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88070-98-8 | HELSS (Haloenol lactone suicide substrate, BEL, Bromoenol lactone)
CAS No: 88070-98-8 Catalog No: AG004EU2 MDL No:MFCD00270871
Product Description
Catalog Number:
AG004EU2
Chemical Name:
HELSS (Haloenol lactone suicide substrate, BEL, Bromoenol lactone)
CAS Number:
88070-98-8
Molecular Formula:
C16H13BrO2
Molecular Weight:
317.1772
MDL Number:
MFCD00270871
IUPAC Name:
(6E)-6-(bromomethylidene)-3-naphthalen-1-yloxan-2-one
InChI:
InChI=1S/C16H13BrO2/c17-10-12-8-9-15(16(18)19-12)14-7-3-5-11-4-1-2-6-13(11)14/h1-7,10,15H,8-9H2/b12-10+
InChI Key:
BYUCSFWXCMTYOI-ZRDIBKRKSA-N
SMILES:
Br/C=C/1\CCC(C(=O)O1)c1cccc2c1cccc2
Properties
Complexity:
377
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
1
Exact Mass:
316.01g/mol
Formal Charge:
0
Heavy Atom Count:
19
Hydrogen Bond Acceptor Count:
2
Hydrogen Bond Donor Count:
0
Isotope Atom Count:
0
Molecular Weight:
317.182g/mol
Monoisotopic Mass:
316.01g/mol
Rotatable Bond Count:
1
Topological Polar Surface Area:
26.3A^2
Undefined Atom Stereocenter Count:
1
Undefined Bond Stereocenter Count:
0
XLogP3:
4.2
Literature
| Title | Journal |
|---|---|
| Group VIA Phospholipase A2 (iPLA2β) Modulates Bcl-x 5'-Splice Site Selection and Suppresses Anti-apoptotic Bcl-x(L) in β-Cells. | The Journal of biological chemistry 20150424 |
| The role of endoplasmic reticulum Ca2+-independent phospholipase a2γ in oxidant-induced lipid peroxidation, Ca2+ release, and renal cell death. | Toxicological sciences : an official journal of the Society of Toxicology 20120801 |
| Haloenol pyranones and morpholinones as antineoplastic agents of prostate cancer. | Bioorganic & medicinal chemistry letters 20120715 |
| Interaction between VEGF and calcium-independent phospholipase A2 in proliferation and migration of retinal pigment epithelium. | Current eye research 20120601 |
| Activation of mitochondrial calcium-independent phospholipase A2γ (iPLA2γ) by divalent cations mediating arachidonate release and production of downstream eicosanoids. | The Journal of biological chemistry 20120427 |
| Group VIA phospholipase A2 is a target for vasopressin signaling in the thick ascending limb. | American journal of physiology. Renal physiology 20120401 |
| The role of calcium-independent phospholipase A2γ in modulation of aqueous humor drainage and Ca2+ sensitization of trabecular meshwork contraction. | American journal of physiology. Cell physiology 20120401 |
| Group VIA PLA2 (iPLA2β) is activated upstream of p38 mitogen-activated protein kinase (MAPK) in pancreatic islet β-cell signaling. | The Journal of biological chemistry 20120217 |
| Bromoenol lactone inhibits voltage-gated Ca2+ and transient receptor potential canonical channels. | The Journal of pharmacology and experimental therapeutics 20111101 |
| GVI phospholipase A2 role in the stimulatory effect of sphingosine-1-phosphate on TRPC5 cationic channels. | Cell calcium 20111001 |
| Role of phospholipase A(2) in retrograde transport of ricin. | Toxins 20110901 |
| Profiling of fatty acids released during calcium-induced mitochondrial permeability transition in isolated rabbit kidney cortex mitochondria. | Toxicology in vitro : an international journal published in association with BIBRA 20110801 |
| Combination therapy of an inhibitor of group VIA phospholipase A2 with paclitaxel is highly effective in blocking ovarian cancer development. | The American journal of pathology 20110701 |
| Lysophosphatidylcholine as an effector of fatty acid-induced insulin resistance. | Journal of lipid research 20110601 |
| Store-operated Ca(2+) entry (SOCE) contributes to normal skeletal muscle contractility in young but not in aged skeletal muscle. | Aging 20110601 |
| Proinflammatory treatment of astrocytes with lipopolysaccharide results in augmented Ca2+ signaling through increased expression of via phospholipase A2 (iPLA2). | American journal of physiology. Cell physiology 20110301 |
