EMPO
(Synonyms: 5-(Ethoxycarbonyl)-5-methyl-1-Pyrroline-N-Oxide) 目录号 : GC41290A free radical spin trap
Cas No.:61856-99-3
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
EMPO is a hydrophilic cyclic nitrone analog of the free radical spin trap DMPO . The EMPO-superoxide adduct (EMPO-OOH) exhibits an ESR spectrum that is similar to the DMPO-OOH spectrum. [1] However, the EMPO-OOH adduct is about 5-8 times more stable (t1/2 = 4.8 - 8.6 min) and does not spontaneously decay to the hydroxyl adduct, making spectral interpretation less difficult. [1][2][3]
Reference:
[1]. Olive, G., Mercier, A., Le Moigne, F., et al. 2-ethoxycarbonyl-2-methyl-3,4-dihydro-2H-pyrrole-1-oxide: evaluation of the spin trapping properties. Free Radic. Biol. Med. 28(3), 403-408 (2000).
[2]. Stolze, K., Udilova, N., and Nohl, H. Spin adducts of superoxide, alkoxyl, and lipid-derived radicals with EMPO and its derivatives. Biol. Chem. 383(5), 813-820 (2002).
[3]. Zhang, H., Joseph, J., Vasquez-Vivar, J., et al. Detection of superoxide anion using an isotopically labeled nitrone spin trap: Potential biological applications. FEBS Lett. 473(1), 58-62 (2000).
| Cas No. | 61856-99-3 | SDF | |
| 别名 | 5-(Ethoxycarbonyl)-5-methyl-1-Pyrroline-N-Oxide | ||
| 化学名 | 3,4-dihydro-2-methyl-2H-pyrrole-2-carboxylic acid 1-oxide, ethyl ester | ||
| Canonical SMILES | [O-][N+]1=CCCC1(C)C(OCC)=O | ||
| 分子式 | C8H13NO3 | 分子量 | 171.2 |
| 溶解度 | 15 mg/ml in DMSO, 30 mg/ml in DMF, 30 mg/ml in Ethanol | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 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。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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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。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 5.8411 mL | 29.2056 mL | 58.4112 mL |
| 5 mM | 1.1682 mL | 5.8411 mL | 11.6822 mL |
| 10 mM | 0.5841 mL | 2.9206 mL | 5.8411 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Spin adducts of superoxide, alkoxyl, and lipid-derived radicals with EMPO and its derivatives
Biol Chem 2002 May;383(5):813-20.PMID:12108546DOI:10.1515/BC.2002.085.
The compound 5-(ethoxycarbonyl)-5-methyl-1-pyrroline N-oxide (EMPO) is a hydrophilic cyclic nitrone spin trap, which, in contrast to DMPO, forms a relatively stable superoxide adduct (t(1/2)=8.6 min) with an EPR spectrum similar to the respective DMPO adduct. In order to find the optimal degree of lipophilicity of this novel type of spin trap with respect to the detection of radicals formed during lipid peroxidation, the ethoxy group of EMPO was replaced by alkoxy substituents of increasing chain length, leading to the methoxy- (MeMPO), 1-propoxy- (PrMPO), 1-butoxy- (BuMPO), and 1-octyloxy- (OcMPO) derivatives of EMPO. The stability of their superoxide adducts was found to be strongly dependent on the size of the alkoxycarbonyl group. Increasing chain length of the alkoxyl substituent decreased the stability of alkoxyl radical adducts of MeMPO, EMPO, and PrMPO, but increased the stability of OcMPO adducts. The stability of alkoxyl radical adducts of BuMPO, on the other hand, were practically independent of the size of the alkoxyl group. Detection of lipid alkoxyl radicals formed by peroxidizing linoleic acid in a stationary system was therefore only possible with the most lipophilic spin trap, OcMPO. However, with the more hydrophilic spin traps MeMPO, EMPO, PrMPO, and BuMPO optimal EPR signal intensity could be obtained when a slow-flow system was used. Thus, within this series EMPO is the best spin trap for the detection of superoxide; OcMPO, on the other hand, is most suitable for the detection of lipid alkoxyl radicals.
Harm reduction for young people who use prescription opioids extra-medically: Obstacles and opportunities
Int J Drug Policy 2016 May;31:25-31.PMID:26919826DOI:10.1016/j.drugpo.2016.01.022.
Extra-medical prescription opioid (EMPO) use - intentional use without a prescription or outside of prescribed parameters - is a public health crisis in the United States and around the world. Epidemiological evidence suggests that the prevalence of EMPO use and adverse sequelae, including opioid overdose and hepatitis C infection, are elevated among people aged 18-25. Despite these preventable health risks, many harm reduction interventions are underutilized by, or inaccessible to, EMPO-using youth. In this commentary, we describe key harm reduction strategies for young people who use prescription opioids. We examine individual, social, and policy-level barriers to the implementation of evidence-based approaches that address EMPO use and related harms among young people. We highlight the need for expanded services and new interventions to engage this diverse and heterogeneous at-risk population. A combination of medical, social, and structural harm reduction interventions are recommended. Furthermore, research to inform strategies that mitigate particularly high-risk practices (e.g., polysubstance use) is warranted. Finally, we discuss how the meaningful involvement of youth in the implementation of harm reduction strategies is a critical component of the public health response to the prescription opioid epidemic.
