Lianguo Chen , Hao Lin , Chen Chen , Fang Hua , Chong-Jing Zhang . Pairs of thiol-substituted 1,2,4-triazole-based isomeric covalent inhibitors with tunable reactivity and selectivity. Chinese Chemical Letters, 2024, 35(7): 109034-. doi: 10.1016/j.cclet.2023.109034
9. [9]
  Caixia Zhu , Qing Hong , Kaiyuan Wang , Yanfei Shen , Songqin Liu , Yuanjian Zhang . Single nanozyme-based colorimetric biosensor for dopamine with enhanced selectivity via reactivity of oxidation intermediates. Chinese Chemical Letters, 2024, 35(10): 109560-. doi: 10.1016/j.cclet.2024.109560
10. [10]
  Shaoming Dong , Yiming Niu , Yinghui Pu , Yongzhao Wang , Bingsen Zhang . Subsurface carbon modification of Ni-Ga for improved selectivity in acetylene hydrogenation reaction. Chinese Chemical Letters, 2024, 35(12): 109525-. doi: 10.1016/j.cclet.2024.109525
11. [11]
  Congyan Liu , Xueyao Zhou , Fei Ye , Bin Jiang , Bo Liu . Confined electric field in nano-sized channels of ionic porous framework towards unique adsorption selectivity. Chinese Chemical Letters, 2025, 36(2): 109969-. doi: 10.1016/j.cclet.2024.109969
12. [12]
  Sanmei Wang , Dengxin Yan , Wenhua Zhang , Liangbing Wang . Graphene-supported isolated platinum atoms and platinum dimers for CO₂ hydrogenation: Catalytic activity and selectivity variations. Chinese Chemical Letters, 2025, 36(4): 110611-. doi: 10.1016/j.cclet.2024.110611
13. [13]
  Dake Liu , Shuyan Liu , Fanlei Hu , Zhongtang Li , Zhongjun Li . N-Glycosylated type Ⅱ collagen peptides as therapeutic saccharide vaccines for rheumatoid arthritis. Chinese Chemical Letters, 2024, 35(5): 108762-. doi: 10.1016/j.cclet.2023.108762
14. [14]
  Lijun Yan , Shiqi Chen , Penglu Wang , Xiangyu Liu , Lupeng Han , Tingting Yan , Yuejin Li , Dengsong Zhang . Hydrothermally stable metal oxide-zeolite composite catalysts for low-temperature NO_x reduction with improved N₂ selectivity. Chinese Chemical Letters, 2024, 35(6): 109132-. doi: 10.1016/j.cclet.2023.109132
15. [15]
  Hui Li , Yanxing Qi , Jia Chen , Juanjuan Wang , Min Yang , Hongdeng Qiu . Synthesis of amine-pillar[5]arene porous adsorbent for adsorption of CO₂ and selectivity over N₂ and CH₄. Chinese Chemical Letters, 2024, 35(11): 109659-. doi: 10.1016/j.cclet.2024.109659
16. [16]
  Shulei Hu , Yu Zhang , Xiong Xie , Luhan Li , Kaixian Chen , Hong Liu , Jiang Wang . Rh(Ⅲ)-catalyzed late-stage C-H alkenylation and macrolactamization for the synthesis of cyclic peptides with unique Trp(C7)-alkene crosslinks. Chinese Chemical Letters, 2024, 35(8): 109408-. doi: 10.1016/j.cclet.2023.109408
17. [17]
  Chuan-Zhi Ni , Ruo-Ming Li , Fang-Qi Zhang , Qu-Ao-Wei Li , Yuan-Yuan Zhu , Jie Zeng , Shuang-Xi Gu . A chiral fluorescent probe for molecular recognition of basic amino acids in solutions and cells. Chinese Chemical Letters, 2024, 35(10): 109862-. doi: 10.1016/j.cclet.2024.109862
18. [18]
  Chong Liu , Ling Li , Jiahui Gao , Yanwei Li , Nazhen Zhang , Jing Zang , Cong Liu , Zhaopei Guo , Yanhui Li , Huayu Tian . The study of antibacterial activity of cationic poly(β-amino ester) regulating by amphiphilic balance. Chinese Chemical Letters, 2025, 36(2): 110118-. doi: 10.1016/j.cclet.2024.110118
19. [19]
  Hong Zhang , Cui-Ping Li , Li-Li Wang , Zhuo-Da Zhou , Wen-Sen Li , Ling-Yi Kong , Ming-Hua Yang . Asperochones A and B, two antimicrobial aromatic polyketides from the endophytic fungus Aspergillus sp. MMC-2. Chinese Chemical Letters, 2024, 35(9): 109351-. doi: 10.1016/j.cclet.2023.109351
20. [20]
  Yaxian Liang , Qingyi Li , Liwei Hu , Ruohan Zhai , Fan Liu , Lin Tan , Xiaofei Wang , Huixu Xie . Environmentally friendly polylysine gauze dressing for an innovative antimicrobial approach to infected wound management. Chinese Chemical Letters, 2024, 35(10): 109459-. doi: 10.1016/j.cclet.2023.109459

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(1231)
HTML views(45)

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