| Role of calcium independent phospholipase A2 in maintaining mitochondrial membrane potential and preventing excessive exocytosis in PC12 cells. | Neurochemical research 20110201 |
| A role for phospholipase A2 activity in membrane tubule formation and TGN trafficking. | Traffic (Copenhagen, Denmark) 20101201 |
| 1-(5-carboxyindol-1-yl)propan-2-one inhibitors of human cytosolic phospholipase A(2)alpha with reduced lipophilicity: synthesis, biological activity, metabolic stability, solubility, bioavailability, and topical in vivo activity. | Journal of medicinal chemistry 20100722 |
| Modulation of melanoma cell phospholipid metabolism in response to heat shock protein 90 inhibition. | Oncotarget 20100701 |
| Inhibition of calcium-independent phospholipase A2 activates p38 MAPK signaling pathways during cytostasis in prostate cancer cells. | Biochemical pharmacology 20100615 |
| Evidence for de novo synthesis of lysophosphatidic acid in the spinal cord through phospholipase A2 and autotaxin in nerve injury-induced neuropathic pain. | The Journal of pharmacology and experimental therapeutics 20100501 |
| Calcium-independent phospholipase A(2) plays a key role in the endothelium-dependent contractions to acetylcholine in the aorta of the spontaneously hypertensive rat. | American journal of physiology. Heart and circulatory physiology 20100401 |
| The roles of iPLA2, TRPM8 and TRPA1 in chemically induced cold hypersensitivity. | Molecular pain 20100101 |
| TLR-4 mediated group IVA phospholipase A(2) activation is phosphatidic acid phosphohydrolase 1 and protein kinase C dependent. | Biochimica et biophysica acta 20091001 |
| Genetic mapping of targets mediating differential chemical phenotypes in Plasmodium falciparum. | Nature chemical biology 20091001 |
| Calcium-independent phospholipase A2 beta is dispensable in inflammasome activation and its inhibition by bromoenol lactone. | Journal of innate immunity 20091001 |
| Regulation of store-operated Ca2+ entry in pulmonary artery smooth muscle cells. | Cell calcium 20090801 |
| Calcium-independent phospholipase A2 participates in KCl-induced calcium sensitization of vascular smooth muscle. | Cell calcium 20090701 |
| Transient receptor potential melastatin 8 channel involvement in the regulation of vascular tone. | American journal of physiology. Heart and circulatory physiology 20090601 |
| [Expression of iPLA2 in human pancreatic islets and its important role in glucose-stimulated insulin secretion]. | Zhonghua yi xue za zhi 20090526 |
| Inhibition of calcium-independent phospholipase A2 prevents inflammatory mediator production in pulmonary microvascular endothelium. | Respiratory physiology & neurobiology 20090227 |
| Discovery and development of fatty acid amide hydrolase (FAAH) inhibitors. | Journal of medicinal chemistry 20081211 |
| The cytotoxic effect of bromoenol lactone, a calcium-independent phospholipase A2 inhibitor, on rat cortical neurons in culture. | Cellular and molecular neurobiology 20081201 |
| Calcium-independent phospholipase A2 in rabbit ventricular myocytes. | Lipids 20080901 |
| Alterations in phospholipid and fatty acid lipid profiles in primary neocortical cells during oxidant-induced cell injury. | Chemico-biological interactions 20080811 |
| Inhibition of Ca2+-independent phospholipase A2 decreases prostate cancer cell growth by p53-dependent and independent mechanisms. | The Journal of pharmacology and experimental therapeutics 20080701 |
| Complex regulation of store-operated Ca2+ entry pathway by PKC-epsilon in vascular SMCs. | American journal of physiology. Cell physiology 20080601 |
| The role of diacylglyceride generation by phospholipase D and phosphatidic acid phosphatase in the activation of 5-lipoxygenase in polymorphonuclear leukocytes. | Journal of leukocyte biology 20080401 |
