| Size | Price | Stock | Qty |
|---|---|---|---|
| 100mg |
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| 500mg |
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| Other Sizes |
| Targets |
Cereblon
CRBN (cereblon), an E3 ubiquitin ligase. |
|---|---|
| ln Vitro |
As a cereblon-binding ligand-linker conjugate, Lenalidomide-C5-NH2 TFA itself has no intrinsic biological activity; its function is to recruit the E3 ubiquitin ligase complex. The terminal primary amine is conjugated to a target protein ligand via amide bond formation using standard coupling reagents (e.g., EDC, HATU). The resulting PROTAC can simultaneously bind to both a target protein and cereblon, leading to ubiquitination and subsequent proteasomal degradation of the target protein. The C5 alkyl linker provides a moderate-length, flexible spacer that is hydrophobic, which can be beneficial for PROTACs targeting intracellular proteins where a certain degree of lipophilicity is required for cellular permeability.
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| ln Vivo |
No specific in vivo activity has been reported for this conjugate 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 of target-driven diseases.
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| Enzyme Assay |
N/A; this compound is not assessed in isolated enzyme/receptor binding assays. As a synthetic intermediate, its quality is confirmed by analytical methods such as HPLC and NMR, with a standard purity of ≥95%. Its binding affinity to cereblon is validated as part of a complete PROTAC construct using biophysical methods such as surface plasmon resonance (SPR) or isothermal titration calorimetry (ITC). The C5 alkyl linker can be characterized by mass spectrometry. The TFA counterion can be detected by ion chromatography.
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| Cell Assay |
N/A; this conjugate is not tested alone in cell-based assays but is used as a building block for constructing PROTACs. In a typical conjugation step, the terminal primary amine is activated (or directly reacted) with a carboxylic acid-containing target protein ligand using EDC and NHS or HATU. The resulting PROTAC is then tested in target-expressing cancer cells for degradation activity by Western blotting to determine the DC50 (half-maximal degradation concentration). The C5 alkyl linker may be optimal for certain target-E3 ligase pairs. The TFA salt improves water solubility.
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| Animal Protocol |
N/A; no animal studies are performed with the ligand-linker conjugate alone. For in vivo studies of a complete PROTAC, the molecule is formulated in a suitable vehicle (e.g., 10% DMSO, 40% PEG300, 5% Tween-80, 45% saline) and administered to animal models via intraperitoneal (IP) or intravenous (IV) injection. Target degradation in tissues and tumor growth inhibition are monitored. The C5 alkyl linker may affect the lipophilicity and cellular permeability of the final PROTAC.
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| ADME/Pharmacokinetics |
This compound has a molecular weight of 432.40, a molecular formula of C18H23F3N4O5, and a standard purity of ≥95%. The IUPAC name is 3-(4-((5-aminopentyl)amino)-1-oxoisoindolin-2-yl)piperidine-2,6-dione 2,2,2-trifluoroacetate. For storage, it should be kept as a solid at -20degC for up to 3 years, sealed, away from moisture. It is soluble in DMSO. The product should be stored in a sealed container, protected from light. CAS: 2550398-71-3.
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| Toxicity/Toxicokinetics |
This product is for research use only and is not for human or veterinary use. Standard chemical safety precautions should be followed during handling. The product is stable under recommended storage conditions. It is not an approved therapeutic drug and has not been cleared for clinical use. Lenalidomide is an immunomodulatory drug (IMiD) clinically used for multiple myeloma and myelodysplastic syndromes; this derivative is for research purposes only.
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| References |
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| Additional Infomation |
The C5 alkyl linker (five-carbon chain) provides a moderate-length, flexible, and hydrophobic spacer that can be optimal for target-E3 ligase pairs requiring a moderate distance between binding sites. This conjugate is a valuable building block for developing cereblon-recruiting PROTACs with alkyl linkers of varying lengths. The terminal primary amine enables direct conjugation to target protein ligands via standard amide coupling. The TFA salt form improves solubility and facilitates handling. This compound is also known as Lenalidomide-C5-NH2 TFA and is widely used in PROTAC research for targeted protein degradation.
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| Exact Mass |
443.167
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|---|---|
| CAS # |
2550398-71-3
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| Related CAS # |
Lenalidomide-C5-NH2 hydrochloride;2595367-27-2
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| PubChem CID |
162640763
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| Appearance |
Light yellow to yellow solid powder
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| Hydrogen Bond Donor Count |
3
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| Rotatable Bond Count |
6
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| Heavy Atom Count |
31
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| Complexity |
591
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| Defined Atom Stereocenter Count |
0
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| SMILES |
C1CC(=O)NC(=O)C1N2CC3=C(C=CC=C3C2=O)CCCCCN.C(=O)(C(F)(F)F)O
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| InChi Key |
XTHUZCHGWIIXLO-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C18H23N3O3.C2HF3O2/c19-10-3-1-2-5-12-6-4-7-13-14(12)11-21(18(13)24)15-8-9-16(22)20-17(15)23;3-2(4,5)1(6)7/h4,6-7,15H,1-3,5,8-11,19H2,(H,20,22,23);(H,6,7)
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| Chemical Name |
3-[7-(5-aminopentyl)-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione;2,2,2-trifluoroacetic acid
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| HS Tariff Code |
2934.99.9001
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| 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)
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| Solubility (In Vitro) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
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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