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G1404

Sigma-Aldrich

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:
92614-59-0
Molecular Weight:
335.38
MDL number:
MFCD00156117
UNSPSC Code:
12161504
PubChem Substance ID:
329799840
NACRES:
NA.26

Quality Level

200

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

Related Categories

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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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)
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)
Alison E M Vickers et al.
Toxicology and applied pharmacology, 244(3), 354-365 (2010-02-11)
A novel in vitro model to investigate time-dependent and concentration-dependent responses in blood cells and hemolytic events is studied for rat, dog, and human tissues. Whole blood is co-cultured with a precision-cut liver slice. Methimazole (MMI) was selected as a
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Stroke, 49(5), 1223-1231 (2018-04-13)
Ischemic brain injury is characterized by 2 temporally distinct but interrelated phases: ischemia (primary energy failure) and reperfusion (secondary energy failure). Loss of cerebral blood flow leads to decreased oxygen levels and energy crisis in the ischemic area, initiating a
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