Calcium-independent phospholipases A2 in murine osteoblastic cells and their inhibition by bromoenol lactone: impact on arachidonate dynamics and prostaglandin synthesis

References

• Funk CD. Prostaglandins and leukotrienes: advances in eicosanoid biology. Science 2001;294:1871–5
   PubMed Web of Science ®Google Scholar
• Moolenaar WH, van Meeteren LA, Giepmans BN. The ins and outs of lysophosphatidic acid signaling. Bioessays 2004;26:870–81
   PubMed Web of Science ®Google Scholar
• Prescott SM, Zimmerman GA, Stafforini DM, McIntyre TM. Platelet-activating factor and related lipid mediators. Annu Rev Biochem 2000;69:419–45
   PubMed Web of Science ®Google Scholar
• Schaloske RH, Dennis EA. The phospholipase A2 superfamily and its group numbering system. Biochim Biophys Acta 2006;1761:1246–59
   PubMed Web of Science ®Google Scholar
• Six DA, Dennis EA. The expanding superfamily of phospholipase A(2) enzymes: classification and characterization. Biochim Biophys Acta 2000;1488:1–19
   PubMed Web of Science ®Google Scholar
• Turk J, Ramanadham S. The expression and function of a group via calcium-independent phospholipase A2 (ipla2beta) in beta-cells. Can J Physiol Pharmacol 2004;82:824–32
   PubMed Web of Science ®Google Scholar
• Balsinde J, Bianco ID, Ackermann EJ, et al. Inhibition of calcium-independent phospholipase A2 prevents arachidonic acid incorporation and phospholipid remodeling in p388d1 macrophages. Proc Natl Acad Sci USA 1995;92:8527–31
   PubMed Web of Science ®Google Scholar
• Perez R, Melero R, Balboa MA, Balsinde J. Role of group via calcium-independent phospholipase A2 in arachidonic acid release, phospholipid fatty acid incorporation, and apoptosis in u937 cells responding to hydrogen peroxide. J Biol Chem 2004;279:40385–91
   PubMed Web of Science ®Google Scholar
• Yellaturu CR, Rao GN. A requirement for calcium-independent phospholipase A2 in thrombin-induced arachidonic acid release and growth in vascular smooth muscle cells. J Biol Chem 2003;278:43831–7
   PubMed Web of Science ®Google Scholar
• Moran JM, Buller RM, McHowat J, et al. Genetic and pharmacologic evidence that calcium-independent phospholipase a2beta regulates virus-induced inducible nitric-oxide synthase expression by macrophages. J Biol Chem 2005;280:28162–8
   PubMed Web of Science ®Google Scholar
• Song K, Zhang X, Zhao C, et al. Inhibition of Ca2+-independent phospholipase A2 results in insufficient insulin secretion and impaired glucose tolerance. Mol Endocrinol 2005;19:504–15
   PubMed Web of Science ®Google Scholar
• Smani T, Zakharov SI, Leno E, et al. Ca2+-independent phospholipase A2 is a novel determinant of store-operated Ca2+ entry. J Biol Chem 2003;278:11909–15
   PubMed Web of Science ®Google Scholar
• Mancuso DJ, Jenkins CM, Gross RW. The genomic organization, complete mRNA sequence, cloning, and expression of a novel human intracellular membrane-associated calcium-independent phospholipase A(2). J Biol Chem 2000;275:9937–45
   PubMed Web of Science ®Google Scholar
• Cummings BS, McHowat J, Schnellmann RG. Role of an endoplasmic reticulum Ca(2+)-independent phospholipase A(2) in oxidant-induced renal cell death. Am J Physiol Renal Physiol 2002;283:F492–8
   PubMed Web of Science ®Google Scholar
• Tanaka H, Takeya R, Sumimoto H. A novel intracellular membrane-bound calcium-independent phospholipase A(2). Biochem Biophys Res Commun 2000;272:320–6
   PubMed Web of Science ®Google Scholar
• Murakami M, Masuda S, Ueda-Semmyo K, et al. Group VIB Ca2+-independent phospholipase A2gamma promotes cellular membrane hydrolysis and prostaglandin production in a manner distinct from other intracellular phospholipases A2. J Biol Chem 2005;280:14028–41
   PubMed Web of Science ®Google Scholar
• Kinsey GR, Blum JL, Covington MD, et al. Decreased iPLA2gamma expression induces lipid peroxidation and cell death and sensitizes cells to oxidant-induced apoptosis. J Lipid Res 2008;49:1477–87
