| HOME | HELP | FEEDBACK | SUBSCRIPTIONS | ARCHIVE | SEARCH | TABLE OF CONTENTS |
|
|
|
|||||||
|
|||||||||
The Journal of Immunology, Vol 156, Issue 1 336-342, Copyright © 1996 by American Association of Immunologists
ARTICLES |
WS Powell, RJ MacLeod, S Gravel, F Gravelle and A Bhakar
Meakins-Christie Laboratories, Department of Medicine, McGill University, Montreal, Quebec, Canada.
5-Oxo-6,8,11,14-eicosatetraenoic acid (5-oxo-ETE) is a recently discovered metabolite of arachidonic acid that activates human neutrophils by a mechanism independent of the receptor for leukotriene B4 (LTB4). The objectives of this study were to identify the major metabolites of 5-oxo-ETE in neutrophils and to compare the biologic activities of 5-oxo-ETE with those of its metabolites and other 5- oxoeicosanoids. Neutrophils rapidly converted 5-oxo-ETE to its omega- oxidation product, 5-oxo-20-hydroxy-6E,8Z,11Z,14Z- eicosatetraenoic acid. This compound was nearly 100 times less potent than 5-oxo-ETE in elevating cytosolic calcium levels in neutrophils. Methylation of the carboxyl group of 5-oxo-ETE resulted in a 20-fold loss of potency, whereas replacement of the 8,9-cis double bond by a trans double bond reduced potency by about sixfold. Similar results were obtained for the effects of the above compounds on neutrophil migration. 5-Oxo-20- hydroxy-6E,8Z,11Z,14Z- eicosatetraenoic acid, 5-oxo-8-trans-ETE, and 5- oxo-ETE methyl ester desensitized neutrophils to 5-oxo-ETE. 5-Oxo-ETE- induced calcium mobilization was inhibited by pretreatment of the cells with pertussis toxin. 5-Oxo metabolites of 6-trans-LTB4 and 12-epi-6- trans-LTB4 had weak stimulatory effects on calcium levels and migration that appeared to be mediated primarily by stimulation of LTB4 receptors. These studies indicate that the 5-oxo group, the omega-end of the molecule, and the carboxyl group are all important for the biologic activity of 5-oxo-ETE, which may be mediated by a G protein- linked receptor. The biologic activity of 5-oxo-ETE can be terminated by omega-oxidation.
This article has been cited by other articles:
|
|
 |
|
  P. Patel, C. Cossette, J. R. Anumolu, S. Gravel, A. Lesimple, O. A. Mamer, J. Rokach, and W. S. Powell Structural Requirements for Activation of the 5-Oxo-6E,8Z, 11Z,14Z-eicosatetraenoic Acid (5-Oxo-ETE) Receptor: Identification of a Mead Acid Metabolite with Potent Agonist Activity J. Pharmacol. Exp. Ther., May 1, 2008; 325(2): 698 - 707. [Abstract] [Full Text] [PDF]
|
|
|
|
 |
|
 C. Cossette, P. Patel, J. R. Anumolu, S. Sivendran, G. J. Lee, S. Gravel, F. D. Graham, A. Lesimple, O. A. Mamer, J. Rokach, et al. Human Neutrophils Convert the Sebum-derived Polyunsaturated Fatty Acid Sebaleic Acid to a Potent Granulocyte Chemoattractant J. Biol. Chem., April 25, 2008; 283(17): 11234 - 11243. [Abstract] [Full Text] [PDF]
|
|
|
|
 |
|
 S. R. McMeekin, I. Dransfield, A. G. Rossi, C. Haslett, and T. R. Walker E-selectin permits communication between PAF receptors and TRPC channels in human neutrophils Blood, June 15, 2006; 107(12): 4938 - 4945. [Abstract] [Full Text] [PDF]
|
|
|
|
|
|
P. B. Stamatiou, C.-C. Chan, G. Monneret, D. Ethier, J. Rokach, and W. S. Powell 5-Oxo-6,8,11,14-eicosatetraenoic Acid Stimulates the Release of the Eosinophil Survival Factor Granulocyte/Macrophage Colony-stimulating Factor from Monocytes J. Biol. Chem., July 2, 2004; 279(27): 28159 - 28164. [Abstract] [Full Text] [PDF]
|
|
|
|
