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Originally published In Press as doi:10.1074/jbc.C000502200 on August 2, 2000

J. Biol. Chem., Vol. 275, Issue 39, 29931-29934, September 29, 2000
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ACCELERATED PUBLICATION
A Novel Glutathione Containing Eicosanoid (FOG7) Chemotactic for Human Granulocytes*

Rebecca C. Bowers, John Hevko, Peter M. Henson, and Robert C. MurphyDagger

From the Division of Cell Biology, Department of Pediatrics, National Jewish Medical and Research Center, Denver, Colorado 80206

A biologically active glutathione adduct of the eicosanoid 5-oxo-eicosatetraenoic acid has been observed as a product formed within the murine peritoneal macrophage. This five-oxo glutathione adduct (FOG7) was structurally characterized using electrospray tandem mass spectrometry as a 1,4 Michael addition product 5-oxo-7-glutathionyl-8,11,14-eicosatrienoic acid. FOG7 was found to be highly potent in stimulating eosinophil as well as neutrophil chemotaxis, also capable of initiating actin polymerization, without elevating intracellular free calcium ion concentration within either the eosinophil or polymorphonuclear leukocyte. These biological responses suggest that either FOG7 activates a subset of receptors mediating the broader biological activity of the parent eicosanoid 5-oxo-6,8,11,14-eicosatetraenoic acid (5-oxo-ETE) or that a receptor not activated by 5-oxo-ETE participates in the chemotactic activity of FOG7. The only other known biologically active glutathione adduct has been leukotriene C4 (LTC4), another eicosanoid that exerts potent effects through the Cys-LT receptor. The biochemical parallel between the formation of LTC4 and FOG7 suggests an interesting mechanism by which biologically active eicosanoids derived from electrophilic intermediates may have unique distribution and prolonged efficacy in vivo.

* This work was supported in part by National Institutes of Health Grant HL25785.The costs of publication of this article were defrayed in part by the payment of page charges. The article must therefore be hereby marked "advertisement" in accordance with 18 U.S.C. Section 1734 solely to indicate this fact.

Dagger To whom correspondence should be addressed: National Jewish Medical and Research Center, 1400 Jackson St., Denver, CO 80206. Tel.: 303-398-1849; Fax: 303-398-1694; E-mail: murphyr@njc.org.

Copyright © 2000 by The American Society for Biochemistry and Molecular Biology, Inc.
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