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4-Octyl Itaconate

Catalog No.: GC31648Purity:>98.00%
4-Octyl Itaconate (4-OI) is a cell-permeable itaconate derivative.

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4-Octyl Itaconate
Cas No.: 3133-16-2
10mM (in 1mL DMSO)In Stock
$58.00
1
50mgIn Stock
$52.00
1
100mgIn Stock
$84.00
1
200mgIn Stock
$147.00
1
500mgIn Stock
$308.00
1

Citations

2 publicationsPublications from researchers using this product

Description

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.

Protocol

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

Product Documents

Purity:>98.00%Appearance:A solid

Chemical Properties

CAS No.
3133-16-2
SMILES
O=C(OCCCCCCCC)CC(C(O)=O)=C
Molecular Formula
C13H22O4
Molecular Weight
242.31
Solubility
DMSO : ≥ 150 mg/mL (619.04 mM)
Storage
Store at -20°C
General tips
Select a suitable solvent according to the product solubility data. Once prepared, aliquot the stock solution to avoid repeated freeze-thaw cycles.
Use stock solutions within 6 months when stored at -80°C or within 1 month when stored at -20°C.
To improve solubility, warm the tube to 37°C and sonicate it for an appropriate period.
Shipping Condition
Evaluation samples are shipped with blue ice. Other available sizes are shipped at room temperature or with blue ice upon request.

CalculatorsMolarity / Dilution / Molecular Weight / Unit Conversion / In Vivo Formulation / Solubility

g/mol

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