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Nifurpirinol

(Synonyms: P-7138) 目录号 : GC68471

Nifurpirinol (P-7138) 是一种硝基芳香抗生素 (Antibiotic),是细菌硝基还原酶 (NTR) 的底物。与甲硝唑相比,Nifurpirinol 是一种更有效的 prodrug,可在表达硝基还原酶的转基因模型中诱导细胞消融。

Nifurpirinol Chemical Structure

Cas No.:13411-16-0

规格 价格 库存 购买数量
5mg
¥1,350.00
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10mg
¥2,250.00
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25mg
¥4,500.00
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50mg
¥7,020.00
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100mg
¥10,350.00
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产品描述

IC50: bacterial nitroreductase (NTR) enzyme[1]

Nifurpirinol (P-7138) is a nitroaromatic Antibiotic and acts as a novel substrate for the bacterial nitroreductase (NTR) enzyme. Nifurpirinol is a more potent prodrug compared to Metronidazole to trigger cell-ablation in nitroreductase expressing transgenic models[1].

[1]. David Bergemann, et al. Nifurpirinol: A more potent and reliable substrate compared to metronidazole for nitroreductase-mediated cell ablations. Wound Repair Regen

Chemical Properties

Cas No. 13411-16-0 SDF Download SDF
别名 P-7138
分子式 C12H10N2O4 分子量 246.22
溶解度 DMSO : ≥ 20.83 mg/mL (84.60 mM) 储存条件 Store at -20°C
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1 mg 5 mg 10 mg
1 mM 4.0614 mL 20.307 mL 40.6141 mL
5 mM 0.8123 mL 4.0614 mL 8.1228 mL
10 mM 0.4061 mL 2.0307 mL 4.0614 mL
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Research Update

Nifurpirinol: A more potent and reliable substrate compared to metronidazole for nitroreductase-mediated cell ablations

Wound Repair Regen 2018 Mar;26(2):238-244.PMID:29663654DOI:10.1111/wrr.12633.

The zebrafish is a popular animal model with well-known regenerative capabilities. To study regeneration in this fish, the nitroreductase/metronidazole-mediated system is widely used for targeted ablation of various cell types. Nevertheless, we highlight here some variability in ablation efficiencies with the metronidazole prodrug that led us to search for a more efficient and reliable compound. Herein, we present Nifurpirinol, another nitroaromatic antibiotic, as a more potent prodrug compared to metronidazole to trigger cell-ablation in nitroreductase expressing transgenic models. We show that Nifurpirinol induces robust and reliable ablations at concentrations 2,000 fold lower than metronidazole and three times below its own toxic concentration. We confirmed the efficiency of Nifurpirinol in triggering massive ablation of three different cell types: the pancreatic beta cells, osteoblasts, and dopaminergic neurons. Our results identify Nifurpirinol as a very potent prodrug for the nitroreductase-mediated ablation system and suggest that its use could be extended to many other cell types, especially if difficult to ablate, or when combined pharmacological treatments are desired.

Mutagenicity of Nifurpirinol (P-7138) in Escherichia coli WP2 and Salmonella typhimurium TA100

Mutat Res 1982 Apr;104(1-3):61-6.PMID:7043255DOI:10.1016/0165-7992(82)90121-x.

Nifurpirinol, 6-hydroxymethyl-2-[2-(5-nitro-2-furyl)vinyl]pyridine, which has been widely used as an antibacterial drug against diseases of fish, was found to be a potent mutagen. The mutagenic effect was dose-related, and the potencies were calculated to be 1.49 X 10(3), 7.24 X 10(4) and 8.49 X 10(5) revertants/1 X 10(-8) survivors at the concentration of 1 microgram/ml to :Escherichia coli B/r WP2, E. coli B/r WP2 hcr- and Salmonella typhimurium TA100, respectively, without metabolic activation. Nifurpirinol is susceptible to photodegradation, and its mutagenic activity to S. typhimurium TA100 was decreased to about one thousandth when the solution of Nifurpirinol was exposed to sunlight at room temperature for 4 h.

