Literature DB >> 18618424

Synthesis of 2-oxoamides based on sulfonamide analogs of gamma-amino acids and their activity on phospholipase A2.

Georgia Antonopoulou1, Victoria Magrioti, Daren Stephens, Violetta Constantinou-Kokotou, Edward A Dennis, George Kokotos.   

Abstract

A variety of lipophilic 2-oxoamides containing n class="Chemical">sulfonamide analogs of gamma-amino acids as well as acyl sulfonamides of gamma-aminobutyric acid were synthesized. Their ability to inhibit intracellular GIVA cPLA2 and GVIA iPLA2 as well as secreted GV sPLA2 was evaluated. The sulfonamide group seems a bioisosteric group suitable to replace the carboxyl group in 2-oxoamide inhibitors of GVIA cPLA2. Copyright 2008 European Peptide Society and John Wiley & Sons, Ltd.

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Year:  2008        PMID： 18618424      PMCID： PMC2678953          DOI： 10.1002/psc.1048

Source DB:  PubMed          Journal:  J Pept Sci        ISSN： 1075-2617            Impact factor:   1.905


  28 in total

Review 1.  Calcium-independent phospholipase A(2): structure and function.

Authors:  M V Winstead; J Balsinde; E A Dennis
Journal:  Biochim Biophys Acta       Date:  2000-10-31

Review 2.  Interfacial enzymology: the secreted phospholipase A(2)-paradigm.

Authors:  O G Berg; M H Gelb; M D Tsai; M K Jain
Journal:  Chem Rev       Date:  2001-09       Impact factor: 60.622

Review 3.  Group V sPLA2: classical and novel functions.

Authors:  Barbara Balestrieri; Jonathan P Arm
Journal:  Biochim Biophys Acta       Date:  2006-07-28

4.  Structure-activity relationship of 2-oxoamide inhibition of group IVA cytosolic phospholipase A2 and group V secreted phospholipase A2.

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
Journal:  J Med Chem       Date:  2007-08-02       Impact factor: 7.446

5.  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

6.  Synthesis of tetrazole analogs of gamma- and delta-amino acids.

Authors:  Panagiota Moutevelis-Minakakis; Maria Filippakou; Charalambos Sinanoglou; George Kokotos
Journal:  J Pept Sci       Date:  2006-06       Impact factor: 1.905

7.  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

8.  Acyl sulfonamides as potent protease inhibitors of the hepatitis C virus full-Length NS3 (protease-helicase/NTPase): a comparative study of different C-terminals.

Authors:  Anja Johansson; Anton Poliakov; Eva Akerblom; Karin Wiklund; Gunnar Lindeberg; Susanne Winiwarter; U Helena Danielson; Bertil Samuelsson; Anders Hallberg
Journal:  Bioorg Med Chem       Date:  2003-06-12       Impact factor: 3.641

Review 9.  Regulation of the specific release of arachidonic acid by cytosolic phospholipase A2.

Authors:  Christina C Leslie
Journal:  Prostaglandins Leukot Essent Fatty Acids       Date:  2004-04       Impact factor: 4.006

10.  Efficient protocols for the synthesis of enantiopure gamma-amino acids with proteinogenic side chains.

Authors:  Vassilios Loukas; Caterina Noula; George Kokotos
Journal:  J Pept Sci       Date:  2003-05       Impact factor: 1.905
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  4 in total

Review 1.  Phospholipase A2 enzymes: physical structure, biological function, disease implication, chemical inhibition, and therapeutic intervention.

Authors:  Edward A Dennis; Jian Cao; Yuan-Hao Hsu; Victoria Magrioti; George Kokotos
Journal:  Chem Rev       Date:  2011-09-12       Impact factor: 60.622

2.  Tuning Side Arm Electronics in Unsymmetrical Cyclotriazadisulfonamide (CADA) Endoplasmic Reticulum (ER) Translocation Inhibitors to Improve their Human Cluster of Differentiation 4 (CD4) Receptor Down-Modulating Potencies.

Authors:  Reena Chawla; Victor Van Puyenbroeck; Nicholas C Pflug; Alekhya Sama; Rameez Ali; Dominique Schols; Kurt Vermeire; Thomas W Bell
Journal:  J Med Chem       Date:  2016-03-14       Impact factor: 7.446

3.  Structure-activity relationships of natural and non-natural amino acid-based amide and 2-oxoamide inhibitors of human phospholipase A(2) enzymes.

Authors:  Georgia Antonopoulou; Efrosini Barbayianni; Victoria Magrioti; Naomi Cotton; Daren Stephens; Violetta Constantinou-Kokotou; Edward A Dennis; George Kokotos
Journal:  Bioorg Med Chem       Date:  2008-11-01       Impact factor: 3.641

4.  2-Oxoamide inhibitors of phospholipase A2 activity and cellular arachidonate release based on dipeptides and pseudodipeptides.

Authors:  Efrosini Barbayianni; Daren Stephens; Andrej Grkovich; Victoria Magrioti; Yuan-Hao Hsu; Panagiotis Dolatzas; Dimitrios Kalogiannidis; Edward A Dennis; George Kokotos
Journal:  Bioorg Med Chem       Date:  2009-05-03       Impact factor: 3.641
  4 in total

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