 |
|
 C. Brink, S.-E. Dahlen, J. Drazen, J. F. Evans, D. W. P. Hay, G. E. Rovati, C. N. Serhan, T. Shimizu, and T. Yokomizo International Union of Pharmacology XLIV. Nomenclature for the Oxoeicosanoid Receptor Pharmacol. Rev., March 1, 2004; 56(1): 149 - 157. [Abstract] [Full Text] [PDF]
|
|
|
|
 |
|
 C. Ferland, M. Guilbert, F. Davoine, N. Flamand, J. Chakir, and M. Laviolette Eotaxin promotes eosinophil transmigration via the activation of the plasminogen-plasmin system J. Leukoc. Biol., May 1, 2001; 69(5): 772 - 778. [Abstract] [Full Text]
|
|
|
|
|
|
J. M. Hevko, R. C. Bowers, and R. C. Murphy Synthesis of 5-Oxo-6,8,11,14-eicosatetraenoic Acid and Identification of Novel omega -Oxidized Metabolites in the Mouse Macrophage J. Pharmacol. Exp. Ther., April 13, 2001; 296(2): 293 - 305. [Abstract] [Full Text]
|
|
|
|
 |
|
 E. M. Brown and R. J. MacLeod Extracellular Calcium Sensing and Extracellular Calcium Signaling Physiol Rev, January 1, 2001; 81(1): 239 - 297. [Abstract] [Full Text] [PDF]
|
|
|
|
|
|
R. J. MacLeod, P. Lembessis, J. R. Hamilton, and W. S. Powell 5-Oxo-6,8,11,14-eicosatetraenoic Acid Stimulates Isotonic Volume Reduction of Guinea Pig Jejunal Crypt Epithelial Cells J. Pharmacol. Exp. Ther., November 1, 1999; 291(2): 511 - 516. [Abstract] [Full Text]
|
|
|
|
 |
|
 H. M. Sarau, R. S. Ames, J. Chambers, C. Ellis, N. Elshourbagy, J. J. Foley, D. B. Schmidt, R. M. Muccitelli, O. Jenkins, P. R. Murdock, et al. ACCELERATED COMMUNICATION: Identification, Molecular Cloning, Expression, and Characterization of a Cysteinyl Leukotriene Receptor Mol. Pharmacol., September 1, 1999; 56(3): 657 - 663. [Abstract] [Full Text]
|
|
|
|
 |
|
 M. Guilbert, C. Ferland, M. Bossé, N. Flamand, S. Lavigne, and M. Laviolette 5-Oxo-6,8,11,14-Eicosatetraenoic Acid Induces Important Eosinophil Transmigration through Basement Membrane Components . Comparison of Normal and Asthmatic Eosinophils Am. J. Respir. Cell Mol. Biol., July 1, 1999; 21(1): 97 - 104. [Abstract] [Full Text]
|
|
|
|
|
|
G. Larfars, F. Lantoine, M.-A. Devynck, J. Palmblad, and H. Gyllenhammar Activation of Nitric Oxide Release and Oxidative Metabolism by Leukotrienes B4, C4, and D4 in Human Polymorphonuclear Leukocytes Blood, February 15, 1999; 93(4): 1399 - 1405. [Abstract] [Full Text] [PDF]
|
|
|
|
|
|
W. S. Powell, S. Gravel, S. P. Khanapure, and J. Rokach Biological Inactivation of 5-oxo-6,8,11,14-Eicosatetraenoic Acid by Human Platelets Blood, February 1, 1999; 93(3): 1086 - 1096. [Abstract] [Full Text] [PDF]
|
|
|
|
|
|
W. S. Powell, S. Gravel, and F. Halwani 5-oxo-6,8,11,14-Eicosatetraenoic Acid Is a Potent Stimulator of L-Selectin Shedding, Surface Expression of CD11b, Actin Polymerization, and Calcium Mobilization in Human Eosinophils Am. J. Respir. Cell Mol. Biol., January 1, 1999; 20(1): 163 - 170. [Abstract] [Full Text]
|
|
|
|
|
|
J. T. O'Flaherty, J. S. Taylor, and M. J. Thomas Receptors for the 5-Oxo Class of Eicosanoids in Neutrophils J. Biol. Chem., December 4, 1998; 273(49): 32535 - 32541. [Abstract] [Full Text] [PDF]
|
|
|
|
|
|
K. Berhane, A. A. Ray, S. P. Khanapure, J. Rokach, and W. S. Powell Calcium/Calmodulin-dependent Conversion of 5-Oxoeicosanoids to 6,7-Dihydro Metabolites by a Cytosolic Olefin Reductase in Human Neutrophils J. Biol. Chem., August 14, 1998; 273(33): 20951 - 20959. [Abstract] [Full Text] [PDF]
|
|
| HOME | HELP | FEEDBACK | SUBSCRIPTIONS | ARCHIVE | SEARCH | TABLE OF CONTENTS |
