| Size | Price | Stock | Qty |
|---|---|---|---|
| 50mg |
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| 100mg |
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| Other Sizes |
| Targets |
Cereblon
CRBN (cereblon), an E3 ubiquitin ligase. |
|---|---|
| ln Vitro |
One ligand is for an E3 ubiquitin ligase, and the other is for the target protein; these two ligands are joined by a linker to form PROTACs. The intracellular ubiquitin-proteasome system is utilized by PROTACs to specifically destroy target proteins[2].
As a cereblon-binding ligand, Lenalidomide-5-aminomethyl hydrochloride itself has no intrinsic degradation activity; its function is to bind to CRBN and recruit the E3 ubiquitin ligase complex. The primary amine can be conjugated to a target protein ligand via a linker, and the resulting PROTAC can ubiquitinate and degrade the target protein. |
| ln Vivo |
No specific in vivo activity has been reported for this ligand alone; its in vivo degradation activity is observed only when conjugated to a target protein ligand to form a complete PROTAC molecule. The in vivo efficacy of such a PROTAC is typically evaluated in animal models.
|
| Enzyme Assay |
N/A; as a ligand, its binding affinity to cereblon is typically determined using biophysical methods such as surface plasmon resonance (SPR) or isothermal titration calorimetry (ITC) as part of the validation of the final PROTAC construct. The compound is used as a synthetic intermediate.
|
| Cell Assay |
N/A; this ligand is not evaluated alone in cell-based assays but is used as a building block to construct cereblon-recruiting PROTACs for cellular degradation studies. In a typical conjugation step, the primary amine is coupled to a carboxylic acid-containing linker or target ligand using EDC/NHS chemistry.
|
| Animal Protocol |
N/A; no animal studies are performed with the ligand alone. In vivo efficacy studies would be conducted using the complete PROTAC molecule synthesized from this building block.
|
| ADME/Pharmacokinetics |
This compound has a molecular weight of 309.75, a molecular formula of C14H16ClN3O3, and appears as an off-white to light yellow solid. It is typically stored as a powder at -20degC, stored under nitrogen and away from moisture. In a solvent, it can be stored at -80degC for 6 months or at -20degC for 1 month, stored under nitrogen and away from moisture. HPLC purity is 98.77%.
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| Toxicity/Toxicokinetics |
This product is for research use only and is not for human therapeutic or clinical applications. Standard chemical safety precautions should be followed during handling. The product has not been fully validated for medical applications. It is for research use only and is not sold to patients.
|
| References | |
| Additional Infomation |
The 5-aminomethyl modification provides a versatile handle for conjugation to linkers and target protein ligands. Unlike the standard lenalidomide, which has a free amine at the glutarimide nitrogen, this compound has an additional aminomethyl group that can be used for orthogonal conjugation strategies. This hydrochloride salt form enhances solubility and stability.
|
| Molecular Formula |
C14H16CLN3O3
|
|---|---|
| Molecular Weight |
309.75
|
| Exact Mass |
309.088
|
| CAS # |
1158264-69-7
|
| Related CAS # |
Lenalidomide-5-aminomethyl;1010100-28-3
|
| PubChem CID |
66589525
|
| Appearance |
Off-white to light yellow solid powder
|
| Hydrogen Bond Donor Count |
3
|
| Hydrogen Bond Acceptor Count |
4
|
| Rotatable Bond Count |
2
|
| Heavy Atom Count |
21
|
| Complexity |
451
|
| Defined Atom Stereocenter Count |
0
|
| SMILES |
Cl[H].O=C1C2C([H])=C([H])C(C([H])([H])N([H])[H])=C([H])C=2C([H])([H])N1C1([H])C(N([H])C(C([H])([H])C1([H])[H])=O)=O
|
| InChi Key |
XTILEMYXOZKSFJ-UHFFFAOYSA-N
|
| InChi Code |
InChI=1S/C14H15N3O3.ClH/c15-6-8-1-2-10-9(5-8)7-17(14(10)20)11-3-4-12(18)16-13(11)19;/h1-2,5,11H,3-4,6-7,15H2,(H,16,18,19);1H
|
| Chemical Name |
3-[6-(aminomethyl)-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione;hydrochloride
|
| 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 Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
|
| Solubility (In Vitro) |
DMSO :~16.67 mg/mL (~53.82 mM )
|
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 1.67 mg/mL (5.39 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 16.7 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 1.67 mg/mL (5.39 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 16.7 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 1.67 mg/mL (5.39 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.2284 mL | 16.1421 mL | 32.2841 mL | |
| 5 mM | 0.6457 mL | 3.2284 mL | 6.4568 mL | |
| 10 mM | 0.3228 mL | 1.6142 mL | 3.2284 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.
Calculation results
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.
(2) Be sure to add the solvent(s) in order.
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