Bromoenol lactone

Bromoenol lactone

Catalog Number:
L002373152APE
Mfr. No.:
APE-C5081
Price:
$297
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      • Overview
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          Background

          Bromoenol lactone is a potent and irreversible inhibitor of myocardial cytosolic calcium-independent phospholipase A2 (iPLA2) [1].
          The iPLA2 has been involved in stimulus-induced arachidonic acid release and lysophospholipid generation. The catalytic action of iPLA2 is responsible for phospholipid remodeling as a housekeeping function. Arachidonic acid and lysophospholipid generated by iPLA2 act as a signaling molecule in cellular functions, including eicosanoid production, glucose-induced insulin secretion, Fas-induced apoptosis, cellular proliferation, membrane traffic in fusion, contribution to myocardial ischemia, and others [2].
          BEL promoted apoptosis in a variety of cell lines, including U937, THP-1, and MonoMac (human phagocyte), RAW264.7 (murine macrophage), Jurkat (human T lymphocyte), and GH3 (human pituitary). Long term treatment with BEL (up to 24 h) increased annexin-V binding to the cell surface and nuclear DNA damage. BEL induced the proteolysis of procaspase-9 and procaspase-3 and increased cleavage of poly (ADP-ribose) polymerase [1]. BEL inhibited cellular phosphatidic acid phosphohydrolase (PAP) activity in intact P388D1 macrophages with an IC50 of ~8 μM. BEL blocked triacylglycerol biosynthesis in P388D1 cells by decreasing diacylglycerol availability [3].

          [1] Fuentes L, Pérez R, Nieto M L, et al. Bromoenol lactone promotes cell death by a mechanism involving phosphatidate phosphohydrolase-1 rather than calcium-independent phospholipase A2[J]. Journal of Biological Chemistry, 2003, 278(45): 44683-44690.
          [2] Akiba S, Sato T. Cellular function of calcium-independent phospholipase A2[J]. Biological and Pharmaceutical Bulletin, 2004, 27(8): 1174-1178.
          [3] Balsinde J, Dennis E A. Bromoenol lactone inhibits magnesium-dependent phosphatidate phosphohydrolase and blocks triacylglycerol biosynthesis in mouse P388D1 macrophages[J]. Journal of Biological Chemistry, 1996, 271(50): 31937-31941.

      • Properties
        • Alternative Name
          6E-(bromomethylene)tetrahydro-3-(1-naphthalenyl)-2H-pyran-2-one
          CAS Number
          88070-98-8
          Molecular Formula
          C16H13BrO2
          Molecular Weight
          317.2
          Appearance
          A crystalline solid
          Purity
          Purity ≥ 95.00%
          Solubility
          ≤2mg/ml in ethanol;25mg/ml in DMSO;50mg/ml in dimethyl formamide
          Storage
          Store at -20°C

          * For Research Use Only

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