| Size | Price | Stock | Qty |
|---|---|---|---|
| 100mg |
|
||
| 500mg |
| Targets |
Cereblon (CRBN), a substrate receptor for the CRL4 E3 ubiquitin ligase complex. The Thalidomide moiety binds CRBN, recruiting the E3 ligase to neosubstrates. No direct target activity in the absence of a target protein ligand.
|
|---|---|
| ln Vitro |
Thalidomide-O-amido-PEG3-C2-NH2 hydrochloride is utilized in PROTAC technology and is made up of a linker and Degron (E3 ubiquitin ligase). Target proteins, such as BRD4, BRD2, and BRD3, are degraded when thalidomide-O-amido-PEG3-C2-NH2 binds to the targeting ligand[1].
Not applicable (PROTAC building block). As a ligand-linker conjugate, it does not have intrinsic activity. It is used to synthesize PROTACs by conjugation to a target protein ligand via the free amine (C2-NH2). The resulting PROTAC induces ubiquitination and proteasomal degradation of the target protein. |
| ln Vivo |
Not applicable; no in vivo activity as a single agent. When incorporated into a PROTAC, in vivo efficacy is determined by the PROTAC structure. The linker influences pharmacokinetic properties (e.g., solubility, metabolic stability) but has no direct pharmacological activity.
|
| Enzyme Assay |
Not applicable (chemical conjugation validation): The linker conjugate is a chemical reagent; no enzyme/receptor binding assays are performed. Quality control may involve NMR and LC-MS to confirm structure and purity (>98%). Solubility testing in DMSO and water may be conducted, but these are not biological assays.
|
| Cell Assay |
Not applicable (no direct cell activity); cells are treated with a PROTAC synthesized using this linker to test target protein degradation. Immunoblotting (Western blot) measures target protein levels after PROTAC treatment (typically 4-24h, 0.1-10 uM) to confirm degradation. Cytotoxicity assays (MTT/CCK-8) may be run to rule out non-specific toxicity.
|
| Animal Protocol |
Not applicable (not a single agent); the linker conjugate is not administered alone. In vivo studies use complete PROTAC molecules, which are typically administered intraperitoneally (IP) or orally (PO) to mice (e.g., xenograft models). Pharmacodynamic endpoints include target protein knockdown in tumor tissue and assessment of tumor growth inhibition.
|
| ADME/Pharmacokinetics |
Not applicable; as a chemical building block for PROTACs, the linker influences the physicochemical properties of the final PROTAC (solubility, permeability, metabolic stability). The PEG3 spacer improves aqueous solubility and reduces aggregation. The free amine enables conjugation to various target ligands via amide bond formation.
|
| Toxicity/Toxicokinetics |
Low toxicity profile as a linker molecule; MSDS reports it is not a hazardous substance or mixture under normal handling. Under fire conditions, may decompose to emit toxic fumes. Thalidomide-based compounds may carry teratogenicity risk (as thalidomide itself is known to be teratogenic), so appropriate precautions should be taken. Standard lab PPE recommended.
|
| References | |
| Additional Infomation |
The compound is a key building block for PROTAC (Proteolysis-Targeting Chimera) synthesis. It has been used to generate PROTACs targeting BRD4, BRD2, and BRD3. The reversible nature of the cereblon-ligand interaction enables catalytic protein degradation. Common for research into targeted protein degradation as a therapeutic modality. Not for human use; no clinical trials with this specific building block.
|
| Molecular Formula |
C23H31CLN4O9
|
|---|---|
| Molecular Weight |
542.9666
|
| Exact Mass |
542.177
|
| CAS # |
2245697-84-9
|
| PubChem CID |
134160246
|
| Appearance |
Off-white to yellow solid powder
|
| Hydrogen Bond Donor Count |
4
|
| Hydrogen Bond Acceptor Count |
10
|
| Rotatable Bond Count |
15
|
| Heavy Atom Count |
37
|
| Complexity |
809
|
| Defined Atom Stereocenter Count |
0
|
| SMILES |
Cl[H].O=C1C([H])(C([H])([H])C([H])([H])C(N1[H])=O)N1C(C2C([H])=C([H])C([H])=C(C=2C1=O)OC([H])([H])C(N([H])C([H])([H])C([H])([H])OC([H])([H])C([H])([H])OC([H])([H])C([H])([H])OC([H])([H])C([H])([H])N([H])[H])=O)=O
|
| InChi Key |
ORRMBTUTYKQYQU-UHFFFAOYSA-N
|
| InChi Code |
InChI=1S/C23H30N4O9.ClH/c24-6-8-33-10-12-35-13-11-34-9-7-25-19(29)14-36-17-3-1-2-15-20(17)23(32)27(22(15)31)16-4-5-18(28)26-21(16)30;/h1-3,16H,4-14,24H2,(H,25,29)(H,26,28,30);1H
|
| Chemical Name |
N-[2-[2-[2-(2-aminoethoxy)ethoxy]ethoxy]ethyl]-2-[2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-4-yl]oxyacetamide;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, 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 : ~125 mg/mL (~230.22 mM)
H2O : ~100 mg/mL (~184.17 mM) |
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (3.83 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 20.8 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: ≥ 2.08 mg/mL (3.83 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 20.8 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: ≥ 2.08 mg/mL (3.83 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 | 1.8417 mL | 9.2086 mL | 18.4172 mL | |
| 5 mM | 0.3683 mL | 1.8417 mL | 3.6834 mL | |
| 10 mM | 0.1842 mL | 0.9209 mL | 1.8417 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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