TEMPONE
(Synonyms: 4-氧-2,2,6,6-四甲基哌啶-1-氧自由基) 目录号 : GC45010
A 4-oxo derivative of the spin trap TEMPO
Cas No.:2896-70-0
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
2,2,6,6-Tetramethylpiperidin-1-oxyl (TEMPO) is a stable radical that will react with reactive oxygen species (ROS). This conversion, followed by ESR, provides an indirect way to monitor ROS production in biological systems. TEMPONE is the 4-oxo derivative of TEMPO. In addition to possible uses as a spin trap, this nitroxyl radical can be used in hydrogen transfer experiments and as a polarizing agent in dynamic nuclear polarization NMR spectroscopy. TEMPONE and other nitroxyl radicals have also been shown to reduce mean arterial pressure in spontaneously hypertensive rats when administered intravenously.
| Cas No. | 2896-70-0 | SDF | |
| 别名 | 4-氧-2,2,6,6-四甲基哌啶-1-氧自由基 | ||
| Canonical SMILES | O=C1CC(C)(C)N([O])C(C)(C)C1 | ||
| 分子式 | C9H16NO2 | 分子量 | 170.2 |
| 溶解度 | DMF: 30 mg/ml,DMSO: 30 mg/ml,Ethanol: 30 mg/ml,PBS (pH 7.2): 10 mg/ml | 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 | 5.8754 mL | 29.3772 mL | 58.7544 mL |
| 5 mM | 1.1751 mL | 5.8754 mL | 11.7509 mL |
| 10 mM | 0.5875 mL | 2.9377 mL | 5.8754 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 | ||||||||||
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。
TEMPONE reduces renal dysfunction and injury mediated by oxidative stress of the rat kidney
Free Radic Biol Med 2002 Dec 1;33(11):1575-89.PMID:12446215DOI:10.1016/s0891-5849(02)01116-4.
Here we investigate the effects of the stable, water-soluble nitroxyl radical, TEMPONE, on renal dysfunction and injury caused by ischemia/reperfusion (I/R) of the rat kidney in vivo. TEMPONE significantly improved both glomerular and tubular function (serum urea, creatinine, creatinine clearance, and fractional excretion of Na(+)) in a dose-dependent manner and significantly attenuated the reperfusion-injury associated with I/R (urinary N-acetyl-beta-D-glucosaminidase, aspartate aminotransferase, assessment of renal histology). TEMPONE also markedly reduced the immunohistochemical evidence of the formation of nitrotyrosine and poly(ADP-ribose), indicating reduction of nitrosative and oxidative stress, respectively. The latter was reflected in vitro, where TEMPONE significantly reduced cellular injury of primary cultures of rat renal proximal tubular (PT) cells caused by hydrogen peroxide in a dose-dependent manner. Importantly, in contrast to its in vivo metabolite TEMPOL (which also provided protective effects against renal I/R and oxidative stress of PT cells), TEMPONE reduced renal dysfunction and injury without causing a significant reduction in blood pressure upon administration. These results suggest, for the first time, that TEMPONE can reduce the renal dysfunction and injury caused by I/R and the injury caused to PT cells by oxidative stress without producing the adverse cardiovascular effects observed when using other nitroxyl radicals.
The products of the reduction of doxyl stearates in cells are hydroxylamines as shown by oxidation by 15N-perdeuterated TEMPONE
Biochim Biophys Acta 1989 Jul 21;992(1):131-3.PMID:2546601DOI:10.1016/0304-4165(89)90060-3.
The use of nitroxides in functional biological systems has increased greatly as it has become evident that such studies can provide valuable biophysical and metabolic data. This has led to a need to understand the nature of the metabolism of nitroxides and their products. This paper presents data indicating the value of 15N-perdeuterated TEMPONE specifically to indicate the amount of hydroxylamines that are present in a cellular system. Using this technique, we found that in the mammalian cells that we studied the principal or only products of reduction of doxyl stearates were the corresponding hydroxylamines.
