| Size | Price | |
|---|---|---|
| 500mg | ||
| 1g | ||
| Other Sizes |
| Targets |
The biological actions of 8(S)-HETE are primarily mediated through the activation of key signaling molecules. This compound acts as a selective activator of peroxisome proliferator-activated receptor alpha (PPARα), with activation observed at concentrations as low as 0.3 μM. Additionally, 8(S)-HETE activates protein kinase C (PKC), effectively stimulating mouse skin PKC at 100 μM and exhibiting an IC₅₀ of 100 μM for mouse keratinocyte PKC. Its PKC-activating capability shows no significant difference between enantiomers, with 8(R)-HETE demonstrating similar activity.
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|---|---|
| ln Vitro |
In vitro studies demonstrate the critical role of 8(S)-HETE in regulating cellular functions. In organ-cultured rat corneal epithelial wound healing models, exogenously added 8(S)-HETE completely reverses the delayed wound closure and disrupted F-actin organization caused by lipoxygenase inhibition. Importantly, 8(S)-HETE shows specificity in reversing these inhibitory effects, whereas 12-HETE and 9-HETE are ineffective. This compound is recognized as the key arachidonic acid metabolite regulating epithelial cell migration during corneal wound healing. 8(S)-HETE can be biosynthesized by various cell types and biological samples, including human neutrophils, phorbol ester-treated mouse epidermis, and hepatic microsomal cytochrome P-450.
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| ln Vivo |
Currently, in vivo studies specifically addressing 8(S)-HETE activity are relatively limited. Based on findings from in vitro corneal wound healing studies, this compound is believed to play a regulatory role in corneal reepithelialization in vivo. Normal rat corneoscleral rim tissues metabolize [³H]arachidonic acid to produce 8-HETE along with other HETEs. The in vivo bioactivity of 8(S)-HETE is closely linked to its ability to modulate PKC and PPARα signaling pathways. As the (S)-enantiomer is the exclusive product of lipoxygenase metabolism, its in vivo activity likely depends on tissue-specific 8-LOX expression and activation of the arachidonic acid metabolic cascade.
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| Enzyme Assay |
Cell-free assays for 8(S)-HETE predominantly utilize radioligand-based or fluorescence-based methodologies. For PPARα binding studies, fluorescence resonance energy transfer (FRET) coactivator recruitment assays can be employed: incubate 8(S)-HETE (0.01-10 μM) with recombinant human PPARα ligand-binding domain and fluorescently labeled coactivator peptides in reaction buffer for 1-2 hours at room temperature, then measure fluorescence signal changes. For PKC activity assays, common methods utilize [γ-³²P]ATP with histone proteins or specific peptides as substrates in reaction systems containing phosphatidylserine, Ca²⁺, and 8(S)-HETE (0.1-100 μM), incubate at 30°C, and assess PKC activation by measuring the radioactivity of phosphorylated substrates. Appropriate positive and negative controls should be included to ensure result reliability.
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| Cell Assay |
The in vitro cell assay protocol for 8(S)-HETE is primarily based on corneal epithelial wound healing models. Standard protocol: 1) Isolate corneas from rat eyes and prepare corneal epithelial cell cultures or use intact corneal organ culture systems; 2) Treat cells with lipoxygenase inhibitors (e.g., esculetin) to inhibit endogenous HETE synthesis, resulting in disrupted F-actin organization and delayed wound closure; 3) Co-treat with various concentrations of 8(S)-HETE (typically 1-100 μM); 4) Assess wound closure rates by microscopic measurement; 5) Assess F-actin cytoskeletal organization by phalloidin fluorescence staining; 6) Assess cell proliferation rates by MTT or BrdU incorporation assays. For neutrophil chemotaxis assays, cells can be placed in the upper chamber of Transwell inserts with gradient concentrations of 8(S)-HETE in the lower chamber, followed by counting of migrated cells after incubation.
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| Animal Protocol |
In vivo studies of 8(S)-HETE primarily focus on its role in corneal wound healing. A typical protocol includes: 1) Use adult male rats under anesthesia and create standardized epithelial defects by corneal epithelial debridement; 2) Experimental groups include vehicle control, lipoxygenase inhibitor treatment group (e.g., esculetin), and 8(S)-HETE co-treatment group; 3) Administration routes may include topical eye drops or subconjunctival injection, with multiple daily doses of the compound; 4) Assess wound closure areas by fluorescein sodium staining, observe and photograph using a slit lamp microscope; 5) Euthanize animals at various time points (e.g., 0, 12, 24, 36, 48 hours), enucleate eyes for histological analysis; 6) Detect F-actin organization and proliferating cell nuclear antigen (PCNA) expression by immunohistochemistry; 7) Measure endogenous 8(S)-HETE and other HETEs levels in corneal tissue by HPLC-MS/MS.
