| Size | Price | Stock | Qty |
|---|---|---|---|
| 100mg |
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| 500mg |
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| Other Sizes |
| Targets |
CRBN (cereblon), an E3 ubiquitin ligase.
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|---|---|
| ln Vitro |
As a cereblon-binding ligand-linker conjugate, Thalidomide-Piperazine 5-fluoride itself has no intrinsic biological activity; its function is to bind to cereblon and recruit the E3 ubiquitin ligase complex. When the piperazine nitrogen is conjugated to a target protein ligand via an appropriate linker, 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 5-fluorine substitution may enhance binding affinity to cereblon compared to unmodified thalidomide.
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| ln Vivo |
No specific in vivo activity has been reported for this conjugate alone; its in vivo degradation effects are 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 ≥98%. 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).
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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 cellular assay, a complete PROTAC synthesized from this conjugate is incubated with target-expressing cancer cells for 4-24 hours, after which target protein levels are measured by Western blotting to determine the DC50 (half-maximal degradation concentration). The piperazine conjugation site allows for linker attachment without interfering with cereblon binding.
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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.
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| ADME/Pharmacokinetics |
This compound has a molecular weight of 360.34, a molecular formula of C17H17FN4O4, and a purity of ≥98%. The IUPAC name is 2-(2,6-dioxopiperidin-3-yl)-5-fluoro-6-(piperazin-1-yl)isoindoline-1,3-dione. It appears as a solid powder and is soluble in DMSO. It is typically stored as a powder at -20degC for up to 3 years or in a solvent at -80degC for 6 months. The product should be protected from light and moisture during storage.
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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 compound should be stored in a sealed and protected environment (e.g., under nitrogen) to avoid moisture absorption. It is not an approved therapeutic drug and has not been cleared for clinical use.
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| References | |
| Additional Infomation |
The piperazine moiety provides a versatile handle for linker attachment via amide bond formation or alkylation, enabling the synthesis of a wide variety of cereblon-recruiting PROTACs. The fluorine atom at the 5-position of the isoindole ring may modulate the pharmacokinetic properties of the resulting PROTACs, such as metabolic stability and binding affinity to cereblon. This compound is an advanced building block for structure-activity relationship studies in targeted protein degradation.
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| Molecular Formula |
C17H17FN4O4
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|---|---|
| Molecular Weight |
360.3397
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| Exact Mass |
360.123
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| CAS # |
2222114-22-7
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| Related CAS # |
Thalidomide-Piperazine 5-fluoride hydrochloride; 2222114-23-8
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| PubChem CID |
134413827
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| Appearance |
Off-white to light green solid powder
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| LogP |
-0.1
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
7
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
26
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| Complexity |
651
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| Defined Atom Stereocenter Count |
0
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| SMILES |
C1CC(=O)NC(=O)C1N2C(=O)C3=CC(=C(C=C3C2=O)F)N4CCNCC4
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| InChi Key |
YNGDWIBEYDEYGU-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C17H17FN4O4/c18-11-7-9-10(8-13(11)21-5-3-19-4-6-21)17(26)22(16(9)25)12-1-2-14(23)20-15(12)24/h7-8,12,19H,1-6H2,(H,20,23,24)
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| Chemical Name |
2-(2,6-dioxopiperidin-3-yl)-5-fluoro-6-piperazin-1-ylisoindole-1,3-dione
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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: This product requires protection from light (avoid light exposure) during transportation and storage. |
| 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) |
DMSO: ~5.8 mg/mL (~16.2 mM; with ultrasonication)
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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.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.7752 mL | 13.8758 mL | 27.7516 mL | |
| 5 mM | 0.5550 mL | 2.7752 mL | 5.5503 mL | |
| 10 mM | 0.2775 mL | 1.3876 mL | 2.7752 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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