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gamma-Glu-Cys

Cat No.:V41419 Purity: ≥98%
Gamma-glutamylcysteine (amma-Glu-Cys) is a substrate for biosynthesis of L-glutathione by glutathione synthetase.
gamma-Glu-Cys
gamma-Glu-Cys Chemical Structure CAS No.: 636-58-8
Product category: New11
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
Gamma-glutamylcysteine (amma-Glu-Cys) is a substrate for biosynthesis of L-glutathione by glutathione synthetase. It is a dipeptide acting as an essential cofactor for the antioxidant enzyme glutathione peroxidase (GPx). It can also increase anti-inflammatory cytokines such as IL-10 and reduce pro-inflammatory cytokines (TNF-α, IL-6, and IL-1β).
gamma-Glu-Cys (Gamma-glutamylcysteine, γ-Glu-Cys) is a natural dipeptide containing cysteine and glutamic acid. It has a molecular weight of 250.27 g/mol, a formula of C8H14N2O5S, and a CAS number of 636-58-8. gamma-Glu-Cys serves as a precursor to glutathione (GSH) and a cofactor for the antioxidant enzyme glutathione peroxidase (GPx). It exhibits anti-inflammatory effects by upregulating IL-10 while downregulating TNF-α, IL-6, and IL-1β.
Biological Activity I Assay Protocols (From Reference)
Targets
gamma-Glu-Cys targets the biosynthesis of glutathione (GSH). It is a substrate for glutathione synthetase, which catalyzes the final step in GSH production. By serving as a precursor and a cofactor for glutathione peroxidase (GPx), it plays a crucial role in the cellular antioxidant defense system.
ln Vitro
The antioxidant enzymes superoxide dismutase (SOD) and glutathione peroxidase (GPx) were activated when 200 μM gamma-glutamylcysteine was co-treated with Aβ40 oligomers. This also led to a considerable rise in total antioxidant levels (TAC) and GSH, as well as a decrease in the GSSG/GSH ratio. Additionally, gamma-glutamylcysteine reduces the levels of pro-inflammatory cytokines (TNF-α, IL-6, and IL-1β), increases the anti-inflammatory cytokine IL-10, and attenuates alterations in metalloproteinase activity in astrocytes treated with oligomeric Aβ40[1].
In vitro, gamma-Glu-Cys (200 μM) has been shown to activate the antioxidant enzymes superoxide dismutase (SOD) and glutathione peroxidase (GPx). It increases total antioxidant capacity (TAC) and GSH levels while decreasing the GSSG/GSH ratio. It also reduces the levels of pro-inflammatory cytokines (TNF-α, IL-6, and IL-1β) and increases the anti-inflammatory cytokine IL-10.
ln Vivo
In vivo activity data for gamma-Glu-Cys are not extensively detailed in the available sources. As a precursor to glutathione and a modulator of inflammation, it has potential applications in research on oxidative stress, inflammatory responses, and neurodegenerative diseases. Its ability to modulate cytokine levels suggests potential for in vivo studies in models of inflammation.
Enzyme Assay
The in vitro assay for gamma-Glu-Cys typically involves treating cells, such as astrocytes, with the compound and then measuring various biochemical markers. For example, human astrocyte-like cells are pre-incubated with gamma-Glu-Cys (200 μM) for 15 minutes, followed by treatment with Aβ40 oligomers (10 nM). After 24 hours, markers of oxidative stress (GSH, GSSG/GSH ratio) and inflammation (cytokine levels) are measured.
Cell Assay
Cellular assays for gamma-Glu-Cys are performed using astrocyte-like cells or other relevant cell types. Cells are pre-treated with gamma-Glu-Cys (200 μM) and then exposed to an inflammatory or oxidative stressor, such as Aβ40 oligomers. After incubation, cell lysates or supernatants are collected to measure antioxidant enzyme activity, GSH levels, and cytokine production using ELISA or other quantitative methods.
Animal Protocol
In vivo animal studies for gamma-Glu-Cys are not detailed in the available sources. The compound is a naturally occurring dipeptide and an endogenous metabolite. Specific animal models and dosing regimens have not been described in the supplier documentation.
ADME/Pharmacokinetics
Pharmacokinetic data for gamma-Glu-Cys are not available in the provided sources. The compound has a molecular weight of 250.27 g/mol and is soluble in DMSO, ethanol, and water. Powder formulations should be stored at -20°C for up to 3 years. Specific PK parameters such as half-life, bioavailability, and clearance have not been reported.
Toxicity/Toxicokinetics
Toxicity data for gamma-Glu-Cys are not reported in the available sources. As a naturally occurring dipeptide and endogenous metabolite, it is generally considered to have a favorable safety profile. Specific toxicological studies have not been described.
References

