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B1552 Sigma

Bromoenol lactone

≥98% (TLC)

Synonym: BEL, E-6-(Bromoethylene)tetrahydro-3-(1-naphthyl)-2H-pyran-2-one

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Properties

Related Categories A to C, B, Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules, Biochemicals and Reagents,
assay   ≥98% (TLC)
solubility   DMSO: soluble (Dilute in aqueous medium immediately prior to use and store on ice for no more than 12 hours.)
  degassed ethanol: soluble (Dilute in aqueous medium immediately prior to use and store on ice for no more than 12 hours.)
absorption   λmax 224 nm
storage temp.   −20°C

Description

Biochem/physiol Actions

Potent, irreversible inhibitor of calcium-independent phospholipase A2 and of magnesium-dependent phosphatidate phosphohydrolase from P388D macrophages (IC50 = 8 μM); enzyme activated irreversible chymotrypsin inhibitor (Ki = 636 nM).

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Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
Hazard Codes (Europe) 
Xi
Risk Statements (Europe) 
Safety Statements (Europe) 
26
WGK Germany 
3

Documents

Certificate of Analysis

Certificate of Origin

Protocols & Articles

Articles

The Role of Inflammation in Neurodegeneration

It is well established that the brain can sense and react to peripheral insults through the rapid induction of fever and other neuroendocrine changes in response to events such as infection and tissu...
Scott Hauser, Technology Transfer Specialist, Sigma® Life Science
Biofiles, Vol. 8, No. 19
Keywords: Adhesion, Biofiles, Central Nervous System, Diseases, Events, Gene expression, Inflammation, Neurodegenerative Diseases, Reductions, Type

Peer-Reviewed Papers

References

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Role Of Calcium-independent Phospholipase A2 In The Pathogenesis Of Barth Syndrome. Malhotra, A., et al. Proc. Natl. Acad. Sci. U. S. A. 106, 2337-41, (2009)

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Inhibition of macrophage Ca2+-independent phospholipase A2 by bromoenol lactone and trifluoromethyl ketones. Ackermann, E.J. J. Biol. Chem. 270, 445, (1995)

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Suicide inhibition of canine myocardial cytosolic calcium-independent phospholipase A2. Hazen. S.L., et al. J. Biol. Chem. 266, 7227-7232, (1991)

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Bromoenol lactone inhibits magnesium-dependent phosphatidate phosphohydrolase and blocks triacylglycerol biosynthesis in mouse P388D1 macrophages. Balsinde, J., Dennis, E.A. J. Biol. Chem. 271, 31937, (1996)

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Haloenol lactones: potent enzyme-activated irreversible inhibitors for α-chymotrypsin. Daniels, S.B. J. Biol. Chem. 258, 15046, (1983)

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Evidence for de novo synthesis of lysophosphatidic acid in the spinal cord through phospholipase A2 and autotaxin in nerve injury-induced neuropathic pain. Ma L, Uchida H, Nagai J, et al. J. Pharmacol. Exp. Ther. 333(2), 540-6, (2010)

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[Expression of iPLA2 in human pancreatic islets and its important role in glucose-stimulated insulin secretion]. Wang RT, Song KY, Shi JY, et al. Zhonghua Yi Xue Za Zhi 89(20), 1426-9, (2009)

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Massive calcium-activated endocytosis without involvement of classical endocytic proteins. Lariccia V, Fine M, Magi S, et al. J. Gen. Physiol. 137(1), 111-32, (2011)

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Interaction between VEGF and calcium-independent phospholipase A2 in proliferation and migration of retinal pigment epithelium. Kehler AK, Andersen C, Andreasen JR, et al. Curr. Eye Res. 37(6), 500-7, (2012)

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Lysophosphatidylcholine as an effector of fatty acid-induced insulin resistance. Han MS, Lim YM, Quan W, et al. J. Lipid Res. 52(6), 1234-46, (2011)

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Inhibition of calcium-independent phospholipase A2 activates p38 MAPK signaling pathways during cytostasis in prostate cancer cells. Sun B, Zhang X, Yonz C, et al. Biochem. Pharmacol. 79(12), 1727-35, (2010)

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Involvement of plasmalogens in post-natal retinal vascular development. Saab S, Buteau B, Leclère L, et al. PLoS ONE 9(6), e101076, (2014)

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Activation of mitochondrial calcium-independent phospholipase A2γ (iPLA2γ) by divalent cations mediating arachidonate release and production of downstream eicosanoids. Moon SH, Jenkins CM, Liu X, et al. J. Biol. Chem. 287(18), 14880-95, (2012)

