PMID: 9535221Apr 16, 1998Paper

Lipoxin B4 regulates human monocyte/neutrophil adherence and motility: design of stable lipoxin B4 analogs with increased biologic activity

FASEB Journal : Official Publication of the Federation of American Societies for Experimental Biology
J F MaddoxC N Serhan

Abstract

Lipoxins are biologically active products of arachidonic acid that are formed via cell-cell interactions, particularly those involving leukocytes. Lipoxin A4 and lipoxin B4 (LXB4), within similar concentration ranges, each inhibit human neutrophil, activate monocyte adherence and motility, and are rapidly converted by initial dehydrogenation to other inactive metabolites by human monocytes. Here, we exposed LXB4 to isolated recombinant 15-hydroxy-prostaglandin dehydrogenase (15-PGDH) and found that it was a good substrate for the enzyme (Km=6.9 microM); we identified the major product as 5-oxo-LXB4 via physical methods including liquid chromatography/tandem mass spectrometry. This is the first evidence of 15-PGDH converting a substrate hydroxyl group at a position other than the omega-6 carbon. Based on these observations, several LXB4 analogs were designed and prepared by total organic synthesis to test as stable mimetics: 5(S)-methyl-LXB4-me, 5(R)-methyl-LXB4-me, and 15-epi-LXB4-me (the aspirin-triggered form of LXB4). Both 5(S)-methyl-LXB4-me and 5(R)-methyl-LXB4-me were resistant to rapid conversion. In addition, actions of the stable analogs were evaluated separately with human mono-cytic cells and neutrophils, and 5(S)-me...Continue Reading

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Citations

Jun 3, 1999·Clinical Chemistry and Laboratory Medicine : CCLM·C N SerhanC B Clish
Jul 8, 1999·Proceedings of the National Academy of Sciences of the United States of America·C B ClishC N Serhan
Oct 3, 2002·Nature Reviews. Immunology·Toby LawrenceDerek W Gilroy
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Jun 10, 2003·The Journal of Immunology : Official Journal of the American Association of Immunologists·Amiram ArielCharles N Serhan
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Apr 15, 2011·Reproduction : the Official Journal of the Society for the Study of Fertility·James L HutchinsonHenry N Jabbour
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Jun 3, 1999·Clinical Chemistry and Laboratory Medicine : CCLM·P DiamondC Godson
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