G1404
Glutathione reduced ethyl ester
≥90% (TLC)
Synonym(s):
γ-Glu-Cys-Gly-OEt, GSH-MEE
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About This Item
Empirical Formula (Hill Notation):
C12H21N3O6S
CAS Number:
Molecular Weight:
335.38
UNSPSC Code:
12161504
PubChem Substance ID:
NACRES:
NA.26
MDL number:
Product Name
Glutathione reduced ethyl ester, ≥90% (TLC)
SMILES string
CCOC(=O)CNC(=O)[C@H](CS)NC(=O)CC[C@H](N)C(O)=O
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
InChI key
JKRODHBGNBKZLE-YUMQZZPRSA-N
assay
≥90% (TLC)
form
powder
color
white to off-white
storage temp.
−20°C
Quality Level
Application
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.
Glutathione reduced ethyl ester inhibits melanin synthesis by inhibiting tyrosinase activity in Melan-A cells. Its antimelanogenic functionality has potential in treating hyperpigmentation skin disorders. GEE supplementation during islets isolation form pancreas reduces reactive oxygen species production and apoptosis.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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Modulation of endothelial GSH concentrations: effect of exogenous GSH and GSH monoethyl ester.
Tsan MF
Journal of Applied Physiology, 66(3), 1029-1034 (1989)
I Rahman et al.
Biochemical pharmacology, 62(6), 787-794 (2001-09-12)
The airway epithelium is injured by oxidants inhaled as atmospheric pollutants or produced during inflammatory responses. We studied the effect of modulating the antioxidant intracellular glutathione, both using thiol compounds and by the adaptive effect of hyperoxia, on oxidant-induced injury
Reticular dysgenesis-associated AK2 protects hematopoietic stem and progenitor cell development from oxidative stress.
Rissone A
The Journal of Experimental Medicine, 212(8), 1185-1202 (2015)
Targeted supplementation design for improved production and quality of enveloped viral particles in insect cell-baculovirus expression system
Monteiro F, et al.
Journal of Biotechnology, 233(2), 34-41 (2016)
M E Anderson et al.
Archives of biochemistry and biophysics, 239(2), 538-548 (1985-06-01)
Glutathione monoethyl ester (L-gamma-glutamyl-L-cysteinylglycyl ethyl ester), in contrast to glutathione itself, is effectively transported into many types of cells. The ester is converted intracellularly into glutathione. Intraperitoneal injection of 35S-labeled ester into mice was followed by rapid appearance of isotope
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