AACOCF - CAS 149301-79-1
Category: Inhibitor
Not Intended for Therapeutic Use. For research use only.
Molecular Formula:
C21H31F3O
Molecular Weight:
356.47
COA:
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Targets:
Others
Description:
AACOCF, an anlogue of arachidonic acid, is a slow-binding inhibitor of cytosolic (85 kDa) phospholipase A2. It also inhibits fatty acid amide hydrolase (FAAH, anandamide amidase) in vitro.
Brife Description:
cytosolic (85 kDa) phospholipase A2 inhibitor
Synonyms:
1,1,1-Trifluoro-6Z,9Z,12Z,15Z-heneicosateraen-2-one; Arachidonyl trifluoromethyl ketone; Arachidonyltrifluoromethane
MSDS:
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InChIKey:
PLWROONZUDKYKG-DOFZRALJSA-N
InChI:
InChI=1S/C21H31F3O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(25)21(22,23)24/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-19H2,1H3/b7-6-,10-9-,13-12-,16-15-
Canonical SMILES:
CCCCCC=CCC=CCC=CCC=CCCCC(=O)C(F)(F)F
1.Mechanisms of the influence of magnolol on eicosanoid metabolism in neutrophils.
Hsu MF;Lu MC;Tsao LT;Kuan YH;Chen CC;Wang JP Biochem Pharmacol. 2004 Mar 1;67(5):831-40.
We have demonstrated that magnolol suppressed thromboxane B2 (TXB2) and leukotriene B4 (LTB4) formation in A23187-stimulated rat neutrophils. Maximum inhibition was obtained with about 10 microM magnolol. Magnolol was more effective in the inhibition of cyclooxygenase (COX) activity than in the inhibition of 5-lipoxygenase (5-LO) activity as assessed by means of enzyme activity determination in vitro and COX and 5-LO metabolic capacity analyses in vivo. Magnolol alone stimulated cytosolic phospholipase A2 (cPLA2) phosphorylation and the translocation of 5-LO and cPLA2 to the membrane, and evoked arachidonic acid (AA) release. Recruitment of both 5-LO and cPLA2 to the membranes was suppressed by EGTA. Arachidonyl trifluoromethyl ketone (AACOCF3), a PLA2 inhibitor, bromoenol lactone (BEL), a Ca2+-independent PLA2 (iPLA2) inhibitor, and EGTA suppressed the magnolol-induced AA release. However, none of the follows affected magnolol-induced AA-release: 4-(4-fluorophenyl)-2-(4-methylsulfinylphenyl)-5-(4-pyridyl)-1H-imidazole (SB203580), a p38 mitogen-activated protein kinase (MAPK) inhibitor, 1,4-diamino-2,3-dicyano-1,4-bis(2-aminophenylthio)butadiene (U0126), a MAPK kinase (MEK) inhibitor, or 2-[1-(3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleimide (GF109203X), a protein kinase C (PKC) inhibitor.
2.85-kDa cytosolic phospholipase A2 mediates peroxisome proliferator-activated receptor gamma activation in human lung epithelial cells.
Pawliczak R;Han C;Huang XL;Demetris AJ;Shelhamer JH;Wu T J Biol Chem. 2002 Sep 6;277(36):33153-63. Epub 2002 Jun 20.
The 85-kDa cytosolic phospholipase A(2) (cPLA(2)) plays an important role in the control of arachidonic acid metabolism. This study was designed to investigate the possible contributions of cPLA(2) and group IIA secretory phospholipase A(2) (sPLA(2)) in the regulation of peroxisome proliferator-activated receptor (PPAR)-mediated gene transcription in human airway epithelial cells. Primary normal human bronchial epithelial cells and human lung epithelial cell lines BEAS 2B, A549, and NCI-H292 all express PPARgamma and -beta. Overexpression of cPLA(2) in BEAS 2B cells and primary bronchial epithelial cells resulted in a significant increase of PPARgamma-mediated reporter activity. In contrast, overexpression of group IIA sPLA(2) had no effect on PPARgamma activation. The PPARgamma activity in A549 cells was significantly inhibited by the cPLA(2) inhibitor arachidonyltrifluoromethyl ketone but not by the sPLA(2) inhibitor LY311727 and the iPLA(2) inhibitor HELSS. Activation of cPLA(2) by the calcium ionophore, induced a dose-dependent increase of PPAR activity in normal human bronchial epithelial cells and in the A549 cells. Electrophoretic mobility shift assays show that the binding between PPAR isolated from A549 cells and peroxisome proliferator response element (PPRE) is enhanced by but partially blocked by the cPLA(2) inhibitors arachidonyltrifluoromethyl ketone and methyl arachidonyl fluorophosphate.
3.Evidence that 85 kDa phospholipase A2 is not linked to CoA-independent transacylase-mediated production of platelet-activating factor in human monocytes.
Winkler JD;Bolognese BJ;Roshak AK;Sung CM;Marshall LA Biochim Biophys Acta. 1997 Jun 2;1346(2):173-84.
Platelet-activating factor (PAF) production is carefully controlled in inflammatory cells. The specific removal of arachidonate (AA) from 1-O-alkyl-2-arachidonoyl-sn-glycero-3-phosphocholine (GPC), thought to be mediated by CoA-independent transacylase (CoA-IT), is required to generate the PAF precursor 1-O-alkyl-2-lyso-GPC in human neutrophils. Exposure of A23187-stimulated human monocytes to the CoA-IT inhibitors SK&F 98625 and SK&F 45905 inhibited PAF formation (IC50s of 10 and 12 microM, respectively), indicating that these cells also need CoA-IT activity for PAF production. Because CoA-IT activity transfers arachidonate to a 2-lyso phospholipid substrate, its activity is obligated to an sn-2 acyl hydrolase to form the 2-lyso phospholipid substrate. SB 203347, an inhibitor of 14 kDa phospholipase A2 (PLA2), and AACOCF3, an inhibitor of 85 kDa PLA2, both inhibited AA release from A23187-stimulated human monocytes. However, AACOCF3 had no effect on A23187-induced PAF formation at concentrations as high as 3 microM. Further, depletion of 85 kDa PLA2 using antisense (SB 7111, 1 microM) had no effect on PAF production, indicating a lack of a role of 85 kDa PLA2 in PAF biosynthesis. Both SB 203347 and the 14 kDa PLA2 inhibitor scalaradial blocked PAF synthesis in monocytes (IC50s of 2 and 0.
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CAS 149301-79-1 AACOCF

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