Citation: Wang Meizi, Zhang Li, Wang Xianwei, Ling Yun, Wu Xiaoqing, Li Xinlu, Mi Yiduo, Yang Xinling. Exploring the N-terminus region:Synthesis, bioactivity and 3D-QSAR of allatostatin analogs as novel insect growth regulators[J]. Chinese Chemical Letters, ;2018, 29(9): 1375-1378. doi: 10.1016/j.cclet.2017.11.022 shu

Exploring the N-terminus region:Synthesis, bioactivity and 3D-QSAR of allatostatin analogs as novel insect growth regulators

Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China

Corresponding author: Yang Xinling, yangxl@cau.edu.cn
Received Date: 25 September 2017
Revised Date: 13 November 2017
Accepted Date: 16 November 2017
Available Online: 20 September 2017

Figures(3)

Allatostatins (ASTs), a family of insect neuropeptide, can inhibit juvenile hormone (JH) biosynthesis by the corpora allata (CA) in Diploptera punctata, and therefore be regarded as potential leads for the discovery of new insect growth regulators (IGRs). But several shortcomings, such as their sensitivity to peptidases and high cost, impeded their practical application in pest management. In order to discover new IGRs, one ASTanalog B1 possessing non-peptide group was discovered with high ability to inhibit JH biosynthesis in vitro (IC₅₀:0.09 μmol/L) in our previous studies. In the present work, two series of B1 analogs with different substituents on the N-terminus region were designed and synthesized. The result suggested that benzene showed better activity than other heterocycles, and the para-substitution on the benzene was beneficial for activity. Moreover, analogs with logP value over 2.0 exhibited good activity, which indicated the hydrophobicity is important to the bioactivity. Three dimension quantitative structure-activity relationship (3D-QSAR) studies were performed to highlight the structural requirements of ASTanalogs, which demonstrated introduction of bulkier substituents on the N-terminus would increase the activity. Analog II12 (IC₅₀:0.08 ǌmol/L) exhibited similar inhibitory activity to the lead B1, but its synthetic route was simpler than B1. Therefore, II12could be used as a new lead compound for the discovery eco-friendly IGRs.
- Allatostatins,
- Juvenile hormone,
- IGRs,
- AST analogs,
- Synthesis,
- 3D-QSAR
1. [1]
  S.M. Olieff, H.J. Mosson, J.P. Edwards, et al., Int. Pest Control 39(1997) 44-45.
2. [2]
  A.P. Woodhead, B. Stay, S.L. Seidel, M.A. Khan, S.S. Tobe, Proc Natl Acad Sci U.S. A. 86(1989) 5997-6001. doi: 10.1073/pnas.86.15.5997
3. [3]
  L. Vilaplana, J.L. Maestro, M.D. Piulachs, X. Bellés, J. Insect Physiol. 45(1999) 1057-1064. doi: 10.1016/S0022-1910(99)00089-X
4. [4]
  D. Martín, M.D. Piulachs, X. Bellés, Mol. Cell. Endocrinol. 121(1996) 191-196. doi: 10.1016/0303-7207(96)03864-6
5. [5]
  M. Fusé, J.R. Zhang, E. Partridge, et al., Peptides 20(1999) 1285-1293. doi: 10.1016/S0196-9781(99)00133-3
6. [6]
  R.J. Nachman, C.S. Garside, S.S. Tobe, Peptides 20(1999) 23-29. doi: 10.1016/S0196-9781(98)00149-1
7. [7]
  B. Stay, A. P. Woodhead, S. Joshi, et al., Allatostatins, in: J. J. Menn, T. J. Kelly, E. P. Masler (Eds. ), Insect Neuropeptides, American Chemical Society, Washington DC, 1991, pp. 164-176.
8. [8]
  A.S. Ripka, D.H. Rich, Curr. Opin. Chem. Biol. 2(1988) 441-452.
9. [9]
  A. Giannis, F. Rübsam, Peptidomimetics in drug design, in: B. Testa, U. A. Meyer (Eds. ), Advances in Drug Research, Academic Press, San Diego, 1997, pp. 1-78.
10. [10]
  Z.P. Kai, Y. Xie, J. Huang, et al., J. Agric. Food Chem. 59(2011) 2478-2485. doi: 10.1021/jf200085d
11. [11]
  Y. Xie, Z.P. Kai, S.S. Tobe, et al., Peptides 32(2011) 581-586. doi: 10.1016/j.peptides.2010.10.016
