| Identification | Back Directory | [Name]
BROMOENOL LACTONE | [CAS]
88070-98-8 | [Synonyms]
BEL
HELSS
HALOENOL LACTONE
BROMOENOL LACTONE
(6E)-Bromoenol lactone
Bromoenol lactone (BEL)
Bromoenol Lactone Solution
HALOENOL LACTONE SUICIDE SUBSTRATE
(6E)-6-(bromomethylidene)-3-naphthalen-1-yloxan-2-one
E-6-(BROMOETHYLENE)TETRAHYDRO-3-(1-NAPHTHYL)-2H-PYRAN-2-ONE
6-(bromomethylene)tetrahydro-3-(1-naphthaleneyl)-2H-pyran-2-one
BEL, E-6-(Bromoethylene)tetrahydro-3-(1-naphthyl)-2H-pyran-2-one
(E)-6-(BROMOMETHYLENE)TETRAHYDRO-3-(1-NAPTHALENYL)-2H-PYRAN-2-ONE
HELSS (Haloenol lactone suicide substrate, BEL, Bromoenol lactone)
(E)-6-(BROMOMETHYLENE)TETRAHYDRO-3-(1-NAPHTHALENYL)-2H-PYRAN-2-ONE | [Molecular Formula]
C16H13BrO2 | [MDL Number]
MFCD00270871 | [MOL File]
88070-98-8.mol | [Molecular Weight]
317.18 |
| Chemical Properties | Back Directory | [Melting point ]
103-106℃ | [Boiling point ]
467.0±45.0 °C(Predicted) | [density ]
1.538±0.06 g/cm3(Predicted) | [storage temp. ]
-20°C | [solubility ]
DMSO: Dilute in aqueous medium immediately prior to use and store on ice for no more than 12 hours.soluble
| [form ]
White solid. | [color ]
White to yellow | [biological source]
synthetic (organic) | [λmax]
224 nm |
| Hazard Information | Back Directory | [Uses]
HELSS (Haloenol lactone suicide substrate, BEL, Bromoenol lactone) is an inhibitor of Ca-independent PLA2 and Mg-dependent PAP. | [Definition]
ChEBI: Bromoenol lactone is a member of naphthalenes. | [Biological Activity]
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]. | [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). | [storage]
Store at -20°C | [References]
[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. |
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