4-Octyl Itaconate |
| Catalog No.GC31648 |
4-Octyl Itaconate (4-OI) is a cell-permeable itaconate derivative.
Products are for research use only. Not for human use. We do not sell to patients.
Cas No.: 3133-16-2
Sample solution is provided at 25 µL, 10mM.
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4-Octyl Itaconate (4-OI) is a cell-permeable itaconate derivative. Itaconate and 4-Octyl Itaconate had similar thiol reactivity, making 4-Octyl Itaconate a suitable itaconate surrogate to study its biological function. 4-Octyl Itaconate is reported to alkylate cysteine residues on kelchlike ECH-associated protein 1 (KEAP1) and then activate nuclear factor (erythroid derived 2)-related factor 2 (Nrf2) to exert antioxidant and anti-inflammatory effects. [1]. 4-Octyl Itaconate can halt the progress of various diseases, including ischemiareperfusion injury, osteoclast-related diseases, and renal fibrosis, by reducing oxidative stress and modifying the immune response of macrophages to lipopolysaccharide (LPS) [2].
The inhibitory effect of 4-octyl itaconate extends to the replication of several other pathogenic viruses including Herpes Simplex Virus-1 and-2, Vaccinia virus, and Zika virus through a type I interferon (IFN)- independent mechanism. In addition, 4-Octyl Itaconate limit host inflammatory responses to SARS-CoV2 infection [3].
Treat Vero cells with 4-octyl itaconate enerated before infection with SARS-CoV2 resulted in a 102–104 eduction in SARS-CoV2 RNA levels in a dose dependent manner, while not affecting cell viability, as determined by lactate dehydrogenase (LDH) release assay. The antiviral effect of 4-Octyl Itaconate was also demonstrated in the lung cancer cell line Calu-3, where SARS-CoV2 RNA levels were reduced by >2-logs, while release of progeny virus was reduced by >6-logs. 4-Octyl Itaconate effect SARSCoV2 in primary human airway epithelial (HAE) cultures, also, 4-Octyl Itaconate treatment significantly reduced viral RNA levels. The antiviral effect of 4-Octyl Itaconate was reproduced using a different SARS-CoV-2 isolate [3].
4-Octyl Itaconate (50 mg/ kg) were administered to 57BL/6J mice or vehicle 2 h before intraperitoneal injection of LPS (5 mg/kg). 4-Octyl Itaconate treatment significantly prolonged the survival rate and simultaneously decreased the serum levels of IL-1β, IL-6 and lactate in mice induced by LPS. 4-Octyl Itaconate protects mice against experimental lethal endotoxaemia partly by inhibiting cytokine release and lactate production [1].
References:
[1] Liao, S. T. et al. 4-Octyl itaconate inhibits aerobic glycolysis by targeting GAPDH to exert anti-inflammatory effects. Nat. Commun. 10, 5091, 2019.
[2] Li, Y., Chen, X., Zhang, H., et al. 4-Octyl Itaconate Alleviates Lipopolysaccharide-Induced Acute Lung Injury in Mice by Inhibiting Oxidative Stress and Inflammation. Dddt 14, 5547–5558. 2020. doi:10.2147/DDDT.S280922.
[3] Olagnier, D. et al. SARS-CoV2-mediated suppression of NRF2-signaling reveals potent antiviral and anti-inflammatory activity of 4-octyl-itaconate and dimethyl fumarate. Nat. Commun. 11, 4938, 2020.
| Cell experiment [1]: | |
|
Cell lines |
C28/I2 chondrocytes |
|
Preparation Method |
Cells were stimulated with 10 ng/mL interleukin 1β(IL-1β) for 24 h. CQ (50 μM) was incubated with chondrocytes for 48 h in the CQ group, chondrocytes were pretreated with 4-Octyl Itaconate (100 μM) for 48 h followed by treatment with IL-1β (1 ng/mL) for 24 h in the IL-1β + 4-Octyl Itaconate group, and chondrocytes were pretreated with 4-Octyl Itaconate (100 μM) for 48 h followed by treatment with CQ (50 μM) for 48 h in the CQ + 4-Octyl Itaconate group. The control group was untreated chondrocytes cultured in regular medium. |
|
Reaction Conditions |
100μM for 48 hours |
|
Applications |
IL-1β (interleukin 1β) treatment significantly inhibited the growth of chondrocytes, but the cell growth of chondrocytes was restored after the pretreatment of 4-Octyl Itaconate. The IL-1β induces chondrocyte apoptosis and participates in the pathogenesis of OA (Osteoarthritis), 4-Octyl Itaconate protected chondrocytes from IL-1β-induced apoptosis. |
| Animal experiment [2]: | |
|
Animal models |
Male C57BL/6 mice aged 8–10-weeks-old |
|
Preparation Method |
The control group (rats were shamoperated and given saline solution on the first day of every week from the 4th to the12th week following surgery, n = 6), the OA group (subjected to DMM, 100 μLof normal saline treatment injected at the same as in the control group, n = 6), and the OA + OI group (subjected to DMM, 100 μL of OI (100 μM) injected at the same as in the control group, n = 6). |
|
Dosage form |
Inject 50 mg/kg or 100 mg/kg |
|
Applications |
The histopathology indicated that 4-Octyl Itaconate reduced the LPS-induced pulmonary edema, hemorrhage and inflammatory cell infiltration. The inflammation scores of 4-Octyl Itaconate intervention groups were lower than those of the ALI group. 4-Octyl Itaconate could alleviate acute lung tissue injury induced by lipopolysaccharide. |
|
References: [1]. X. Pan, H. Shan, J. Bai et al. Four-octyl itaconate improves osteoarthritis by enhancing autophagy in chondrocytes via PI3K/AKT/mTOR signalling pathway inhibition. Communications Biology, vol. 5, no. 1, p. 641, 2022. [2]. Li, Y., Chen, X., Zhang, H., et al. 4-Octyl Itaconate Alleviates Lipopolysaccharide-Induced Acute Lung Injury in Mice by Inhibiting Oxidative Stress and Inflammation. Dddt 14, 5547–5558. 2020. doi:10.2147/DDDT.S280922 |
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| Cas No. | 3133-16-2 | SDF | |
| Canonical SMILES | O=C(OCCCCCCCC)CC(C(O)=O)=C | ||
| Formula | C13H22O4 | M.Wt | 242.31 |
| Solubility | DMSO : ≥ 150 mg/mL (619.04 mM) | Storage | Store at -20°C |
| General tips | Please select the appropriate solvent to prepare the stock solution according to the
solubility of the product in different solvents; once the solution is prepared, please store it in
separate packages to avoid product failure caused by repeated freezing and thawing.Storage method
and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored
at -20°C, please use it within 1 month. To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time. |
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| Shipping Condition | Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request. | ||
| Prepare stock solution | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 4.1269 mL | 20.6347 mL | 41.2694 mL |
| 5 mM | 0.8254 mL | 4.1269 mL | 8.2539 mL |
| 10 mM | 0.4127 mL | 2.0635 mL | 4.1269 mL |
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g
μL
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Method for preparing in vivo formulation: Take μL DMSO master liquid, next addμL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O, mix and clarify.
Method for preparing in vivo formulation: Take μL DMSO master liquid, next add μL Corn oil, mix and clarify.
Note: 1. Please make sure the liquid is clear before adding the next solvent.
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3. All of the above co-solvents are available for purchase on the GlpBio website.
Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Average Rating: 5 (Based on Reviews and 24 reference(s) in Google Scholar.)
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