Epsilon-(gamma-glutamyl)-lysine TFA
Based on 1 Customer Validation
Epsilon-(gamma-glutamyl)-lysine TFA (H-Glu (H-Lys-OH)-OH) is an isodipeptide formed during the proteolytic degradation of proteins containing Nε-(γ-glutamyl)-lysine cross-links. Epsilon-(gamma-glutamyl)-lysine TFA serves as a substrate for γ-glutamylamine cyclotransferase, which specifically cleaves it. Epsilon-(gamma-glutamyl)-lysine TFA is applicable to studies related to transglutaminase-mediated protein cross-linking and turnover, γ-glutamylamine cyclotransferase activity, glaucoma, and tissue scar formation.
For research use only. We do not sell to patients.
- Purity : 99.88%
- Formula: C15H23F6N3O9
- Molecular Weight:503.35
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Storage:
Sealed storage, away from moisture.
Powder -80°C, 2 years , -20°C, 1 year* In solvent : -80°C, 6 months; -20°C, 1 month (sealed storage, away from moisture)
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Tel: 609-228-6898 E-mail: [email protected] [email protected]
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Biological Activity
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Chemical Information
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Solvent & Solubility
- Purity & Documentation
- References
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Help & FAQs
All Endogenous Metabolite Isoforms
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Biological Activity
Description
IC50 & Target
[1]|
γ-glutamylamine cyclotransferase |
In Vitro
Epsilon-(gamma-glutamyl)-lysine TFA (H-Glu (H-Lys-OH)-OH TFA) is specifically cleaved in the presence of γ-glutamyl cyclotransferase (25 μg/mL) at 37°C for 3 h. The radiolabeled heterodipeptide peak almost completely disappears, while a lysine peak appears, indicating that Epsilon-(gamma-glutamyl)-lysine TFA is a substrate of this enzyme[1].
When exogenously radiolabeled ε-(γ-glutamyl)-lysine is added to pre-fusion CHO cells (24 h), it can be fully recovered in the unmodified form of Nε-(γ-glutamyl)-lysine, indicating that this heterodipeptide is not taken up by CHO cells nor modified in the culture medium[1].
The content of ε-(γ-glutamyl)-lysine in the free protein fraction reaches 188-238 pmol/107 cells, and that in the culture medium reaches 35-48 pmol/mL when CHO cells are cultured for 48 h. Its content increases with the rise of cell density, peaking at 460 pmol/107 cells in the free protein fraction and 61 pmol/mL in the culture medium respectively when cells are confluent[1].
The formation of ε-(gamma-glutamyl)-lysine in CHO cells and culture medium is inhibited by intracellular protein degradation inhibitors; Methylamine (20 mM) almost completely prevents its occurrence, Leupeptin (HY-18234) (0.2 mM) also exerts a significant inhibitory effect, while Chymostatin (HY-P3042) (0.2 mM) shows a weaker effect. Meanwhile, protein-bound Nε-(γ-glutamyl)-lysine increases, which supports that the free heterodipeptide originates from proteolytic degradation of cross-linked proteins[1].
Epsilon-(gamma-glutamyl)-lysine TFA exists as protein cross-links in renal tissues of human diabetic nephropathy (DN). Its immunofluorescence intensity increases from 3.02 mV/μm2 in normal renal tissues to 14.68 mV/μm2 in DN renal tissues. It mainly distributes in the extracellular regions around glomeruli and renal tubules, and correlates with the degree of renal scarring and the estimated glomerular filtration rate[2].
Epsilon-(gamma-glutamyl)-lysine TFA exists in the form of protein cross-links in all examined scar tissues of failed filtering blebs after glaucoma filtering surgery. Its staining is most prominent at the edge of the Tenon's capsule and shows almost complete colocalization with fibronectin, suggesting that it can reflect tissue transglutaminase-mediated extracellular matrix cross-linking[3].
Epsilon-(gamma-glutamyl)-lysine TFA cross-links show weak staining in the untreated incision area of the ex vivo trabeculectomy model using human donor eyes[3].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only. .
Chemical Information
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Appearance Solid
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Molecular Weight 503.35
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Formula C15H23F6N3O9
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Color White to off-white
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SMILES
OC([C@@H](N)CCC(NCCCC[C@H](N)C(O)=O)=O)=O.OC(C(F)(F)F)=O.OC(C(F)(F)F)=O
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Synonyms
H-Glu(H-Lys-OH)-OH TFA; γ-Glu-ε-Lys TFA
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Structure Classification
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Initial Source
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Shipping
Room temperature in continental US; may vary elsewhere.
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Storage
Sealed storage, away from moisture
Powder -80°C 2 years -20°C 1 year * In solvent : -80°C, 6 months; -20°C, 1 month (sealed storage, away from moisture)
Solvent & Solubility
In Vitro:
DMSO : 100 mg/mL (198.67 mM; Need ultrasonic; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month (sealed storage, away from moisture). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month (sealed storage, away from moisture). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
In Vivo:
Select the appropriate dissolution method based on your experimental animal and administration route.
