2,3-Dimethoxy-5-methyl-p-benzoquinone (coenzyme Q0) disrupts carbohydrate metabolism of HeLa cells by adduct formation with intracellular free sulfhydryl-groups, and induces ATP depletion and necrosis was written by Takahashi, Takayuki;Mine, Yukitoshi;Okamoto, Tadashi. And the article was included in Biological & Pharmaceutical Bulletin in 2018.Category: ethers-buliding-blocks This article mentions the following:
2,3-Dimethoxy-5-methyl-p-benzoquinone is a common chem. structure of coenzyme Q (CoQ) that conjugates different lengths of an isoprenoid side chain at the 6-position of the p-benzoquinone ring. In a series of studies to explore the cytotoxic mechanism of CoQ homologues with a short isoprenoid side chain, we found that a CoQ analog without an isoprenoid side chain, CoQ0, showed marked toxicity against HeLa cells in comparison with cytotoxic homologues. The CoQ0-induced cell death was accompanied by a decrease in endogenous non-protein and protein-associated sulfhydryl (SH)-groups, but this improved with the concomitant addition of compounds with SH-groups but not antioxidants without SH-groups. In addition, UV-spectrum anal. suggested that CoQ0 could rapidly form S-conjugated adducts with compounds with SH-groups by Michael addition On the other hand, enzyme activities of both glyceraldehyde-3-phosphate dehydrogenase, which has a Cys residue in the active site, and a-ketoglutarate dehydrogenase complex, which requires cofactors with SH-groups, CoA and protein-bound a-lipoic acid, and CoA and ATP contents in the cells were significantly decreased by the addition of CoQ0 but not CoQ1. These results suggest that CoQ0 rapidly forms S-conjugate adducts with these endogenous non-protein and protein-associated SH-groups of HeLa cells, which disrupts carbohydrate metabolism followed by intracellular ATP depletion and necrotic cell death. In the experiment, the researchers used many compounds, for example, 2,3-Dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione (cas: 605-94-7Category: ethers-buliding-blocks).
2,3-Dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione (cas: 605-94-7) belongs to ethers. Ether is less polar than esters, alcohols or amines because of the oxygen atom that is unable to participate in hydrogen bonding due to the presence of bulky alkyl groups on both sides of the oxygen atom. But ether is more polar than alkenes. Autoxidation is the spontaneous oxidation of a compound in air. In the presence of oxygen, ethers slowly autoxidize to form hydroperoxides and dialkyl peroxides. If concentrated or heated, these peroxides may explode. To prevent such explosions, ethers should be obtained in small quantities, kept in tightly sealed containers, and used promptly.Category: ethers-buliding-blocks
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem