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Glycylglutamine

Alias: L-Glutamine, N2-glycyl-; Gly-gln; Glycylglutamine
Cat No.:V21681 Purity: ≥98%
Glycyl-glutamine (Glycyl-L-glutamine), an enzymatic cleavage product of β-endorphin, is an endogenous antagonist of β-endorphin (1-31).
Glycylglutamine
Glycylglutamine Chemical Structure CAS No.: 13115-71-4
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
Glycyl-glutamine (Glycyl-L-glutamine), an enzymatic cleavage product of β-endorphin, is an endogenous antagonist of β-endorphin (1-31). Glycyl-glutamine (Glycyl-L-glutamine) is an active neuropeptide that is more stable than glutamine (Gln).
Glycylglutamine (CAS 13115-71-4), also known as Glycyl-L-glutamine or Gly-Gln, is an enzymatic cleavage product of β-endorphin and functions as an endogenous antagonist of β-endorphin (1-31) in several systems. It is a stable and active neuropeptide containing glutamine that is more stable than free glutamine. The dipeptide is composed of glycine and L-glutamine residues and has a molecular weight of 203.19.
Biological Activity I Assay Protocols (From Reference)
Targets
Glycylglutamine targets β-endorphin (1-31) as an endogenous antagonist. In animal models of opioid use, it inhibits opioid-induced dopamine signaling, preventing reward and suppressing development of tolerance and withdrawal. It also inhibits nicotine-induced reward signaling in conditioned place preference (CPP) paradigms and the development of nicotine withdrawal. The compound inhibits β-endorphin-induced cardiorespiratory depression.
ln Vitro
Glycylglutamine, also known as glycyl-L-glutamine, is a neuropeptide that contains glutamine and is both stable and active. When it comes to growth factors for cell culture during autoclaving and storage, glycylglutamine (also known as glycyl-L-glutamine) is superior to free glutamine (Gln) [2].
In vitro, glycylglutamine is superior to free glutamine as a growth factor for cell culture during autoclaving and storage. It is an active neuropeptide that is both stable and active in cell culture applications. As a β-endorphin antagonist, it inhibits the effects of β-endorphin in various in vitro systems.
ln Vivo
Rats anesthetized with pentobarbital are shown to be resistant to β-End-(1-31)-induced hypoxia when given varying doses of glycyl-L-glutamine (0.3, 0.6, 1.0, and 10.0 nM). blood pressure [1].
In vivo, glycylglutamine administered at varying doses (0.3, 0.6, 1.0, and 10.0 nM) to rats anesthetized with pentobarbital protects against β-endorphin (1-31)-induced hypoxia. It inhibits β-endorphin-induced cardiorespiratory depression. In animal models of opioid use, it prevents reward and suppresses development of tolerance and withdrawal.
Enzyme Assay
β-Endorphin antagonism assays: Cells or tissue preparations expressing β-endorphin receptors are treated with β-endorphin (1-31) in the presence or absence of glycylglutamine at various concentrations (typically 0.1-100 nM). Functional readouts such as cAMP levels, calcium flux, or receptor binding are measured. Inhibition of β-endorphin-induced effects is calculated to determine antagonist potency.
Cell Assay
For cell culture studies, various mammalian cell lines are cultured in media supplemented with glycylglutamine as a stable glutamine source替代 free glutamine. Cells are maintained at 37°C with 5% CO₂, and growth and viability are compared to cultures supplemented with free glutamine. Cell proliferation is assessed using cell counting or metabolic assays.
Animal Protocol
In animal studies, glycylglutamine is administered intravenously or intracerebroventricularly to rats at doses of 0.3, 0.6, 1.0, and 10.0 nM. Cardiovascular and respiratory parameters (blood pressure, heart rate, respiratory rate) are monitored. β-Endorphin (1-31) is co-administered to induce cardiorespiratory depression, and the protective effect of glycylglutamine is assessed.
ADME/Pharmacokinetics
Glycylglutamine (molecular weight 203.19, formula C₇H₁₃N₃O₄) is a white to off-white solid powder. It has density 1.4±0.1 g/cm³, boiling point 643.1±55.0°C at 760 mmHg, and LogP -2.5. The compound is more stable than free glutamine and is suitable for cell culture applications. It is both a metabolite and has protective functions.
References
[1]. Unal CB1, et al. Beta-endorphin-induced cardiorespiratory depression is inhibited by glycyl-L-glutamine, a dipeptide derived from beta-endorphin processing.J Pharmacol Exp Ther. 1994 Nov;271(2):952-8
[2]. Roth E, et al. Influence of two glutamine-containing dipeptides on growth of mammalian cells.In Vitro Cell Dev Biol. 1988 Jul;24(7):696-8.
Additional Infomation
Glycine-glutamine (Gly-Gln) is a dipeptide composed of glycine and L-glutamine residues. It is both a metabolite and has protective functions. It is the zwitterion tautomer of Gly-Gln.
Glycylglutamine is an inhibitory neuropeptide derived from β-endorphin. It has been studied for its potential to inhibit opioid and nicotine addiction by preventing reward signaling and suppressing tolerance and withdrawal. The dipeptide is more stable than free glutamine and is useful as a glutamine source in cell culture media. It inhibits β-endorphin-induced cardiorespiratory depression, suggesting potential therapeutic applications.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C7H13N3O4
Molecular Weight
203.19
Exact Mass
203.09
CAS #
13115-71-4
PubChem CID
123913
Appearance
White to off-white solid powder
Density
1.4±0.1 g/cm3
Boiling Point
643.1±55.0 °C at 760 mmHg
Melting Point
194°C
Flash Point
342.7±31.5 °C
Vapour Pressure
0.0±4.1 mmHg at 25°C
Index of Refraction
1.538
LogP
-2.5
Hydrogen Bond Donor Count
4
Hydrogen Bond Acceptor Count
5
Rotatable Bond Count
6
Heavy Atom Count
14
Complexity
241
Defined Atom Stereocenter Count
1
SMILES
NC(CC[C@H](NC(CN)=O)C(O)=O)=O
InChi Key
PNMUAGGSDZXTHX-BYPYZUCNSA-N
InChi Code
InChI=1S/C7H13N3O4/c8-3-6(12)10-4(7(13)14)1-2-5(9)11/h4H,1-3,8H2,(H2,9,11)(H,10,12)(H,13,14)/t4-/m0/s1
Chemical Name
(2S)-5-amino-2-[(2-aminoacetyl)amino]-5-oxopentanoic acid
Synonyms
L-Glutamine, N2-glycyl-; Gly-gln; Glycylglutamine
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 : ~62.5 mg/mL (~307.58 mM)
Solubility (In Vivo)
Solubility in Formulation 1: 100 mg/mL (492.13 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 4.9215 mL 24.6075 mL 49.2150 mL
5 mM 0.9843 mL 4.9215 mL 9.8430 mL
10 mM 0.4922 mL 2.4608 mL 4.9215 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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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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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.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
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