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The roles of iPLA2, TRPM8 and TRPA1 in chemically induced cold hypersensitivity. Gentry C, Stoakley N, Andersson DA, et al. Mol. Pain 6, 4, (2010)

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Role of calcium independent phospholipase A2 in maintaining mitochondrial membrane potential and preventing excessive exocytosis in PC12 cells. Ma MT, Yeo JF, Farooqui AA, et al. Neurochem. Res. 36(2), 347-54, (2011)

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Modulation of melanoma cell phospholipid metabolism in response to heat shock protein 90 inhibition. Beloueche-Babari M, Arunan V, Jackson LE, et al. Oncotarget 1(3), 185-97, (2010)

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Group VIA PLA2 (iPLA2β) is activated upstream of p38 mitogen-activated protein kinase (MAPK) in pancreatic islet β-cell signaling. Song H, Wohltmann M, Tan M, et al. J. Biol. Chem. 287(8), 5528-41, (2012)

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Calcium-independent phospholipase A(2) plays a key role in the endothelium-dependent contractions to acetylcholine in the aorta of the spontaneously hypertensive rat. Wong MS, Man RY, and Vanhoutte PM Am. J. Physiol. Heart Circ. Physiol. 298(4), H1260-6, (2010)

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The role of calcium-independent phospholipase A2γ in modulation of aqueous humor drainage and Ca2+ sensitization of trabecular meshwork contraction. Pattabiraman PP, Lih FB, Tomer KB, et al. Am. J. Physiol. Cell Physiol. 302(7), C979-91, (2012)

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Calcium-independent phospholipase A2 beta is dispensable in inflammasome activation and its inhibition by bromoenol lactone. Franchi L, Chen G, Marina-Garcia N, et al. J. Innate Immun. 1(6), 607-17, (2009)

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Store-operated Ca(2+) entry (SOCE) contributes to normal skeletal muscle contractility in young but not in aged skeletal muscle. Thornton AM, Zhao X, Weisleder N, et al. Aging (Albany. NY.) 3(6), 621-34, (2011)

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Group VIA phospholipase A2 is a target for vasopressin signaling in the thick ascending limb. Paliege A, Roeschel T, Neymeyer H, et al. Am. J. Physiol. Renal Physiol. 302(7), F865-74, (2012)

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Bromoenol lactone inhibits voltage-gated Ca2+ and transient receptor potential canonical channels. Chakraborty S, Berwick ZC, Bartlett PJ, et al. J. Pharmacol. Exp. Ther. 339(2), 329-40, (2011)

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Role of phospholipase A(2) in retrograde transport of ricin. Klokk TI, Lingelem AB, Myrann AG, et al. Toxins (Basel.) 3(9), 1203-19, (2011)

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Combination therapy of an inhibitor of group VIA phospholipase A2 with paclitaxel is highly effective in blocking ovarian cancer development. Li H, Zhao Z, Antalis C, et al. Am. J. Pathol. 179(1), 452-61, (2011)

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Inhibition of calcium-independent phospholipase A impairs agonist-induced calcium entry in keratinocytes. Ross K Br. J. Dermatol. 158(1), 31-7, (2008)

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The absence of myocardial calcium-independent phospholipase A2γ results in impaired prostaglandin E2 production and decreased survival in mice with acute Trypanosoma cruzi infection. Sharma J, Eickhoff CS, Hoft DF, et al. Infect. Immun. 81(7), 2278-87, (2013)

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GVI phospholipase A2 role in the stimulatory effect of sphingosine-1-phosphate on TRPC5 cationic channels. AL-Shawaf E, Tumova S, Naylor J, et al. Cell Calcium 50(4), 343-50, (2011)

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A role for phospholipase A2 activity in membrane tubule formation and TGN trafficking. Schmidt JA, Kalkofen DN, Donovan KW, et al. Traffic 11(12), 1530-6, (2010)

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Calcium-independent phospholipase A2 participates in KCl-induced calcium sensitization of vascular smooth muscle. Ratz PH, Miner AS, and Barbour SE Cell Calcium 46(1), 65-72, (2009)

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Regulation of store-operated Ca2+ entry in pulmonary artery smooth muscle cells. McElroy SP, Drummond RM, and Gurney AM Cell Calcium 46(2), 99-106, (2009)

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Store-operated Ca(2+) entry is not essential for PDGF-BB induced phenotype modulation in rat aortic smooth muscle. Emter CA and Bowles DK Cell Calcium 48(1), 10-8, (2010)

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