HELSS

Names

[ Name ]:
HELSS

[Synonym ]:
Haloenol lactone suicide substrate
MFCD00270871
bromoenol lactone
2H-Pyran-2-one, 6-(bromomethylene)tetrahydro-3-(1-naphthalenyl)-, (6Z)-
6-Btnpo
L66J B- FT6VOYTJ CU1E
HELSS
BEL
(6Z)-6-(Bromomethylene)-3-(1-naphthyl)tetrahydro-2H-pyran-2-one
BTNP

Biological Activity

[Description]:

Bromoenol lactone ((6E)-Bromoenol lactone) is a suicide-based irreversible, selective, potent inhibitor of calcium-independent phospholipase A2 (iPLA2β) with an IC50 value of approximately 7 μM, which inhibits antigen-stimulated mast cell exocytosis without blocking Ca2+ influx[1][2].

[Related Catalog]:

Signaling Pathways >> Metabolic Enzyme/Protease >> Phospholipase

Research Areas >> Others

[Target]

PLA2:7 μM (IC50)

[In Vitro]

In RBL 2H3 and bone marrow-derived mast cells (BMMCs), Ca2+ entry is critical for exocytosis. Bromoenol lactone inhibits exocytosis when stimulated using a Ca2+ ionophore A23187, which passively transports Ca2+ down a concentration gradient and also in permeabilised mast cells where Ca2+ entry is no longer relevant. Moreover, Bromoenol lactone has only a minor effect on antigen- or thapsigargin-stimulated Ca2+ signalling, both the release from internal stores and sustained elevation due to Ca2+ influx[1].

[References]

[1]. Fensome-Green A, et al. Bromoenol lactone, an inhibitor of Group V1A calcium-independent phospholipase A2 inhibits antigen-stimulated mast cell exocytosis without blocking Ca2+ influx. Cell Calcium. 2007 Feb;41(2):145-53.

[2]. Takuma T, et al. Role of Ca2+-independent phospholipase A2 in exocytosis of amylase from parotid acinar cells. J Biochem. 1997 Jun;121(6):1018-24.

Chemical & Physical Properties

[ Density]:
1.5±0.1 g/cm3

[ Boiling Point ]:
467.0±45.0 °C at 760 mmHg

[ Molecular Formula ]:
C₁₆H₁₃BrO₂

[ Molecular Weight ]:
317.177

[ Flash Point ]:
236.2±28.7 °C

[ Exact Mass ]:
316.009888

[ PSA ]:
26.30000

[ LogP ]:
4.36

[ Vapour Pressure ]:
0.0±1.2 mmHg at 25°C

[ Index of Refraction ]:
1.716

[ Storage condition ]:
-20°C

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H319-H335

[ Precautionary Statements ]:
P261-P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xi: Irritant;

[ Risk Phrases ]:
36/37/38

[ Safety Phrases ]:
26

[ RIDADR ]:
NONH for all modes of transport

Articles

Persistent Nociception Triggered by Nerve Growth Factor (NGF) Is Mediated by TRPV1 and Oxidative Mechanisms.

J. Neurosci. 35 , 8593-603, (2015)

Nerve growth factor (NGF) is elevated in certain chronic pain conditions and is a sufficient stimulus to cause lasting pain in humans, but the actual mechanisms underlying the persistent effects of NG...

Bromoenol Lactone Attenuates Nicotine-Induced Breast Cancer Cell Proliferation and Migration.

PLoS ONE 10 , e0143277, (2015)

Calcium independent group VIA phospholipase A2 (iPLA2β) and Matrix Metalloproteinase-9 (MMP-9) are upregulated in many disease states; their involvement with cancer cell migration has been a recent su...

Cytosolic phospholipase A2 plays a crucial role in ROS/NO signaling during microglial activation through the lipoxygenase pathway.

J. Neuroinflammation 12 , 199, (2015)

Oxidative stress and inflammation are important factors contributing to the pathophysiology of numerous neurological disorders, including Alzheimer's disease, Parkinson's disease, acute stroke, and in...

Related Compounds

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