Arachidonyl trifluoromethyl ketone

Last updated
Arachidonyl trifluoromethyl ketone
Arachidonyl trifluoromethyl ketone.svg
Names
Preferred IUPAC name
(6Z,9Z,12Z,15Z)-1,1,1-Trifluorohenicosa-6,9,12,15-teraen-2-one
Other names
  • Arachidonic acid trifluoromethyl ketone
  • Arachidonyltrifluoromethane
  • Arach-CF3
  • AACOCF3
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • 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-
    Key: PLWROONZUDKYKG-DOFZRALJSA-N
  • CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)C(F)(F)F
Properties
C21H31F3O
Molar mass 356.473 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Arachidonyl trifluoromethyl ketone (ATK) is an analog of arachidonic acid. [1] that inhibits some isoforms of the enzyme phospholipase A2. [2] Specifically it inhibits the 85 kDa cystolic PLA2 (cPLA2). [2]

It has been studied as a neuroprotective agent after spinal cord injury, [2] [3] and in animal models of multiple sclerosis. [4]

See also

References

  1. ↑ Street, Ian P.; Lin, Hung Kuei; Laliberte, France; Ghomashchi, Farideh; Wang, Zhaoyin; Perrier, Helene; Tremblay, Nathalie M.; Huang, Zheng; Weech, Philip K.; Gelb, Michael H. (1993). "Slow- and tight-binding inhibitors of the 85-k Da human phospholipase A2". Biochemistry. 32 (23): 5935–5940. doi:10.1021/bi00074a003. PMID   8018213.
  2. 1 2 3 Khan, Mushfiquddin; Shunmugavel, Anandakumar; Dhammu, Tajinder S; Matsuda, Fumiyo; Singh, Avtar K; Singh, Inderjit (2015). "Oral administration of cytosolic PLA2 inhibitor arachidonyl trifluoromethyl ketone ameliorates cauda equina compression injury in rats". Journal of Neuroinflammation. 12 94. doi: 10.1186/s12974-015-0311-y . PMC   4436116 . PMID   25971887.
  3. ↑ Huang, Wenlong; Bhavsar, Amar; Ward, Rachael E; Hall, Jodie C.E.; Priestley, John V.; Michael-Titus, Adina T. (2009). "Arachidonyl trifluoromethyl ketone is neuroprotective after spinal cord injury". Journal of Neurotrauma. 26 (8): 1429–1434. doi:10.1089/neu.2008-0835. PMID   19371144.
  4. ↑ Vana, Adam C.; Li, Shihe; Ribeiro, Rachel; Tchantchou, Flaubert; Zhang, Yumin (2011). "Arachidonyl trifluoromethyl ketone ameliorates experimental autoimmune encephalomyelitis via blocking peroxynitrite formation in mouse spinal cord white matter" . Experimental Neurology. 231 (1): 45–55. doi:10.1016/j.expneurol.2011.05.014. PMID   21683698. S2CID   8652522.


This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.