A potential insect growth regulator for cockroach control: design, synthesis and bioactivity of N‐terminal‐modified allatostatin analogues

Wu, Xiaoqing; Wang, Meizi; Huang, Juan; Zhang, Li; Zhang, Zhe; Ling, Yun; Yang, Xinling; Tobe, Stephen S.

doi:10.1002/ps.4444

Cited by 7 publications

(9 citation statements)

References 26 publications

(57 reference statements)

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“…Briefly, Leu-Rink amide-AM was prepared from Rink Amide-AM resin using the standard Fmoc/tBu chemistry and HBTU/HOBt protocol. 24 Then, to replace amino acids protected by Fmoc (containing an R group) and (E)-3-(4-nitrophenyl)-acrylic acid in turn, Fmoc-Gly-OH and Fmoc-Phe-OH were activated with HBTU, HOBt, and N,N-diisopropylethylamine (DIEA) in dimethylformamide (DMF) for 5 min. Fmoc-Gly-OH and Fmoc-Phe-OH replacing amino acids protected by Fmoc (containing an R group) and (E)-3-(4-nitrophenyl)-acrylic acid were activated in turn with HBTU, HOBt, and N,N-diisopropylethylamine (DIEA) in dimethylformamide (DMF) for 5 min, and couplings were run for 4 h at room temperature.…”

Section: Structural Analysis Of the Modeled Dippu-astrmentioning

confidence: 99%

“…5 H17 was therefore considered a lead compound for further exploration of IGRs, and several H17 analogs were found to have good JHinhibiting activity as well as Dippu-AstR binding activity. 19,24 In this study, to find highly active IGRs that disturb JH biosynthesis, the 3D structure of Dippu-AstR was first modeled and qualified using RoseTTAFold (http://robetta.bakerlab. org/) and Structure Analysis and Verification Server (SAVES) (http://services.mbi.ucla.edu/SAVES/).…”

Section: ■ Introductionmentioning

confidence: 99%

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A Novel Peptidomimetic Insecticide: Dippu-AstR-Based Rational Design and Biological Activity of Allatostatin Analogs

Zhang,

Liu,

et al. 2024

J. Agric. Food Chem.

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Insect neuropeptides play an essential role in regulating growth, development, reproduction, nerve conduction, metabolism, and behavior in insects; therefore, G protein-coupled receptors of neuropeptides are considered important targets for designing green insecticides. Cockroach-type allatostatins (ASTs) (FGLamides allatostatins) are important insect neuropeptides in Diploptera punctata that inhibit juvenile hormone (JH) synthesis in the corpora allata and affect growth, development, and reproduction of insects. Therefore, the pursuit of novel insecticides targeting the allatostatin receptor (AstR) holds significant importance. Previously, we identified an AST analogue, H17, as a promising candidate for pest control. Herein, we first modeled the 3D structure of AstR in D. punctata (Dippu-AstR) and predicted the binding mode of H17 with Dippu-AstR to study the critical interactions and residues favorable to its bioactivity. Based on this binding mode, we designed and synthesized a series of H17 derivatives and assessed their insecticidal activity against D. punctata. Among them, compound Q6 showed higher insecticidal activity than H17 against D. punctata by inhibiting JH biosynthesis, indicating that Q6 is a potential candidate for a novel insect growth regulator (IGR)-based insecticide. Moreover, Q6 exhibited insecticidal activity against Plutella xylostella, indicating that these AST analogs may have a wider insecticidal spectrum. The underlying mechanisms and molecular conformations mediating the interactions of Q6 with Dippu-AstR were explored to understand its effects on the bioactivity. The present work clarifies how a target-based strategy facilitates the discovery of new peptide mimics with better bioactivity, enabling improved IGR-based insecticide potency in sustainable agriculture.

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Section: Structural Analysis Of the Modeled Dippu-astrmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

A Novel Peptidomimetic Insecticide: Dippu-AstR-Based Rational Design and Biological Activity of Allatostatin Analogs

Zhang,

Liu,

et al. 2024

J. Agric. Food Chem.

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“…Using the H17, as the lead compound, Xie et al (2016) designed new AST analogues which exhibited strong potency to inhibit JH production by CA of D. punctata. Recently, Wu et al (2017) designed and synthesized 30 analogues, modified with various substituents on the benzene ring at the N-terminus of the lead compound H17. Depending on their results, all analogues exhibited various effects on JH biosynthesis by CA of D. punctata.…”

Section: Fgl-amide Allatostatinsmentioning

confidence: 99%

“…Although the discovery of the first AST almost forty years ago, the exact mode(s) of action is still unknown or remains poorly understood (Weaver and Audsley, 2009;Stay and Tobe, 2007;Chowański et al, 2016). However, the AST compound H17, as well as Ketomethylene, methyleneamino and Dippu-AST (pseudopeptide analogues of ASTs) had been reported as potent inhibitors of JH biosynthesis in some insects (Nachman et al, 1999;Garside et al, 2000;Bendena and Tobe, 2012;Wu et al, 2017). According to the current literature, Nouzova et al (2015) carried out a study aiming to understand the mode of AST compounds in Aedes aegypti.…”

Section: Mode Of Action Of Fgl-amide Allatostatinsmentioning

confidence: 99%

Physiological Activities of Anti-Juvenile Hormone Agents Against Insects and Their Role For Devising Fourth Generation Insecticides: A Comprehensive Review

Ghoneim

Bakr

2018

Egyptian Academic Journal of Biological Sciences. A, Entomology

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“…In previous studies, approximately 200 FGLamide AST analogues were synthesized by Yang’s group with the C-terminal pentapeptide as the lead compound. − Their results suggested that an aromatic group, a linker of an appropriate length, and an FGLa moiety should appear in bioactive AST analogues. The subsequent study showed an alteration of the peptide backbone.…”

Section: Introductionmentioning

confidence: 99%

Structure-Based Discovery of Nonpeptide Allatostatin Analogues for Pest Control

Huang

Chen

Zhang

et al. 2018

J. Agric. Food Chem.

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FGLamide allatostatins (ASTs) are regarded as possible insecticide candidates, although their lack of in vivo effects, rapid degradation, poor water solubility, and high production costs preclude their practical use in pest control. In contrast to previous research, the C-terminal tripeptide (FGLa) was selected as the lead compound in this study. Five nonpeptide AST analogues (2-amino-1-[3-oxo-3-(substituted-anilino)propyl]pyridinium nitrate derivatives) were designed on the basis of the structure-activity relationship and docking results of FGLa. All of the nonpeptide analogues (S1-S5) were more potent against juvenile-hormone (JH) biosynthesis than the lead compound. They significantly inhibited the biosynthesis of JH in vivo following injection. A pest-control application demonstrated that S1 and S3 have larvicidal effects following oral administration (the IC values were 0.020 and 0.0016 mg/g, respectively). The good oral toxicities and excellent water solubilities of S1 and S3 suggest that they have considerable potential as insecticides for pest management.

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A potential insect growth regulator for cockroach control: design, synthesis and bioactivity of N‐terminal‐modified allatostatin analogues

Cited by 7 publications

References 26 publications

A Novel Peptidomimetic Insecticide: Dippu-AstR-Based Rational Design and Biological Activity of Allatostatin Analogs

A Novel Peptidomimetic Insecticide: Dippu-AstR-Based Rational Design and Biological Activity of Allatostatin Analogs

Physiological Activities of Anti-Juvenile Hormone Agents Against Insects and Their Role For Devising Fourth Generation Insecticides: A Comprehensive Review

Structure-Based Discovery of Nonpeptide Allatostatin Analogues for Pest Control

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