Collagen fibers provide guidance cues for capillary regrowth during regenerative angiogenesis in zebrafish

Sci Rep 2021 Sep 30;11(1):19520.PMID:34593884DOI:10.1038/s41598-021-98852-6.

Although well investigated, the importance of collagen fibers in supporting angiogenesis is not well understood. In this study, we demonstrate that extracellular collagen fibers provide guidance cues for endothelial cell migration during regenerative angiogenesis in the caudal zebrafish fin. Inhibition of collagen cross-linking by β-Aminopropionitrile results in a 70% shorter regeneration area with 50% reduced vessel growth and disintegrated collagen fibers. The disrupted collagen scaffold impedes endothelial cell migration and induces formation of abnormal angioma-like blood vessels. Treatment of the Fli//colRN zebrafish line with the prodrug Nifurpirinol, which selectively damages the active collagen-producing 1α2 cells, reduced the regeneration area and vascular growth by 50% with wider, but less inter-connected, capillary segments. The regenerated area contained larger vessels partially covered by endothelial cells embedded in atypical extracellular matrix containing cell debris and apoptotic bodies, macrophages and granulocytes. Similar experiments performed in early embryonic zebrafish suggested that collagens are important also during embryonic angiogenesis. In vitro assays revealed that collagen I allows for the most efficient endothelial cell migration, followed by collagen IV relative to the complete absence of exogenous matrix support. Our data demonstrates severe vascular defects and restricted fin regeneration when collagens are impaired. Collagen I therefore, provides support and guidance for endothelial cell migration while collagen IV is responsible for proper lumen formation and vascular integrity.

Stakeholder position paper: aquaculture producer

Prev Vet Med 2006 Feb 24;73(2-3):197-202.PMID:16289382DOI:10.1016/j.prevetmed.2005.09.013.

The use of antimicrobials in domestic aquaculture is limited. There are only two approved and available antimicrobials for food fish (Terramycin for Fish) and Romet-30 and one approved for ornamental fish (Nifurpirinol). These antimicrobials are only approved to treat specific diseases in specific aquatic animal species. Antimicrobial use data, as well as environmental fate information and analysis of barriers to transmission, are valuable for assessing qualitative or quantitative risk. In the US, the limited availability of antimicrobials and use in aquaculture suggests the best quantitative source of antimicrobial use information is directly from drug manufacturers.

Development of a multi-class method to determine nitroimidazoles, nitrofurans, pharmacologically active dyes and chloramphenicol in aquaculture products by liquid chromatography-tandem mass spectrometry

Food Chem 2020 May 1;311:125924.PMID:31865112DOI:10.1016/j.foodchem.2019.125924.

LC-MS/MS method was developed for the efficient identification and quantification of 21 banned substances including various nitroimidazoles, nitrofurans, pharmacologically-active dyes and chloramphenicol, respectively in aquaculture products. The sample preparation was started by acid-treatment with 2-nitrobenzaldehyde (NBA) to liberate matrix-bound residues of nitrofurans. A modified QuEChERS method was optimized for the extraction and clean-up of the target analytes. The metabolites of the four conventional nitrofurans (nitrofurantoin, furazolidone, nitrofurazone and furaltadone) and of three other nitrofurans (nifursol, nifuroxazide, and nitrovin), and an underivatizable nitrofuran (Nifurpirinol) were simultaneously detected. Furthermore, 21 banned substances were quantified by LC-MS/MS with ESI using one single injection. To evaluate and validate the performance of the method, the criteria of the Decision (EC) no 2002/657 were applied. Decision limit (CCα) of target analytes ranged 0.067-1.655 μg/kg in aquaculture products. The recovery ranged 77.2%-125.6%, and the relative standard deviations of inter-day analyses (RSD) were less than 25%.