- For the following dissolution methods, please ensure to first prepare a clear stock solution using an In Vitro approach and then sequentially add co-solvents:
- To ensure reliable experimental results, the clarified stock solution can be appropriately stored based on storage conditions. As for the working solution for In Vivo experiments, it is recommended to prepare freshly and use it on the same day.
- The percentages shown for the solvents indicate their volumetric ratio in the final prepared solution. If precipitation or phase separation occurs during preparation, heat and/or sonication can be used to aid dissolution.
Add each solvent one by one: 10% DMSO 40% PEG300 5% Tween-80 45% Saline
Solubility: ≥ 2.08 mg/mL (4.13 mM); Clear solution
This protocol yields a clear solution of ≥ 2.08 mg/mL (saturation unknown).
Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (20.8 mg/mL) to 400 μL PEG300, and mix evenly; then add 50 μL Tween-80 and mix evenly; then add 450 μL Saline to adjust the volume to 1 mL.
Preparation of Saline: Dissolve 0.9 g sodium chloride in ddH₂O and dilute to 100 mL to obtain a clear Saline solution.
Add each solvent one by one: 10% DMSO 90% (20% SBE-β-CD in Saline)
Solubility: ≥ 2.08 mg/mL (4.13 mM); Clear solution
This protocol yields a clear solution of ≥ 2.08 mg/mL (saturation unknown).
Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (20.8 mg/mL) to 900 μL 20% SBE-β-CD in Saline, and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C, storage for one week): 2 g SBE-β-CD powder is dissolved in 10 mL Saline, completely dissolve until clear.
In Vivo Dissolution Calculator
Please enter the basic information of animal experiments:
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Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.
Please enter your animal formula composition:
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%DMSO +
Recommended: Keep the proportion of DMSO in working solution below 2% if your animal is weak.
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%+
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+%Tween-80 + +
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%Saline +
The co-solvents required include: DMSO, . All of co-solvents are available by MedChemExpress (MCE). , Tween 80. All of co-solvents are available by MedChemExpress (MCE).
Working solution concentration: 0.22 mg/mL
Method for preparing stock solution: mg drug dissolved in μL DMSO. Stock solution concentration: mg/mL. * In solvent : -80°C, 6 months; -20°C, 1 month (sealed storage, away from moisture)
1. Take μL DMSO stock solution;
2. Add μL .
μL , mix evenly;
3. Then add μL Tween 80, mix evenly;
4. Then add μL
Please ensure that the stock solution in the first step is dissolved to a clear state, and add co-solvents in sequence. You can use ultrasonic heating (ultrasonic cleaner, recommended frequency 20-40 kHz), vortexing, etc. to assist dissolution.
Purity & Documentation
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Data Sheet (285 KB)
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SDS (252 KB)
- English - EN (252 KB)
- Français - FR (252 KB)
- Deutsch - DE (252 KB)
- Norwegian - NO (252 KB)
- Español - ES (252 KB)
- Swedish - SV (252 KB)
- Italian - IT (252 KB)
- Korean - KR (252 KB)
- Portuguese - PT (252 KB)
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Handling Instructions (2659 KB)
References
[2]. El Nahas AM, et al. Elevated ε-(γ-Glutamyl)lysine in Human Diabetic Nephropathy Results from Increased Expression and Cellular Release of Tissue Transglutaminase. Nephron Clin Pract. 2004;97:c108-c117. [Content Brief]
[3]. Priglinger SG, et al. Potential role of tissue transglutaminase in glaucoma filtering surgery. Investigative ophthalmology & visual science. 2006 Sep;47(9):3835-45. [Content Brief]
Complete Stock Solution Preparation Table
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month (sealed storage, away from moisture). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
| Optional Solvent | Concentration Solvent Mass | 1 mg | 5 mg | 10 mg | 25 mg |
|---|---|---|---|---|---|
| DMSO | 1 mM | 1.9867 mL | 9.9334 mL | 19.8669 mL | 49.6672 mL |
| 5 mM | 0.3973 mL | 1.9867 mL | 3.9734 mL | 9.9334 mL | |
| 10 mM | 0.1987 mL | 0.9933 mL | 1.9867 mL | 4.9667 mL | |
| 15 mM | 0.1324 mL | 0.6622 mL | 1.3245 mL | 3.3111 mL | |
| 20 mM | 0.0993 mL | 0.4967 mL | 0.9933 mL | 2.4834 mL | |
| 25 mM | 0.0795 mL | 0.3973 mL | 0.7947 mL | 1.9867 mL | |
| 30 mM | 0.0662 mL | 0.3311 mL | 0.6622 mL | 1.6556 mL | |
| 40 mM | 0.0497 mL | 0.2483 mL | 0.4967 mL | 1.2417 mL | |
| 50 mM | 0.0397 mL | 0.1987 mL | 0.3973 mL | 0.9933 mL | |
| 60 mM | 0.0331 mL | 0.1656 mL | 0.3311 mL | 0.8278 mL | |
| 80 mM | 0.0248 mL | 0.1242 mL | 0.2483 mL | 0.6208 mL | |
| 100 mM | 0.0199 mL | 0.0993 mL | 0.1987 mL | 0.4967 mL |
Epsilon-(gamma-glutamyl)-lysine TFA Related Classifications
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