   PubMed Web of Science ®Google Scholar
• Saavedra G, Zhang W, Peterson B, Cummings BS. Differential roles for cytosolic and microsomal Ca2+-independent phospholipase A2 in cell growth and maintenance of phospholipids. J Pharmacol Exp Ther 2006;318:1211–19
   PubMed Web of Science ®Google Scholar
• Jenkins CM, Han X, Mancuso DJ, Gross RW. Identification of calcium-independent phospholipase A2 (iPLA2) beta, and not iPLA2gamma, as the mediator of arginine vasopressin-induced arachidonic acid release in A-10 smooth muscle cells. Enantioselective mechanism-based discrimination of mammalian iPLA2s. J Biol Chem 2002;277:32807–14
   PubMed Web of Science ®Google Scholar
• van Tienhoven M, Atkins J, Li Y, Glynn P. Human neuropathy target esterase catalyzes hydrolysis of membrane lipids. J Biol Chem 2002;277:20942–8
   PubMed Web of Science ®Google Scholar
• Jenkins CM, Mancuso DJ, Yan W, et al. Identification, cloning, expression, and purification of three novel human calcium-independent phospholipase A2 family members possessing triacylglycerol lipase and acylglycerol transacylase activities. J Biol Chem 2004;279:48968–75
   PubMed Web of Science ®Google Scholar
• Ackermann EJ, Conde-Frieboes K, Dennis EA. Inhibition of macrophage Ca(2+)-independent phospholipase A2 by bromoenol lactone and trifluoromethyl ketones. J Biol Chem 1995;270:445–50
   PubMed Web of Science ®Google Scholar
• Daniels SB, Katzenellenbogen JA. Halo enol lactones: Studies on the mechanism of inactivation of alpha-chymotrypsin. Biochemistry 1986;25:1436–44
   PubMed Web of Science ®Google Scholar
• Daniels SB, Cooney E, Sofia MJ, et al. Haloenol lactones. Potent enzyme-activated irreversible inhibitors for alpha-chymotrypsin. J Biol Chem 1983;258:15046–53
   PubMed Web of Science ®Google Scholar
• Balsinde J, Dennis EA. Bromoenol lactone inhibits magnesium-dependent phosphatidate phosphohydrolase and blocks triacylglycerol biosynthesis in mouse p388d1 macrophages. J Biol Chem 1996;271:31937–41
   PubMed Web of Science ®Google Scholar
• Zheng J, Mitchell AE, Jones AD, Hammock BD. Haloenol lactone is a new isozyme-selective and active site-directed inactivator of glutathione s-transferase. J Biol Chem 1996;271:20421–5
   PubMed Web of Science ®Google Scholar
• Song H, Ramanadham S, Bao S, et al. A bromoenol lactone suicide substrate inactivates group via phospholipase A2 by generating a diffusible bromomethyl keto acid that alkylates cysteine thiols. Biochemistry 2006;45:1061–73
   PubMed Web of Science ®Google Scholar
• Akiba S, Sato T. Cellular function of calcium-independent phospholipase A2. Biol Pharm Bull 2004;27:1174–8
   PubMed Web of Science ®Google Scholar
• Kudo I, Murakami M. Phospholipase A2 enzymes. Prostaglandins Other Lipid Mediat 2002;6869:3–58
   Web of Science ®Google Scholar
• Smith WL, DeWitt DL, Garavito RM. Cyclooxygenases: structural, cellular, and molecular biology. Annu Rev Biochem 2000;69:145–82
   PubMed Web of Science ®Google Scholar
• Akiba S, Hayama M, Sato T. Inhibition of Ca2+-independent phospholipase A2 by bromoenol lactone attenuates prostaglandin generation induced by interleukin-1 beta and dibutyryl camp in rat mesangial cells. FEBS Lett 1998;437:225–8
   PubMed Web of Science ®Google Scholar
• Murakami M, Kambe T, Shimbara S, Kudo I. Functional coupling between various phospholipase A2s and cyclooxygenases in immediate and delayed prostanoid biosynthetic pathways. J Biol Chem 1999;274:3103–15
   PubMed Web of Science ®Google Scholar
• Wilkins WP III, Barbour SE. Group VI phospholipases A2: homeostatic phospholipases with significant potential as targets for novel therapeutics. Curr Drug Targets 2008;9:683–97
   PubMed Web of Science ®Google Scholar
