2. Immunology/Inflammation Metabolic Enzyme/Protease Anti-infection Membrane Transporter/Ion Channel Cell Cycle/DNA Damage Others
  3. COX Lipoxygenase Orthopoxvirus Potassium Channel DNA/RNA Synthesis Drug Derivative
  4. Eicosatetraynoic acid

Eicosatetraynoic acid  (Synonyms: ETYA)

Cat. No.: HY-124108 Purity: 99.9%
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Eicosatetraynoic acid (ETYA) is a non-metabolizable analog of Arachidonic acid (HY-109590) and also an inhibitor of the lipoxygenase (LOX)/cyclooxygenase (COX) pathway (ID50 = 8 μM and 4 μM). Eicosatetraynoic acid acts as a suicide substrate to inhibit the production of inflammatory mediators such as leukotrienes and prostaglandins. Eicosatetraynoic acid acts directly on cell membranes and membrane proteins to exert a wide range of effects, including blocking potassium channels, increasing cell membrane fluidity, elevating intracellular calcium levels, inhibiting DNA synthesis in tumor cells, inducing differentiation of certain cells, and specifically inhibiting the assembly and replication of orthopoxviruses. Eicosatetraynoic acid alleviates acute lung injury induced by chemicals such as phosgene.

For research use only. We do not sell to patients.

Eicosatetraynoic acid

Eicosatetraynoic acid Chemical Structure

CAS No. : 1191-85-1

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Based on 1 publication(s) in Google Scholar

Eicosatetraynoic acid Related Antibodies

Top Publications Citing Use of Products

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COX COX-1 COX-2 COX-3

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5-LOX 12-LOX 15-LOX

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RNASE L DNA Polymerases RNA Polymerases Helicases DNA Ligase

  • Biological Activity

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Description

Eicosatetraynoic acid (ETYA) is a non-metabolizable analog of Arachidonic acid (HY-109590) and also an inhibitor of the lipoxygenase (LOX)/cyclooxygenase (COX) pathway (ID50 = 8 μM and 4 μM). Eicosatetraynoic acid acts as a suicide substrate to inhibit the production of inflammatory mediators such as leukotrienes and prostaglandins. Eicosatetraynoic acid acts directly on cell membranes and membrane proteins to exert a wide range of effects, including blocking potassium channels, increasing cell membrane fluidity, elevating intracellular calcium levels, inhibiting DNA synthesis in tumor cells, inducing differentiation of certain cells, and specifically inhibiting the assembly and replication of orthopoxviruses. Eicosatetraynoic acid alleviates acute lung injury induced by chemicals such as phosgene[1][2][3][4][5].

IC50 & Target[2]

COX

8 μM (ID50)

In Vitro

Eicosatetraynoic acid dose-dependently reduces MDA production in cultured human umbilical vein endothelial cells co-incubated with low-density lipoprotein[1].
Eicosatetraynoic acid (40 μM; 4-72 h) reversibly inhibits DNA synthesis and blocks the proliferation of PC3, U937 and A172 cells without inducing significant cytotoxicity[2].
Eicosatetraynoic acid (40 μM; 3-7 d) induces partial monocyte-like differentiation in U937 cells, and induces partial glial-like differentiation in A172 cells after 72 h of incubation; in addition, the differentiation of U937 cells progresses gradually over 5 to 7 days[2].
Incubation with eicosatetraynoic acid (40 μM; 72 h) for 72 h induces cell type-specific ultrastructural changes, including severe oxidative stress-related mitochondrial damage in PC3 cells, milder damage in A172 cells, and immature monocyte morphology in U937 cells[2].
Eicosatetraynoic acid (40 μM) rapidly regulates multiple signal transduction pathways in PC3 and U937 cells, including increasing membrane fluidity and intracellular Ca2+ levels, inhibiting O2 uptake, reversibly blocking DNA synthesis, downregulating c-myc, inhibiting eicosanoid synthesis, and altering the localization of protein kinase C[2].
Eicosatetraynoic acid non-selectively inhibits 12-lipoxygenase (ID50 = 4 μM) and fatty acid cyclooxygenase (ID50 = 8 μM) in washed human platelets[3].
Eicosatetraynoic acid (79-316 μM) specifically and effectively blocks the replication of orthopoxviruses (vaccinia, vaccinia vaccine, and ectromelia viruses)[4].

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

Eicosatetraynoic acid Related Antibodies

Cell Proliferation Assay[2]

Cell Line: PC3 prostate, U937 monoblastoid, A172 glioblastoma cells
Concentration: 40 μM
Incubation Time: 4 h, 72 h (DNA synthesis and cell number measurements); 4 h, 72 h (viability assays)
Result: Inhibited DNA synthesis in all three cell lines.
Reduced PC3 cell proliferation over 72 h, with control cells increasing from 1.3 million to 3.1 million while treated cells remained at 0.99 million, and maintained >95% viability.
Showed reversible inhibition of DNA synthesis at 4 h and 72 h, with no induced change in Cr51 release from prelabelled PC3 and U937 cells, and kept PC3/A172 cells attached to substrates.

