2,3-Butanedione-2-monoxime
(Synonyms: 2,3-丁烷二酮一肟,BDM|Diacetyl Monoxime|NSC 660|NSC 116103) 目录号 : GC12469
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2,3-Butanedione-2-monoxime是一种肌球蛋白ATP酶的非竞争性抑制剂，可抑制肌球蛋白-V和非肌肉肌球蛋白-II的ATP酶速率，但对驱动蛋白和动力蛋白无抑制作用。
Cas No.:57-71-6
Sample solution is provided at 25 µL, 10mM.
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2,3-Butanedione-2-monoxime, a non-competitive inhibitor of myosin ATPase, inhibits the ATPase rate of myosin-V and non-muscle myosin-II but not of kinesin or dynein.
2,3-Butanedione-2-monoxime also acts as a reactivator of phosphorylated acetylcholinesterase by removing the phosphate group from the enzyme[1].
In vitro, 2,3-Butanedione-2-monoxime (50mM; 6h or 48h) decreased protein secretion in C. cinerea[2]. 2,3-Butanedione-2-monoxime (50mM; 2h or 4h) resulted in Golgi aggregation but did not alter ER localization in C. cinerea[2]. 2,3-Butanedione-2-monoxime (30mM; 10min; 37℃) decreased accumulated sarcoplasmic reticulum (SR) Ca2+ in Canine ventricular myocytes in the absence of efflux inhibitors[3].
In vivo, 2,3-Butanedione-2-monoxime (5-200mg/kg; i.v.; once) dose-dependently reduced blood pressure in Male spontaneously hypertensive (SHR) and age-matched Wistar-Kyoto (WKY) rat, with a greater antihypertensive effect in SHR rats[4]. 2,3-Butanedione-2-monoxime (0-205mg/kg; i.p.; once) dose-dependently suppressed clonic and tonic-clonic seizures induced by picrotoxin (PTX) in adult mice[5].
References:
[1] Ostap, E Michael. “2,3-Butanedione monoxime (BDM) as a myosin inhibitor.” Journal of muscle research and cell motility vol. 23,4 (2002): 305-8.
[2] Hashimoto, Kohsuke et al. “The myosin ATPase inhibitor, 2,3-butanedione 2-monoxime, prevents protein secretion by the basidiomycete Coprinopsis cinerea.” Biotechnology letters vol. 33,4 (2011): 769-75.
[3] Phillips, R M, and R A Altschuld. “2,3-Butanedione 2-monoxime (BDM) induces calcium release from canine cardiac sarcoplasmic reticulum.” Biochemical and biophysical research communications vol. 229,1 (1996): 154-7.
[4] Xiao, Y F, and J J McArdle. “Effects of 2,3-butanedione monoxime on blood pressure, myocardial Ca2+ currents, and action potentials of rats.” American journal of hypertension vol. 8,12 Pt 1 (1995): 1232-40. doi:10.1016/0895-7061(95)00251-0
[5] Brightman, T et al. “2,3-Butanedione monoxime protects mice against the convulsant effect of picrotoxin by facilitating GABA-activated currents.” Brain research vol. 678,1-2 (1995): 110-6.
2,3-Butanedione-2-monoxime是一种肌球蛋白ATP酶的非竞争性抑制剂，可抑制肌球蛋白-V和非肌肉肌球蛋白-II的ATP酶速率，但对驱动蛋白和动力蛋白无抑制作用。
2,3-Butanedione-2-monoxime还可作为磷酸化乙酰胆碱酯酶的再活化剂，通过去除酶上的磷酸基团使其恢复活性[1]。
体外实验中，50mM的2,3-Butanedione-2-monoxime处理6小时或48小时，抑制灰盖拟鬼伞菌（C. cinerea）中的蛋白质分泌[2]。50mM的2,3-Butanedione-2-monoxime处理2小时或4小时，会导致灰盖拟鬼伞菌细胞中高尔基体聚集，但不改变内质网的定位[2]。在无外排抑制剂存在的情况下，30mM的2,3-Butanedione-2-monoxime在37°C下处理10分钟，降低了犬心室肌细胞中的肌浆网（SR）钙含量[3]。
体内实验中，2,3-Butanedione-2-monoxime（5-200mg/kg；i.v.；once）剂量依赖性降低雄性自发性高血压（SHR）和同龄Wistar-Kyoto（WKY）大鼠血压，其中SHR大鼠降压效果更明显[4]。2,3-Butanedione-2-monoxime (0-205mg/kg；i.p.；once)剂量依赖性地抑制了成年小鼠中由PTX诱导的阵挛性和强直-阵挛性发作[5]。
| Kinase experiment [1]: | |
Preparation Method | All experiments were performed at 25±0.1℃ in KMg50–MOPS buffer (10mM MOPS, pH 7.0, 50mM KCl, 1mM MgCl2, 1mM EGTA, 1mM DTT). 160mM 2,3-Butanedione-2-monoxime (BDM) stock solution was made in KMg50–MOPS immediately before each set of experiments. Solutions of 2,3-Butanedione-2-monoxime were used within 2h of preparation. The reaction was initiated by mixing 4mM MgATP with an equal volume of myosin or actomyosin in 2·-reaction mix (400µM NADH, 1mM phosphoenolpyruvate, 40U/ml lactate dehydrogenase, 200U/ml pyruvate kinase, KMg50–MOPS buffer). 2,3-Butanedione-2-monoxime (0-50mM) did not inhibit the NADH-coupled reaction as measured by direct mixing with MgADP. 2,3-Butanedione-2-monoxime was added tomyosin solutions from concentrated stock 5min before each ATPase measurement. |
