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HELSS (Haloenol lactone suicide substrate, BEL, Bromoenol lactone) (CAS 88070-98-8)

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Alternate Names:
6-(Bromomethylene)tetrahydro-3-(1-naphthaleneyl)-2H-pyran-2-one
Application:
HELSS (Haloenol lactone suicide substrate, BEL, Bromoenol lactone) is an inhibitor of Ca-independent PLA2 and Mg-dependent PAP
CAS Number:
88070-98-8
Purity:
≥95%
Molecular Weight:
317.18
Molecular Formula:
C16H13BrO2
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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HELSS (Haloenol lactone suicide substrate, BEL, Bromoenol lactone) is a potent and irreversible inhibitor that selectively targets and forms a covalent bond with myocardial group VI iPLA2 (calcium-independent phospholipase A2). Group VI iPLA2 (Calcium-independent phospholipase A2) is a mediator of arachidonic acid release from aortic smooth cells induced by vasopressin. Inhibition of arachidonic acid release was found to be saturable and specific due to HELSS′s 1,000-fold selectivity for inhibition of calcium-independent versus calcium-dependent PLA2. HELSS (Haloenol lactone suicide substrate, BEL, Bromoenol lactone) has also been observed to inhibit cellular cytosolic magnesium-dependent PAP (phosphatidic acid phosphohydrolase) activity in intact P388D1 macrophages. It is noted that this compound is also a GST (glutathione S-transferases) inhibitor that could help prevent GST-mediated drug resistance. HELSS (Haloenol lactone suicide substrate, BEL, Bromoenol lactone) is an inhibitor of Chymotrypsin.


HELSS (Haloenol lactone suicide substrate, BEL, Bromoenol lactone) (CAS 88070-98-8) References

  1. Regulation of lung surfactant secretion by phospholipase A2.  |  Liu, L. 1999. J Cell Biochem. 72: 103-10. PMID: 10025671
  2. Formation of reactive oxygen species by the contracting diaphragm is PLA(2) dependent.  |  Nethery, D., et al. 1999. J Appl Physiol (1985). 87: 792-800. PMID: 10444641
  3. Involvement of cytosolic phospholipase A2 and secretory phospholipase A2 in arachidonic acid release from human neutrophils.  |  Marshall, J., et al. 2000. J Immunol. 164: 2084-91. PMID: 10657662
  4. Protease-activated receptor-1 mediates thrombin-induced persistent sodium current in human cardiomyocytes.  |  Pinet, C., et al. 2008. Mol Pharmacol. 73: 1622-31. PMID: 18326052
  5. Calcium-independent phospholipase A2 beta is dispensable in inflammasome activation and its inhibition by bromoenol lactone.  |  Franchi, L., et al. 2009. J Innate Immun. 1: 607-17. PMID: 20160900
  6. Suicide inhibition of canine myocardial cytosolic calcium-independent phospholipase A2. Mechanism-based discrimination between calcium-dependent and -independent phospholipases A2.  |  Hazen, SL., et al. 1991. J Biol Chem. 266: 7227-32. PMID: 2016324
  7. Inhibition of auxin transport and auxin signaling and treatment with far red light induces root coiling in the phospholipase-A mutant ppla-I-1. Significance for surface penetration?  |  Perrineau, F., et al. 2016. J Plant Physiol. 196-197: 53-9. PMID: 27058428
  8. Arachidonic acid release from aortic smooth muscle cells induced by [Arg8]vasopressin is largely mediated by calcium-independent phospholipase A2.  |  Lehman, JJ., et al. 1993. J Biol Chem. 268: 20713-6. PMID: 8407892
  9. Rat and human pancreatic islet cells contain a calcium ion independent phospholipase A2 activity selective for hydrolysis of arachidonate which is stimulated by adenosine triphosphate and is specifically localized to islet beta-cells.  |  Gross, RW., et al. 1993. Biochemistry. 32: 327-36. PMID: 8418853
  10. Inhibition of arachidonate release by secretagogue-stimulated pancreatic islets suppresses both insulin secretion and the rise in beta-cell cytosolic calcium ion concentration.  |  Ramanadham, S., et al. 1993. Biochemistry. 32: 337-46. PMID: 8418854
  11. Bromoenol lactone inhibits magnesium-dependent phosphatidate phosphohydrolase and blocks triacylglycerol biosynthesis in mouse P388D1 macrophages.  |  Balsinde, J. and Dennis, EA. 1996. J Biol Chem. 271: 31937-41. PMID: 8943239
  12. Haloenol lactone: a new synergist of chemotherapy in vitro.  |  Zheng, J., et al. 1997. Biochem Biophys Res Commun. 241: 13-7. PMID: 9405226
  13. Cloning and expression of a group IV cytosolic Ca2+-dependent phospholipase A2 from rat pancreatic islets. Comparison of the expressed activity with that of an islet group VI cytosolic Ca2+-independent phospholipase A2.  |  Ma, Z., et al. 1998. Biochim Biophys Acta. 1391: 384-400. PMID: 9555100

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

HELSS (Haloenol lactone suicide substrate, BEL, Bromoenol lactone), 5 mg

sc-201418
5 mg
$163.00

HELSS (Haloenol lactone suicide substrate, BEL, Bromoenol lactone), 25 mg

sc-201418A
25 mg
$609.00