Diethyl maleate

Diethyl maleate (DEM) is an orally available, effective glutathione (GSH) depletor that crosses the blood-brain barrier. Diethyl maleate covalently binds irreversibly to GSH via glutathione S-transferase with an in vitro IC50 of 0.1-0.5 mM. Diethyl maleate selectively depletes GSH in liver, lung, and brain tissues, exacerbating oxidative stress and enhancing hyperbaric oxygen toxicity. Diethyl maleate promotes precursor amino acid uptake and in turn promotes GSH synthesis by upregulating the activity of the cystine-glutamate transporter XO-. Diethyl maleate can be used to study redox homeostasis and GSH protection mechanisms in oxidative stress-related diseases such as hyperbaric oxygen injury and metabolic diseases[1][2][3].

Product Specifications

CAS Number

[141-05-9]

Product Name Alternative

Maleic acid diethyl ester

UNSPSC

12352200

Hazard Statement

H317, H319, H412

Target

Biochemical Assay Reagents

Type

Biochemical Assay Reagents

Related Pathways

Others

Field of Research

Others

Assay Protocol

https://www.medchemexpress.com/diethyl-maleate.html

Purity

99.57

Solubility

DMSO : 100 mg/mL (ultrasonic) |Ethanol : ≥ 100 mg/mL

Smiles

O=C(OCC)/C=C\C(OCC)=O

Molecular Formula

C8H12O4

Molecular Weight

172.18

Precautions

H317, H319, H412

References & Citations

[1]Andrea Gille, et al. Nuclear trapping of inactive FOXO1 by the Nrf2 activator diethyl maleate. Redox Biol. 2019 Jan;20:19-27.|[2]Weber CA, et al. Depletion of tissue glutathione with diethyl maleate enhances hyperbaric oxygen toxicity. Am J Physiol. 1990 Jun;258 (6 Pt 1) :L308-12.|[3]Deneke SM, et al. Increase in endothelial cell glutathione and precursor amino acid uptake by diethyl maleate and hyperoxia. Am J Physiol. 1989 Oct;257 (4 Pt 1) :L265-71.