DEPMPO
(Synonyms: 5-(二乙氧基磷酰)-5-甲基-1-吡咯啉-N-氧化物,5-(Diethoxyphosphoryl)-5-methyl-1-pyrroline-N-oxide) 目录号 : GC43410A spin trap for superoxide radical detection
Cas No.:157230-67-6
Sample solution is provided at 25 µL, 10mM.
Quality Control & SDS
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- Purity: >98.00%
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- SDS (Safety Data Sheet)
- Datasheet
DEPMPO is a phosphorylated derivative of the widely used DMPO spin trap. It has been reported to produce spin adducts with increased stability particularly for the adduct of superoxide. [1] [2] [3] DEPMPO displays a detectable spin adduct signal at a concentration as low as 1 mM, as compared to 5 mM for DMPO.[3] A significant advantage of using DEPMPO in trapping superoxide radical is that the decomposition of DEPMPO/O2•- does not produce the OH• adduct, which can be a drawback when using DMPO. [2][3]
Reference:
[1]. Khan, N., Wilmont, C.M., Rosen, G.M., et al. Spin traps: In vitro toxicity and stability of radical adducts. Free Radical Biology & Medicine 34(11), 1473-1481 (2003).
[2]. Anzai, K., Aikawa, T., Furukawa, Y., et al. ESR measurement of rapid penetration of DMPO and DEPMPO spin traps through lipid bilayer membranes. Archives of Biochemistry and Biophysics 415, 251-256 (2003).
[3]. Liu, K.J., Miyake, M., Panz, T., et al. Evaluation of DEPMPO as a spin trapping agent in biological systems. Free Radical Biology & Medicine 26, 714-721 (1999).
| Cas No. | 157230-67-6 | SDF | |
| 别名 | 5-(二乙氧基磷酰)-5-甲基-1-吡咯啉-N-氧化物,5-(Diethoxyphosphoryl)-5-methyl-1-pyrroline-N-oxide | ||
| 化学名 | P-(3,4-dihydro-2-methyl-1-oxido-2H-pyrrol-2-yl)-phosphonic acid, diethyl ester | ||
| Canonical SMILES | [O-][N+]1=CCCC1(P(OCC)(OCC)=O)C | ||
| 分子式 | C9H18NO4P | 分子量 | 235.2 |
| 溶解度 | Soluble in water to 100 mM, in ethanol and in DMSO to 25 mM | 储存条件 | Store at -80°C,protect from light |
| 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 | 4.2517 mL | 21.2585 mL | 42.517 mL |
| 5 mM | 0.8503 mL | 4.2517 mL | 8.5034 mL |
| 10 mM | 0.4252 mL | 2.1259 mL | 4.2517 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 |
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| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
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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。
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Evaluation of DEPMPO as a spin trapping agent in biological systems
Free Radic Biol Med 1999 Mar;26(5-6):714-21.PMID:10218661DOI:10.1016/s0891-5849(98)00251-2.
Cellular toxicity, pharmacokinetics, and the in vitro and in vivo stability of the SO3*- spin adduct of the spin trap, 5-diethoxyphosphoryl-5-methyl-1-pyrroline-n-oxide (DEPMPO), was investigated, and the results were compared with those of the widely used spin trap 5,5-dimethyl-1-pyrroline-N-oxide (DMPO). Similar to DMPO, DEPMPO was quickly taken up (<15 min) after intraperitoneal injection, and distributed evenly in the liver, heart, and blood of the mice. In the presence of ascorbate the in vitro stability of the adduct DEPMPO/SO3*- was 7 times better than DMPO/SO3*-. Under in vivo conditions, the spin adduct DEPMPO/SO3*- was 2-4 times more stable than DMPO/ SO3*-, depending on the route of administration of the adducts. Using a low frequency EPR spectrometer, we were able to observe the spin trapped SO3*- radical both with DMPO and DEPMPO directly in the intact mouse. DEPMPO had a detectable spin adduct signal at a concentration as low as 1 mM, as compared to 5 mM for DMPO. We conclude that DEPMPO is potentially a good candidate for trapping radicals in functioning biological systems, and represents an improvement over the commonly used trap DMPO.
DEPMPO: an efficient tool for the coupled ESR-spin trapping of alkylperoxyl radicals in water
Org Biomol Chem 2011 Apr 7;9(7):2473-80.PMID:21347497DOI:10.1039/c0ob00876a.
