Citation: Jintao Shen, Jia Liu, Shuo Yu, Yunzhou Yu, Chao Huang, Xianghua Xiong, Junjie Yue, Qiuyun Dai. Diaminodiacid bridge improves enzymatic and in vivo inhibitory activity of peptide CPI-1 against botulinum toxin serotype A[J]. Chinese Chemical Letters, ;2021, 32(12): 4049-4052. doi: 10.1016/j.cclet.2021.03.055 shu

Diaminodiacid bridge improves enzymatic and in vivo inhibitory activity of peptide CPI-1 against botulinum toxin serotype A

Beijing Institute of Biotechnology, Beijing 100071, China

yue_junjie@126.com

daiqy@bmi.ac.cn

Received Date: 29 January 2021
Revised Date: 4 March 2021
Accepted Date: 22 March 2021
Available Online: 23 March 2021

Figures(5)

The replacement of the disulfide bridge of CPI-1, a peptide inhibitor of light chain of Botulinum toxin serotype A, with the thioether-containing and biscarba-containing diaminodiacid bridge leads to a significant decrease in the degradation by trypsin and increase in the detoxification activity in vivo, the addition of hydrophobic or positive amino acid at C-terminus of modified peptides further improves the inhibitory activity.
- Botulinum neurotoxin serotype A,
- Light chain inhibitor,
- Peptide CPI-1,
- Diaminodiacid bridges,
- Inhibitory activity
1. [1]
  G. Schiavo, O. Rossetto, A. Santucci, et al., J. Biol. chem. 267 (1992) 23479-23483. doi: 10.1016/S0021-9258(18)35863-0
2. [2]
  O. Rossetto, M. Pirazzini, C. Montecucco, Nat. Rev. Microbiol. 12 (2014) 535-549. doi: 10.1038/nrmicro3295
3. [3]
  R.M. Benoit, D. Frey, M.M. Wieser, et al., Toxicon 107 (2015) 25-31. doi: 10.1016/j.toxicon.2015.08.002
4. [4]
  C.N. Mayers, J.L. Holley, T. Brooks, Rev. Med. Microbiol. 12 (2001) 29-37. doi: 10.1097/00013542-200101000-00004
5. [5]
  A.A. Adalja, E. Toner, T.V. Inglesby, N. Engl. J. Med. 372 (2015) 954-962. doi: 10.1056/NEJMra1409755
6. [6]
  T.J. Dickerson, G.R. Smith, J.C. Pelletier, et al., Curr. Top. Med. Chem. 14 (2014) 2094-2102. doi: 10.2174/1568026614666141022095114
7. [7]
  P. Silhar, N.R. Silvaggi, S. Pellett, et al., Bioorg. Med. Chem. 21 (2013) 1344-1348. doi: 10.1016/j.bmc.2012.12.001
8. [8]
  R. Chauhan, V. Chauhan, P. Sonkar, et al., Mini-Rev. Med. Chem. 19 (2019) 1694-1706. doi: 10.2174/1389557519666190906120228
9. [9]
  P.T. Bremer, M. Adler, C.H. Phung, et al., J. Med. Chem. 60 (2017) 338-348. doi: 10.1021/acs.jmedchem.6b01393
10. [10]
  W.A. Harrell Jr, R.C. Vieira, S.M. Ensel, et al., Bioorg. Med. Chem. Lett. 27 (2017) 675-678. doi: 10.1016/j.bmcl.2016.11.019
11. [11]
  J.J. Schmidt, R.G. Stafford, FEBS Lett. 532 (2002) 423-426. doi: 10.1016/S0014-5793(02)03738-9
12. [12]
  D. Kumaran, R. Rawat, M.L. Ludivico, et al., J. Biol. Chem. 283 (2008) 18883-18891. doi: 10.1074/jbc.M801240200
13. [13]
  G. Kumar, D. Kumaran, S.A. Ahmed, et al., Acta Crystallogr. Sect. D: Struct Biol. 68 (2012) 511-520.
14. [14]
  J. Guo, J. Wang, S. Gao, et al., Sci. Rep. 5 (2015) 16981. doi: 10.1038/srep16981
15. [15]
  D. Kumaran, M. Adler, M. Levit, et al., Bioorg. Med. Chem. 23 (2015) 7264-7273. doi: 10.1016/j.bmc.2015.10.024
16. [16]
  H. Seki, S. Xue, M.S. Hixon, et al., Chem. Commun. 51(2015) 6226-6229. doi: 10.1039/C5CC00677E
