An ω-3 endocannabinoid epoxide; decreases LPS-induced IL-6 and nitrite production and increases the production of IL-10 in BV-2 microglia; inhibits arachidonic acid-induced platelet aggregation at 50 µM; induces relaxation of preconstricted bovine coronary arteries (ED50 = 1.1 µM); inhibits VEGF-stimulated tubulogenesis in HMVECs; activates CB1 and CB2 receptors (EC50s = 18.5 and 1.4 nM

(±)17(18)-EpETE-Ethanolamide – 100 µg

Brand:
Cayman
CAS:
2123491-23-4
Storage:
-20
UN-No:
Excepted Quantity - 1170 / 3

(±)17(18)-EpETE-Ethanolamide is an ω-3 endocannabinoid epoxide.{40186} It is formed from the endocannabinoid eicosapentaenoic ethanolamide (EPEA) via cytochrome P450 (CYP) epoxygenases and hydrolyzed by soluble epoxide hydrolase (sEH) and fatty acid amide hydrolase (FAAH). It is endogenously produced in LPS-stimulated BV-2 microglia cells and in BV-2 microglia cells supplemented with EPEA, an effect that can be reduced by the CYP inhibitor ketoconazole. (±)17(18)-EpETE-ethanolamide decreases IL-6 and nitrite production induced by LPS in BV-2 microglia and increases the production of IL-10. It inhibits platelet aggregation induced by arachidonic acid (Item Nos. 90010 | 90010.1 | 10006607) when used at a concentration of 50 µM but not aggregation induced by ADP (Item Nos. 16778 | 21121), collagen, or ristocetin. It also induces relaxation of preconstricted bovine coronary arteries (ED50 = 1.1 µM) and inhibits VEGF-stimulated tubulogenesis in human microvascular endothelial cells (HMVECs). (±)17(18)-EpETE-ethanolamide is the predominant EPEA metabolite found in rat brain, and it has also been found in rat heart, kidney, spleen, and liver, as well as in pig brain. It activates cannabinoid receptor 1 (CB1) and CB2 with EC50 values of 18.5 and 1.4 nM, respectively, in a β-arrestin recruitment assay.  

 

Available on backorder

Add to quotes
SKU: 25920 - 100 µg Category:

Description

An ω-3 endocannabinoid epoxide; decreases LPS-induced IL-6 and nitrite production and increases the production of IL-10 in BV-2 microglia; inhibits arachidonic acid-induced platelet aggregation at 50 µM; induces relaxation of preconstricted bovine coronary arteries (ED50 = 1.1 µM); inhibits VEGF-stimulated tubulogenesis in HMVECs; activates CB1 and CB2 receptors (EC50s = 18.5 and 1.4 nM, respectively)

Formal name: 16-(3-ethyl-2-oxiranyl)-N-(2-hydroxyethyl)-5Z,8Z,11Z,14Z-hexadecatetraenamide

Synonyms:  ,17,18-EEQ-EA|(±)17(18)-EpETE-EA|(±)17,18-EEQ-Ethanolamide|17,18-epoxy-Eicosatetraenoic Acid Ethanolamide

Molecular weight: 361.5

CAS: 2123491-23-4

Purity: ≥98%

Formulation: A solution in ethanol

Product Type|Biochemicals|Lipids|Hydroxy/Hydroperoxy/ Epoxy/Oxo Eicosanoids||Product Type|Biochemicals|Receptor Pharmacology|Agonists||Research Area|Cardiovascular System|Blood|Coagulation & Hemostasis||Research Area|Cardiovascular System|Vasculature|Vasodilation||Research Area|Immunology & Inflammation|Innate Immunity||Research Area|Lipid Biochemistry|Cytochrome P450 Pathways||Research Area|Lipid Biochemistry|Endocannabinoid/Endocannabinoid-like||Research Area|Neuroscience|Cannabinoid Research|Endocannabinoids

Related products

  • A zwitterionic glycerophospholipid commonly used in the formation of lipid monolayers

    1,2-Dipalmitoyl-sn-glycero-3-PC – 50 mg

    1,2-Dipalmitoyl-sn-glycero-3-PC (DPPC) is a zwitterionic glycerophospholipid commonly used in the formation of lipid monolayers, bilayers, and liposomes for use in a variety of applications.{14480,24261,14478,14479} It has been used in the formation of proteoliposomes for implantation of γ-glutamyl transpeptidase into human erythrocyte membranes.{14478} Incorporation of glycosphingolipid antigens into DPPC-containing liposomes increases the immunogenicity of the antigens in mice.{14479}  

     

    Brand:
    Cayman
    SKU:10009473 - 50 mg

    Available on backorder

    Add to quotes
    Add to quotes
    View product page
  • A small molecule activator of stem cell renewal that allows the propagation of OG2 mES cells for at least 10 passages in an undifferentiated state; activity is mediated by the combined inhibition of RasGAP and ERK1 with Kd values of 98 and 212 nM

    SC-1 – 1 mg

    The maintenance of embryonic stem cells in culture typically requires feeder cells and various exogenous factors found in serum. Murine embryonic stem (mES) cells can be maintained in the absence of feeder cells and serum but require the leukemia inhibitor factor (LIF) and bone morphogenic protein (BMP) to prevent differentiation and promote self-renewal. SC-1 is a small molecule activator of stem cell renewal that allows the propagation of OG2 mES cells for at least 10 passages in an undifferentiated state.{14533} The activity of SC-1 is mediated by the combined inhibition of RasGAP and ERK1 with Kd values of 98 and 212 nM, respectively.{14533} Inhibition of RasGAP increases Ras signaling via the PI3-kinase pathway which promotes self-renewal, whereas inhibition of ERK blocks differentiation.  

     

    Brand:
    Cayman
    SKU:10009557 - 1 mg

    Available on backorder

    Add to quotes
    Add to quotes
    View product page
  • A zwitterionic glycerophospholipid commonly used in the formation of lipid monolayers

    1,2-Dipalmitoyl-sn-glycero-3-PC – 250 mg

    1,2-Dipalmitoyl-sn-glycero-3-PC (DPPC) is a zwitterionic glycerophospholipid commonly used in the formation of lipid monolayers, bilayers, and liposomes for use in a variety of applications.{14480,24261,14478,14479} It has been used in the formation of proteoliposomes for implantation of γ-glutamyl transpeptidase into human erythrocyte membranes.{14478} Incorporation of glycosphingolipid antigens into DPPC-containing liposomes increases the immunogenicity of the antigens in mice.{14479}  

     

    Brand:
    Cayman
    SKU:10009473 - 250 mg

    Available on backorder

    Add to quotes
    Add to quotes
    View product page
  • PtdIns-(3

    PtdIns-(3,4,5)-P3-biotin (sodium salt) – 25 µg

    The PtdIn phosphates play an important role in the generation and transduction of intracellular signals.{8344,4096,14518} PtdIns-(3,4,5)-P3-biotin is an affinity probe which allows the PIP3 to be detected through an interaction with the biotin ligand. This design allows PtdIns-(3,4,5)-P3-biotin to serve as a general probe for any protein with a high affinity binding interaction with inositol-(3,4,5)-triphosphate phospholipids, such as phosphatidylinositol 3-kinase, PTEN, or PH-domain-containing proteins.  

     

    Brand:
    Cayman
    SKU:10009531 - 25 µg

    Available on backorder

    Add to quotes
    Add to quotes
    View product page