Peroxidation is an important process both in chemistry and biology, and peroxyl radicals play a crucial role in various pathological situations involving lipid and protein peroxidation. A few secondary and tertiary peroxyl radicals can be detected directly by Electron Spin Resonance (ESR). However, primary and secondary alkylperoxyl radicals have extremely short lifetimes and their direct observation is impossible in biological samples. DMPO has been used to trap alkylperoxyl radicals generated in biological systems and the characterization of DMPO-alkylperoxyl spin adducts has been claimed by different authors. However, it was then clearly shown that all the assignments made previously to DMPO-OOR adducts were actually due to DMPO-OR adducts. We have investigated the potential of DEPMPO to characterize the formation of alkylperoxyl radicals in biological milieu. Various DEPMPO-OOR (R = Me, primary or secondary alkyl group) spin adducts were unambiguously characterized and the formation of DEPMPO-OOCH(3) was clearly established during the reaction of tert-butylhydroperoxide with chloroperoxidase and cytochrome c.
Mito-DEPMPO synthesized from a novel NH2-reactive DEPMPO spin trap: a new and improved trap for the detection of superoxide
Chem Commun (Camb) 2007 Mar 14;(10):1083-5.PMID:17325813DOI:10.1039/b616076j.
Mito-DEPMPO, a new DEPMPO analogue bearing a triphenylphosphonium group, was synthesized via a novel NH2-reactive DEPMPO. The half-life of the Mito-DEPMPO superoxide adduct was estimated to be ca. 40 min. Using Mito-DEPMPO, reactive oxygen species generated in intact mitochondria were detected and characterized by EPR.
Detection, characterization, and decay kinetics of ROS and thiyl adducts of mito-DEPMPO spin trap
Chem Res Toxicol 2007 Jul;20(7):1053-60.PMID:17559235DOI:10.1021/tx700101d.
We report here the detection and characterization of spin adducts formed from the trapping of reactive oxygen species (superoxide and hydroxyl radicals) and glutathiyl and carbon-centered radicals by a newly synthesized nitrone, Mito-DEPMPO. This is a cationic nitrone spin trap with a triphenyl phosphonium cation conjugated to the DEPMPO analogue. The Mito-DEPMPO-OOH adduct, formed from the trapping of superoxide by Mito-DEPMPO, was enzymatically generated using xanthine/xanthine oxidase and neuronal nitric oxide synthase, and chemically generated by KO2 in 18-crown-6. The Mito-DEPMPO-OOH adduct exhibits an eight-line EPR spectrum with partial asymmetry arising from the alternate line-width effect. The half-life of the Mito-DEPMPO-OOH adduct is 2-2.5-times greater than that of the DEPMPO-OOH. The Mito-DEPMPO-SG adduct, formed from the trapping of glutathiyl radicals by Mito-DEPMPO, is 3-times more persistent than the analogue DEPMPO-SG adduct. In this study, we describe the EPR characterization of spin adducts formed from Mito-DEPMPO. The EPR parameters of Mito-DEPMPO adducts are distinctly different and highly characteristic. The detection of superoxide from an intact mitochondrion was feasible with Mito-DEPMPO but not with DEPMPO. We conclude that Mito-DEPMPO nitrone and its analogues are more effective than most nitrone spin traps for trapping superoxide, hydroxyl, and thiyl radicals formed in biological systems, including mitochondria.
Detection of hydrogen atom adduct of spin-trap DEPMPO. The relevance for studies of biological systems
J Chem Inf Model 2005 Nov-Dec;45(6):1716-8.PMID:16309278DOI:10.1021/ci050173d.
We proposed EPR spectroscopy using spin-trap DEPMPO as a novel method for the detection of a hydrogen atom (*H) produced by chemical and biological systems. In complex EPR spectra of DEPMPO adducts in biological systems, spectral lines of unknown origin have been observed. We have assumed (Bacić, G.; Mojović, M. Ann. N. Y. Acad. Sci. 2005, 1048, 230-243) that those lines represent the spectrum of a hydrogen atom (*H) adduct i.e., DEPMPO/H. An electrochemical system known to produce only *H radicals was used here in order to obtain a separate spectrum of the DEPMPO/H adduct. An acquired spectrum as well as a computer spectral simulation of the DEPMPO/H adduct showed considerable resemblance with additional lines in the EPR spectra of DEPMPO adducts in biological systems-plant plasma membranes and cell walls. This shows that such a radical is produced by plants as well as that DEPMPO is suitable for detection in both electrochemical and biological systems.