12-Hydroxyeicosatetraenoic acid (original) (raw)
L’acide 12-hydroxyeicosatétraénoïque (12-HETE) est un eicosanoïde dérivé de l'acide arachidonique sous l'action de l'. C'est un ligand très sélectif utilisé pour marquer les récepteurs aux opiacés mu.
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| dbo:abstract | 12-Hydroxyeicosatetraenoic acid (12-HETE) is a derivative of the 20 carbon polyunsaturated fatty acid, arachidonic acid, containing a hydroxyl residue at carbon 12 and a 5Z,8Z,10E,14Z Cis–trans isomerism configuration (Z=cis, E=trans) in its four double bonds. It was first found as a product of arachidonic acid metabolism made by human and bovine platelets through their 12S-lipoxygenase (i.e. ALOX12) enzyme(s). However, the term 12-HETE is ambiguous in that it has been used to indicate not only the initially detected "S" stereoisomer, 12S-hydroxy-5Z,8Z,10E,14Z-eicosatetraenoic acid (12(S)-HETE or 12S-HETE), made by platelets, but also the later detected "R" stereoisomer, 12(R)-hydroxy-5Z,8Z,10E,14Z-eicosatetraenoic acid (also termed 12(R)-HETE or 12R-HETE) made by other tissues through their 12R-lipoxygenase enzyme, ALOX12B. The two isomers, either directly or after being further metabolized, have been suggested to be involved in a variety of human physiological and pathological reactions. Unlike hormones which are secreted by cells, travel in the circulation to alter the behavior of distant cells, and thereby act as Endocrine signalling agents, these arachidonic acid metabolites act locally as Autocrine signalling and/or Paracrine signaling agents to regulate the behavior of their cells of origin or of nearby cells, respectively. In these roles, they may amplify or dampen, expand or contract cellular and tissue responses to disturbances. (en) L’acide 12-hydroxyeicosatétraénoïque (12-HETE) est un eicosanoïde dérivé de l'acide arachidonique sous l'action de l'. C'est un ligand très sélectif utilisé pour marquer les récepteurs aux opiacés mu. (fr) L'acido 12-idrossieicosatetraenoico (in sigla dall'inglese 12-HETE ) è un acido grasso con 20 atomi di carbonio, 4 doppi legami in posizione 5=6, 8=9, 10=11, 14=15 e un gruppo ossidrile sostituente in posizione 12. I doppi legami sono in configurazione cis eccetto il doppio legame 13=14 che è in configurazione trans. La sua notazione delta è: 12-OH-20:4Δ5c,8c,10t,14c. È stato scoperto per la prima volta nel 1974 dal premio Nobel, Bengt Samuelsson, e colleghi come prodotto del metabolismo dell'acido arachidonico prodotto dalle piastrine umane e bovine attraverso enzimi 12 S-lipossigenasi (in sigla ALOX12 ). Sono noti 2 stereoisomeri in funzione della configurazione S o R del gruppo ossidrile. È stato suggerito che i due isomeri, direttamente o dopo essere stati ulteriormente metabolizzati, siano coinvolti in una varietà di reazioni fisiologiche e patologiche nell'uomo. A differenza degli ormoni che vengono secreti dalle cellule, viaggiano nella circolazione per alterare il comportamento delle cellule distanti e quindi agiscono come agenti di segnalazione endocrina Appartengono alla famiglia degli eicosanoidi, metaboliti strutturalmente correlati che condividono un meccanismo comune per l'attivazione delle cellule e un insieme comune di attività biologiche e conseguenti potenziali effetti sulla salute.Gli studi sugli animali e una serie limitata di studi sull'uomo suggeriscono che questa famiglia di metaboliti funga da agente di segnalazione autocrina e paracrina, simile agli ormoni, che possono regolare il comportamento delle loro cellule di origine o di cellule vicine. In questi ruoli, possono amplificare o smorzare, espandere o contrarre le risposte cellulari e tissutali ai disturbi. Nell'uomo, l'arachidonato di 12-lipossigenasi è codificato dal gene ALOX12 ed espresso principalmente nelle piastrine e nellapelle. L'ALOX12 metabolizza l'acido arachidonico quasi esclusivamente a 12(S)-idroperossieicosatetraenoico, (12(S )-HPETE). L'arachidonato 12-lipossigenasi, tipo 12R, codificato dal gene ALOX12B, che è espresso principalmente nella pelle e nella cornea, metabolizza l'acido arachidonico a 12(R)-HPETE. Gli enzimi del citocromo P450 convertono l'acido arachidonico in una varietà di derivati idroperossidici , epossidici e diidrossi tra cui miscele racemiche di 12(S) -HPETE e 12 (R)-HPETE o 12(S)-HETE e 12(R)-HETE dove lo stereoisomero R predomina. Gli intermedi 12(S)-HPETE e 12(R)-HPETE, indipendentemente dal loro percorso di formazione, vengono rapidamente ridotti a 12(S)-HETE e 12(R)-HETE mediante glutatione perossidasi cellulari onnipresenti o, in alternativa, vengono ulteriormente metabolizzate. (it) |
| dbo:alternativeName | 12-HETE; 12(S)-HETE (en) |
| dbo:iupacName | (5Z,8Z,10E,12S,14Z)-12-Hydroxyicosa-5,8,10,14-tetraenoic acid (en) |
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| dcterms:subject | dbc:Animal_physiology dbc:Cell_biology dbc:Eicosanoids dbc:Fatty_acids dbc:Human_physiology dbc:Immunology dbc:Inflammations |
| gold:hypernym | dbr:Derivative |
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| rdfs:comment | L’acide 12-hydroxyeicosatétraénoïque (12-HETE) est un eicosanoïde dérivé de l'acide arachidonique sous l'action de l'. C'est un ligand très sélectif utilisé pour marquer les récepteurs aux opiacés mu. (fr) 12-Hydroxyeicosatetraenoic acid (12-HETE) is a derivative of the 20 carbon polyunsaturated fatty acid, arachidonic acid, containing a hydroxyl residue at carbon 12 and a 5Z,8Z,10E,14Z Cis–trans isomerism configuration (Z=cis, E=trans) in its four double bonds. It was first found as a product of arachidonic acid metabolism made by human and bovine platelets through their 12S-lipoxygenase (i.e. ALOX12) enzyme(s). However, the term 12-HETE is ambiguous in that it has been used to indicate not only the initially detected "S" stereoisomer, 12S-hydroxy-5Z,8Z,10E,14Z-eicosatetraenoic acid (12(S)-HETE or 12S-HETE), made by platelets, but also the later detected "R" stereoisomer, 12(R)-hydroxy-5Z,8Z,10E,14Z-eicosatetraenoic acid (also termed 12(R)-HETE or 12R-HETE) made by other tissues through the (en) L'acido 12-idrossieicosatetraenoico (in sigla dall'inglese 12-HETE ) è un acido grasso con 20 atomi di carbonio, 4 doppi legami in posizione 5=6, 8=9, 10=11, 14=15 e un gruppo ossidrile sostituente in posizione 12. I doppi legami sono in configurazione cis eccetto il doppio legame 13=14 che è in configurazione trans. La sua notazione delta è: 12-OH-20:4Δ5c,8c,10t,14c. Nell'uomo, l'arachidonato di 12-lipossigenasi è codificato dal gene ALOX12 ed espresso principalmente nelle piastrine e nellapelle. (it) |
| rdfs:label | 12-Hydroxyeicosatetraenoic acid (en) Acide 12-hydroxyeicosatétraénoïque (fr) Acido 12-idrossieicosatetraenoico (it) |
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