CYPMPO
(Synonyms: 2-(5,5-二甲基-2-氧代-1,3,2-二氧磷杂环己烷-2-基)-1-羟基-2-甲基-3,4-二氢-2H-1lambda5-吡咯-1-基,RR 071) 目录号 : GC43352A novel spin trap for hydroxyl and superoxide radical detection
Cas No.:934182-09-9
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >95.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
CYPMPO is a free radical spin trap with excellent trapping capabilities toward hydroxyl and superoxide radicals in biological and chemical systems. Decay of the superoxide adduct of CYPMPO proceeds in an apparent first order fashion with half-lives of 15 and 51 minutes in a UV-illuminated hydrogen peroxide solution and a hypoxanthine/xanthine oxidase system, respectively. CYPMPO traps superoxide radicals generated by bovine neutrophils as effectively as DEPMPO.[1] The high melting point (126°C), low hygroscopic properties, and long shelf-life in aqueous solutions offer significant practical advantages for use of CYPMPO over DEPMPO and DMPO.
Reference:
[1]. Kamibayashi, M., Oowada, S., Kameda, H., et al. Synthesis and characterization of a practically better DEPMPO-type spin trap, 5-(2,2-dimethyl-1,3-propoxy cyclophosphoryl)-5-methyl-1-pyrroline N-oxide (CYPMPO). Free Radical Research 40(11), 1166-1172 (2006).
| Cas No. | 934182-09-9 | SDF | |
| 别名 | 2-(5,5-二甲基-2-氧代-1,3,2-二氧磷杂环己烷-2-基)-1-羟基-2-甲基-3,4-二氢-2H-1lambda5-吡咯-1-基,RR 071 | ||
| 化学名 | 5-(2,2-dimethyl-1,3-propoxycyclophosphoryl)-5-methyl-1-pyrroline N-oxide | ||
| Canonical SMILES | O[N]1=CCCC1(C)P1(=O)OCC(C)(C)CO1 | ||
| 分子式 | C10H18NO4P | 分子量 | 247.2 |
| 溶解度 | 25mg/mL in ethanol or DMF, 20mg/mL in DMSO | 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 | 4.0453 mL | 20.2265 mL | 40.4531 mL |
| 5 mM | 0.8091 mL | 4.0453 mL | 8.0906 mL |
| 10 mM | 0.4045 mL | 2.0227 mL | 4.0453 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。
Influences of organic solvents on CYPMPO-electron spin resonance spectra in in vitro radical generating systems
J Vet Med Sci 2010 Dec;72(12):1547-50.PMID:20661003DOI:10.1292/jvms.10-0232.
Estimation of radical scavenging capacity of lipophilic antioxidants by electron spin resonance (ESR) in vitro is a challenging issue due to their poor solubility in aqueous radical generating and measuring systems. Water-miscible organic solvents are used for this purpose. A novel radical trapping agent, 5-(2,2-dimethyl-1,3-propoxy cyclophosphoryl)-5-methyl-1-pyrroline N-oxide (CYPMPO), that has practical advantages over well-known trapping agents was synthesized. However, no available data for the influence of solvents in an ESR system that uses CYPMPO has been presented. The influences of six water-miscible organic solvents, acetonitrile (AcN), acetone, dimethyl sulfoxide (DMSO), ethanol, polyethylene glycol (PEG), and dimethoxyethane (DME), on ESR responses to Fenton Fe(2+)/H (2)O(2 )OH· and hypoxanthine/xanthine oxidase superoxide generation systems in vitro were studied. Reduction of the ESR signal to CYPMPO-OH· adducts by 55.86 ± 5.95 and 83.17 ± 2.50% compared with the control was observed in the presence of AcN and acetone, respectively, at a final concentration of 5% (v/v). AcN of less than 1% had minimal effects. DMSO, ethanol, PEG and DME at 5% (v/v) strongly inhibited the ESR signals and/or caused derangement in the signal patterns. The six water-miscible solvents at 5% (v/v) had no influence on the ESR spectra of CYPMPO-superoxide adducts. From these results, AcN, at less than 1% (v/v), is a useful water-miscible organic solvent for assessing radical scavenging capacities of lipophilic compounds in the CYPMPO-Fenton Fe(2+)/H(2)O(2) OH· reaction system in an ESR assay. Any of the solvents used in the present study can be used in a hypoxanthine/xanthine oxidase superoxide generation system.
Synthesis and characterization of a practically better DEPMPO-type spin trap, 5-(2,2-dimethyl-1,3-propoxy cyclophosphoryl)-5-methyl-1-pyrroline N-oxide (CYPMPO)
Free Radic Res 2006 Nov;40(11):1166-72.PMID:17050170DOI:10.1080/10715760600883254.