| On the importance of plasmalogen status in stimulated arachidonic acid release in the macrophage cell line RAW 264.7. | Biochimica et biophysica acta 20080401 |
| Anti-angiogenic pigment epithelium-derived factor regulates hepatocyte triglyceride content through adipose triglyceride lipase (ATGL). | Journal of hepatology 20080301 |
| Inhibition of calcium-independent phospholipase A impairs agonist-induced calcium entry in keratinocytes. | The British journal of dermatology 20080101 |
| Role of calcium-independent phospholipase A2 in cortex striatum thalamus cortex circuitry-enzyme inhibition causes vacuous chewing movements in rats. | Psychopharmacology 20071201 |
| The increase of cell-membranous phosphatidylcholines containing polyunsaturated fatty acid residues induces phosphorylation of p53 through activation of ATR. | Journal of cell science 20071201 |
| Induction of group VIA phospholipase A2 activity during in vitro ischemia in C2C12 myotubes is associated with changes in the level of its splice variants. | American journal of physiology. Cell physiology 20071101 |
| Arachidonic acid signaling is involved in the mechanism of imidazoline-induced KATP channel-independent stimulation of insulin secretion. | Cellular and molecular life sciences : CMLS 20071101 |
| Inhibition of calcium-independent phospholipase A2 suppresses proliferation and tumorigenicity of ovarian carcinoma cells. | The Biochemical journal 20070915 |
| Group VIA phospholipase A2 (iPLA2beta) participates in angiotensin II-induced transcriptional up-regulation of regulator of g-protein signaling-2 in vascular smooth muscle cells. | The Journal of biological chemistry 20070831 |
| A novel role of group VIB calcium-independent phospholipase A2 (iPLA2gamma) in the inducible expression of group IIA secretory PLA2 in rat fibroblastic cells. | The Journal of biological chemistry 20070713 |
| The transfer of VLDL-associated phospholipids to activated platelets depends upon cytosolic phospholipase A2 activity. | Journal of lipid research 20070701 |
| Activation and inactivation of the volume-sensitive taurine leak pathway in NIH3T3 fibroblasts and Ehrlich Lettre ascites cells. | American journal of physiology. Cell physiology 20070701 |
| Agonist-induced calcium entry correlates with STIM1 translocation. | Journal of cellular physiology 20070601 |
| Role of Ca2+-independent phospholipase A2gamma in Ca2+-induced mitochondrial permeability transition. | The Journal of pharmacology and experimental therapeutics 20070501 |
| Bromoenol lactone, an inhibitor of Group V1A calcium-independent phospholipase A2 inhibits antigen-stimulated mast cell exocytosis without blocking Ca2+ influx. | Cell calcium 20070201 |
| Identification of calcium-independent phospholipase A2gamma in mitochondria and its role in mitochondrial oxidative stress. | American journal of physiology. Renal physiology 20070201 |
| Caspase-dependent and -independent induction of phosphatidylserine externalization during apoptosis in human renal carcinoma Cak(1)-1 and A-498 cells. | Toxicology 20070105 |
| Calcium-independent phospholipase A2-catalyzed plasmalogen hydrolysis in hypoxic human coronary artery endothelial cells. | American journal of physiology. Cell physiology 20070101 |
| Phospholipase A2-catalyzed hydrolysis of plasmalogen phospholipids in thrombin-stimulated human platelets. | Thrombosis research 20070101 |
| Inhibition of phospholipase A2 reduces neurite outgrowth and neuronal viability. | Prostaglandins, leukotrienes, and essential fatty acids 20070101 |
| Calcium-independent phospholipase A(2) influences AMPA-mediated toxicity of hippocampal slices by regulating the GluR1 subunit in synaptic membranes. | Hippocampus 20070101 |
| Phospholipase A2 activation regulates cytotoxicity of methylmercury in vascular endothelial cells. | International journal of toxicology 20070101 |
