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Chemical Compound Review

HELSS     (6E)-6-(bromomethylidene)-3- naphthalen-1...

Synonyms: BTNP, AC1NZRTK, CHEMBL6206, SureCN2060001, B1552_SIGMA, ...
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Disease relevance of bromoenol lactone (BEL)


High impact information on bromoenol lactone (BEL)


Chemical compound and disease context of bromoenol lactone


Biological context of bromoenol lactone


Anatomical context of bromoenol lactone


Associations of bromoenol lactone with other chemical compounds

  • Inhibition of PAP-1 activity by three different strategies (i.e. use of bromoenol lactone, propranolol, and ethanol) resulted in inhibition of COX-2 expression and hence of PGE(2) production [18].
  • Identical inhibition of TG-induced Ca(2+) and Mn(2+) influx (but not Ca(2+) release) was observed in SMC, human platelets, and Jurkat T-lymphocytes when functional activity of iPLA(2) was inhibited by its mechanism-based suicidal substrate, bromoenol lactone (BEL) [19].
  • Co-application of the DAG antagonist and a phospholipase A(2) (PLA(2)) inhibitor such as aristolochic acid, arachidonyltrifluoromethyl ketone, or bromoenol lactone inhibited the purinergic receptor-mediated translocation of PKC epsilon although each PLA(2) inhibitor alone did not block the translocation [20].
  • Bromoenol lactone (BEL), an inhibitor of the Group VI Ca2+-independent phospholipase A2 (iPLA2), diminished both lysophosphatidylcholine levels and the incorporation of AA into phospholipids [21].
  • PLD activation was fully blocked by the cytosolic phospholipase A(2) (PLA(2)) inhibitor ONO-RS-082 and partially attenuated by the selective Ca(2+)-dependent cytosolic PLA(2) inhibitor, arachidonyl trifluoromethylketone (AACOCF(3)), or by bromoenol lactone, an inhibitor of Ca(2+)-independent cytosolic PLA(2) [22].

Gene context of bromoenol lactone

  • In contrast, bromoenol lactone (BEL), a specific inhibitor of iPLA2 had no effect on the release of AA [13].
  • The present study shows that the iPLA2 inhibitor bromoenol lactone, when introduced into hippocampal CA1 pyramidal cells through a patch pipette, generated a dose-dependent increase in the amplitude of alpha-amino-3-hydroxy-5-methylisoxazole-4-propionate (AMPA) receptor-mediated excitatory postsynaptic currents (EPSCs) [23].
  • Although a significant inhibitory effect of MAFP on both TNF-induced AA release and PLA(2) activity in MCF7 was observed, BEL had no effect [24].
  • The selective iPLA(2) suicide substrate inhibitor bromoenol lactone prevents dsRNA- and EMCV-stimulated inducible NO synthase expression; however, bromoenol lactone does not attenuate dsRNA- or EMCV-induced COX-2 expression by macrophages [25].
  • Based on the use of the Group VI Ca2+-independent phospholipase A2 (iPLA2) inhibitor bromoenol lactone (BEL), we previously suggested a role for the iPLA2 in mediating phospholipid fatty acid turnover (Balsinde, J., Bianco, I. D., Ackermann, E. J., Conde-Frieboes, K., and Dennis, E. A. (1995) Proc. Natl. Acad. Sci. U. S. A. 92: 8527-8531) [26].

