Arachidonyl trifluoromethyl ketone

Names

[ Name ]:
Arachidonyl trifluoromethyl ketone

[Synonym ]:
Arachidonic acid trifluoromethyl ketone
AACOCF3
Arachidonyl trifluoromethyl ketone
UNII:00XIW1CR0F
Arachidonic acid trifluoromethylketone
MFCD00236427
6,9,12,15-Heneicosatetraen-2-one, 1,1,1-trifluoro-, (6Z,9Z,12Z,15Z)-
(6Z,9Z,12Z,15Z)-1,1,1-Trifluoro-6,9,12,15-henicosatetraen-2-one
Arach-CF3
Arachidonyltrifluoromethane
(6Z,9Z,12Z,15Z)-1,1,1-Trifluorohenicosa-6,9,12,15-tetraen-2-one

Biological Activity

[Description]:

AACOCF3 (Arachidonyl trifluoromethyl ketone) is a cell-permeant trifluoromethyl ketone analog of arachidonic acid. AACOCF3 is a potent and selective slow binding inhibitor of the 85-kDa cytosolic phospholipase A2 (cPLA2). AACOCF3 blocks production of arachidonate and 12-hydroxyeicosatetraenoic acid by calcium ionophore-challenged platelets. AACOCF3 inhibits glucose-induced insulin secretion from isolated rat islets. AACOCF3 has the potential for the research of cardiovascular disease[1][2][3].

[Related Catalog]:

Research Areas >> Cardiovascular Disease

Signaling Pathways >> Metabolic Enzyme/Protease >> Phospholipase

[In Vitro]

AACOCF3 inhibits the release of arachidonic acid from calcium ionophore-challenged U937 cells (IC50= 8 μM, 2 x 106 cells ml-1) and from platelets (IC50= 2 μM, 4 x 107 cells ml-1)[1]. AACOCF3 (10 μM) suppresses phosphate-induced calcification and osteogenic/chondrogenic signaling in HAoSMCs. AACOCF3 significantly inhibits both basal and Pi-induced release of arachidonic acid, the product of PLA2 activity[2].

[In Vivo]

AACOCF3 (10 mg/kg; gavage; 5 days a week; ApoE–/– mice (6-week-old males) were fed a high-cholesterol diet) significantly reduces type III collagen plaque expression but had no significant influence on total collagen accumulation[3].

[References]

[1]. Riendeau D, et al. Arachidonyl trifluoromethyl ketone, a potent inhibitor of 85-kDa phospholipase A2, blocks production of arachidonate and 12-hydroxyeicosatetraenoic acid by calcium ionophore-challenged platelets. J Biol Chem. 1994;269(22):15619-15624.

[2]. Schanstra JP, et al. Systems biology identifies cytosolic PLA2 as a target in vascular calcification treatment. JCI Insight. 2019;4(10):e125638. Published 2019 May 16.

[3]. Loweth AC, et al. A specific inhibitor of cytosolic phospholipase A2 activity, AACOCF3, inhibits glucose-induced insulin secretion from isolated rat islets. Biochem Biophys Res Commun. 1996;218(2):423-427.

Chemical & Physical Properties

[ Density]:
1.0±0.1 g/cm3

[ Boiling Point ]:
421.7±45.0 °C at 760 mmHg

[ Molecular Formula ]:
C₂₁H₃₁F₃O

[ Molecular Weight ]:
356.465

[ Flash Point ]:
288.7±20.2 °C

[ Exact Mass ]:
356.232697

[ PSA ]:
17.07000

[ LogP ]:
7.78

[ Vapour Pressure ]:
0.0±1.0 mmHg at 25°C

[ Index of Refraction ]:
1.463

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;half-mask respirator (US);multi-purpose combination respirator cartridge (US)

[ Hazard Codes ]:
Xi

[ RIDADR ]:
NONH for all modes of transport

Articles

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...

Cytoplasmic phospholipase A₂ modulation of adolescent rat ethanol-induced protein kinase C translocation and behavior.

Neurochem. Res. 40 , 1023-31, (2015)

Ethanol consumption typically begins during adolescence, a developmental period which exhibits many age-dependent differences in ethanol behavioral sensitivity. Protein kinase C (PKC) activity is larg...

Inhibition of cytosolic phospholipase A(2) alpha protects against focal ischemic brain damage in mice.

Brain Res. 1471 , 129-37, (2012)

It is postulated that inhibition of cytosolic phospholipase A(2) alpha (cPLA(2)α) can reduce severity of stroke injury. This is supported by the finding that cPLA(2)α-deficient mice are partially prot...

Related Compounds

The content on this webpage is sourced from various professional data sources. If you have any questions or concerns regarding the content, please feel free to contact service1@chemsrc.com.