BROMOENOL LACTONE
Synonym(s):BEL;E-6-(Bromoethylene)tetrahydro-3-(1-naphthyl)-2H-pyran-2-one
- CAS NO.:88070-98-8
- Empirical Formula: C16H13BrO2
- Molecular Weight: 317.18
- MDL number: MFCD00270871
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-07-02 08:55:03
What is BROMOENOL LACTONE?
The Uses of BROMOENOL LACTONE
HELSS (Haloenol lactone suicide substrate, BEL, Bromoenol lactone) is an inhibitor of Ca-independent PLA2 and Mg-dependent PAP.
What are the applications of Application
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).
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.
Properties of BROMOENOL LACTONE
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 |
Safety information for BROMOENOL LACTONE
Pictogram(s) |
Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation |
Precautionary Statement Codes |
P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P304+P340:IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. P405:Store locked up. |
Computed Descriptors for BROMOENOL LACTONE
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