Diethylmaleate 141-05-9_Others_Signaling Pathways_Products

Diethylmaleate is the diethyl ester of maleic acid and a glutathione-depleting compound that inhibits NFkB. DEM induces upregulation of GSH(L-c-glutamyl-L-cysteinyl-glycine) metabolism, and the downregulation of pathways of cancer, chemokine signaling, cytokine-cytokine receptor, and focal adhesion in transformed cells. DEM appears to modify microenvironment of transformed cells thereby restraining tumor cell growth.

Physicochemical Properties

Molecular Formula

C8H12O4

Molecular Weight

172.18

Exact Mass

172.073

CAS #

141-05-9

Related CAS #

141-05-9

PubChem CID

5271566

Appearance

Colorless to light yellow liquid

Density

1.1±0.1 g/cm3

Boiling Point

214.0±0.0 °C at 760 mmHg

Melting Point

−10 °C(lit.)

Flash Point

93.3±0.0 °C

Vapour Pressure

0.2±0.4 mmHg at 25°C

Index of Refraction

1.443

LogP

1.68

Hydrogen Bond Donor Count

Hydrogen Bond Acceptor Count

Rotatable Bond Count

Heavy Atom Count

Complexity

164

Defined Atom Stereocenter Count

SMILES

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

InChi Key

IEPRKVQEAMIZSS-WAYWQWQTSA-N

InChi Code

InChI=1S/C8H12O4/c1-3-11-7(9)5-6-8(10)12-4-2/h5-6H,3-4H2,1-2H3/b6-5-

Chemical Name

2-Butenedioic acid (2Z)-, diethyl ester

Synonyms

Ethyl maleate; Maleic acid|diethyl ester, Maleic acid diethyl ester;NSC 8394; NSC-8394; NSC8394; AI3-00678; AI3 00678; AI300678

HS Tariff Code

2934.99.9001

Storage

Powder-20°C 3 years

4°C 2 years

In solvent -80°C 6 months

-20°C 1 month

Shipping Condition

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

ln Vitro

In vitro activity: DEM induces upregulation of GSH(L-c-glutamyl-L-cysteinyl-glycine) metabolism, and the downregulation of pathways of cancer, chemokine signaling, cytokine-cytokine receptor, and focal adhesion in transformed cells. DEM appears to modify microenvironment of transformed cells thereby restraining tumor cell growth. DEM is cytotoxic to the transformed cells in a concentration dependent manner. DEM at 0.25 mM decreases cell viability to 75%. The co-exposure of cells to DEM+GSHe inhibits DEM induced cytotoxicity. DEM exposure increases the ROS generation by multiple orders of magnitude in transformed cells. This is evident from the dose and time dependent increase in fluorescence intensity of CMH2DCFDA. Moreover, DEM activates MAPK pathway and DEM induced activation of ERK is found to be due to phosphorylation at Thr 202/204.

Cell Assay: A stock solution of DEM is prepared in 100% DMSO and diluted in DMEM to achieve the desired concentration with less than 0.1% DMSO in the culture wells. Briefly, cells are seeded (1 ×104 cells/well) in 96-well plates and allowed to adhere overnight. Subsequently, these cells are exposed to DEM at various test concentrations (0.05-1 mM) or co-exposed to equimolar (0.25 mM) DEM+GSHe for 24 h. Cell viability is determined by recording the OD at 570 nm in an Elisa microplate reader.

ln Vivo

Sperm motility and epididymal sperm count are significantly reduced in the DEM treated animals. Fertility status is also affected by DEM exposure as is evident from the percent fertility and the litter size. consequences of the oxidative stress produced by the DEM induces glutathione depletion, on the reproductive ability of male mice and modulation of the various components of the antioxidant defense system at the transcriptional level.

Animal Protocol

Dissolved in corn oil; 6mmol/kg; i.p.

Sprague-Dawley rats

References

Chem Biol Interact.2014 Aug 5;219:37-47;Biochem Pharmacol.1992 Feb 4;43(3):451-6.

Additional Infomation

Diethyl maleate is a maleate ester resulting from the formal condensation of both carboxy groups of maleic acid with ethanol. A colourless liquid at room temperature (m.p. -10℃) with boiling point 220℃ at 1 atm., it is commonly used as a dienophile for Diels-Alder-type cycloaddition reactions in organic synthesis. It has a role as a glutathione depleting agent. It is a maleate ester and an ethyl ester. It is functionally related to an ethanol.
See also: 2-Butenedioic acid (2Z)-, di-C8-15-alkyl esters (annotation moved to).

Solubility Data

Solubility (In Vitro)

DMSO: N/A

Water:N/A

Ethanol:N/A

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 9.09 mg/mL (52.79 mM) (saturation unknown) in 10% DMSO + 40% PEG300 +5% Tween-80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 90.9 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 + to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

(Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	5.8079 mL	29.0394 mL	58.0788 mL
	5 mM	1.1616 mL	5.8079 mL	11.6158 mL
	10 mM	0.5808 mL	2.9039 mL	5.8079 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

PeptideDB

Diethylmaleate 141-05-9

CAS No.: 141-05-9

Physicochemical Properties

Biological Activity

Solubility Data