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(Synonyms: A-(4-吡啶基-1-氧)-N-叔丁基硝基酮,4-POBN) 目录号 : GC44666

A spin trap

POBN Chemical Structure

Cas No.:66893-81-0

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Sample solution is provided at 25 µL, 10mM.

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产品描述

POBN is a cell permeable, hydrophilic spin trap that can be used to detect free radical adducts in in vitro studies. It is a water soluble analog of N-tert-butyl-α-phenylnitrone .

Chemical Properties

Cas No. 66893-81-0 SDF
别名 A-(4-吡啶基-1-氧)-N-叔丁基硝基酮,4-POBN
Canonical SMILES [O-][N+]1=CC=C(/C=[N+]([O-])/C(C)(C)C)C=C1
分子式 C10H14N2O2 分子量 194.2
溶解度 DMF: 30 mg/mL,DMSO: 25 mg/mL,Ethanol: 30 mg/mL,PBS (pH 7.2): 1 mg/mL 储存条件 Store at -20°C
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储备液的保存方式和期限:-80°C 储存时,请在 6 个月内使用,-20°C 储存时,请在 1 个月内使用。
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Shipping Condition 评估样品解决方案:配备蓝冰进行发货。所有其他可用尺寸:配备RT,或根据请求配备蓝冰。

溶解性数据

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1 mg 5 mg 10 mg
1 mM 5.1493 mL 25.7467 mL 51.4933 mL
5 mM 1.0299 mL 5.1493 mL 10.2987 mL
10 mM 0.5149 mL 2.5747 mL 5.1493 mL
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Research Update

Spin trapping agents (Tempol and POBN) protect HepG2 cells overexpressing CYP2E1 against arachidonic acid toxicity

Free Radic Biol Med 2001 Apr 1;30(7):734-46.PMID:11275473DOI:10.1016/s0891-5849(01)00461-0.

Polyunsaturated fatty acids such as arachidonic acid were previously shown to be toxic to HepG2 cells expressing CYP2E1 by a mechanism involving oxidative stress and lipid peroxidation. This study investigated the effects of the spin trapping agents Tempol and POBN on the arachidonic acid toxicity. Arachidonic acid caused toxicity and induced lipid peroxidation and mitochondrial membrane damage in cells overexpressing CYP2E1 but had little or no effect in control cells not expressing CYP2E1. The toxicity appeared to be both apoptotic and necrotic in nature. 4-Hydroxy-[2,2,6,6-tetramethylpiperidine-1-oxyl] (Tempol) and alpha-(4-pyridyl-1-oxide)-N-tert-butyl nitrone (POBN) protected against the decrease in cell viability and the apoptosis and necrosis. These spin traps prevented the enhanced lipid peroxidation and the loss of mitochondrial membrane potential. Tempol and POBN had little or no effect on cellular viability or on CYP2E1 activity at concentrations which were protective. It is proposed that elevated production of reactive oxygen intermediates by cells expressing CYP2E1 can cause lipid peroxidation, which subsequently damages the mitochondrial membrane leading to a loss in cell viability when the cells are enriched with arachidonic acid. Tempol and POBN, which scavenge various radical intermediates, prevent in this way the enhanced lipid peroxidation, mitochondrial dysfunction, and the cell toxicity. Since oxidative stress appears to play a key role in ethanol hepatotoxicity, it may be of interest to evaluate whether such spin trapping agents are useful candidates for the prevention or improvement of ethanol-induced liver injury.

ESR and HPLC-EC analysis of ethanol oxidation to 1-hydroxyethyl radical: rapid reduction and quantification of POBN and PBN nitroxides

Free Radic Biol Med 1998 Sep;25(4-5):536-45.PMID:9741590DOI:10.1016/s0891-5849(98)00081-1.

Extensive ESR spin-trapping studies have shown that ethanol is oxidized to 1-hydroxyethyl radical (HER) by rat and deer mice liver microsomal systems. The ESR detection of POBN/HER nitroxide in bile, and formation of antibodies, which recognize HER adducts in alcoholics, suggest that HER is produced in vivo. In liver, where ethanol is primarily metabolized, only traces of PBN/HER nitroxide are documented. One limitation of the ESR spin-trapping technique, however, is that the nitroxides formed in the presence of cellular reductants can be metabolized to the corresponding ESR "silent" hydroxylamines. Ascorbate and NADPH plus liver microsomes were found to reduce rapidly both POBN/HER and PBN/HER nitroxides to their ESR "silent" hydroxylamine derivatives. An HPLC method with electrochemical detection was developed for the detection and quantification of both POBN/HER and PBN/HER nitroxides, as well as their hydroxylamines. Both the diastereomers of the POBN/HER nitroxide and hydroxylamine can be detected, as can both isomers of the PBN/HER nitroxide, and it is estimated that the sensitivity of the HPLC procedure is in the nM range when using EC detection. The hydroxylamines are stable in ethanol, while pH-dependent auto-oxidation occurs in aqueous buffers. Some of the characteristics associated with HER formation by microsomes as detected with ESR (e.g., sensitivity to SOD and catalase, increase after induction of CYP2E1) are reproduced with the HPLC method. By quantification of the POBN/HER hydroxylamine, the NADPH-dependent rates of HER formation by microsomes from pyrazole-treated rats are estimated to be about 1-1.5 nmol HER per min per mg microsomal protein. This rate is less, as compared to the two electron-dependent rate of acetaldehyde formation by these microsomes, about 10-15 nmol per min per mg protein. Thus, at first approximation, the one electron-dependent rate of ethanol oxidation is about 10% the two electron-dependent rate by isolated microsomes. The HPLC procedure can readily detect the POBN/HER and PBN/HER nitroxides and their hydroxylamine derivatives in the same sample and may be of value in detecting HER spin-trapped adducts under biological reducing conditions.

