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
MDL number:
UNSPSC Code:
12161504
PubChem Substance ID:
NACRES:
NA.26
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Product Name
Glutathione reduced ethyl ester, ≥90% (TLC)
Quality Level
Assay
≥90% (TLC)
form
powder
color
white to off-white
storage temp.
−20°C
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
Amino Acid Sequence
Glu-Cys-Gly-OEt
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 Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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The glutathione derivative, GSH monoethyl ester, may effectively whiten skin but GSH does not
Chung B, et al.
International Journal of Molecular Sciences, 17(5), 629-629 (2016)
Cytotoxic effects induced by oxidative stress in cultured mammalian cells and protection provided by Hsp27 expression
Arrigo A, et al.
Methods, 35(2), 126-138 (2005)
Glutathione ethyl ester supplementation during pancreatic islet isolation improves viability and transplant outcomes in a murine marginal islet mass model
do Amaral ASR, et al.
Testing, 8(2), e55288-e55288 (2013)
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
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)
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