Literature DB >> 19443224

2-Oxoamide inhibitors of phospholipase A2 activity and cellular arachidonate release based on dipeptides and pseudodipeptides.

Efrosini Barbayianni1, Daren Stephens, Andrej Grkovich, Victoria Magrioti, Yuan-Hao Hsu, Panagiotis Dolatzas, Dimitrios Kalogiannidis, Edward A Dennis, George Kokotos.   

Abstract

A series of 2-oxoamides based on dipeptides and pseudodipeptides were synthesized and their activities towards two human intracellular phospholipases A(2) (GIVA cPLA(2) and GVIA iPLA(2)) and one human secretory phospholipase A(2) (GV sPLA(2)) were evaluated. Derivatives containing a free carboxyl group are selective GIVA cPLA(2) inhibitors. A derivative based on the ethyl ester of an ether pseudodipeptide is the first 2-oxoamide, which preferentially inhibits GVIA iPLA(2). The effect of 2-oxoamides on the generation of arachidonic acid from RAW 264.7 macrophages was also studied and it was found that selective GIVA cPLA(2) inhibitors preferentially inhibited cellular arachidonic acid release; one pseudodipeptide gave an IC(50) value of 2muM.

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Year:  2009        PMID： 19443224      PMCID： PMC2695835          DOI： 10.1016/j.bmc.2009.03.069

Source DB:  PubMed          Journal:  Bioorg Med Chem        ISSN： 0968-0896            Impact factor:   3.641


  27 in total

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Authors:  David A Six; Efrosini Barbayianni; Vassilios Loukas; Violetta Constantinou-Kokotou; Dimitra Hadjipavlou-Litina; Daren Stephens; Alan C Wong; Victoria Magrioti; Panagiota Moutevelis-Minakakis; Sharon F Baker; Edward A Dennis; George Kokotos
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Review 3.  Inhibitors of secretory phospholipase A2 group IIA.

Authors:  Robert C Reid
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4.  Localization and functional interrelationships among cytosolic Group IV, secreted Group V, and Ca2+-independent Group VI phospholipase A2s in P388D1 macrophages using GFP/RFP constructs.

Authors:  Yasuhito Shirai; Jesús Balsinde; Edward A Dennis
Journal:  Biochim Biophys Acta       Date:  2005-07-15

5.  Arachidonic acid release from mammalian cells transfected with human groups IIA and X secreted phospholipase A(2) occurs predominantly during the secretory process and with the involvement of cytosolic phospholipase A(2)-alpha.

Authors:  Carine M Mounier; Farideh Ghomashchi; Margaret R Lindsay; Scott James; Alan G Singer; Robert G Parton; Michael H Gelb
Journal:  J Biol Chem       Date:  2004-03-08       Impact factor: 5.157

6.  Renin inhibitors containing psi[CH2O] pseudopeptide inserts.

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7.  Role of group V phospholipase A2 in zymosan-induced eicosanoid generation and vascular permeability revealed by targeted gene disruption.

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8.  TLR-4 and sustained calcium agonists synergistically produce eicosanoids independent of protein synthesis in RAW264.7 cells.

Authors:  Matthew W Buczynski; Daren L Stephens; Rebecca C Bowers-Gentry; Andrej Grkovich; Raymond A Deems; Edward A Dennis
Journal:  J Biol Chem       Date:  2007-05-29       Impact factor: 5.157

9.  Synthesis and biological evaluation of analogues of Pro-Leu-Gly-NH2 modified at the leucyl residue.

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Review 10.  Regulation of the specific release of arachidonic acid by cytosolic phospholipase A2.

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  13 in total

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Authors:  Edward A Dennis; Jian Cao; Yuan-Hao Hsu; Victoria Magrioti; George Kokotos
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2.  Computer-aided drug design guided by hydrogen/deuterium exchange mass spectrometry: A powerful combination for the development of potent and selective inhibitors of Group VIA calcium-independent phospholipase A2.

Authors:  Varnavas D Mouchlis; Christophe Morisseau; Bruce D Hammock; Sheng Li; J Andrew McCammon; Edward A Dennis
Journal:  Bioorg Med Chem       Date:  2016-05-10       Impact factor: 3.641

3.  Potent and selective fluoroketone inhibitors of group VIA calcium-independent phospholipase A2.

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Journal:  J Med Chem       Date:  2010-05-13       Impact factor: 7.446

Review 4.  Calcium-independent phospholipases A2 and their roles in biological processes and diseases.

Authors:  Sasanka Ramanadham; Tomader Ali; Jason W Ashley; Robert N Bone; William D Hancock; Xiaoyong Lei
Journal:  J Lipid Res       Date:  2015-05-28       Impact factor: 5.922

5.  Inhibition of secreted phospholipases A₂ by 2-oxoamides based on α-amino acids: Synthesis, in vitro evaluation and molecular docking calculations.

Authors:  Varnavas D Mouchlis; Victoria Magrioti; Efrosini Barbayianni; Nathan Cermak; Rob C Oslund; Thomas M Mavromoustakos; Michael H Gelb; George Kokotos
Journal:  Bioorg Med Chem       Date:  2010-12-16       Impact factor: 3.641

6.  2-Oxoamides based on dipeptides as selective calcium-independent phospholipase A2 inhibitors.

Authors:  Anneta Smyrniotou; Maroula G Kokotou; Varnavas D Mouchlis; Efrosini Barbayianni; George Kokotos; Edward A Dennis; Violetta Constantinou-Kokotou
Journal:  Bioorg Med Chem       Date:  2016-12-08       Impact factor: 3.641

7.  Regulation of calcium release from the endoplasmic reticulum by the serine hydrolase ABHD2.

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8.  2-Oxoamide inhibitors of cytosolic group IVA phospholipase A2 with reduced lipophilicity.

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9.  Off-target effect of the cPLA2α inhibitor pyrrophenone: Inhibition of calcium release from the endoplasmic reticulum.

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10.  Serine hydrolase inhibitors block necrotic cell death by preventing calcium overload of the mitochondria and permeability transition pore formation.

Authors:  Bogeon Yun; HeeJung Lee; Moumita Ghosh; Benjamin F Cravatt; Ku-Lung Hsu; Joseph V Bonventre; Heather Ewing; Michael H Gelb; Christina C Leslie
Journal:  J Biol Chem       Date:  2013-12-02       Impact factor: 5.157
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