| Size | Price | Stock | Qty |
|---|---|---|---|
| 500mg |
|
||
| Other Sizes |
| Targets |
Cereblon (CRBN) .
|
|---|---|
| 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 ligand, it binds to the CRBN E3 ligase complex. It can be conjugated via the 5-carboxyl group to a linker and a target protein ligand to form a PROTAC molecule. The resulting PROTAC induces ubiquitination and subsequent proteasomal degradation of the target protein . |
| ln Vivo |
No in vivo activity data available for the ligand alone. Its activity is demonstrated only after being incorporated into a complete PROTAC molecule.
|
| Enzyme Assay |
Not typically performed for the ligand alone. The binding affinity of Thalidomide and its derivatives for CRBN is well-established. A competitive binding assay using recombinant CRBN and a labeled probe (e.g., FITC- Thalidomide) could be used to determine the IC50 of Thalidomide-5-COOH.
|
| Cell Assay |
Not applicable. As an un-conjugated ligand, it lacks the ability to recruit a target protein and thus has no specific degradation activity in cells. It serves as a negative control or a building block for cellular studies.
|
| Animal Protocol |
Not applicable. This ligand is not intended for direct in vivo administration. The final PROTAC molecule containing this ligand would be used for animal experiments.
|
| ADME/Pharmacokinetics |
Molecular weight is 302.24 g/mol. It has a predicted LogP of 0.22, indicating moderate hydrophilicity. The pKa of the carboxylic acid is approximately 4.0. The compound is a solid powder, typically pale purple to purple .
|
| Toxicity/Toxicokinetics |
No specific toxicity data for this derivative. Thalidomide and its analogs are known teratogens, and appropriate safety precautions (e.g., use of closed systems, PPE) must be taken when handling this compound.
|
| References |
[1]. Liu K, et, al. Design and biological characterization of hybrid compounds of curcumin and thalidomide for multiple myeloma. Org Biomol Chem. 2013 Aug 7;11(29):4757-63.
|
| Additional Infomation |
This is a key building block for PROTAC synthesis. The 5-carboxyl substitution allows for site-specific conjugation, which is important for structure-activity relationship (SAR) studies. The parent compound, Thalidomide, is an immunomodulatory drug, but this derivative is solely for research use.
|
| Molecular Formula |
C14H10N2O6
|
|---|---|
| Molecular Weight |
302.24
|
| Exact Mass |
302.053
|
| CAS # |
1216805-11-6
|
| PubChem CID |
25195297
|
| Appearance |
Pale purple to purple solid powder
|
| Density |
1.6±0.1 g/cm3
|
| Boiling Point |
648.3±50.0 °C at 760 mmHg
|
| Flash Point |
345.9±30.1 °C
|
| Vapour Pressure |
0.0±2.0 mmHg at 25°C
|
| Index of Refraction |
1.676
|
| LogP |
0.22
|
| Hydrogen Bond Donor Count |
2
|
| Hydrogen Bond Acceptor Count |
6
|
| Rotatable Bond Count |
2
|
| Heavy Atom Count |
22
|
| Complexity |
586
|
| Defined Atom Stereocenter Count |
0
|
| SMILES |
O=C1C(CCC(N1)=O)N1C(C2C=CC(C(=O)O)=CC=2C1=O)=O
|
| InChi Key |
YIBCNIAUDQMKRO-UHFFFAOYSA-N
|
| InChi Code |
InChI=1S/C14H10N2O6/c17-10-4-3-9(11(18)15-10)16-12(19)7-2-1-6(14(21)22)5-8(7)13(16)20/h1-2,5,9H,3-4H2,(H,21,22)(H,15,17,18)
|
| Chemical Name |
2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindole-5-carboxylic acid
|
| 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 (In Vitro) |
DMSO :~125 mg/mL (~413.58 mM)
|
|---|---|
| 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.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.3086 mL | 16.5431 mL | 33.0863 mL | |
| 5 mM | 0.6617 mL | 3.3086 mL | 6.6173 mL | |
| 10 mM | 0.3309 mL | 1.6543 mL | 3.3086 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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