1. Membrane Transporter/Ion Channel
    Immunology/Inflammation
    NF-κB
    Metabolic Enzyme/Protease
  2. Potassium Channel
    NF-κB
    NO Synthase
    Reactive Oxygen Species
    NADPH Oxidase
    Endogenous Metabolite
  3. 20-HETE

20-HETE (Synonyms: 20-hydroxy Arachidonic Acid)

Cat. No.: HY-15598
Handling Instructions

20-HETE (20-hydroxy Arachidonic Acid) is a CYP450 metabolite and a potent vasoconstrictor. 20-HETE is an endogenous inhibitor of the large-conductance Ca2+-activated K+ channel in renal arterioles. 20-HETE constricts smooth muscles, stimulates smooth muscle proliferation and migration. 20-HETE increases NADPH oxidase, ROS, and NF-κB activity. 20-HETE also inhibits endothelial NO synthase and inhibits apoptosis of pulmonary artery smooth muscle cells.

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20-HETE Chemical Structure

20-HETE Chemical Structure

CAS No. : 79551-86-3

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Description

20-HETE (20-hydroxy Arachidonic Acid) is a CYP450 metabolite and a potent vasoconstrictor. 20-HETE is an endogenous inhibitor of the large-conductance Ca2+-activated K+ channel in renal arterioles. 20-HETE constricts smooth muscles, stimulates smooth muscle proliferation and migration. 20-HETE increases NADPH oxidase, ROS, and NF-κB activity. 20-HETE also inhibits endothelial NO synthase and inhibits apoptosis of pulmonary artery smooth muscle cells[1][2].

IC50 & Target

Human Endogenous Metabolite

 

In Vitro

Addition of 20-HETE to the bath (1-100 nM), reduces the frequency of opening of the large-conductance Ca2+-activated K+ channel recorded using cell-attached patches on vascular smooth muscle cells (VSM)[1].
20-HETE (1-1000 nM) reduces the diameter of isolated perfused small renal arteries of the rat by approximately 15% tetraethylammonium (1 mM) blocked the vasoconstrictor response to 20-HETE (100 nM)[1].
20-HETE induces the phosphorylation of ERK1/2, a MAPK that plays a pivotal role in the proliferation induced by the activation of receptor tyrosine kinases and G protein-coupled receptors. 20-HETE promotes platelet-derived growth factor-stimulated vascular smooth muscle cell migration via pathways that involve MEK and phosphatidylinositol 3-kinase activation[2].

In Vivo

In Sprague-Dawley rats, administration of the 20-HETE inhibitor HET0016 or the 20-HETE antagonist 20-HEDE preventes DHT-induced increases in blood pressure as well as abrogates DHT-induced increases in the media-to-lumen ratio (M/L), media thickness, and collagen IV deposition in renal interlobar arteries. 20-HETE contributes to DHT-induced vascular remodeling independent of blood pressure elevation[2].
In Cyp4a14-/- mice, which display androgen-driven and 20-HETE-dependent hypertension, treatment with the 20-HETE antagonist abolishes remodeling of renal resistance arteries measured as media thickness and M/L. 20-HETE is a key regulator of microvascular remodeling in hypertension; its effect is independent of blood pressure elevation and androgen levels[2].

Molecular Weight

320.47

Formula

C₂₀H₃₂O₃

CAS No.

79551-86-3

SMILES

O=C(O)CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCCO

Shipping

Room temperature in continental US; may vary elsewhere.

Storage

-20°C, protect from light, stored under argon

*In solvent : -80°C, 6 months; -20°C, 1 month (protect from light, stored under argon)

Solvent & Solubility
In Vitro: 

DMSO : 110 mg/mL (343.25 mM; Need ultrasonic)

Ethanol : 6.67 mg/mL (20.81 mM; Need ultrasonic)

Preparing
Stock Solutions
Concentration Solvent Mass 1 mg 5 mg 10 mg
1 mM 3.1204 mL 15.6021 mL 31.2042 mL
5 mM 0.6241 mL 3.1204 mL 6.2408 mL
10 mM 0.3120 mL 1.5602 mL 3.1204 mL
*Please refer to the solubility information to select the appropriate solvent.
In Vivo:
  • 1.

    Add each solvent one by one:  10% DMSO    90% corn oil

    Solubility: ≥ 2.75 mg/mL (8.58 mM); Clear solution

*All of the co-solvents are provided by MCE.
References
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Keywords:

20-HETE20-hydroxy Arachidonic AcidPotassium ChannelNF-κBNO SynthaseReactive Oxygen SpeciesNADPH OxidaseEndogenous MetaboliteKcsANuclear factor-κBNuclear factor-kappaBNitric oxide synthasesNOSNOXVasoconstrictorCa2+-activatedVSMCYP450metabolitehypertensionNF-kBinflammatoryapoptosisROSInhibitorinhibitorinhibit

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20-HETE
Cat. No.:
HY-15598
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