ESR and HPLC-EC analysis of the interaction of hydroxyl radical with DMSO: rapid reduction and quantification of POBN and PBN nitroxides

Anal Chem 1999 Feb 1;71(3):715-21.PMID:9989388DOI:10.1021/ac980657r.

The low stability of hydroxyl radical (OH.)-derived nitroxides is a limiting factor for direct spin-trapping of OH. in biological systems. The latter experimental difficulty is partly solved with the introduction of dimethyl sulfoxide (DMSO) into the studied systems. Hydroxyl radical oxidizes DMSO to methyl radical, which forms relatively stable nitroxides. The results of the present work provide evidence that in alpha-(4-pyridyl-1-oxide)-N-tert-butylnitrone (POBN) and alpha-phenyl-N-tert-butylnitrone (PBN) spin-trapping experiments aimed to detect methyl radical in biological systems, the nitroxides formed can be reduced to their ESR-"silent" hydroxylamine derivatives. The nitroxides and their hydroxylamine derivatives were successfully analyzed by HPLC with electrochemical (EC) and UV detection. The lowest limits of UV and EC detection of POBN/CH3 hydroxylamine was evaluated to be in the micro- and nanomolar range, respectively. In parallel ESR and HPLC-EC analysis of the metabolism of menadione by either HepG2 cells or isolated rat hepatocytes in the presence of DMSO, the HPLC-EC method has proven to be more sensitive in detecting the production of methyl radical. The use of the HPLC-EC detection of POBN/CH3 and PBN/CH3 is expected to be advantageous in detection of hydroxyl radical in biological systems in the presence of DMSO.

Relationship between postoperative bulla neogenesis at the staple line and the resected lung volume in primary spontaneous pneumothorax

Gen Thorac Cardiovasc Surg 2015 Oct;63(10):572-5.PMID:26104239DOI:10.1007/s11748-015-0568-1.

Purpose: In patients with primary spontaneous pneumothorax (PSP), bullae are generally resected using autosutures under video-assisted thoracoscopic surgery (VATS). However, postoperative bulla neogenesis (POBN) along the staple line is not rare and is a factor promoting PSP recurrence. POBN is attributed to tension along the staple line, and we surmise that the resected lung volume affects this tension. Therefore, in this study, we retrospectively examined the relationship between POBN and the resected lung volume in patients who underwent surgical treatment of PSP. Methods: Between February 2011 and May 2015, 70 lung resection sites in 56 PSP patients who underwent primary VATS at our hospital were evaluated. POBN was diagnosed on high-resolution computed tomography 1 year postoperatively in principle. Results: POBN was detected at 26 of 70 (37.1 %) sites. On univariate analysis, lung weight ≥1.5 g, lung length ≥4.0 cm, resected site: apical, age <25 years old and non-smoking habit were identified as significant, and the POBN rates for cases with lung weight ≥1.5 g or lung length ≥4.0 cm were 47.9 % (P = 0.004) and 44.1 % (P < 0.001), respectively. On multivariate analysis, lung weight ≥1.5 g was only significant factor for POBN (P = 0.043). Conclusion: A resected lung weight ≥1.5 g was only significant risk factor of POBN in patients with PSP.

Association between postoperative bulla neogenesis at the staple line and resected lung weight for primary spontaneous pneumothorax: a retrospective study using the inverse-probability of treatment weighted method in patients grouped according to age

J Thorac Dis 2016 Dec;8(12):3676-3681.PMID:28149563DOI:10.21037/jtd.2016.12.14.

Background: Bullectomy using autosutures is the standard procedure in patients with primary spontaneous pneumothorax (PSP). However, postoperative bulla neogenesis (POBN) along the staple line is relatively common and promotes PSP recurrence. We have previously reported the relationship between POBN and resected lung weight (LW). However, recently published data indicate that young patients with PSP have a high postoperative recurrence rate. Therefore, we evaluated the relationship between POBN and LW in PSP patients, subdivided according to age. Methods: Between February 2011 and April 2016, 96 lung-resection sites in 67 patients who underwent bullectomy were evaluated. Patients were subdivided into two groups by age: Y group (<25 years, 56 sites) and O group (≥25 years, 40 sites). We used the inverse-probability of treatment weighted (IPTW) method to adjust for the heterogeneity in their backgrounds. POBN was diagnosed by computed tomography. Results: Cox regression analysis for the O group indicated that LW ≥3.0 g was a significant risk factor for POBN (P=0.049). For the Y group, no association between lung weight and POBN was observed. Conclusions: A LW ≥3.0 g is a significant risk factor for POBN in individuals aged ≥25 years.