Reaction Conditions | 0-50mM; 5min |
Applications | The 2,3-Butanedione-2-monoxime concentration at half maximal inhibition (KI) in KMg50–MOPS is 4.1±1.0mM. The steady-state ATPase rates of myole and Acanthamoeba myosin-IC were not inhibited by 2,3-Butanedione monoxime |
| Cell experiment [2]: | |
Cell lines | Canine ventricular myocytes |
Preparation Method | Myocytes were washed twice and resuspended in the following buffer at room temperature: in (mM) NaCl 50, Na2HPO4/NaH2PO4 50, glucose 11, N,N-bis[2-hydroxyethyl]-2-aminoethanesulfonic acid (BES) 20, rotenone 0.016, EGTA 0.2. The buffer was then supplemented with oligomycin 0.01, phosphocreatine 10, dithiothreitol 1, MgATP 10, and 0.2units/ml creatine phosphokinase. Where indicated, ruthenium red 0.03, and procaine 10 were added to inhibit SR Ca2+ efflux. All cells were lysed with 16mg digitonin/mg myocyte protein, and pH was adjusted to 7.2. At this point, the lysed myocytes were divided into 1.5ml aliquots, and the proper quantity of 2,3-Butanedione-2-monoxime (1M stock) and/or vehicle (water) was added. Cells were warmed to 37℃ during a 5 minute pre-incubation and the appropriate 45Ca2+ EGTA buffer was added. The cells were incubated for 5 minutes at 37℃, when duplicate 0.5ml samples were sedimented through a layer of 97% bromododecane/3% dodecane into 0.1ml of 2N perchloric acid, all layered in a 1.5ml microcentrifuge tube. SR 45Ca2+ uptake was determined by counting a 75ml aliquot of the acid extract using Beckman Ready Caps in a Beckman LS 6800 liquid scintillation counter. |
Reaction Conditions | 30mM; 5+5min |
Applications | 2,3-Butanedione-2-monoxime has no effect on sarcoplasmic reticulum (SR) Ca2+ uptake when efflux is prevented with ruthenium red and procaine. In the absence of efflux inhibitors, a substantial decrease in accumulated SR Ca2+ is observed in the curve with 30mM 2,3-Butanedione-2-monoxime and a synergistic relationship between 2,3-Butanedione-2-monoxime and free Ca2+ concentration is observed. |
| Animal experiment [3]: | |
Animal models | Male spontaneously hypertensive (SHR) and age-matched Wistar-Kyoto (WKY) rat |
Preparation Method | 2,3-Butanedione-2-monoxime was freshly dissolved in physiological saline. Doses of 2,3-Butanedione-2-monoxime ranging from 5 to 200mg/kg were slowly given by intravenous injection over 30sec. The volume of 2,3-Butanedione-2-monoxime solution injected was about 1ml/kg. |
Dosage form | 5, 30, 100 and 200mg/kg; i.v.; once |
Applications | 5, 30, 100 and 200mg/kg 2,3-Butanedione-2-monoxime (intravenously) reduced blood pressure (BP) of the SHR by 9±3, 20±3, 49±5, and 63±7mmHg, respectively. The same doses of 2,3-Butanedione-2-monoxime reduced BP of the WKY by 0, 2±0.4, 18±3, and 26±3mmHg. |
References: | |
| Cas No. | 57-71-6 | SDF | |
| 别名 | 2,3-丁烷二酮一肟,BDM|Diacetyl Monoxime|NSC 660|NSC 116103 | ||
| 化学名 | 2,3-butanedione, 2-oxime | ||
| Canonical SMILES | CC(/C(C)=N/O)=O | ||
| 分子式 | C4H7NO2 | 分子量 | 101.1 |
| 溶解度 | DMF: 30 mg/ml,DMSO: 30 mg/ml,Ethanol: 30 mg/ml,PBS (pH 7.2): 2 mg/ml | 储存条件 | Store at -20°C |
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1 mg | 5 mg | 10 mg |
| 1 mM | 9.8912 mL | 49.456 mL | 98.912 mL |
| 5 mM | 1.9782 mL | 9.8912 mL | 19.7824 mL |
| 10 mM | 989.1 μL | 4.9456 mL | 9.8912 mL |
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动物数量 | 只 |
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- Purity: >98.00% Appearance: A solid
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