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Literature summary extracted from

  • Barbayianni, E.; Stephens, D.; Grkovich, A.; Magrioti, V.; Hsu, Y.H.; Dolatzas, P.; Kalogiannidis, D.; Dennis, E.A.; Kokotos, G.
    2-Oxoamide inhibitors of phospholipase A2 activity and cellular arachidonate release based on dipeptides and pseudodipeptides (2009), Bioorg. Med. Chem., 17, 4833-4843.
    View publication on PubMedView publication on EuropePMC

Inhibitors

EC Number Inhibitors Comment Organism Structure
3.1.1.4 (2E,4E,6S)-6-[(2-oxohexadecanoyl)amino]deca-2,4-dienoic acid reduces the cellular release of arachidonic acid by 6% Homo sapiens
3.1.1.4 (2E,4S)-4-[(2-oxohexadecanoyl)amino]oct-2-enoic acid reduces the cellular release of arachidonic acid by 74% Homo sapiens
3.1.1.4 (4R)-6-methyl-4-[(2-oxohexadecanoyl)amino]heptanoic acid reduces the cellular release of arachidonic acid by 62% Homo sapiens
3.1.1.4 (4S)-4-[(2-oxododecanoyl)amino]octanoic acid reduces the cellular release of arachidonic acid by 56% Homo sapiens
3.1.1.4 (4S)-4-[(2-oxohexadecanoyl)amino]octanoic acid reduces the cellular release of arachidonic acid by 79% Homo sapiens
3.1.1.4 (5S)-5-[(2-oxohexadecanoyl)amino]nonanoic acid reduces the cellular release of arachidonic acid by 59% Homo sapiens
3.1.1.4 (S)-2-(2-(2-oxohexadecanamido)hexanamido)acetic acid contains a free carboxyl group, inhibits GIVA cPLA2 without affecting the activity of the other intracellular enzyme GVIA iPLA2 Homo sapiens
3.1.1.4 (S)-2-(2-(2-oxohexadecanamido)hexyloxy)acetic acid selectively inhibits GIVA cPLA2, due to its free carboxyl group. Most potent inhibitor of GIVA cPLA2. Reduces the cellular release of arachidonic acid by 68% Homo sapiens
3.1.1.4 (S)-2-(3-methyl-2-(2-oxohexadecanamido)butanamido)acetic acid contains a free carboxyl group, inhibits GIVA cPLA2 without affecting the activity of the other intracellular enzyme GVIA iPLA2 Homo sapiens
3.1.1.4 (S)-ethyl 2-(2-(2-oxohexadecanamido)hexanamido)acetate ethyl ester based on Nle-Gly dipeptide, potent inhibition of GVIA iPLA2, inhibits GIVA cPLA2 (73%) and GV sPLA2 (63%) Homo sapiens
3.1.1.4 (S)-ethyl 2-(2-(2-oxohexadecanamido)hexyloxy)acetate preferentially inhibits GVIA iPLA2, is a potent inhibitor of GVIA iPLA2, inhibits GIVA cPLA2 by 52% and GV sPLA2 by 81% Homo sapiens
3.1.1.4 (S)-methyl 2-(2-(2-oxohexadecanamido)hexanamido)acetate methyl ester based on dipeptide Nle-Gly, inhibits both GIVA cPLA2 and GVIA iPLA2, showing a small preference for GIVA cPLA2, inhibits GV sPLA2 by 65% Homo sapiens
3.1.1.4 (S)-methyl 2-(3-methyl-2-(2-oxohexadecanamido)butanamido)acetate methyl ester based on dipeptide Val-Gly, inhibits activity of GIVA cPLA2 by 25% Homo sapiens
3.1.1.4 (S)-tert-butyl 2-(2-(2-oxohexadecanamido)hexanamido)acetate tert-butyl ester based on Nle-Gly dipeptide, potent inhibition of GVIA iPLA2, inhibits GIVA cPLA2 (72%) and GV sPLA2 (59%) Homo sapiens
3.1.1.4 (S)-tert-butyl 2-(2-(2-oxohexadecanamido)hexyloxy)acetate preferentially inhibits GVIA iPLA2 (81% inhibition), inhibits GIVA cPLA2 by 44% and GV sPLA2 by 57% Homo sapiens
3.1.1.4 (S)-tert-butyl 2-(3-methyl-2-(2-oxohexadecanamido)butanamido)acetate tert-butyl ester based on dipeptide Val-Gly, inhibits both GIVA cPLA2 and GVIA iPLA2, showing a small preference for GIVA cPLA2, reduces GV sPLA2 activity by 78%. Reduces the cellular release of arachidonic acid by 30% Homo sapiens
3.1.1.4 4-[(2-oxohexadecanoyl)amino]butanoic acid reduces the cellular release of arachidonic acid by 52% Homo sapiens
3.1.1.4 AX006 inhibits GIVA cPLA2 Homo sapiens
3.1.1.4 AX048 inhibits GIVA cPLA2 and GVIA iPLA2 Homo sapiens
3.1.1.4 ethyl (2E,4S)-4-[(2-oxohexadecanoyl)amino]oct-2-enoate reduces the cellular release of arachidonic acid by 16% Homo sapiens
3.1.1.4 methyl N-(2-oxohexadecanoyl)glycinate reduces the cellular release of arachidonic acid by 30% Homo sapiens
3.1.1.4 additional information replacement of the amino acid unit of a 2-oxoamide inhibitor by a dipeptide unit may shift the selectivity in favour of GVIA iPLA2 Homo sapiens
3.1.1.4 N-(2-oxododecanoyl)-L-norleucine reduces the cellular release of arachidonic acid by 21% Homo sapiens
3.1.1.4 tert-butyl 5-[(2-oxohexadecanoyl)amino]pentanoate reduces the cellular release of arachidonic acid by 11% Homo sapiens

