| 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 |
Lenalidomide-I can be joined via a linker to the protein ligand to create PROTACs. Cancer-promoting proteins are degraded by ubiquitination, which is induced by PROTACs[1].
As a cereblon-binding ligand, Lenalidomide-I itself has no intrinsic degradation activity; its function is to bind to CRBN and recruit the E3 ubiquitin ligase complex. The iodo substituent provides a handle for further functionalization, such as Suzuki-Miyaura cross-coupling or Ullmann coupling, to attach linkers or target protein ligands. |
| 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. A PROTAC BET degrader (QCA570) has been synthesized using a Lenalidomide-based analog.
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| 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 iodine atom enables radioiodination for tracer studies.
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| 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. The iodine atom can be used for radiolabeling (e.g., with 125I) to study PROTAC tissue distribution and binding.
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| 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. The iodine label can be used for SPECT imaging or autoradiography in animal models.
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| ADME/Pharmacokinetics |
This compound has a molecular weight of 370.14, a molecular formula of C13H11IN2O3, and is typically stored as a powder at -20degC for up to 3 years. It is soluble in DMSO (25 mg/mL, 67.54 mM). The IUPAC name is 3-(4-iodo-1-oxoisoindolin-2-yl)piperidine-2,6-dione. Purity is typically ≥95% up to >98%.
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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 iodine atom is light-sensitive and the product should be protected from light.
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| References | |
| Additional Infomation |
The iodo substituent provides a versatile handle for further functionalization via transition metal-catalyzed cross-coupling reactions. This enables the introduction of a wide variety of linkers and target protein ligands that are not accessible through standard amide bond formation. Lenalidomide-I can also be used as a chemical probe or intermediate in targeted protein degradation and bioconjugation research. The PROTAC BET degrader QCA570, which incorporates a Lenalidomide-based analog, has been developed for the treatment of BET-dependent cancers.
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| Molecular Formula |
C13H11IN2O3
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|---|---|
| Molecular Weight |
370.142515420914
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| Exact Mass |
369.981
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| CAS # |
2207541-30-6
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| PubChem CID |
134348132
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| Appearance |
Light yellow to yellow solid powder
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| LogP |
0.8
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
1
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| Heavy Atom Count |
19
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| Complexity |
440
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| Defined Atom Stereocenter Count |
0
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| SMILES |
C1CC(=O)NC(=O)C1N2CC3=C(C2=O)C=CC=C3I
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| InChi Key |
BKIUJJLYXXEGFT-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C13H11IN2O3/c14-9-3-1-2-7-8(9)6-16(13(7)19)10-4-5-11(17)15-12(10)18/h1-3,10H,4-6H2,(H,15,17,18)
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| Chemical Name |
3-(7-iodo-3-oxo-1H-isoindol-2-yl)piperidine-2,6-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 |
| 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 :~25 mg/mL (~67.54 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: 2.5 mg/mL (6.75 mM) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), suspension solution; with sonication.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 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: ≥ 2.5 mg/mL (6.75 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (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 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.7017 mL | 13.5084 mL | 27.0168 mL | |
| 5 mM | 0.5403 mL | 2.7017 mL | 5.4034 mL | |
| 10 mM | 0.2702 mL | 1.3508 mL | 2.7017 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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