Diethylmaleate - CAS 141-05-9
Category: Inhibitor
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Molecular Formula:
C8H12O4
Molecular Weight:
172.18
COA:
Inquire
Targets:
NF-κB
Description:
Diethylmaleate, a glutathione-depleting compound, is the diethyl ester of maleic acid and inhibits NF-kB. It is used as a reagent in the synthesis of several organic compounds including that of polyaspartic acid ester based polyurea coatings.
Brife Description:
An inhibitor of NF-kB
Purity:
99.07 %
Appearance:
Colourless liquid
Synonyms:
Diethyl maleate; NSC 8394; NSC-8394; NSC8394; AI3-00678; AI3 00678; AI300678; diethyl (Z)-but-2-enedioate; (2Z)-2-Butenedioic Acid Diethyl Ester; Diethyl (Z)-2-Butenedioate; Ethyl Maleate; Staflex DEM
Storage:
Store in a cool and dry place (or refer to the Certificate of Analysis).
MSDS:
Inquire
Boiling Point:
223 °C
Melting Point:
-8.8 °C
Density:
1.0690 g/cm3
InChIKey:
IEPRKVQEAMIZSS-WAYWQWQTSA-N
InChI:
1S/C8H12O4/c1-3-11-7(9)5-6-8(10)12-4-2/h5-6H,3-4H2,1-2H3/b6-5-
Canonical SMILES:
CCOC(=O)C=CC(=O)OCC
1.Enhancement of acetyl-CoA: 1-O-alkyl-2-lyso-sn-glycero-3-phosphocholine acetyltransferase activity by hydrogen peroxide.
Tosaki T;Sakamoto H;Kitahara J;Imai H;Nakagawa Y Biol Pharm Bull. 2007 Feb;30(2):272-8.
The synthesis of platelet-activating factor (PAF) by human umbilical vein endothelial cell (HUVEC) in response to H2O2 was significantly increased in a concentration-dependent manner. When HUVEC were pretreated with diethyl maleate, which depletes intracellular glutathione, PAF synthesis was enhanced 3-fold upon 5 mM H2O2-treatment. Intracellular redox was involved in regulating PAF synthesis, since the addition of antioxidants such as N-acetylcysteine, pyrrolidinecarbodithioic acid (PDTC), and Trolox reduced PAF production in H2O2-treated HUVEC. The activity of acetyl-CoA: 1-O-alkyl-2-lyso-sn-glycero-3-phosphocholine acetyltransferase, which is involved in the last step of PAF synthesis, was also activated in H2O2-treated cells. However, exogenous lyso-PAF addition had not effected to acetyltransferase activity. The acetyltransferase activity responded quickly to H2O2-treatment, but the activation was transitory. A tyrosine kinase inhibitor and a calmodulin antagonist blocked acetyltransferase activity in H2O2-stimulated cells, suggesting that tyrosine kinase and calcium/calmodulin-dependent protein kinase are involved in regulating acetyltransferase activity. These observations suggest that H2O2 is one of the modulators of lyso-PAF acetyltransferase activity via a phosphorylation system and platelet-activating factor (PAF) synthesis.
2.Enzymes mediating resistance to lambda-cyhalothrin in Eriopis connexa (Coleoptera: Coccinellidae).
Rodrigues AR;Siqueira HA;Torres JB Pestic Biochem Physiol. 2014 Mar;110:36-43. doi: 10.1016/j.pestbp.2014.02.005. Epub 2014 Mar 5.
Resistance to widely used insecticide, lambda-cyhalothrin, was recently reported in the predatory lady beetle Eriopis connexa (Germar) (Coleoptera: Coccinellidae). However, to understand whether metabolic mechanisms underlie such resistance, synergism bioassays and in vitro studies were carried out by using inhibitors and model substrates for enzymatic assays, respectively. The LD50s estimated for susceptible and resistant populations ηg of lambda-cyhalothrin/insect, and thus, a 22-fold difference in resistance ratio. Synergism ratios for the susceptible population with piperonyl butoxide (PBO), diethyl maleate (DEM), triphenyl phosphate (TPP), and S,S,S-tributylphosphorotrithioate (DEF) were respectively 33.8-, 0.24-, 0.35-, and 4.25-fold, while for the resistant population, they were 1463.0-, 0.79-, 0.85-, and 282.6-fold, respectively. The synergized resistance ratios were 0.50-, 2.00-, 6.75-, and 8.77-fold with PBO, DEF, DEM, and TPP, respectively, while resistance was virtually suppressed with DEF. The esterase exhibited 4.16-, 4.03-, and 5.38-fold greater activity towards formation of α-naphthol, β-naphthol, and 4-nitrophenol in the resistant population of E. connexa than in the susceptible population.
3.Cross-resistance and biochemical mechanisms of resistance to indoxacarb in the diamondback moth, Plutella xylostella.
Zhang S;Zhang X;Shen J;Li D;Wan H;You H;Li J Pestic Biochem Physiol. 2017 Aug;140:85-89. doi: 10.1016/j.pestbp.2017.06.011. Epub 2017 Jun 20.
Indoxacarb belongs to a class of insecticides known as oxadiazines and is the first commercialized pyrazoline-type voltage-dependent sodium channel blocker. A moderate level of resistance to indoxacarb has evolved in field populations of Plutella xylostella from Central China. In the present study, cross-resistance, resistance stability and metabolic mechanisms of indoxacarb resistance were investigated in this moth species. A P. xylostella strain with a high level of resistance to indoxacarb was obtained through continuous selection in the laboratory. The strain showed cross-resistance to metaflumizone, beta-cypermethrin and chlorfenapyr, but no resistance to cyantraniliprole, chlorantraniliprole, abamectin, chlorfluazuron, spinosad and diafenthiuron compared with the susceptible strain. Synergism tests revealed that piperonyl butoxide (PBO) (synergistic ratio, SR=7.8) and diethyl maleate (DEF) (SR=3.5) had considerable synergistic effects on indoxacarb toxicity in the resistant strain (F;58;). Enzyme activity data showed there was an approximate 5.8-fold different in glutathione S-transferase (GST) and a 6.8-fold different in cytochrome P450 monooxygenase between the resistant strain (F;58;) and susceptible strain, suggesting that the increased activity of these two enzymes is likely the main detoxification mechanism responsible for the species' resistance to indoxacarb.
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CAS 141-05-9 Diethylmaleate

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