Sulfonyl-acetohydrazide derivatives as juvenile hormone mimics to be insect growth regulators

IF 4.5 2区 医学 Q1 BIOCHEMISTRY & MOLECULAR BIOLOGY Bioorganic Chemistry Pub Date : 2024-09-05 DOI:10.1016/j.bioorg.2024.107781
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Abstract

The need for targeted pest control strategies has led to the development of juvenile hormone (JH) mimics that selectively disrupt the life cycles of harmful insect species. Present study focuses on the synthesis, characterization and evaluation of sulfonyl-acetohydrazide derivatives (H1-H8) as novel JH mimics on two different insect species, with an emphasis on their insect-specific action. The yellow fever mosquito, Aedes aegypti and cabbage leaf borer, Spodoptera litura, were selected for this investigation. Our results indicate that while these compounds exhibit negligible effects on the development of Aedes aegypti, they demonstrate a potent and specific action against Spodoptera litura. The sulfonyl-acetohydrazide derivatives induced significant developmental abnormalities and increased mortality rates in Spodoptera litura larvae, leading to a marked disruption in their life cycle. Additionally, Density Functional Theory methods were employed to elucidate the electronic structure and corelate the reactivity of the synthesized compounds with the insect growth regulating activity (IGR). The DNA-binding study of synthesized JH analogs has been carried out using UV–vis spectroscopy for toxicity assessment against biomolecule DNA. All the synthesized JH analogs (H1-H8) show IGR action and exhibit better reactivity and reduced toxicity as compared to the commercial in use IGR, pyriproxyfen.

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磺酰-乙酰肼衍生物作为昆虫生长调节剂的幼虫激素模拟物
由于需要采取有针对性的害虫控制策略,因此开发了能选择性地破坏有害昆虫物种生命周期的幼虫激素(JH)模拟物。本研究的重点是磺酰基乙酰肼衍生物(H1-H8)的合成、表征和评估,这些衍生物作为新型的 JH 模拟物可用于两种不同的昆虫物种,重点是它们对昆虫的特异性作用。这项研究选择了黄热病蚊子埃及伊蚊和卷心菜卷叶螟。我们的研究结果表明,虽然这些化合物对埃及伊蚊的发育影响微乎其微,但它们对鳞翅目卷叶螟却具有强大的特异性作用。磺酰乙酰肼衍生物会诱导鞘翅目幼虫出现明显的发育异常,并增加其死亡率,导致其生命周期明显中断。此外,还采用密度泛函理论方法阐明了合成化合物的电子结构,并将其反应活性与昆虫生长调节活性(IGR)联系起来。利用紫外可见光谱对合成的 JH 类似物进行了 DNA 结合研究,以评估其对生物大分子 DNA 的毒性。所有合成的 JH 类似物(H1-H8)都具有 IGR 作用,与商用 IGR 吡丙醚相比,反应性更好,毒性更低。
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来源期刊
Bioorganic Chemistry
Bioorganic Chemistry 生物-生化与分子生物学
CiteScore
9.70
自引率
3.90%
发文量
679
审稿时长
31 days
期刊介绍: Bioorganic Chemistry publishes research that addresses biological questions at the molecular level, using organic chemistry and principles of physical organic chemistry. The scope of the journal covers a range of topics at the organic chemistry-biology interface, including: enzyme catalysis, biotransformation and enzyme inhibition; nucleic acids chemistry; medicinal chemistry; natural product chemistry, natural product synthesis and natural product biosynthesis; antimicrobial agents; lipid and peptide chemistry; biophysical chemistry; biological probes; bio-orthogonal chemistry and biomimetic chemistry. For manuscripts dealing with synthetic bioactive compounds, the Journal requires that the molecular target of the compounds described must be known, and must be demonstrated experimentally in the manuscript. For studies involving natural products, if the molecular target is unknown, some data beyond simple cell-based toxicity studies to provide insight into the mechanism of action is required. Studies supported by molecular docking are welcome, but must be supported by experimental data. The Journal does not consider manuscripts that are purely theoretical or computational in nature. The Journal publishes regular articles, short communications and reviews. Reviews are normally invited by Editors or Editorial Board members. Authors of unsolicited reviews should first contact an Editor or Editorial Board member to determine whether the proposed article is within the scope of the Journal.
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