Analytical, diagnostic and therapeutic context of bromoenol lactone


  1. Group VIA phospholipase A2 forms a signaling complex with the calcium/calmodulin-dependent protein kinase IIbeta expressed in pancreatic islet beta-cells. Wang, Z., Ramanadham, S., Ma, Z.A., Bao, S., Mancuso, D.J., Gross, R.W., Turk, J. J. Biol. Chem. (2005) [Pubmed]
  2. Glyburide-reversible cardioprotective effects of calcium-independent phospholipase A2 inhibition in ischemic rat hearts. Sargent, C.A., Wilde, M.W., Dzwonczyk, S., Tuttle, J.G., Murray, H.N., Atwal, K., Grover, G.J. Cardiovasc. Res. (1996) [Pubmed]
  3. Signalling pathways regulating human neutrophil migration induced by secretory phospholipases A2. Gambero, A., Thomazzi, S.M., Cintra, A.C., Landucci, E.C., De Nucci, G., Antunes, E. Toxicon (2004) [Pubmed]
  4. Lipopolysaccharide-induced Cyclooxygenase-2 Expression in Human U937 Macrophages Is Phosphatidic Acid Phosphohydrolase-1-dependent. Grkovich, A., Johnson, C.A., Buczynski, M.W., Dennis, E.A. J. Biol. Chem. (2006) [Pubmed]
  5. Group VIA Calcium-independent Phospholipase A2 Mediates Endothelial Cell S Phase Progression. Herbert, S.P., Walker, J.H. J. Biol. Chem. (2006) [Pubmed]
  6. Genetic and pharmacologic evidence that calcium-independent phospholipase A2beta regulates virus-induced inducible nitric-oxide synthase expression by macrophages. Moran, J.M., Buller, R.M., McHowat, J., Turk, J., Wohltmann, M., Gross, R.W., Corbett, J.A. J. Biol. Chem. (2005) [Pubmed]
  7. Rat brain cortex mitochondria release group II secretory phospholipase A(2) under reduced membrane potential. Macchioni, L., Corazzi, L., Nardicchi, V., Mannucci, R., Arcuri, C., Porcellati, S., Sposini, T., Donato, R., Goracci, G. J. Biol. Chem. (2004) [Pubmed]
  8. Male mice that do not express group VIA phospholipase A2 produce spermatozoa with impaired motility and have greatly reduced fertility. Bao, S., Miller, D.J., Ma, Z., Wohltmann, M., Eng, G., Ramanadham, S., Moley, K., Turk, J. J. Biol. Chem. (2004) [Pubmed]
  9. Bromoenol lactone inhibits voltage-gated Ca2+ and transient receptor potential canonical channels. Chakraborty, S., Berwick, Z.C., Bartlett, P.J., Kumar, S., Thomas, A.P., Sturek, M., Tune, J.D., Obukhov, A.G. J. Pharmacol. Exp. Ther. (2011) [Pubmed]
  10. Urocortin protects cardiac myocytes from ischemia/reperfusion injury by attenuating calcium-insensitive phospholipase A2 gene expression. Lawrence, K.M., Scarabelli, T.M., Turtle, L., Chanalaris, A., Townsend, P.A., Carroll, C.J., Hubank, M., Stephanou, A., Knight, R.A., Latchman, D.S. FASEB J. (2003) [Pubmed]
  11. Protein kinase C activation precedes arachidonic acid release during IgG-mediated phagocytosis. Karimi, K., Lennartz, M.R. J. Immunol. (1995) [Pubmed]
  12. Electrospray ionization/mass spectrometric analyses of human promonocytic U937 cell glycerolipids and evidence that differentiation is associated with membrane lipid composition changes that facilitate phospholipase A2 activation. Hsu, F.F., Ma, Z., Wohltmann, M., Bohrer, A., Nowatzke, W., Ramanadham, S., Turk, J. J. Biol. Chem. (2000) [Pubmed]
  13. Phospholipase A2 enzymes regulate alpha IIb beta3-mediated, but not Fc gammaRII receptor-mediated, pp125FAK phosphorylation in platelets. Haimovich, B., Ji, P., Ginalis, E., Kramer, R., Greco, R. Thromb. Haemost. (1999) [Pubmed]