5-(2,2-dimethyl-1,3-propoxy cyclophosphoryl)-5-methyl-1-pyrroline N-oxide (CYPMPO), a new cyclic DEPMPO-type nitrone was evaluated for spin-trapping capabilities toward hydroxyl and superoxide radicals. CYPMPO is colorless crystalline and freely soluble in water. Both the solid and diluted aqueous solution did not develop electron spin resonance (ESR) signal for at least 1 month at ambient conditions. CYPMPO can spin-trap superoxide and hydroxyl radicals in both chemical and biological systems, and the ESR spectra are readily assignable. Half life for the superoxide adduct of CYPMPO produced in UV-illuminated hydrogen peroxide solution was approximately 15 min, and in biological systems such as hypoxanthine (HX)/xanthine oxidase (XOD) the half-life of the superoxide adduct was approximately 50 min. In UV-illuminated hydrogen peroxide solution, there was no conversion from the superoxide adduct to the hydroxyl adduct. Although overall spin-trapping capabilities of CYPMPO are similar to DEPMPO, its high melting point, low hygroscopic property, and the long shelf-life would be highly advantageous for the practical use.
Comparison of superoxide detection abilities of newly developed spin traps in the living cells
Free Radic Res 2009 Jul;43(7):668-76.PMID:19479584DOI:10.1080/10715760902988850.
This study compared the superoxide detection abilities of four spin traps, 5,5-dimethyl-1-pyrroline-N-oxide (DMPO), 5-(diethoxyphosphoryl)-5-methyl-1-pyrroline N-oxide (DEPMPO), 5-(diphenylphosphinoyl)-5-methyl-1pyrroline N-oxide (DPPMPO) and 5-(2,2-dimethyl-1,3-propoxy cyclophosphoryl)-5-methyl-1-pyrroline N-oxide (CYPMPO) in living cells. Electron spin resonance (ESR) signals of the superoxide adducts were observed when spin traps were added to a suspension of human oral polymorphonuclear leukocytes (OPMNs) stimulated by phorbol 12-myristate 13-acetate. The ESR signal of the CYPMPO-superoxide adduct (CYPMPO-OOH) increased for 24 min after the initiation of the reaction, whereas the signals from DMPO-OOH and DPPMPO-OOH peaked at 6 and 10 min, respectively. The maximum concentrations of DMPO-OOH, DPPMPO-OOH and CYPMPO-OOH in OPMNs were 1.9, 6.0 and 10.7 microM, respectively. Furthermore, CYPMPO could more efficiently trap superoxide in blood PMNs compared with DEPMPO. From these results, it was concluded that CYPMPO performs better than DMPO, DPPMPO and DEPMPO for superoxide measurements in living cell systems because it has lower cytotoxicity and its superoxide adduct has a longer lifetime.
In vitro reactive oxygen species production by histatins and copper(I,II)
J Biol Inorg Chem 2009 Feb;14(2):243-51.PMID:18975018DOI:10.1007/s00775-008-0444-x.
The ability of the histidine-rich peptides, histatin-5 (Hst-5) and histatin-8 (Hst-8), to support the generation of reactive oxygen species during the Cu-catalyzed oxidation of ascorbate and cysteine has been evaluated. High levels of hydrogen peroxide (70-580 mol/mol Cu/h) are produced by aqueous solutions containing Cu(II), Hst-8 or Hst-5, and a reductant, either ascorbate or cysteine, as determined by the postreaction Amplex Red assay. When the reactions are conducted in the presence of superoxide dismutase, the total hydrogen peroxide produced is decreased, more so in the presence of the peptides (up to 50%), suggesting the intermediacy of superoxide in these reactions. On the other hand, the presence of sodium azide or sodium formate, traps for hydroxyl radicals, has no appreciable effect on the total hydrogen peroxide production for the Cu-Hst systems. EPR spin-trapping studies using 5-(2,2-dimethyl-1,3-propoxy cyclophosphoryl)-5-methyl-1-pyrroline N-oxide (CYPMPO) in the cysteine-Cu(II) reactions reveal the formation of the CYPMPO-hydroperoxyl and CYPMPO-hydroxyl radical adducts in the presence of Hst-8, whereas only the latter was observed with Cu alone.
Redox regulation in radiation-induced cytochrome c release from mitochondria of human lung carcinoma A549 cells
Cancer Lett 2009 May 8;277(1):64-71.PMID:19117669DOI:10.1016/j.canlet.2008.11.021.
Mitochondria in mammalian cells are well-known to play an important role in the intrinsic pathway of genotoxic-agent-induced apoptosis by releasing cytochrome c into cytosol and to be a major source of reactive oxygen species (ROS). The aim of this study was to examine whether mitochondrial ROS are involved in radiation-induced apoptotic signaling in A549 cells. Post-irradiation treatment with N-acetyl-L-cysteine (NAC) inhibited cytochrome c release from mitochondria but did not affect expression levels of Bcl-2, Bcl-X(L) and Bax, suggesting that late production of ROS triggered cytochrome c release. Experiments using DCFDA (a classical ROS fluorescence probe) and MitoAR (a novel mitochondrial ROS probe) demonstrated that intracellular and mitochondrial ROS were enhanced 6h after X irradiation. Furthermore, the O(2)(-*) production ability of mitochondria isolated from A549 cells was evaluated by ESR spectroscopy combined with a spin-trapping reagent (CYPMPO). When isolated mitochondria were incubated with NADH, succinate and CYPMPO, an ESR spectrum due to CYPMPO-OOH was detected. This NADH/succinate-dependent O(2)(-*) production from mitochondria of irradiated cells was significantly increased in comparison with that of unirradiated cells. These results indicate that ionizing radiation enhances O(2)(-*) production from mitochondria to trigger cytochrome c release in A549 cells.