| Roles of phospholipase A2 isoforms in swelling- and melittin-induced arachidonic acid release and taurine efflux in NIH3T3 fibroblasts. | American journal of physiology. Cell physiology 20061201 |
| Group VIA calcium-independent phospholipase A2 mediates endothelial cell S phase progression. | The Journal of biological chemistry 20061124 |
| Lipopolysaccharide-induced cyclooxygenase-2 expression in human U937 macrophages is phosphatidic acid phosphohydrolase-1-dependent. | The Journal of biological chemistry 20061103 |
| Prostacyclin production in tryptase and thrombin stimulated human bladder endothelial cells: effect of pretreatment with phospholipase A2 and cyclooxygenase inhibitors. | The Journal of urology 20061001 |
| Ca2+-independent phospholipase A2 enhances store-operated Ca2+ entry in dystrophic skeletal muscle fibers. | Journal of cell science 20060915 |
| Neuroprotection of rat hippocampal slices exposed to oxygen-glucose deprivation by enrichment with docosahexaenoic acid and by inhibition of hydrolysis of docosahexaenoic acid-containing phospholipids by calcium independent phospholipase A2. | Neuroscience 20060630 |
| Gestation age-related increase in 50-kDa rat uterine calcium-independent phospholipase A2 expression influences uterine sensitivity to polychlorinated biphenyl stimulation. | Biology of reproduction 20060501 |
| Disruption of G1-phase phospholipid turnover by inhibition of Ca2+-independent phospholipase A2 induces a p53-dependent cell-cycle arrest in G1 phase. | Journal of cell science 20060315 |
| Lysophosphatidic acid is constitutively produced by human peritoneal mesothelial cells and enhances adhesion, migration, and invasion of ovarian cancer cells. | Cancer research 20060315 |
| Calcium-independent phospholipase A2 modulates cytosolic oxidant activity and contractile function in murine skeletal muscle cells. | Journal of applied physiology (Bethesda, Md. : 1985) 20060201 |
| A bromoenol lactone suicide substrate inactivates group VIA phospholipase A2 by generating a diffusible bromomethyl keto acid that alkylates cysteine thiols. | Biochemistry 20060124 |
| A small-molecule FRET probe to monitor phospholipase A2 activity in cells and organisms. | Angewandte Chemie (International ed. in English) 20060109 |
| A novel role for calcium-independent phospholipase A in alpha-amino-3-hydroxy-5-methylisoxazole-propionate receptor regulation during long-term potentiation. | The European journal of neuroscience 20060101 |
| Potential role for mast cell tryptase in recruitment of inflammatory cells to endothelium. | American journal of physiology. Cell physiology 20051201 |
| Modulation of phospholipase A2 activity in primary cultures of rat cortical neurons. | Journal of neural transmission (Vienna, Austria : 1996) 20051001 |
| Inhibition of calcium-independent phospholipase A2 activity in rat hippocampus impairs acquisition of short- and long-term memory. | Psychopharmacology 20050901 |
| The endocannabinoid system: drug targets, lead compounds, and potential therapeutic applications. | Journal of medicinal chemistry 20050811 |
| Genetic and pharmacologic evidence that calcium-independent phospholipase A2beta regulates virus-induced inducible nitric-oxide synthase expression by macrophages. | The Journal of biological chemistry 20050729 |
| Ca(2+)-independent phospholipase A2 participates in the vesicular transport of milk proteins. | Biochimica et biophysica acta 20050415 |
| Identification and distribution of endoplasmic reticulum iPLA2. | Biochemical and biophysical research communications 20050204 |
| Inhibition of Ca2+-independent phospholipase A2 results in insufficient insulin secretion and impaired glucose tolerance. | Molecular endocrinology (Baltimore, Md.) 20050201 |
| Identification, cloning, expression, and purification of three novel human calcium-independent phospholipase A2 family members possessing triacylglycerol lipase and acylglycerol transacylase activities. | The Journal of biological chemistry 20041119 |