  14. A bromoenol lactone suicide substrate inactivates group VIA phospholipase A2 by generating a diffusible bromomethyl keto acid that alkylates cysteine thiols. Song, H., Ramanadham, S., Bao, S., Hsu, F.F., Turk, J. Biochemistry (2006) [Pubmed]
  15. Apoptosis of insulin-secreting cells induced by endoplasmic reticulum stress is amplified by overexpression of group VIA calcium-independent phospholipase A2 (iPLA2 beta) and suppressed by inhibition of iPLA2 beta. Ramanadham, S., Hsu, F.F., Zhang, S., Jin, C., Bohrer, A., Song, H., Bao, S., Ma, Z., Turk, J. Biochemistry (2004) [Pubmed]
  16. Novel role for calcium-independent phospholipase A(2) in the macrophage antiviral response of inducible nitric-oxide synthase expression. Maggi, L.B., Moran, J.M., Scarim, A.L., Ford, D.A., Yoon, J.W., McHowat, J., Buller, R.M., Corbett, J.A. J. Biol. Chem. (2002) [Pubmed]
  17. Human calcium-independent phospholipase A2 mediates lymphocyte proliferation. Roshak, A.K., Capper, E.A., Stevenson, C., Eichman, C., Marshall, L.A. J. Biol. Chem. (2000) [Pubmed]
  18. Regulation of cyclooxygenase-2 expression by phosphatidate phosphohydrolase in human amnionic WISH cells. Johnson, C.A., Balboa, M.A., Balsinde, J., Dennis, E.A. J. Biol. Chem. (1999) [Pubmed]
  19. Ca2+-independent phospholipase A2 is a novel determinant of store-operated Ca2+ entry. Smani, T., Zakharov, S.I., Leno, E., Csutora, P., Trepakova, E.S., Bolotina, V.M. J. Biol. Chem. (2003) [Pubmed]
  20. Phospholipase A(2) and its products are involved in the purinergic receptor-mediated translocation of protein kinase C in CHO-K1 cells. Shirai, Y., Kashiwagi, K., Sakai, N., Saito, N. J. Cell. Sci. (2000) [Pubmed]
  21. Roles of various phospholipases A2 in providing lysophospholipid acceptors for fatty acid phospholipid incorporation and remodelling. Balsinde, J. Biochem. J. (2002) [Pubmed]
  22. Activation of phospholipase D-2 by P2X(7) agonists in rat submandibular gland acini. Pérez-Andrés, E., Fernández-Rodriguez, M., González, M., Zubiaga, A., Vallejo, A., García, I., Matute, C., Pochet, S., Dehaye, J.P., Trueba, M., Marino, A., Gómez-Muñoz, A. J. Lipid Res. (2002) [Pubmed]
  23. Postsynaptic injection of calcium-independent phospholipase A2 inhibitors selectively increases AMPA receptor-mediated synaptic transmission. St-Gelais, F., Ménard, C., Congar, P., Trudeau, L.E., Massicotte, G. Hippocampus. (2004) [Pubmed]
  24. Resistance to TNF-induced cytotoxicity correlates with an abnormal cleavage of cytosolic phospholipase A2. El Mahdani, N.E., Ameyar, M., Cai, Z., Colard, O., Masliah, J., Chouaib, S. J. Immunol. (2000) [Pubmed]
  25. Regulation of cyclooxygenase-2 expression by macrophages in response to double-stranded RNA and viral infection. Steer, S.A., Moran, J.M., Maggi, L.B., Buller, R.M., Perlman, H., Corbett, J.A. J. Immunol. (2003) [Pubmed]
  26. Antisense inhibition of group VI Ca2+-independent phospholipase A2 blocks phospholipid fatty acid remodeling in murine P388D1 macrophages. Balsinde, J., Balboa, M.A., Dennis, E.A. J. Biol. Chem. (1997) [Pubmed]
  27. Studies of phospholipid metabolism, proliferation, and secretion of stably transfected insulinoma cells that overexpress group VIA phospholipase A2. Ma, Z., Bohrer, A., Wohltmann, M., Ramanadham, S., Hsu, F.F., Turk, J. Lipids (2001) [Pubmed]
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