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| ADME/Pharmacokinetics |
Pharmacokinetic data for 8(S)-HETE are limited in publicly available literature. As an endogenous metabolite produced from arachidonic acid via the 8-LOX pathway, the in vivo concentrations of 8(S)-HETE are regulated by tissue-specific lipoxygenase expression levels and substrate availability. In biological samples (such as cell supernatants and tissue homogenates), extraction and detection of 8(S)-HETE are typically performed using solid-phase extraction combined with UPLC-MS/MS for quantitative analysis. This compound can be stored at -20°C, with protein precipitation by methanol and purification via C18 solid-phase extraction cartridges prior to LC-MS/MS detection. Deuterated internal standards such as d8-5S-HETE are commonly used for correction in lipid mediator analysis. Storage conditions: powder can be stored long-term at -20°C, while solutions should be stored at -80°C to prevent degradation. This compound is classified as a dangerous good for transport.
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| Toxicity/Toxicokinetics |
According to the supplier's Material Safety Data Sheet, 8(S)-HETE is classified as a dangerous good for transport, requiring additional shipping charges. This product is intended for research use only and is not for diagnostic or therapeutic purposes. Systematic toxicological data for 8(S)-HETE (including acute toxicity, genotoxicity, and reproductive toxicity) are not fully reported in the available literature. As an endogenous lipid mediator, it typically does not exhibit obvious toxicity at physiological concentrations. At higher concentrations (e.g., 100 μM), 8(S)-HETE can activate PKC signaling pathways, but its cytotoxic effects have not been systematically evaluated. Appropriate personal protective equipment should be used during handling and storage, following standard chemical safety practices.
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| References | |
| Additional Infomation |
8(S)-Hete is a HETE containing an (8S)-hydroxyl group and (5Z)-, (9E)-, (11Z)-, and (14Z)- double bonds. Functionally, it is associated with icosanoic acid (EAC)-5,9,11,14-tetraenoic acid. It is the conjugate acid of 8(S)-HETE(1-) and the enantiomer of 8(R)-HETE.
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| Molecular Formula |
C20H32O3
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|---|---|
| Molecular Weight |
320.47
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| Exact Mass |
320.235
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| CAS # |
98462-03-4
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| Related CAS # |
98462-03-4; 79495-84-4; 70968-93-3; 105500-09-2
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| PubChem CID |
5283154
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| Appearance |
Typically exists as solids at room temperature
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| Density |
1.0±0.1 g/cm3
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| Boiling Point |
471.1±45.0 °C at 760 mmHg
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| Flash Point |
252.8±25.2 °C
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| Vapour Pressure |
0.0±2.7 mmHg at 25°C
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| Index of Refraction |
1.514
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| LogP |
5.45
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
14
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| Heavy Atom Count |
23
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| Complexity |
392
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| Defined Atom Stereocenter Count |
1
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| SMILES |
CCCCC/C=C\C/C=C\C=C\[C@H](C/C=C\CCCC(=O)O)O
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| InChi Key |
NLUNAYAEIJYXRB-VYOQERLCSA-N
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| InChi Code |
InChI=1S/C20H32O3/c1-2-3-4-5-6-7-8-9-10-13-16-19(21)17-14-11-12-15-18-20(22)23/h6-7,9-11,13-14,16,19,21H,2-5,8,12,15,17-18H2,1H3,(H,22,23)/b7-6-,10-9-,14-11-,16-13+/t19-/m1/s1
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| Chemical Name |
(5Z,8S,9E,11Z,14Z)-8-hydroxyicosa-5,9,11,14-tetraenoic acid
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| Synonyms |
8(S)-Hydroxyeicosatetraenoic acid; 8S-HETE; 8(S)-HETE; 98462-03-4; (5Z,8S,9E,11Z,14Z)-8-hydroxyicosa-5,9,11,14-tetraenoic acid; 8S-hydroxyeicosatetraenoic acid;
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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|---|---|
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 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 |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
Products are for research use only; We do not sell to patients
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