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
1
Street, I.P., Lin, H., Laliberté, F., et al. Slow- and tight-binding inhibitors of the 85-kDa human phospholipase A2. Biochemistry325935-5940(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. J Biol Chem270445-450(1995).
3
Conde-Frieboes, K., Reynolds, L.J., Lio, Y., et al. Activated ketones as inhibitors of intracellular Ca2+-dependent and Ca2+-independent phospholipase A2. J Am Chem Soc1185519-5525(1996).
4
Bartoli, F., Lin, H., 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. J Biol Chem26915625-15630(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. J Biol Chem26915619-15624(1994).
Room temperature
in continental US; may vary elsewhere
SMILES
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CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)C(F)(F)F
Background Reading
Street, I.P., Lin, H., Laliberté, F., et al. Slow- and tight-binding inhibitors of the 85-kDa human phospholipase A2. Biochemistry325935-5940(1993).
Bartoli, F., Lin, H., 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. J Biol Chem26915625-15630(1994).
Conde-Frieboes, K., Reynolds, L.J., Lio, Y., et al. Activated ketones as inhibitors of intracellular Ca2+-dependent and Ca2+-independent phospholipase A2. J Am Chem Soc1185519-5525(1996).
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. J Biol Chem26915619-15624(1994).
Ackermann, E.J., Conde-Frieboes, K., and Dennis, E.A. Inhibition of macrophage Ca2+-independent phospholipase A2 by bromoenol lactone and trifluoromethyl ketones. J Biol Chem270445-450(1995).