BMPO |
| (Synonyms: BocMPO) Catalog No.: GC41397 |
BMPO is a cyclic nitrone spin trap agent, it is a water-soluble white solid which makes BMPO purification easier than other spin trap agents.
Products are for research use only. Not for human use. We do not sell to patients.
Cas No.:387334-31-8
Sample solution is provided at 25 µL, 10mM.
Quality Control & SDS
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Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
| Cell experiment [1]: | |
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Cell lines |
Human normal lymphocytes and MEC-1 leukemia cells |
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Preparation Method |
Cells were irradiated with UV radiation (290 – 315 nm). Then add 20 μl of BMPO to 80μ l cell suspension (20 mM), then mixed in an eppendorf tube. After that, transferred the mixture to microhaematocrit capillaries and sealed with Paraffin. Then put it into EPR Pyrex tubes and inserted into the cavity of a Bruker EMX-131 X-band spectrometer. |
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Reaction Conditions |
The final concentration of BMPO is 100 mM. Samples were exposed to UVB radiation (290-315 nm) and to UVA radiation (315-400 nm) for 3 and 10 min at 47.7 and 159 mJ/cm2 and 53.7 mJ/cm2. The spectrometer was operated at ~9.5 GHz, while the spectra were recorded at room temperature. |
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Applications |
BMPO combined with EPR spectroscopy provides detection and identification of cellular ROS. Which might contribute to the understanding of some fundamental mechanisms leading to oxidative stress or damage in biological systems. |
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References: [1]. Tepe Çam S, et al. Tea extracts protect normal lymphocytes but not leukemia cells from UV radiation-induced ROS production: An EPR spin trap study. Int J Radiat Biol. 2015 Aug;91(8):673-80. |
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BMPO is a cyclic nitrone spin trap agent, it is a water-soluble white solid which makes BMPO purification easier than other spin trap agents. Even after prolonged storage at 220°C, there was no artificial signal formation from aqueous solutions containing BMPO (25–100 mM). BMPO offers several advantages over the existing spin traps in the detection and characterization of thiyl radicals, hydroxyl radicals, and superoxide anions in biological systems. One of the perceived advantages of BMPO is that the BMPO/•OOH adduct does not readily decay nonenzymatically to the BMPO/•OH adduct. [1]
The in vitro experiment took advantage of Rabbit aortic segments, which were treated with ADR and incubation with 0.1 M BMPO, a novel solid superoxide spin trap. Results showed that BMPO-hydroxyl radical adduct was detected in supernatants upon 10-min incubation of aortic segment with incremental doses of ADR.[2] Time-dependent changes in the ESR spectra of superoxide adducts of BMPO was generated in a xanthine/xanthine oxidase incubation system. BMPO superoxide adducts did not decay to the corresponding hydroxyl adducts. Results also indicate that the BMPO superoxide adduct is persistent. The decay kinetics of BMPO/•OOH also demonstrate this feature. In this system, the ESR spectrum of the BMPO/•OOH adduct could be detected even up to 35 min. Although BMPO/•OOH is intrinsically more stable, it is likely to be enzymatically reduced to BMPO/•OH in biological systems.[1]
References:
[1]. Zhao H, Joseph J, Zhang H, Karoui H, Kalyanaraman B. Synthesis and biochemical applications of a solid cyclic nitrone spin trap: a relatively superior trap for detecting superoxide anions and glutathiyl radicals. Free Radic Biol Med. 2001 Sep 1;31(5):599-606.
[2]. Duquaine D, Hirsch GA, Chakrabarti A, Han Z, Kehrer C, Brook R, Joseph J, Schott A, Kalyanaraman B, Vasquez-Vivar J, Rajagopalan S. Rapid-onset endothelial dysfunction with adriamycin: evidence for a dysfunctional nitric oxide synthase. Vasc Med. 2003 May;8(2):101-7.
| Cas No. | 387334-31-8 | SDF | |
| Synonyms | BocMPO | ||
| Chemical Name | 3,4-dihydro-2-methyl-1,1-dimethylethyl ester-2H-pyrrole-2-carboxylic acid-1-oxide | ||
| Canonical SMILES | [O-][N+]1=CCCC1(C)C(OC(C)(C)C)=O | ||
| Formula | C10H17NO3 | M.Wt | 199.2 |
| Solubility | 33mg/mL in ethanol, 25mg/mL in DMSO or in DMF, 10mg/mL in water | Storage | Store at -20°C |
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. | ||
| Shipping Condition | Evaluation sample solution : ship with blue ice All other available size: ship with RT , or blue ice upon request |
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Method for preparing DMSO master liquid: mg drug pre-dissolved in μL DMSO ( Master liquid concentration mg/mL, Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug. )
Method for preparing in vivo formulation: Take μL DMSO master liquid, next addμL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL saline, mix and clarify.
Method for preparing in vivo formulation: Take μL DMSO master liquid, next add μL Corn oil, mix and clarify.