17. [17]
  G.E. Boldt, L.M. Eubanks, K.D. Janda, Chem. Commun. 29 (2006) 3063-3065. doi: 10.1039/b603099h
18. [18]
  L. Lin, M.E. Olson, T. Sugane, et al., J. Med. Chem. 63 (2020) 11100-11120. doi: 10.1021/acs.jmedchem.0c01006
19. [19]
  L. Lin, M.E. Olson, L.M. Eubanks, et al., Acc. Chem. Res. 52 (2019) 2322-2331. doi: 10.1021/acs.accounts.9b00261
20. [20]
  L.K. Buckton, M.N. Rahimi, S.R. McAlpine, Chemistry 27 (2021) 1487-1513. doi: 10.1002/chem.201905385
21. [21]
  G.M. Fang, X.X. Chen, Q.Q. Yang, et al., Chin. Chem. Lett. 29 (2018) 1033-1042. doi: 10.1016/j.cclet.2018.02.002
22. [22]
  H.K. Cui, Y. Guo, Y. He, et al., Angew. Chem. Int. Ed. 52 (2013) 9558-9562. doi: 10.1002/anie.201302197
23. [23]
  T. Wang, Y.F. Kong, Y. Xu, et al., Tetrahedron. Lett. 58 (2017) 3970-3973. doi: 10.1016/j.tetlet.2017.09.006
24. [24]
  X. Li, Y Zou, H.G. Hu, Chin. Chem. Lett. 29 (2018) 1088-1092. doi: 10.1016/j.cclet.2018.01.018
25. [25]
  P.J. Knerr, A. Tzekou, D. Ricklin, et al., Acc. Chem. Biol. 6 (2011) 753-760. doi: 10.1021/cb2000378
26. [26]
  F. Cai, N. Xu, Z. Liu, et al., J. Med. Chem. 61 (2018) 10198-10205. doi: 10.1021/acs.jmedchem.8b01343
27. [27]
  M.R. Baldwin, M. Bradshaw, E.A. Johnson, et al., Protein Expr. Purif. 37 (2004) 187-195. doi: 10.1016/j.pep.2004.05.009
28. [28]
  G.E. Boldt, J.P. Kennedy, M.S. Hixon, et al., J. Comb. Chem. 8 (2006) 513-521. doi: 10.1021/cc060010h
1. [1]
  Zheng-Biao Zou , Tai-Zong Wu , Chun-Lan Xie , Yuan Wang , Yan Li , Gang Zhang , Rong Chao , Lian-Zhong Luo , Li-Sheng Li , Xian-Wen Yang . neo-Dicitrinols A–C: Unprecedented PKS-NRPS hybrid citrinin dimers with ferroptosis inhibitory activity from the deep-sea-derived Penicillium citrinum W22. Chinese Chemical Letters, 2024, 35(12): 109723-. doi: 10.1016/j.cclet.2024.109723
2. [2]
  Jia Chen , Yun Liu , Zerong Long , Yan Li , Hongdeng Qiu . Colorimetric detection of α-glucosidase activity using Ni-CeO₂ nanorods and its application to potential natural inhibitor screening. Chinese Chemical Letters, 2024, 35(9): 109463-. doi: 10.1016/j.cclet.2023.109463
3. [3]
  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
4. [4]
  Huiju Cao , Lei Shi . sp¹-Hybridized linear and cyclic carbon chain. Chinese Chemical Letters, 2025, 36(4): 110466-. doi: 10.1016/j.cclet.2024.110466
5. [5]
  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
6. [6]
  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
7. [7]
  Fuyun Chi , Man Zhang , Yiman Han , Fukui Shen , Shijie Peng , Bo Su , Yuanyuan Hou , Gang Bai . Covalent modulation of mPGES1 activity via α,β-unsaturated aldehyde group: Implications for downregulating PGE2 expression and antipyretic response. Chinese Chemical Letters, 2025, 36(4): 109913-. doi: 10.1016/j.cclet.2024.109913
8. [8]
  Zuyou Song , Yong Jiang , Qiao Gou , Yini Mao , Yimin Jiang , Wei Shen , Ming Li , Rongxing He . Promoting the generation of active sites through "Co-O-Ru" electron transport bridges for efficient water splitting. Chinese Chemical Letters, 2025, 36(4): 109793-. doi: 10.1016/j.cclet.2024.109793
9. [9]