• Ramanadham S, Yarasheski KE, Silva MJ, et al. Age-related changes in bone morphology are accelerated in group VIA phospholipase A2 (iPLA2beta)-null mice. Am J Pathol 2008;172:868–81
   PubMed Web of Science ®Google Scholar
• Bligh EG, Dyer WJ. A rapid method of total lipid extraction and purification. Can J Biochem Physiol 1959;37:911–17
   PubMedGoogle Scholar
• Ackermann EJ, Kempner ES, Dennis EA. Ca(2+)-independent cytosolic phospholipase A2 from macrophage-like P388D1 cells. Isolation and characterization. J Biol Chem 1994;269:9227–33
   PubMed Web of Science ®Google Scholar
• Lio YC, Dennis EA. Interfacial activation, lysophospholipase and transacylase activity of group VI Ca2+-independent phospholipase A2. Biochim Biophys Acta 1998;1392:320–32
   PubMed Web of Science ®Google Scholar
• CondeFrieboes K, Reynolds LJ, Lio YC, et al. Activated ketones as inhibitors of intracellular Ca2+-dependent and Ca2+-independent phospholipase A(2). J Am Chem Soc 1996;118:5519–25
   Web of Science ®Google Scholar
• Leis HJ, Hohenester E, Gleispach H, et al. Measurement of prostaglandins, thromboxanes and hydroxy fatty acids by stable isotope dilution gas chromatography/mass spectrometry. Biomed Environ Mass Spectrom 1987;14:617–21
   PubMedGoogle Scholar
• Balsinde J, Balboa MA. Cellular regulation and proposed biological functions of group VIA calcium-independent phospholipase A2 in activated cells. Cell Signal 2005;17:1052–62
   PubMed Web of Science ®Google Scholar
• Larsson Forsell PK, Kennedy BP, Claesson HE. The human calcium-independent phospholipase A2 gene multiple enzymes with distinct properties from a single gene. Eur J Biochem 1999;262:575–85
   PubMedGoogle Scholar
• Hsu YH, Burke JE, Li S, et al. Localizing the membrane binding region of group VIA Ca2+-independent phospholipase A2 using peptide amide hydrogen/deuterium exchange mass spectrometry. J Biol Chem 2009;284:23652–61
   PubMed Web of Science ®Google Scholar
• Ma Z, Wang X, Nowatzke W, et al. Human pancreatic islets express mrna species encoding two distinct catalytically active isoforms of group vi phospholipase A2 (iPLA2) that arise from an exon-skipping mechanism of alternative splicing of the transcript from the iPLA2 gene on chromosome 22q13.1. J Biol Chem 1999;274:9607–16
   PubMed Web of Science ®Google Scholar
• Lands WE. Metabolism of glycerolipides: a comparison of lecithin and triglyceride synthesis. J Biol Chem 1958;231:883–8
   PubMed Web of Science ®Google Scholar
• Perez-Chacon G, Astudillo AM, Balgoma D, et al. Control of free arachidonic acid levels by phospholipases A2 and lysophospholipid acyltransferases. Biochim Biophys Acta 2009;1791:1103–13
   PubMed Web of Science ®Google Scholar
• Pastore A, Massoud R, Motti C, et al. Fully automated assay for total homocysteine, cysteine, cysteinylglycine, glutathione, cysteamine, and 2-mercaptopropionylglycine in plasma and urine. Clin Chem 1998;44:825–32
   PubMed Web of Science ®Google Scholar
• Kramer BC, Yabut JA, Cheong J, et al. Toxicity of glutathione depletion in mesencephalic cultures: a role for arachidonic acid and its lipoxygenase metabolites. Eur J Neurosci 2004;19:280–6
   PubMed Web of Science ®Google Scholar
• Buckley BJ, Kent RS, Whorton AR. Regulation of endothelial cell prostaglandin synthesis by glutathione. J Biol Chem 1991;266:16659–66
   PubMed Web of Science ®Google Scholar
• Rouzer CA, Scott WA, Griffith OW, et al. Arachidonic acid metabolism in glutathione-deficient macrophages. Proc Natl Acad Sci USA 1982;79:1621–5
   PubMed Web of Science ®Google Scholar
• Smith WL, Urade Y, Jakobsson PJ. Enzymes of the cyclooxygenase pathways of prostanoid biosynthesis. Chem Rev 2011;111:5821–65
   PubMed Web of Science ®Google Scholar
• Griffith OW, Meister A. Potent and specific inhibition of glutathione synthesis by buthionine sulfoximine (s-n-butyl homocysteine sulfoximine). J Biol Chem 1979;254:7558–60
   PubMed Web of Science ®Google Scholar