12(R)-HETE 

12(R)-HETE is a CYP-dependent arachidonic acid metabolite that acts as a proinflammatory lipid mediator. 12 (R)-HETE widely exists in various tissues including the eye, skin and liver. In the cornea, 12(R)-HETE is metabolized via pathways such as β-oxidation into the precursor of 12(R)-HETrE. Without direct receptor binding, 12(R)-HETE indirectly activates AHR-mediated target gene transcription, while inhibiting the enzymatic activity of Na+,K+-ATPase and the intracellular calcium elevation induced by TP agonists. 12(R)-HETE also possesses multiple physiological effects such as chemotaxis, proangiogenesis, vasodilation, natriuresis, diuresis and intraocular pressure reduction, and can be widely used in studies related to psoriasis, inflammatory skin diseases and ocular inflammation^[1][2][3].

12 (R)-HETE (10-25 μM; 6 h) dose-dependently activates AHR-mediated transcription in human hepatocellular carcinoma HepG2 40/6 cells^[1].
12 (R)-HETE (0.25-4.0 μM; 3 h) dose-dependently induces the mRNA expression of the AHR target gene CYP1A1 in human hepatocellular carcinoma HepG2 cells, and this inductive effect is not blocked by treatment with Cycloheximide (HY-12320)^[1].
12 (R)-HETE activates AHR-mediated transcription of CYP1A1, CYP1B1 and AhRR in human keratinocyte HaCaT cells in an AHR-dependent manner^[1].
12 (R)-HETE (1 μM; 10 min) potently relaxes mouse mesenteric arteries precontracted with U46619 (HY-108566) via a thromboxane receptor-dependent mechanism (EC₅₀=0.05 μM, maximal relaxation rate=91.4%), inhibits U46619-induced contraction, and does not induce vasoconstriction or alter phenylephrine-mediated responses^[2].
12 (R)-HETE (0.001-10 μM; 30 min) competes for binding to the thromboxane receptor (TXA) binding site in mouse platelets, with an IC₅₀ of 0.32 μM, and exhibits stronger activity than 12 (S)-HETE^[2].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

320.47

C₂₀H₃₂O₃

82337-46-0

Liquid

Colorless to light yellow

CCCCC/C=C\C[C@H](/C=C/C=C\C/C=C\CCCC(O)=O)O

Room temperature in continental US; may vary elsewhere.

Solution, -20°C, 2 years

• [1]. Chiaro C R, et al. 12 (R)-Hydroxy-5 (Z), 8 (Z), 10 (E), 14 (Z)-eicosatetraenoic acid [12 (R)-HETE], an arachidonic acid derivative, is an activator of the aryl hydrocarbon receptor[J]. Molecular pharmacology, 2008, 74(6): 1649-1656.

  [2]. Siangjong L, et al. Endothelial 12(S)-HETE vasorelaxation is mediated by thromboxane receptor inhibition in mouse mesenteric arteries. Am J Physiol Heart Circ Physiol. 2013;304(3):H382-H392.

  [3]. Nishimura M, et al. Metabolism of 12 (R)-hydroxy-5, 8, 10, 14-eicosatetraenoic acid (12 (R)-HETE) in corneal tissues: formation of novel metabolites[J]. Archives of biochemistry and biophysics, 1991, 290(2): 326-335.