12. [12]
  E.G. Brown, J.M. Nuss, Tetrahedron Lett. 38(1997) 8457-8460. doi: 10.1016/S0040-4039(97)10279-9
13. [13]
  L.A. Carpino, Acc. Chem. Res. 20(1987) 401-407. doi: 10.1021/ar00143a003
14. [14]
  W.C. Chan, P.D. White, Fmoc Solid Phase Peptide Synthesis:A Practical Approach, Oxford University Press, New York, 2000.
15. [15]
  X.Q. Wu, J. Huang, M.Z. Wang, et al., Chin. Chem. Lett. 27(2016) 559-562. doi: 10.1016/j.cclet.2016.02.010
1. [1]
  Yulong Shi , Fenbei Chen , Mengyuan Wu , Xin Zhang , Runze Meng , Kun Wang , Yan Wang , Yuheng Mei , Qionglu Duan , Yinghong Li , Rongmei Gao , Yuhuan Li , Hongbin Deng , Jiandong Jiang , Yanxiang Wang , Danqing Song . Chemical construction and anti-HCoV-OC43 evaluation of novel 10,12-disubstituted aloperine derivatives as dual cofactor inhibitors of TMPRSS2 and SR-B1. Chinese Chemical Letters, 2024, 35(5): 108792-. doi: 10.1016/j.cclet.2023.108792
2. [2]
  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
3. [3]
  Xinyi Zhang , Kai Ren , Yanning Liu , Zhenyi Gu , Zhixiong Huang , Shuohang Zheng , Xiaotong Wang , Jinzhi Guo , Igor V. Zatovsky , Junming Cao , Xinglong Wu . Progress on Entropy Production Engineering for Electrochemical Catalysis. Acta Physico-Chimica Sinica, 2024, 40(7): 2307057-0. doi: 10.3866/PKU.WHXB202307057
4. [4]
  Lei Feng , Ze-Min Zhu , Ying Yang , Zongbin He , Jiafeng Zou , Man-Bo Li , Yan Zhao , Zhikun Wu . Long-Pursued Structure of Au₂₃(S-Adm)₁₆ and the Unexpected Doping Effects. Acta Physico-Chimica Sinica, 2024, 40(5): 2305029-0. doi: 10.3866/PKU.WHXB202305029
5. [5]
  Ying Chen , Ronghua Yan , Weiyan Yin . Research Progress on the Synthesis of Metal Single-Atom Catalysts and Their Applications in Electrocatalytic Hydrogen Evolution Reactions. University Chemistry, 2025, 40(9): 344-353. doi: 10.12461/PKU.DXHX202503066
6. [6]
  Jiaming Xu , Yu Xiang , Weisheng Lin , Zhiwei Miao . Research Progress in the Synthesis of Cyclic Organic Compounds Using Bimetallic Relay Catalytic Strategies. University Chemistry, 2024, 39(3): 239-257. doi: 10.3866/PKU.DXHX202309093
7. [7]
  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
8. [8]
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10. [10]
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11. [11]
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12. [12]
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13. [13]
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14. [14]
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15. [15]
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16. [16]
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17. [17]
  Rong-Nan Yi , Wei-Min He . Photocatalytic Minisci-type multicomponent reaction for the synthesis of 1-(halo)alkyl-3-heteroaryl bicyclo[1.1.1]pentanes. Chinese Chemical Letters, 2024, 35(10): 110115-. doi: 10.1016/j.cclet.2024.110115
18. [18]
  Yuexiang Liu , Xiangqiao Yang , Tong Lin , Guantian Yang , Xiaoyong Xu , Bubing Zeng , Zhong Li , Weiping Zhu , Xuhong Qian . Efficient continuous synthesis of 2-[3-(trifluoromethyl)phenyl]malonic acid, a key intermediate of Triflumezopyrim, coupling with esterification-condensation-hydrolysis. Chinese Chemical Letters, 2025, 36(1): 109747-. doi: 10.1016/j.cclet.2024.109747
19. [19]
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20. [20]
  Huimin Luan , Qinming Wu , Jianping Wu , Xiangju Meng , Feng-Shou Xiao . Templates for the synthesis of zeolites. Chinese Journal of Structural Chemistry, 2024, 43(4): 100252-100252. doi: 10.1016/j.cjsc.2024.100252

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