Inclusion complexes of EMPO derivatives with 2,6-di-O-methyl-beta-cyclodextrin: synthesis, NMR and EPR investigations for enhanced superoxide detection
Org Biomol Chem 2006 Aug 7;4(15):2874-82.PMID:16855735DOI:10.1039/b606062e.
The free radical trapping properties of eight 5-alkoxycarbonyl-5-methyl-1-pyrroline N-oxide (EMPO) type nitrones and those of 5,5-dimethyl-1-pyrroline N-oxide (DMPO) were evaluated for trapping of superoxide anion radicals in the presence of 2,6-di-O-methyl-beta-cyclodextrin (DM-beta-CD). (1)H-NMR titrations were performed to determine both stoichiometries and binding constants for the diamagnetic nitrone-DM-beta-CD equilibria. EPR titrations were then performed and analyzed using a two-dimensional EPR simulation program affording 1 : 1 and 1 : 2 stoichiometries for the nitroxide spin adducts with DM-beta-CD and the associated binding constants after spin trapping. The nitroxide spin adducts associate more strongly with DM-beta-CD than the nitrones. The ability of the nitrones to trap superoxide, the enhancement of the EPR signal intensity and the supramolecular protection by DM-beta-CD against sodium L-ascorbate reduction were evaluated.
Synthesis and characterization of EMPO-derived 5,5-disubstituted 1-pyrroline N-oxides as spin traps forming exceptionally stable superoxide spin adducts
Biol Chem 2003 Mar;384(3):493-500.PMID:12715901DOI:10.1515/BC.2003.056.
EMPO [5-(ethoxycarbonyl)-5-methyl-1-pyrroline N-oxide] is a highly hydrophilic cyclic nitrone spin trap, whose superoxide adduct is considerably more stable (t 1/2 = 8.6 min) than DMPO (5,5-dimethyl-1-pyrroline N-oxide, t 1/2=45 s). EPR spectra of spin adducts of EMPO and its derivatives are very similar to those of the respective DMPO spin adducts, in contrast to the rather complex spectra obtained using DEPMPO [5-(diethoxyphosphoryl)-5-methyl-1-pyrroline N-oxide]. Several EMPO derivatives, with both the ethoxycarbonyl group and the methyl group at position 5 of the pyrroline ring being replaced by other substituents, were synthesized and characterized by 1H and 13C NMR spectroscopy. Thus, a series of derivatives was obtained that exhibit large differences in the stability of their superoxide adducts, ranging from less than one to more than 25 min. The stability of the superoxide adducts was mainly determined by the steric environment of the nitroxyl group: in compounds with less bulky 5-alkoxycarbonyl substituents the nitroxyl group is sterically less shielded, which resulted in a lower stability of the superoxide adducts. The spin density distribution, as obtained from DFT computations, was found to be nearly identical for all compounds, so that in contrast to the steric influences the spin density did not seem to be a crucial factor for the stability of the superoxide adducts.
Spin adduct formation from lipophilic EMPO-derived spin traps with various oxygen- and carbon-centered radicals
Biochem Pharmacol 2005 Jan 15;69(2):297-305.PMID:15627482DOI:10.1016/j.bcp.2004.09.021.
Free radicals are involved in the onset of many diseases, therefore the availability of adequate spin traps is crucial to the identification and localization of free radical formation in biological systems. In recent studies several hydrophilic compounds of 2-ethoxycarbonyl-2-methyl-pyrroline-N-oxide (EMPO) have been found to form rather stable superoxide spin adducts with half-lives up to twenty minutes at physiological pH. This is a major improvement over DMPO (t1/2=ca. 45 s), and even over DEPMPO (t1/2=ca. 14 min), the best commercially available spin trap for the unambiguous detection of superoxide radicals. In order to allow the detection of superoxide and also other radicals in lipid environment a series of more lipophilic derivatives of EMPO was synthesized and their structure unambiguously characterized by 1H and 13C NMR spectroscopy. In this way, six different compounds with a n-butyl group in position 5 and either an ethoxy- (EBPO), propoxy- (PBPO), iso-propoxy- (iPBPO), butoxy- (BBPO), sec-butoxy- (sBBPO) or tert-butoxycarbonyl group (tBBPO) in position 5 of the pyrroline ring were obtained and fully analytically characterized (NMR, IR). The stability of the superoxide adducts of all investigated spin traps were comparable with EMPO (t1/2=ca. 8 min), except for the two compounds bearing an additional methyl group in position 3 or 4 of the pyrroline ring, 5-butyl-5-ethoxycarbonyl-3-methyl-pyrroline-N-oxide (BEMPO-3) and 5-butyl-5-ethoxycarbonyl-4-methyl-pyrroline-N-oxide (BEMPO-4), of which the superoxide adducts were stable for more than 30 min. Spin adducts of other carbon- and oxygen-centered radicals were also investigated.