An inhibitor of cPLA2 and iPLA2
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Arachidonyl Trifluoromethyl Ketone

Item No. 62120

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
1,1,1-trifluoro-6Z,9Z,12Z,15Z-heneicosatetraen-2-one
CAS Number
149301-79-1
Synonyms
  • ATK
  • AATFMK
Molecular Formula
C21H31F3O
Formula Weight
356.5
Purity
≥98%
Formulation (Request formulation change)
A 50 mg/ml solution in methyl acetate
Solubility(Learn about Variance in Solubility)
DMF: >25 mg/mlDMSO: > 25 mg/mlPBS pH 7.2: <50 µg/ml
SMILES
CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)C(F)(F)F
InChi Code
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-
InChi Key
PLWROONZUDKYKG-DOFZRALJSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    5 mg

    $70

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    10 mg

    $118

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    50 mg

    $477

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    Product Description

    ATK is an analog of arachidonic acid in which the carboxyl group is replaced by a trifluoromethyl ketone group.1 It inhibits the activity of the 85 kDa cPLA2 and the 80 kDa macrophage iPLA2 without altering the activity of the 14 kDa sPLA2s.1,2,3 ATK is useful for differentiating the effects of cPLA2 and iPLA2 from sPLA2.4,5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Street, I.P., Lin, H.K., Laliberté, F., et al. Slow- and tight-binding inhibitors of the 85-kDa human phospholipase A2. Biochemistry 32, 5935-5940 (1993).

    2. Ackermann, E.J., Conde-Frieboes, K., and Dennis, E.A. Inhibition of macrophage Ca2+-independent phospholipase A2 by bromoenol lactone and trifluoromethyl ketones. The Journal of Biological Chemisty 270(1), 445-450 (1995).

    3. Conde-Frieboes, K., Reynolds, L.J., Lio, Y.C., et al. Activated ketones as inhibitors of intracellular Ca2+-dependent and Ca2+-independent phospholipase A2. J. Am. Chem. Soc. 118, 5519-5525 (1996).

    4. Bartoli, F., Lin, H.K., Ghomashchi, F., et al. Tight binding inhibitors of 85-kDa phospholipase A2 but not 14-kDa phospholipase A2 inhibit release of free arachidonate in thrombin-stimulated human platelets. The Journal of Biological Chemisty 269, 15625-15630 (1994).

    5. Riendeau, D., Guay, J., Weech, P.K., 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. The Journal of Biological Chemisty 269, 15619-15624 (1994).

    Product Citations

    Roy, D., Mondal, S., Khurana, A., et al. Loss of HSulf-1: The missing link between autophagy and lipid droplets in ovarian cancer. Sci. Rep. 7:41977, (2017).

    Ueda, N., Kurahashi, Y., Yamamoto, S., et al. Partial purification and characterization of the porcine brain enzyme hydrolyzing and synthesizing anandamide. The Journal of Biological Chemisty 270(40), 23823-23827 (1995).