3133-16-2Relevant academic research and scientific papers
4-Octyl itaconate protects against renal fibrosis via inhibiting TGF-β/Smad pathway, autophagy and reducing generation of reactive oxygen species
Tian, Feng,Wang, Zhe,He, Junqiu,Zhang, Zhihao,Tan, Ninghua
, (2020)
Renal fibrosis is an inevitable course of all kinds of progressive chronic kidney disease (CKD). Itaconic acid is an endogenous metabolite that has shown anti-inflammatory and antioxidant effects. 4-octyl itaconate (OI), a derivative of itaconic acid with higher fat solubility, can penetrate the cell membranes and be metabolized into itaconic acid in vitro. However, whether OI has an anti-renal fibrotic effect is still unclear. The current study purposed to investigate the anti-fibrotic effect in renal and the underlying mechanisms of OI. The unilateral ureteral occlusion (UUO) model and adenine-induced fibrosis model in Sprague-Dawley (SD) rats and Transforming growth factor-β1 (TGF-β1) induced HK-2 cells were applied to investigate the renoprotective effects of OI. This study reports for the first time that OI ameliorated renal fibrosis by suppressing the activation of TGF-β/Smad and nuclear factor kappa B (NF-κB) pathways, reducing generation of reactive oxygen species and inhibiting autophagy. These results clearly suggest that OI has great clinical potential for managing renal fibrosis.
One-Step Synthesis of 4-Octyl Itaconate through the Structure Control of Lipase
Liu, Changsheng,Wang, Yilin,Liu, Jiahao,Chen, An'nan,Xu, Juntao,Zhang, Renwei,Wang, Fang,Nie, Kaili,Deng, Li
, p. 7895 - 7903 (2021)
4-Octyl itaconate is a novel antiviral and immunoregulatory small molecule showing great potential in the treatment of various autoimmune diseases and viral infections. It is difficult to selectively esterify the C4 carboxyl group of itaconate acid via one-step direct esterification using chemical catalysts, while the two-step route with itaconic anhydride as an intermediate is environmentally unfriendly and costly. This research investigated the one-step and green synthesis of 4-octyl itaconate through the structure control of lipase, obtaining 4-octyl itaconate with over 98% yield and over 99% selectivity. Multiscale molecular dynamics simulations were applied to investigate the reaction mechanism. The cavity pocket of lipases resulted in a 4-octyl itaconate selectivity by affecting distribution of substrates toward the catalytic site. Toluene could enhance monoesterification in the C4 carboxyl group and contribute to a nearly 100% conversion from itaconate acid into 4-octyl itaconate by adjusting the catalytic microenvironment around the lipase, producing a shrinkage effect on the channel.
A comparative study of the thermal properties of homologous series of crystallisable n-alkyl maleate and itaconate monoesters
Richard, Jean-Victor,Delaite, Christelle,Riess, Gérard,Schuller, Anne-Sophie
, p. 136 - 143 (2015/12/26)
Homologous series of crystallisable C8-C22 even-numbered alkane oligomers with either maleate or itaconate monoesters end-groups were synthesized. Their total phase change enthalpy (ΔHtpce) and entropy (ΔStpce) on melting, determined by DSC, show a linear dependence with the number of carbons of the alkyl chain. A comparison was performed with corresponding succinate derivatives. The influence of the end functions on ΔStpce was examined in view of ΔStpce values estimated by the group additivity approach. A fair agreement between the experimental and the estimated entropy values could be demonstrated. Thermogravimetric analysis (TGA) has shown that the maleate oligomers are less stable than the corresponding succinate and itaconate derivatives. This behaviour could be confirmed by the activation energies of the degradation process.
