Literature DB >> 21377873

C20-trifluoro-5-oxo-ETE: a metabolically stable 5-oxo-ETE derivative.

Pranav Patel1, Vivek Gore, William S Powell, Joshua Rokach.   

Abstract

The total synthesis of C(20)-trifluoro-6(E),8(Z),11(Z),14(Z) 5-oxo-ETE is reported. This compound was designed as an ω-oxidation-resistant analog of 5-oxo-ETE that would be resistant to metabolism. The trifluoro derivative of 5-oxo-ETE stimulated calcium mobilization in neutrophils and desensitized these cells to subsequent exposure to 5-oxo-ETE.
Copyright © 2011 Elsevier Ltd. All rights reserved.

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Year:  2011        PMID： 21377873      PMCID： PMC3062511          DOI： 10.1016/j.bmcl.2011.02.021

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN： 0960-894X            Impact factor:   2.823


  23 in total

1.  A series of prostaglandin F2-like compounds are produced in vivo in humans by a non-cyclooxygenase, free radical-catalyzed mechanism.

Authors:  J D Morrow; K E Hill; R F Burk; T M Nammour; K F Badr; L J Roberts
Journal:  Proc Natl Acad Sci U S A       Date:  1990-12       Impact factor: 11.205

2.  Expression and characterization of a 5-oxo-6E,8Z,11Z,14Z-eicosatetraenoic acid receptor highly expressed on human eosinophils and neutrophils.

Authors:  Carol E Jones; Suzanne Holden; Laurent Tenaillon; Umesh Bhatia; Klaus Seuwen; Pamela Tranter; Jonathan Turner; Rachel Kettle; Rochdi Bouhelal; Steven Charlton; N R Nirmala; Gabor Jarai; Peter Finan
Journal:  Mol Pharmacol       Date:  2003-03       Impact factor: 4.436

3.  5-Oxo-6,8,11,14-eicosatetraenoic acid is a potent stimulator of human eosinophil migration.

Authors:  W S Powell; D Chung; S Gravel
Journal:  J Immunol       Date:  1995-04-15       Impact factor: 5.422

4.  Metabolism of 5(S)-hydroxy-6,8,11,14-eicosatetraenoic acid and other 5(S)-hydroxyeicosanoids by a specific dehydrogenase in human polymorphonuclear leukocytes.

Authors:  W S Powell; F Gravelle; S Gravel
Journal:  J Biol Chem       Date:  1992-09-25       Impact factor: 5.157

5.  Stimulation of human neutrophils by 5-oxo-6,8,11,14-eicosatetraenoic acid by a mechanism independent of the leukotriene B4 receptor.

Authors:  W S Powell; S Gravel; R J MacLeod; E Mills; M Hashefi
Journal:  J Biol Chem       Date:  1993-05-05       Impact factor: 5.157

6.  5-Oxo-eicosatetraenoate, a potent human neutrophil stimulus.

Authors:  J T O'Flaherty; J Cordes; J Redman; M J Thomas
Journal:  Biochem Biophys Res Commun       Date:  1993-04-15       Impact factor: 3.575

7.  Metabolism and biologic effects of 5-oxoeicosanoids on human neutrophils.

Authors:  W S Powell; R J MacLeod; S Gravel; F Gravelle; A Bhakar
Journal:  J Immunol       Date:  1996-01-01       Impact factor: 5.422

8.  Leukotriene C: a slow-reacting substance from murine mastocytoma cells.

Authors:  R C Murphy; S Hammarström; B Samuelsson
Journal:  Proc Natl Acad Sci U S A       Date:  1979-09       Impact factor: 11.205

9.  5-Oxo-eicosanoids are potent eosinophil chemotactic factors. Functional characterization and structural requirements.

Authors:  U Schwenk; J M Schröder
Journal:  J Biol Chem       Date:  1995-06-23       Impact factor: 5.157

10.  Identification of a novel human eicosanoid receptor coupled to G(i/o).

Authors:  Takeshi Hosoi; Yutaka Koguchi; Emiko Sugikawa; Aiko Chikada; Koji Ogawa; Naoki Tsuda; Naoki Suto; Shiho Tsunoda; Tomoyasu Taniguchi; Tetsuo Ohnuki
Journal:  J Biol Chem       Date:  2002-06-13       Impact factor: 5.157
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