Itaconic acid 4-octyl ester 2-Methylidene-4-octoxy-4-oxobutanoic acid CAS NO.: 3133-16-2
4-Octyl itaconate is a derivative of itaconic acid, a metabolite. Its structure features an α,β-unsaturated ketone. It can form itaconylation modifications by undergoing Michael addition reactions with cysteine residues in proteins. This modification, known to participate in various pathways, including glycolysis and immune-inflammatory responses, involves binding to the cysteine residues and influencing cellular processes. 4-Octyl itaconate is a novel, synthetically accessible small molecule with potential applications as an antiviral and immune-modulating agent. It holds promise as a candidate for researching a variety of autoimmune diseases and viral infections.
Anti-inflammatory effects: 4-Octyl itaconate can modulate the activity of a series of inflammation-related signaling pathways in cells (such as NF-κB, GAPDH, Nrf2, etc.), promoting or inhibiting the anti-inflammatory or pro-inflammatory mechanisms during the occurrence of inflammation. As a widely used compound with anti-inflammatory effects, 4-Octyl itaconate provides a new avenue for the development of drugs related to inflammatory disorders, such as sepsis.
Immunomodulatory effects: 4-Octyl itaconate is capable of inhibiting the acetylation of STING by alkylating modification, thereby suppressing the activation of STING and consequently inhibiting cGAS-STING-mediated immune inflammation. This offers a new strategy for the treatment of related autoimmune diseases.
Antioxidant effects: 4-Octyl itaconate can directly alkylate the cysteine residues at positions 151, 257, 288, 273, and 297 on KEAP1, leading to increased expression of downstream Nrf2 genes and exerting antioxidant capabilities. This mechanism promotes the prevention and treatment of clinically relevant diseases associated with inflammation and oxidative stress.
Regulation of lipid metabolism: Itaconic acid is upregulated in human non-alcoholic fatty liver disease and non-alcoholic fatty liver disease mouse models. Treatment of mice with the itaconate derivative 4-Octyl itaconate can reverse blood lipid abnormalities associated with a high-fat diet. Mechanistically, treating primary liver cells with 4-Octyl itaconate can reduce lipid accumulation and increase oxidative phosphorylation in a fatty acid-dependent manner. As a candidate for lipid metabolism regulation, 4-Octyl itaconate shows significant potential.
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