BROMOENOL LACTONE Chemical Properties

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

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26

WGK Germany 

3

MSDS

• Language:English Provider:SigmaAldrich

BROMOENOL LACTONE Usage And Synthesis

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).

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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