| Contribution of lipid second messengers to the regulation of phosphatidylcholine synthesis during cell cycle re-entry. | Biochimica et biophysica acta 20041108 |
| Amyloid beta(1-42) and its beta(25-35) fragment induce activation and membrane translocation of cytosolic phospholipase A2 in bovine retina capillary pericytes. | Biochimica et biophysica acta 20041108 |
| Signalling pathways regulating human neutrophil migration induced by secretory phospholipases A2. | Toxicon : official journal of the International Society on Toxinology 20041001 |
| Male mice that do not express group VIA phospholipase A2 produce spermatozoa with impaired motility and have greatly reduced fertility. | The Journal of biological chemistry 20040910 |
| Differing caspase-1 activation states in monocyte versus macrophage models of IL-1beta processing and release. | Journal of leukocyte biology 20040901 |
| Laminar flow activates peroxisome proliferator-activated receptor-gamma in vascular endothelial cells. | Circulation 20040831 |
| Inactivation of endoplasmic reticulum bound Ca2+-independent phospholipase A2 in renal cells during oxidative stress. | Journal of the American Society of Nephrology : JASN 20040601 |
| Mechanisms of caspase-1 activation by P2X7 receptor-mediated K+ release. | American journal of physiology. Cell physiology 20040501 |
| Mercury- and copper-induced lysosomal membrane destabilisation depends on [Ca2+]i dependent phospholipase A2 activation. | Aquatic toxicology (Amsterdam, Netherlands) 20040210 |
| Apoptosis of insulin-secreting cells induced by endoplasmic reticulum stress is amplified by overexpression of group VIA calcium-independent phospholipase A2 (iPLA2 beta) and suppressed by inhibition of iPLA2 beta. | Biochemistry 20040203 |
| Involvement of p38 and p42/44 MAP kinases and protein kinase C in the interferon-gamma and interleukin-1alpha-induced phosphorylation of 85-kDa cytosolic phospholipase A(2) in primary human bronchial epithelial cells. | Cytokine 20040107 |
| Postsynaptic injection of calcium-independent phospholipase A2 inhibitors selectively increases AMPA receptor-mediated synaptic transmission. | Hippocampus 20040101 |
| Pancreatic islets and insulinoma cells express a novel isoform of group VIA phospholipase A2 (iPLA2 beta) that participates in glucose-stimulated insulin secretion and is not produced by alternate splicing of the iPLA2 beta transcript. | Biochemistry 20031202 |
| Urocortin protects cardiac myocytes from ischemia/reperfusion injury by attenuating calcium-insensitive phospholipase A2 gene expression. | FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20031201 |
| Bromoenol lactone promotes cell death by a mechanism involving phosphatidate phosphohydrolase-1 rather than calcium-independent phospholipase A2. | The Journal of biological chemistry 20031107 |
| A requirement for calcium-independent phospholipase A2 in thrombin-induced arachidonic acid release and growth in vascular smooth muscle cells. | The Journal of biological chemistry 20031031 |
| Dopamine D1 receptor-dependent inhibition of NaCl transport in the rat thick ascending limb: mechanism of action. | European journal of pharmacology 20030725 |
| Ca2+-independent phospholipase A2 is a novel determinant of store-operated Ca2+ entry. | The Journal of biological chemistry 20030404 |
| Phospholipase A2 modulates respiratory burst developed by neutrophils in patients with rheumatoid arthritis. | Journal of cellular and molecular medicine 20030101 |
| Phospholipid metabolite production in human urothelial cells after protease-activated receptor cleavage. | American journal of physiology. Renal physiology 20021101 |
| Essential role of Ca2+ -dependent phospholipase A2 in estradiol-induced lysosome activation. | American journal of physiology. Cell physiology 20021101 |
