Flupyrimin
目录号 : GC64394Flupyrimin 是昆虫烟碱乙酰胆碱受体 (nAChR) 的拮抗剂。
Cas No.:1689566-03-7
Sample solution is provided at 25 µL, 10mM.
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Flupyrimin acts as an antagonist at the insect nicotinic acetylcholine receptor (nAChR)[1].
[1]. Terajima T, et al. Deciphering the Flupyrimin Binding Surface on the Insect Nicotinic Acetylcholine Receptor. J Agric Food Chem. 2021;69(33):9551-9556.
Cas No. | 1689566-03-7 | SDF | Download SDF |
分子式 | C13H9ClF3N3O | 分子量 | 315.68 |
溶解度 | DMSO : 250 mg/mL (791.94 mM; Need ultrasonic) | 储存条件 | Store at -20°C |
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1 mg | 5 mg | 10 mg | |
1 mM | 3.1678 mL | 15.8388 mL | 31.6776 mL |
5 mM | 0.6336 mL | 3.1678 mL | 6.3355 mL |
10 mM | 0.3168 mL | 1.5839 mL | 3.1678 mL |
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Comparison of the interactions of Flupyrimin and nitenpyram with serum albumins via multiple analysis methods
Chemosphere 2022 Feb;289:133139.PMID:34863729DOI:10.1016/j.chemosphere.2021.133139.
Flupyrimin and nitenpyram are emerging neonicotinoid insecticides that may cause potential harm to the human body. In the present work, the interactions of Flupyrimin/nitenpyram with serum albumins under normal physiological conditions were thoroughly studied by using multiple spectroscopic techniques, DFT calculations and molecular docking. Flupyrimin/nitenpyram can quench the endogenous fluorescence of HSA/BSA and form a complex with HSA/BSA through a static process, causing conformational and secondary structure changes of HSA/BSA. Thermodynamic analysis shows that the combination of Flupyrimin/nitenpyram with HSA/BSA is a spontaneous process, mainly driven by hydrogen bonds and hydrophobic forces. Site marking and molecular docking experiments indicated that Flupyrimin/nitenpyram binds with HSA/BSA at site II (subdomain IIIA). The binding constant Ka in HSA-flupyrimin, HSA-nitenpyram, BSA-flupyrimin and BSA-nitenpyram systems at 298 K was 2.11 × 105 M-1, 2.35 × 105 M-1, 1.91 × 105 M-1 and 2.11 × 105 M-1, respectively. The binding constant Ka of nitenpyram with HSA/BSA was greater than Flupyrimin, indicating that nitenpyram binds HSA/BSA was more stable than that of Flupyrimin, which was consistent with the DFT calculation. In addition, the acute toxicity bioassay showed that Flupyrimin and nitenpyram exhibited low toxicity to zebrafish, with 96 h LC50 values of 181.662 and 250.658 mg a. i. L-1, respectively. These results can help understand the interactions of Flupyrimin/nitenpyram with HSA/BSA.
Deciphering the Flupyrimin Binding Surface on the Insect Nicotinic Acetylcholine Receptor
J Agric Food Chem 2021 Aug 25;69(33):9551-9556.PMID:34374535DOI:10.1021/acs.jafc.1c03241.
A novel insecticide Flupyrimin (FLP) with a trifluoroacetyl pharmacophore acts as an antagonist at the insect nicotinic acetylcholine receptor (nAChR). This investigation examines a hypothesis that the FLP C(O)CF3 moiety is primarily recognized by the β subunit-face in the ligand-binding pocket (interface between α and β subunits) of the insect nAChR. Accordingly, we evaluate the atomic interaction between a fluorine atom of FLP and the partnering amino acid side chain on the β subunit employing a recombinant hybrid nAChR consisting of aphid Mpα2 and rat Rβ2 subunits (with a mutation at T77 on the Rβ2). The H-donating T77R, T77K, T77N, or T77Q nAChR enhances the FLP binding potency relative to that of the wild-type receptor, whereas the affinity of neonicotinoid imidaclprid (IMI) with a nitroguanidine pharmacophore remains unchanged. These results facilitate the establishment of the unique FLP molecular recognition at the Mpα2/Mpβ1 interface structural model, thereby underscoring a distinction in its binding mechanism from IMI.
