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5-Hydroxyicosatetraenoic acid and 5-oxo-eicosatetraenoic acid : ウィキペディア英語版
5-Hydroxyicosatetraenoic acid

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5-Hydroxyicosatetraenoic acid (5-HETE) is an eicosanoid, i.e. a metabolite of arachidonic acid, made by a wide variety of cell types of mammals and other species. It is more properly termed 5(''S'')-hydroxyicosatetraenoic acid (i.e., 5(''S'')-HETE) to signify the (''S'') stereochemical configuration of its 5-hydroxy residue as opposed to its 5(''R'')-hydroxyicosatetraenoic acid (i.e., 5(''R'')-HETE) stereoisomer. A shortened but still unambiguous version of 5(''S'')-HETE's IUPAC name is 5S-hydroxy-6''E'',8''Z'',11''Z'',14''Z''-eicosatetraenoic acid where ''Z'' and ''E'' signify the cis and trans configurations of its four double bonds. 5(''S'')-HETE along with its hydroperoxy precursor (5(''S'')-HpETE) and its several metabolites have actions that are hormone-like. Hormones are secreted by cells, travel in the circulation to alter the behavior of distant cells, and thereby act as Endocrine signalling agents. The 5-HETE-related arachidonic acid metabolites have similar messaging function; however, they are released by cells to act either locally as Autocrine signalling agents to regulate the behavior of their cells of origin or as Paracrine signalling agents to regulate the function of nearby cells. In these roles, the 5-HETE family of agonists can amplify or dampen, expand or contract cellular and tissue responses to disturbances and thereby play roles in an array of physiological and pathological reactions in various animal species including humans.
== History of discovery ==

5-HETE was first described in 1976 as a product made by neutrophils.〔J Biol Chem. 1976 Dec 25;251(24):7816-20.〕 Several years later it was found to stimulate human neutrophil chemotaxis〔Immunology. 1980 Apr;39(4):491-501.〕 and a racemic mixture of 5-(''S'')-HETE and 5(''R'')-HETE was found to be the most potent stimulator among a series of racemic mono-hydroxy eicosatetraenoates (i.e. HETEs) of human neutrophil aggregation. These effects, it was suggested, may have reflected the ability of 5-(''S'')-HETE to act through the same Cell surface receptor used by leukotriene B4 (LTB4); LTB4 is also a 5-(''S'')-hydroxy-eicosateraenoate and has neutrophil chemotactic and aggregating activity that is similar to (but far more potent than) that of 5-(''S'')-HETE. However, further studies in neutrophils indicated that 5-(''S'')-HETE had a somewhat different set of actions than LTB4 and acted through a receptor system distinct from that used by LTB4. Subsequent studies identified several other polyunsaturated fatty acid metabolites with key structural similarities to 5-(''S'')-HETE that operated through this receptor.〔J Biol Chem. 1993 Jul 15;268(20):14708-14.〕 Thus, 5-(''S'')-HETE is the first described member of a structurally and functionally related family of metabolites of which its 5-keto analog, 5-oxo-eicosatetraenoic acid (5-oxo-6''E'',8''Z'',11''Z'',14''Z''-eicosatetraenoic acid, 5-oxo-ETE, or 5-oxoETE), because of its potency, gives its name to the family's common receptor viz., the Oxoeicosanoid receptor 1 or OXER1.〔Prog Lipid Res. 2005 Mar-May;44(2-3):154-83. Epub 2005 Apr 20. Review.〕

抄文引用元・出典: フリー百科事典『 ウィキペディア(Wikipedia)
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