| Novel role for calcium-independent phospholipase A(2) in the macrophage antiviral response of inducible nitric-oxide synthase expression. | The Journal of biological chemistry 20021011 |
| 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. | The Journal of biological chemistry 20020906 |
| Role of an endoplasmic reticulum Ca(2+)-independent phospholipase A(2) in oxidant-induced renal cell death. | American journal of physiology. Renal physiology 20020901 |
| Pore formation and uncoupling initiate a Ca2+-independent degradation of mitochondrial phospholipids. | Biochemistry 20020618 |
| Roles of various phospholipases A2 in providing lysophospholipid acceptors for fatty acid phospholipid incorporation and remodelling. | The Biochemical journal 20020615 |
| Dopamine D(2) receptor-induced COX-2-mediated production of prostaglandin E(2) in D(2)-transfected Chinese hamster ovary cells without simultaneous administration of a Ca(2+)-mobilizing agent. | Biochemical pharmacology 20020615 |
| Sustained ER Ca2+ depletion suppresses protein synthesis and induces activation-enhanced cell death in mast cells. | The Journal of biological chemistry 20020419 |
| PTH and DA regulate Na-K ATPase through divergent pathways. | American journal of physiology. Renal physiology 20020301 |
| Identification of the phospholipase A(2) isoforms that contribute to arachidonic acid release in hypoxic endothelial cells: limits of phospholipase A(2) inhibitors. | Biochemical pharmacology 20020115 |
| A calcium-independent phospholipase activity insensitive to bromoenol lactone mediates arachidonic acid release by lindane in rat myometrial cells. | Life sciences 20011214 |
| Endothelial cell PAF synthesis following thrombin stimulation utilizes Ca(2+)-independent phospholipase A(2). | Biochemistry 20011211 |
| Proliferative and morphological effects of endothelins in Schwann cells: roles of p38 mitogen-activated protein kinase and Ca(2+)-independent phospholipase A2. | Journal of neurochemistry 20011201 |
| Calcium-independent phospholipase A(2) is required for human monocyte chemotaxis to monocyte chemoattractant protein 1. | Journal of immunology (Baltimore, Md. : 1950) 20010915 |
| Calcium-independent phospholipase A(2) mediates CREB phosphorylation and c-fos expression during ischemia. | American journal of physiology. Heart and circulatory physiology 20010701 |
| Anti-CD3 and concanavalin A-induced human T cell proliferation is associated with an increased rate of arachidonate-phospholipid remodeling. Lack of involvement of group IV and group VI phospholipase A2 in remodeling and increased susceptibility of proliferating T cells to CoA-independent transacyclase inhibitor-induced apoptosis. | The Journal of biological chemistry 20010518 |
| Clinical concentrations of doxorubicin inhibit activity of myocardial membrane-associated, calcium-independent phospholipase A(2). | Cancer research 20010515 |
| The Ca2+-sensing receptor activates cytosolic phospholipase A2 via a Gqalpha -dependent ERK-independent pathway. | The Journal of biological chemistry 20010427 |
| Studies of insulin secretory responses and of arachidonic acid incorporation into phospholipids of stably transfected insulinoma cells that overexpress group VIA phospholipase A2 (iPLA2beta ) indicate a signaling rather than a housekeeping role for iPLA2beta. | The Journal of biological chemistry 20010420 |
| Docosahexaenoic acid improves long-term potentiation attenuated by phospholipase A(2) inhibitor in rat hippocampal slices. | British journal of pharmacology 20010401 |
| Arachidonyltrifluoromethy ketone, a phospholipase A(2) antagonist, induces dispersal of both Golgi stack- and trans Golgi network-resident proteins throughout the cytoplasm. | Biochemical and biophysical research communications 20010223 |
| Oxidant-induced inhibition of myocardial calcium-independent phospholipase A2. | Cardiovascular toxicology 20010101 |
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