  Xiao-Ming Chen , Lianhui Song , Jun Pan , Fei Zeng , Yi Xie , Wei Wei , Dong Yi . Visible-light-induced four-component difunctionalization of alkenes to construct phosphorodithioate-containing quinoxalin-2(1H)-ones. Chinese Chemical Letters, 2024, 35(11): 110112-. doi: 10.1016/j.cclet.2024.110112
10. [10]
  Yijia Jiao , Yuzhu Li , Yuting Zhou , Peipei Cen , Yi Ding , Yan Guo , Xiangyu Liu . Structural evolution and zero-field SMM behaviour in ferromagnetically-coupled disk-type Co₇ clusters bearing exclusively end-on azido bridges. Chinese Chemical Letters, 2024, 35(8): 109082-. doi: 10.1016/j.cclet.2023.109082
11. [11]
  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
12. [12]
  Qihang Wu , Hui Wen , Wenhai Lin , Tingting Sun , Zhigang Xie . Alkyl chain engineering of boron dipyrromethenes for efficient photodynamic antibacterial treatment. Chinese Chemical Letters, 2024, 35(12): 109692-. doi: 10.1016/j.cclet.2024.109692
13. [13]
  Ting Wang , Xin Yu , Yaqiang Xie . Unlocking stability: Preserving activity of biomimetic catalysts with covalent organic framework cladding. Chinese Chemical Letters, 2024, 35(6): 109320-. doi: 10.1016/j.cclet.2023.109320
14. [14]
  Fangping Yang , Jin Shi , Yuansong Wei , Qing Gao , Jingrui Shen , Lichen Yin , Haoyu Tang . Mixed-charge glycopolypeptides as antibacterial coatings with long-term activity. Chinese Chemical Letters, 2025, 36(2): 109746-. doi: 10.1016/j.cclet.2024.109746
15. [15]
  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
16. [16]
  Di ZHANG , Tianxiang XIE , Xu HE , Wanyu WEI , Qi FAN , Jie QIAO , Gang JIN , Ningbo LI . Construction and antitumor activity of pH/GSH dual-responsive magnetic nanodrug. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 786-796. doi: 10.11862/CJIC.20240329
17. [17]
  Yiran Tao , Chunlei Dai , Zhaoxiang Xie , Xinru You , Kaiwen Li , Jun Wu , Hai Huang . Redox responsive polymeric nanoparticles enhance the efficacy of cyclin dependent kinase 7 inhibitor for enhanced treatment of prostate cancer. Chinese Chemical Letters, 2024, 35(8): 109170-. doi: 10.1016/j.cclet.2023.109170
18. [18]
  Yifei Zhang , Yuncong Xue , Laiwei Gao , Rui Liao , Feng Wang , Fei Wang . Merging non-covalent and covalent crosslinking: En route to single chain nanoparticles. Chinese Chemical Letters, 2024, 35(6): 109217-. doi: 10.1016/j.cclet.2023.109217
19. [19]
  Haoran Shi , Jiaxin Wang , Yuqin Zhu , Hongyang Li , Guodong Ju , Lanlan Zhang , Chao Wang . Highly selective α-C(sp³)-H arylation of alkenyl amides via nickel chain-walking catalysis. Chinese Chemical Letters, 2024, 35(7): 109333-. doi: 10.1016/j.cclet.2023.109333
20. [20]
  Chao Chen , Wenwen Yu , Guangen Huang , Xuelian Ren , Xiangli Chen , Yixin Li , Shenggui Liang , Mengmeng Xu , Mingyue Zheng , Yaxi Yang , He Huang , Wei Tang , Bing Zhou . Asymmetric macrocyclization enabled by Rh(Ⅲ)-catalyzed CH activation: Enantioenriched macrocyclic inhibitor of Zika virus infection. Chinese Chemical Letters, 2024, 35(11): 109574-. doi: 10.1016/j.cclet.2024.109574

Get Citation

PDF

XML

Metrics

PDF Downloads(2)
Abstract views(814)
HTML views(59)

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