Note: 1. Please make sure the liquid is clear before adding the next solvent.
2. Be sure to add the solvent(s) in order. You must ensure that the solution obtained, in the previous addition, is a clear solution before proceeding to add the next solvent. Physical methods such as vortex, ultrasound or hot water bath can be used to aid dissolving.
3. All of the above co-solvents are available for purchase on the GlpBio website.
•BMPO-OOH Spin-Adduct as a Model for Study of Decomposition of Organic Hydroperoxides and the Effects of Sulfide/Selenite Derivatives. An EPR Spin-Trapping Approach
Antioxidants (Basel) 2020 Sep 26;9(10):918.PMID:32993108DOI:10.3390/antiox9100918.
Lipid hydroperoxides play an important role in various pathophysiological processes. Therefore, a simple model for organic hydroperoxides could be helpful to monitor the biologic effects of endogenous and exogenous compounds. The electron paramagnetic resonance (EPR) spin-trapping technique is a useful method to study superoxide (O2•-) and hydroxyl radicals. The aim of our work was to use EPR with the spin trap 5-tert-butoxycarbonyl-5-methyl-1-pyrroline-N-oxide (BMPO), which, by trapping O2•- produces relatively stable •BMPO-OOH spin-adduct, a valuable model for organic hydroperoxides. We used this experimental setup to investigate the effects of selected sulfur/selenium compounds on •BMPO-OOH and to evaluate the antioxidant potential of these compounds. Second, using the simulation of time-dependent individual BMPO adducts in the experimental EPR spectra, the ratio of •BMPO-OH/•BMPO-OOH-which is proportional to the transformation/decomposition of •BMPO-OOH-was evaluated. The order of potency of the studied compounds to alter •BMPO-OOH concentration estimated from the time-dependent •BMPO-OH/•BMPO-OOH ratio was as follows: Na2S4 > Na2S4/SeO32- > H2S/SeO32- > Na2S2 ~Na2S2/SeO32- ~H2S > SeO32- ~SeO42- ~control. In conclusion, the presented approach of the EPR measurement of the time-dependent ratio of •BMPO-OH/•BMPO-OOH could be useful to study the impact of compounds to influence the transformation of •BMPO-OOH.
EPR Study of KO2 as a Source of Superoxide and •BMPO-OH/OOH Radical That Cleaves Plasmid DNA and Detects Radical Interaction with H2S and Se-Derivatives
Antioxidants (Basel) 2021 Aug 13;10(8):1286.PMID:34439533DOI:10.3390/antiox10081286.
Superoxide radical anion (O2•-) and its derivatives regulate numerous physiological and pathological processes, which are extensively studied. The aim of our work was to utilize KO2 as a source of O2•- and the electron paramagnetic resonance (EPR) spin trapping 5-tert-butoxycarbonyl-5-methyl-1-pyrroline N-oxide (BMPO) technique for the preparation of •BMPO-OOH and/or •BMPO-OH radicals in water solution without DMSO. The method distinguishes the interactions of various compounds with •BMPO-OOH and/or •BMPO-OH radicals over time. Here, we show that the addition of a buffered BMPO-HCl mixture to powdered KO2 formed relatively stable •BMPO-OOH and •BMPO-OH radicals and H2O2, where the •BMPO-OOH/OH ratio depended on the pH. At a final pH of ~6.5-8.0, the concentration of •BMPO-OOH radicals was ≥20 times higher than that of •BMPO-OH, whereas at pH 9.0-10.0, the •BMPO-OH radicals prevailed. The •BMPO-OOH/OH radicals effectively cleaved the plasmid DNA. H2S decreased the concentration of •BMPO-OOH/OH radicals, whereas the selenium derivatives 1-methyl-4-(3-(phenylselanyl) propyl) piperazine and 1-methyl-4-(4-(phenylselanyl) butyl) piperazine increased the proportion of •BMPO-OH over the •BMPO-OOH radicals. In conclusion, the presented approach of using KO2 as a source of O2•-/H2O2 and EPR spin trap BMPO for the preparation of •BMPO-OOH/OH radicals in a physiological solution could be useful to study the biological effects of radicals and their interactions with compounds.
Impact of SOD-Mimetic Manganoporphyrins on Spin Trapping of Superoxide and Related Artifacts
Appl Magn Reson 2011 Feb;40(1):125-134.PMID:23853422DOI:10.1007/s00723-010-0188-y.
