Glutathione Ethyl Ester

Product NameGlutathione Ethyl Ester
CAS92614-59-0
MFC12H21N3O6S
MW335.38
EINECS000-000-0
MOL File92614-59-0.mol

Chemical Properties

Boiling point	644.3±55.0 °C(Predicted)
Density	1.314±0.06 g/cm3(Predicted)
storage temp.	-20°C
solubility	PBS (pH 7.2): 10 mg/ml; Water: 20 mg/ml
form	A crystalline solid
pka	2.21±0.10(Predicted)
color	White to off-white
InChI	1S/C12H21N3O6S/c1-2-21-10(17)5-14-11(18)8(6-22)15-9(16)4-3-7(13)12(19)20/h7-8,22H,2-6,13H2,1H3,(H,14,18)(H,15,16)(H,19,20)/t7-,8-/m0/s1
InChIKey	JKRODHBGNBKZLE-YUMQZZPRSA-N
SMILES	CCOC(=O)CNC(=O)[C@H](CS)NC(=O)CC[C@H](N)C(O)=O

Safety Information

WGK Germany	3
Storage Class	11 - Combustible Solids

Usage And Synthesis

Description

Glutathione (GSH) serves as a nucleophilic co-substrate to glutathione transferase in the detoxification of xenobiotics and is an essential electron donor to glutathione peroxidases in the reduction of hydroperoxides. GSH ethyl ester is a cell-permeable derivative of GSH that undergoes hydrolysis by intracellular esterases to release GSH. Effective transport of GSH ethyl ester has been used to protect cells against damage from radiation, oxidants, and various toxic compounds including heavy metals.

Uses

Glutathione (GSH) serves as a nucleophilic co-substrate to glutathione transferase in the detoxification of xenobiotics and is an essential electron donor to glutathione peroxidases in the reduction of hydroperoxides. GSH ethyl ester is a cell permeable derivative of GSH that undergoes hydrolysis by intracellular esterases to release GSH. Effective transport of GSH ethyl ester has been used to protect cells against damage from radiation, oxidants, and various toxic compounds including heavy metals.

Uses

Glutathione reduced ethyl ester has been used:

to increase intracellular glutathione levels in mouse fibroblast L929 cells
as a medium supplement in Spodoptera frugiperda (Sf)9 cells
to evaluate its effect on lipid peroxidation after spinal cord injury

Biochem/physiol Actions

Glutathione reduced ethyl ester (GSH-MEE) is a membrane/lipid permeable derivative of GSH that may be used to partially supplement the GSH supply within cells subjected to cysteine and/or GSH depletion. GSH-MEE is hydrolysed by intracellular esterases to release GSH, thereby increases the concentrations of intracellular GSH. It prevents the toxic effects of acetaminophen in animal cells. It protects human lymphoid cells and skin fibroblasts against the damage caused due to radiation.

in vivo

Glutathione ethyl ester (6 mmol/kg; intraperitoneal injection; once; administered 1 h before the experiment) increases the swimming endurance and reduces exercise-induced muscle lipid peroxidation in mice starved for 24 h. However, it has certain metabolic and oxidative stress side effects on the kidney^[2]. X

Animal Model:	Male Swiss-Webster mice (age 2 mo, body wt 25-30 g), a model of exercise-induced oxidative stress^[2].
Dosage:	6 mmol/kg (saline)
Administration:	Intraperitoneal injection, once, 1 h before the experiment.
Result:	Normalized endurance performance in starved mice. Decreased muscle GSH content and the GSH:GSSG ratio. Also significantly increased endurance time and suppressed exercise-induced muscle lipid peroxidation .

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