Metabolism of the stable nitroxyl radical 4-oxo-2,2,6, 6-tetramethylpiperidine-N-oxyl (TEMPONE)
Eur J Pharm Sci 1999 Apr;8(1):5-9.PMID:10072473DOI:10.1016/s0928-0987(98)00047-5.
The formation of new metabolites of the stable nitroxyl radical 4-oxo-2,2,6,6-tetramethylpiperidine-N-oxyl (TEMPONE) inside the isolated perfused rat liver was examined. The paramagnetic 4-hydroxy derivative (TEMPOL) and the diamagnetic 1,4-dihydroxy derivative were found to be the major metabolites besides the well-known corresponding hydroxylamine of TEMPONE. No reoxidation of the hydroxyl group in the 4-position was observed. The conversion of nitroxides to the sterically hindered secondary amines remains speculative. A redox cycle of nitroxide and hydroxylamine including the secondary amines is discussed. For the first time the biotransformation of the stable nitroxyl radical TEMPONE detected by means of GC and GC-MS has been examined and new metabolites have been described, i.e. the newly discussed metabolites have to be considered for the interpretation of electron paramagnetic resonance (EPR), magnetic resonance imaging (MRI) and dynamic nuclear polarization (DNP) measurements on using the spin probe TEMPONE.
Electron spinal resonance analysis of the nitroxide spin label 2,2,6,6-tetramethylpipidone-N-oxyl (TEMPONE) in single crystals of the reduced TEMPONE matrix
Biophys J 1974 Jan;14(1):20-32.PMID:4359744DOI:10.1016/s0006-3495(74)85900-x.
The nitroxide spin label TEMPONE (2,2,6,6-tetramethylpiperidone-N-oxyl) can be reduced with ascorbic acid to give a nonparamagnetic species. Single crystals of reduced TEMPONE serve as a suitable host matrix to orient trace quantities of TEMPONE for ESR analysis. In these crystals the majority of the TEMPONE molecules are well-oriented, but a smaller fraction of the molecules tumble freely to give an isotropic electron spin resonance (ESR) spectrum. ESR transitions for the oriented molecules are saturated at much lower microwave power levels than for the tumbling molecules. For the oriented molecules, an analysis of the anisotropy of the spectroscopic splitting factor (g) gives principal values of g(1) = 2.0094, g(2) = 2.0061, g(3) = 2.0021. The hyperfine coupling tensor is nearly axially symmetric, with principal values (in gauss) of A(1) = 6.5, A(2) = 6.7, A(3) = 33.0. Within experimental error, the principal axis systems for the g tensor and the hyperfine tensor are identical. Comparison of the average values of g and A with the isotropic values of these parameters for TEMPONE in solvents of different polarity suggests a method for choosing the most appropriate tensor elements to be used for spin label experiments in various solvent systems.
Reduction of the spin-label TEMPONE by ubiquinol in the electron transport chain of intact rabbit spermatozoa
Biol Reprod 1985 May;32(4):884-93.PMID:4005351DOI:10.1095/biolreprod32.4.884.
When the hydrophilic spin label TEMPONE (deuterated 2,2,6,6-tetramethylpiperidine-N-oxyl) was incubated with intact rabbit spermatozoa at concentrations greater than 0.3 X 10(9) cells/ml, the electron spin resonance signal height decreased with time. This loss of signal amplitude was reversed by the oxidizing reagent potassium dichromate, indicating that the signal loss was due to a reduction of the paramagnetic nitroxide species to the nonparamagnetic hydroxylamine. Using inhibitors that act on the respiratory chain, we observed that, relative to controls, the rate of TEMPONE reduction was decreased in the presence of rotenone, but increased in the presence of antimycin A and potassium cyanide (KCN). Parallel studies measuring oxygen consumption showed decreases with all three inhibitors. We interpret these observations to mean that TEMPONE is reduced by ubiquinol in the respiratory chain. Supporting this conclusion is the observation that the midpoint potential of TEMPONE was determined by be +48mV, which is close to the midpoint potential of +40 mV for the ubiquinone/ubiquinol couple. Furthermore, in a cell-free test system, ubiquinol reduced TEMPONE, but ubiquinone, NADH, and succinate did not.