Localization

EC Number Localization Comment Organism GeneOntology No. Textmining

Organism

EC Number Organism UniProt Comment Textmining
3.1.1.4 Homo sapiens
-
-
-

Source Tissue

EC Number Source Tissue Comment Organism Textmining
3.1.1.4 macrophage primary lung macrophage Homo sapiens
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
3.1.1.4 1-palmitoyl-2-arachidonoylglycerophosphocholine + H2O GIVA cPLA2 substrate and GIVA iPLA2 Homo sapiens 1-palmitoyl-glycerophosphorylcholine + arachidonic acid
-
 ?
3.1.1.4 dipalmitoyl-phosphatidylcholine + H2O GIVA iPLA2 and GV sPLA2 Homo sapiens 1-palmitoyl-glycerophosphocholine + palmitic acid
-
 ?

Synonyms

EC Number Synonyms Comment Organism
3.1.1.4 GIVA cPLA2
-
 Homo sapiens
3.1.1.4 GV sPLA2
-
 Homo sapiens
3.1.1.4 GVIA iPLA2
-
 Homo sapiens
3.1.1.4 phospholipase A2
-
 Homo sapiens
3.1.1.4 secretory phospholipase A2
-
 Homo sapiens

IC50 Value

EC Number IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
3.1.1.4 0.002
-
 at 37°C, pH not specified in the publication Homo sapiens (S)-2-(2-(2-oxohexadecanamido)hexyloxy)acetic acid
3.1.1.4 0.007
-
 at 37°C, pH not specified in the publication Homo sapiens (5S)-5-[(2-oxohexadecanoyl)amino]nonanoic acid
3.1.1.4 0.01
-
 at 37°C, pH not specified in the publication Homo sapiens (4S)-4-[(2-oxododecanoyl)amino]octanoic acid
3.1.1.4 0.025
-
 at 37°C, pH not specified in the publication Homo sapiens 4-[(2-oxohexadecanoyl)amino]butanoic acid
3.1.1.4 0.025
-
 at 37°C, pH not specified in the publication Homo sapiens (4R)-6-methyl-4-[(2-oxohexadecanoyl)amino]heptanoic acid
3.1.1.4 0.025
-
 at 37°C, pH not specified in the publication Homo sapiens (4S)-4-[(2-oxohexadecanoyl)amino]octanoic acid
3.1.1.4 0.025
-
 at 37°C, pH not specified in the publication Homo sapiens (2E,4S)-4-[(2-oxohexadecanoyl)amino]oct-2-enoic acid