Cell Differentiation Assay[2]

Cell Line: U937 monoblastoid, A172 glioblastoma cells
Concentration: 40 μM
Incubation Time: 72 h; 5 to 7 days (extended U937 cell cultures)
Result: Induced reduced nuclear-to-cytoplasmic ratio, increased cytoplasm, irregular plasma membranes, increased nonspecific acid phosphatase activity, latex bead ingestion, and increased expression of the monocyte-associated surface epitope leu M3 (cd14) in U937 cells.
Caused spindle-shaped morphology, increased glial fibrillary acidic protein (GFAP) expression, and prominent bundles of 8 nm glial filaments in A172 cells.
Produced a progressive increase in differentiated cell functions in U937 cells during extended 5 to 7 day culture.
In Vivo

Eicosatetraynoic acid (50-100 µM/200 μL ethanol solution; i.p. or isolated lung perfusion; single administration) exerts antioxidant effects and effectively alleviates pulmonary edema and oxidative damage.
Eicosatetraynoic acid (300 μM; topical administration) significantly reduces pock formation on the chorioallantoic membranes of chicken embryos infected with the vaccinia virus CPV-BR.D1[4].

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

Animal Model: Hartley (male, 600-700 g, phosgene-induced acute lung injury)[1]
Dosage: 100 µM (i.p. post-exposure); 50 µM (perfusate, every 40 mins starting 60 mins post-exposure)
Administration: i.p.; single dose (5 mins post-phosgene exposure); perfusate; every 40 minutes (starting 60 mins post-exposure initiation)
Result: Prevented phosgene-induced acute lung injury in male Hartley guinea pigs by maintaining lung GSH levels, reducing pulmonary edema, and increasing the GSH/TBARS protection ratio to 12.
Animal Model: 12-day-old chick embryo[4]
Dosage: 300 μM
Administration: topical (alongside virus infection)
Result: Severely reduced the number of pocks detected on chorioallantoic membranes.
Molecular Weight

296.40

Formula

C20H24O2
CAS No.
Appearance

Solid

Color

Light yellow to brown

SMILES

CCCCCC#CCC#CCC#CCC#CCCCC(O)=O
Shipping

Room temperature in continental US; may vary elsewhere.
Storage
Powder -20°C 3 years

*The compound is unstable in solutions, freshly prepared is recommended.

Solvent & Solubility
In Vitro: 

DMSO : 2 mg/mL (6.75 mM; Need ultrasonic; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)

Ethanol : < 1 mg/mL (insoluble)

Preparing
Stock Solutions
Concentration Solvent Mass 1 mg 5 mg 10 mg
1 mM 3.3738 mL 16.8691 mL 33.7382 mL
5 mM 0.6748 mL 3.3738 mL 6.7476 mL
View the Complete Stock Solution Preparation Table

* Please refer to the solubility information to select the appropriate solvent. The compound is unstable in solutions, freshly prepared is recommended.

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This equation is commonly abbreviated as: C1V1 = C2V2

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Purity & Documentation

Purity: 99.9%

SDS (252 KB)

COA (237 KB)

Handling Instructions (2659 KB)
References

Complete Stock Solution Preparation Table

* Please refer to the solubility information to select the appropriate solvent. The compound is unstable in solutions, freshly prepared is recommended.

Optional Solvent Concentration Solvent Mass 1 mg 5 mg 10 mg 25 mg
DMSO 1 mM 3.3738 mL 16.8691 mL 33.7382 mL 84.3455 mL
5 mM 0.6748 mL 3.3738 mL 6.7476 mL 16.8691 mL
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Eicosatetraynoic acid Related Classifications

Help & FAQs
  • Do most proteins show cross-species activity?

    Species cross-reactivity must be investigated individually for each product. Many human cytokines will produce a nice response in mouse cell lines, and many mouse proteins will show activity on human cells. Other proteins may have a lower specific activity when used in the opposite species.

Keywords:

Eicosatetraynoic acid1191-85-1ETYACOXLipoxygenaseOrthopoxvirusPotassium ChannelDNA/RNA SynthesisDrug DerivativeCyclooxygenaseLOXKcsADrug derivativelipoxygenase/cyclooxygenase pathwayprostate cancerprostaglandinarachidonic acidhistiocytic lymphomaBS-C-1 African green monkey kidney cellsPC3 cellsleukotrieneglioblastomaorthopoxvirusInhibitorinhibitorinhibit

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