The superoxide dismutase (SOD)-mimetic effectiveness of [meso-tetrakis (R)porphyrinato]manganese with R = 1,3-di-N-ethylimidazolium-2-yl (Mn-TDEIP), 1,3-di-N-methylimidazolium-2-yl (Mn-TDMIP), 1,3-di-N-propylimidazolium-2-yl (Mn-TDPIP), N-ethyl-2-pyridyl (Mn-T2EPyP), 4-sulphonatophenyl (Mn-TSP), 1-methyl-4-pyridyl (Mn-T4PyP), 4-carboxyphenyl (Mn-TBAP), and β-octabromomeso-tetrakis(4-carboxyphenyl porphyrinato)manganese (MnBr8TBAP) was compared with Cu, Zn SOD. Superoxide generated by reaction of xanthine oxidase with hypoxanthine was trapped with 5-tert-butoxycarbonyl-5-methyl-1-pyrroline N-oxide (BMPO), forming BMPO-OOH, which was monitored by electron paramagnetic resonance. Manganoporphyrins with redox potentials ranging from -0.190 to 0.346 V relative to the standard hydrogen electrode were selected for this study. With 0.1 µM manganoporphyrins and 20 mM BMPO, the effectiveness of the manganoporphyrins in inhibiting formation of BMPO-OOH increases in the order Mn-TSP < Mn-TBAP < MnBr8TBAP < Mn-T4PyP < Mn-T2EPyP < Mn-TDEIP ~ Mn-TDMIP ~ Mn-TDPIP ~ Cu, Zn SOD. However, at higher concentrations of manganoporphyrin and BMPO, a BMPO-OH signal was observed. The formation of BMPO-OH was not inhibited by catalase or dimethylsulfoxide, which demonstrated that it was not produced from hydroxyl radical. The artifactual formation of BMPO-OH is attributed to oxidation of the water adduct of BMPO by the manganoporphyrins or decomposition of BMPO-OOH. Although spin trapping is an effective method for evaluating SOD-mimetic efficacy, caution must be exercised to ensure that artifact signals are not interpreted improperly.
Ionic liquid-mediated bis[(3-methyldimethoxysilyl)propyl] polypropylene oxide-based polar sol-gel coatings for capillary microextraction
J Chromatogr A 2009 Sep 4;1216(36):6349-55.PMID:19643422DOI:10.1016/j.chroma.2009.07.028.
Two ionic liquids (IL), namely, 1-methyl-3-octylimidazolium chloride (MOIC) and trihexyltetradecylphosphonium tetrafluoroborate (TTPT) were used to prepare polar and nonpolar sol-gel coatings for capillary microextraction (CME). Bis[(3-methyldimethoxysilyl)propyl] polypropylene oxide (BMPO), containing sol-gel active terminal methoxysilyl groups and polar propylene oxide repeating units, was used to prepare polar sol-gel hybrid organic-inorganic coatings. Hydroxy-terminated poly(dimethyl-co-diphenylsiloxane) was used as the sol-gel active organic component for nonpolar sol-gel hybrid coatings. Compared to a sol-gel BMPO coating prepared without IL, the sol-gel BMPO coatings prepared with the use of both of these ILs provided more efficient extraction as is evidenced by more pronounced GC peak areas. The MOIC-mediated sol-gel BMPO coating provided larger GC peak areas compared to the TTPT-mediated sol-gel BMPO coating. Scanning electron microscopy results suggested that MOIC provided a more porous morphology of the sol-gel BMPO extraction media compared to that prepared with TTPT. Thus, individual ILs can affect the porosity of sol-gel materials to different degrees. Overall, the sol-gel BMPO coating prepared with the ILs could extract nonpolar to polar analytes directly from aqueous samples. Detection limits were on the order of nanograms per liter (1.9-330.5 ng/L) depending on the analyte class. Furthermore, the MOIC-mediated sol-gel BMPO coating demonstrated high thermal stability (330 degrees C), solvent resistance, and fast extraction equilibrium (10-15 min) for polar and moderately polar analytes.
Use of rapid-scan EPR to improve detection sensitivity for spin-trapped radicals
Biophys J 2013 Jul 16;105(2):338-42.PMID:23870255DOI:10.1016/j.bpj.2013.06.005.
The short lifetime of superoxide and the low rates of formation expected in vivo make detection by standard continuous wave (CW) electron paramagnetic resonance (EPR) challenging. The new rapid-scan EPR method offers improved sensitivity for these types of samples. In rapid-scan EPR, the magnetic field is scanned through resonance in a time that is short relative to electron spin relaxation times, and data are processed to obtain the absorption spectrum. To validate the application of rapid-scan EPR to spin trapping, superoxide was generated by the reaction of xanthine oxidase and hypoxanthine with rates of 0.1-6.0 μM/min and trapped with 5-tert-butoxycarbonyl-5-methyl-1-pyrroline-N-oxide (BMPO). Spin trapping with BMPO to form the BMPO-OOH adduct converts the very short-lived superoxide radical into a more stable spin adduct. There is good agreement between the hyperfine splitting parameters obtained for BMPO-OOH by CW and rapid-scan EPR. For the same signal acquisition time, the signal/noise ratio is >40 times higher for rapid-scan than for CW EPR. Rapid-scan EPR can detect superoxide produced by Enterococcus faecalis at rates that are too low for detection by CW EPR.
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