Flupyrimin: A Novel Insecticide Acting at the Nicotinic Acetylcholine Receptors
J Agric Food Chem 2017 Sep 13;65(36):7865-7873.PMID:28820587DOI:10.1021/acs.jafc.7b02924.
A novel chemotype insecticide Flupyrimin (FLP) [N-[(E)-1-(6-chloro-3-pyridinylmethyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetamide], discovered by Meiji Seika Pharma, has unique biological properties, including outstanding potency to imidacloprid (IMI)-resistant rice pests together with superior safety toward pollinators. Intriguingly, FLP acts as a nicotinic antagonist in American cockroach neurons, and [3H]FLP binds to the multiple high-affinity binding components in house fly nicotinic acetylcholine (ACh) receptor (nAChR) preparation. One of the [3H]FLP receptors is identical to the IMI receptor, and the alternative is IMI-insensitive subtype. Furthermore, FLP is favorably safe to rats as predicted by the very low affinity to the rat α4β2 nAChR. Structure-activity relationships of FLP analogues in terms of receptor potency, featuring the pyridinylidene and trifluoroacetyl pharmacophores, were examined, thereby establishing the FLP molecular recognition at the Aplysia californica ACh-binding protein, a suitable structural surrogate of the insect nAChR. These FLP pharmacophores account for the excellent receptor affinity, accordingly revealing differences in its binding mechanism from IMI.
Design, Synthesis and Bioactivity of Novel Low Bee-Toxicity Compounds Based on Flupyrimin
Molecules 2022 Sep 19;27(18):6133.PMID:36144866DOI:10.3390/molecules27186133.
Neonicotinoids are important insecticides for controlling aphids in agriculture. Growing research suggested that neonicotinoid insecticides are a key factor causing the decline of global pollinator insects, such as bees. Flupyrimin (FLP) is a novel nicotinic insecticide with unique biological properties and no cross-resistance, and is safe for pollinators. Using FLP as the lead compound, a series of novel compounds were designed and synthesized by replacing the amide fragment with a sulfonamideone. Their structures were confirmed by 1H NMR, 13C NMR and HRMS spectra. Bioassay results showed that compound 2j had good insecticidal activity against Aphis glycines with an LC50 value of 20.93 mg/L. Meanwhile, compound 2j showed significantly lower acute oral and contact toxicity to Apis mellifera. In addition, compound 2j interacted well with the protein in insect acetylcholine binding protein (AChBP). The molecular docking on honeybee nicotinic acetylcholine receptor (nAChR) indicated that the sulfonamide group of compound 2j did not form a hydrogen bond with Arg173 of the β subunit, which conforms to the reported low bee-toxicity conformation. In general, target compound 2j can be regarded as a bee-friendly insecticide candidate.
Design, synthesis, and insecticidal activity of a novel series of Flupyrimin analogs bearing 1-aryl-1H-pyrazol-4-yl subunits
Front Chem 2022 Oct 3;10:1019573.PMID:36262338DOI:10.3389/fchem.2022.1019573.
To discover new potential insecticides to protect agricultural crops from damage, a series of novel Flupyrimin derivatives containing an arylpyrazole core were designed and synthesized. Their structures were confirmed by 1H NMR, 13C NMR, and HRMS. Bioassays indicated that the 31 compounds synthesized possessed excellent insecticidal activity against Plutella xylostella. Among these target compounds, the lethality of A3, B1-B6, D4, and D6 reached 100% at 400 μg/ml. Moreover, when the concentration dropped to 25 μg/ml, the insecticidal activities against the Plutella xylostella for compounds B2, B3, and B4 still reached more than 70%. The structure-activity relationship of the Plutella xylostella was discussed. The density functional theory analysis of Flupyrimin and B4 was carried out to support the abovementioned structure-activity relationship. The possible binding modes between receptor and active groups in title compounds were also verified by docking simulation. These results provided new ideas for the development of these novel candidate insecticides in the future.