[1]. The Precursor to Glutathione (GSH), γ-Glutamylcysteine (GGC), Can Ameliorate Oxidative Damage and Neuroinflammation Induced by Aβ40 Oligomers in Human Astrocytes. Front Aging Neurosci. 2019 Aug 8;11:177.

Additional Infomation
L-γ-Glutamyl-L-cysteine is a molecular entity formed by the combination of the amino group of L-cysteine and the γ-carbonyl group of L-glutamic acid. It is a human metabolite, as well as a metabolite in Saccharomyces cerevisiae, Escherichia coli, and mice. Its function is related to both L-glutamic acid and L-cysteine. It is the conjugate acid of L-γ-glutamyl-L-cysteine (1-). γ-Glutamyl-cysteine is a metabolite found or produced in Escherichia coli (K12 strain, MG1655 strain). γ-Glutamyl-cysteine has been reported to exist in Homo sapiens, grapes, and other organisms with relevant data. γ-Glutamyl-cysteine is a metabolite found or produced in Saccharomyces cerevisiae.
gamma-Glu-Cys is a natural dipeptide and endogenous metabolite that serves as a precursor to glutathione (GSH) and a cofactor for glutathione peroxidase (GPx). It exhibits anti-inflammatory effects by modulating cytokine levels. The compound is used in research on oxidative stress, inflammation, and neurodegenerative diseases. It is available from commercial suppliers for research purposes only.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C8H14N2O5S
Molecular Weight
250.2722
Exact Mass
250.062
CAS #
636-58-8
PubChem CID
123938
Appearance
White to off-white solid powder
Density
1.436g/cm3
Boiling Point
592.4ºC at 760 mmHg
Melting Point
167℃
Flash Point
312.1ºC
Index of Refraction
1.57
LogP
-3.8
Hydrogen Bond Donor Count
5
Hydrogen Bond Acceptor Count
7
Rotatable Bond Count
7
Heavy Atom Count
16
Complexity
284
Defined Atom Stereocenter Count
2
SMILES
S([H])C([H])([H])[C@@]([H])(C(=O)O[H])N([H])C(C([H])([H])C([H])([H])[C@@]([H])(C(=O)O[H])N([H])[H])=O
InChi Key
RITKHVBHSGLULN-WHFBIAKZSA-N
InChi Code
InChI=1S/C8H14N2O5S/c9-4(7(12)13)1-2-6(11)10-5(3-16)8(14)15/h4-5,16H,1-3,9H2,(H,10,11)(H,12,13)(H,14,15)/t4-,5-/m0/s1
Chemical Name
(2S)-2-amino-5-[[(1R)-1-carboxy-2-sulfanylethyl]amino]-5-oxopentanoic acid
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)
Solubility Data
Solubility (In Vitro)
H2O : ~100 mg/mL (~399.57 mM)
Solubility (In Vivo)
Solubility in Formulation 1: 100 mg/mL (399.57 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with sonication.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 3.9957 mL 19.9784 mL 39.9568 mL
5 mM 0.7991 mL 3.9957 mL 7.9914 mL
10 mM 0.3996 mL 1.9978 mL 3.9957 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.

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Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

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