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D9150 Sigma

2,3-Dimethoxy-5-methyl-p-benzoquinone

apoptosis inducer

Synonym: Coenzyme Q0

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Properties

Related Categories Biochemicals and Reagents, Coenzymes, Nucleosides, Nucleotides, Oligonucleotides More...
mp   58-60 °C(lit.)
storage temp.   2-8°C

Description

Packaging

1, 5 g in glass bottle

Application

Coenzyme Q0 inhibits (via radical quenching) reactions of gamma-irradiation induced homolytic cleavage of O-glycoside bonds in polysaccharides. Coenzyme Q0 induces apoptosis and modulates the cell cycle in estrogen receptor negative breast cancer cells. It is toxic to other cells such as insulin producing cells.

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Safety & Documentation

Safety Information

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GHS07  GHS07
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WGK Germany 
2

Documents

Certificate of Analysis

Certificate of Origin

Protocols & Articles

Peer-Reviewed Papers

References

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Coenzyme Q0 induces apoptosis and modulates the cell cycle in estrogen receptor negative breast cancer cells. Somers-Edgar TJ, Rosengren RJ. Anticancer Drugs 20, 33-40, (2009)

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Immunochemical identification of coenzyme Q0-dihydrolipoamide adducts in the E2 components of the alpha-ketoglutarate and pyruvate dehydrogenase complexes partially explains the cellular toxicity of coenzyme Q0. MacDonald MJ, Husain RD, et al J. Biol. Chem. 279, 27278-27285, (2004)

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Effects of vitamins, coenzymes and amino acids on reactions of homolytic cleavage of the O-glycoside bond in carbohydrates. Shadyro OI, Kisel RM, Vysotskii VV, Edimecheva IP. Bioorg. Med. Chem. Lett. 16, 4763-4766, (2006)

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Escherichia coli-catalyzed bioelectrochemical oxidation of acetate in the presence of mediators. Wang YF, Cheng SS, Tsujimura S, et al. Bioelectrochemistry 69(1), 74-81, (2006)

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Ubiquinone analogs: a mitochondrial permeability transition pore-dependent pathway to selective cell death. Devun F, Walter L, Belliere J, et al. PLoS ONE 5, e11792, (2010)

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Properties of the permeability transition pore in mitochondria devoid of Cyclophilin D. Basso E, Fante L, Fowlkes J, et al. J. Biol. Chem. 280(19), 18558-61, (2005)

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Uncoupling proteins 2 and 3 are highly active H(+) transporters and highly nucleotide sensitive when activated by coenzyme Q (ubiquinone). Echtay KS, Winkler E, Frischmuth K, et al. Proc. Natl. Acad. Sci. U. S. A. 98(4), 1416-21, (2001)

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The reaction of nitric oxide with ubiquinol: kinetic properties and biological significance. Poderoso JJ, Carreras MC, Schöpfer F, et al. Free Radic. Biol. Med. 26(7-8), 925-35, (1999)

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Prerequisites for ubiquinone analogs to prevent mitochondrial permeability transition-induced cell death. Belliere J, Devun F, Cottet-Rousselle C, et al. J. Bioenerg. Biomembr. 44(1), 207-12, (2012)

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The mitochondrial phosphate carrier interacts with cyclophilin D and may play a key role in the permeability transition. Leung AW, Varanyuwatana P, and Halestrap AP J. Biol. Chem. 283(39), 26312-23, (2008)

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Properties of Ca(2+) transport in mitochondria of Drosophila melanogaster. von Stockum S, Basso E, Petronilli V, et al. J. Biol. Chem. 286(48), 41163-70, (2011)

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Cytokinin oxidase/dehydrogenase genes in barley and wheat: cloning and heterologous expression. Galuszka P, Frébortová J, Werner T, et al. Eur. J. Biochem. 271(20), 3990-4002, (2004)

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The unorthodox histidine kinases BvgS and EvgS are responsive to the oxidation status of a quinone electron carrier. Bock A and Gross R Eur. J. Biochem. 269(14), 3479-84, (2002)

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Site-specific binding of quinones to proteins through thiol addition and addition-elimination reactions. Li WW, Heinze J, and Haehnel W J. Am. Chem. Soc. 127(17), 6140-1, (2005)

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Thiol metabolomics of endothelial cells using capillary liquid chromatography mass spectrometry with isotope coded affinity tags. Yuan W and Edwards JL J. Chromatogr. A 1218(18), 2561-8, (2011)

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Photolabile ubiquinone analogues for identification and characterization of quinone binding sites in proteins. Zhichao Pei et al Bioorg. Med. Chem. 18, 3457-66, (2010)

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Ubiquinone-0 (2,3-dimethoxy-5-methyl-1,4-benzoquinone) as effective catalyzer of ascorbate and epinephrine oxidation and damager of neuroblastoma cells. Roginsky VA, Bruchelt G, and Bartuli O Biochem. Pharmacol. 55(1), 85-91, (1998)

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Quinones facilitate the self-assembly of the phosphorylated tubulin binding region of tau into fibrillar polymers. Santa-María I, Hernández F, Martín CP, et al. Biochemistry 43(10), 2888-97, (2004)

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Plasma membrane NADH-coenzyme Q0 reductase generates semiquinone radicals and recycles vitamin E homologue in a superoxide-dependent reaction. Kagan VE, Arroyo A, Tyurin VA, et al. FEBS Lett. 428(1-2), 43-6, (1998)

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Sonochemistry of quinones in argon-saturated aqueous solutions: enhanced cytochrome c reduction. Lawson RC, Ferrer A, Flores W, et al. Chem. Res. Toxicol. 12(9), 850-4, (1999)

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Ca2+-reversible inhibition of the mitochondrial megachannel by ubiquinone analogues. Martinucci S, Szabò I, Tombola F, et al. FEBS Lett. 480(2-3), 89-94, (2000)

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Antioxidant activities of extracts and metabolites isolated from the fungus Antrodia cinnamomea. Wu MD, Cheng MJ, Wang WY, et al. Nat. Prod. Res. 25(16), 1488-96, (2011)

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Electron spin resonance investigation of semiquinone radicals formed from the reaction of ubiquinone 0 with human oxyhemoglobin. Guo Q, Corbett JT, Yue G, et al. J. Biol. Chem. 277(8), 6104-10, (2002)

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The raised midpoint potential of the [2Fe2S] cluster of cytochrome bc1 is mediated by both the Qo site occupants and the head domain position of the Fe-S protein subunit. Cooley JW, Roberts AG, Bowman MK, et al. Biochemistry 43(8), 2217-27, (2004)

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Inhibitory copper binding site on the spinach cytochrome b6f complex: implications for Qo site catalysis. Rao BK, Tyryshkin AM, Roberts AG, et al. Biochemistry 39(12), 3285-96, (2000)

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Electrophysiological characterization of the Cyclophilin D-deleted mitochondrial permeability transition pore. De Marchi U, Basso E, Szabò I, et al. Mol. Membr. Biol. 23(6), 521-30, (2006)

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Turnover of ubiquinone-0 at the acceptor side of photosynthetic reaction center. Gerencsér L and Maróti P Eur. Biophys. J. 37(7), 1195-205, (2008)

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Quinone analogue irrecoverably paralyses the filarial parasites in vitro. Sivan VM and Kaleysa Raj R Biochem. Biophys. Res. Commun. 256(1), 81-3, (1999)

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Beil. 8,IV,2721

Corp MSDS 1 (1), 1316:C / RegBook 1 (1), 495:A / Structure Index 1, 71:D:3

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