| Size | Price | Stock | Qty |
|---|---|---|---|
| 100mg |
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| 1g |
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| Other Sizes |
| Targets |
Alkyl/ether
PROTAC Linkers. |
|---|---|
| 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[1].
As a linker molecule, Br-Boc-C2-azido itself has no intrinsic biological activity; it serves as a structural connector to join a target protein ligand and an E3 ubiquitin ligase ligand in PROTAC synthesis. The bromide group is a good leaving group that can undergo nucleophilic substitution (SN2) with nucleophiles such as thiols, amines, or carboxylates to attach a ligand. The azide group is a click chemistry handle that can undergo copper-catalyzed azide-alkyne cycloaddition (CuAAc) or strain-promoted azide-alkyne cycloaddition (SPAAC) with alkyne-containing molecules. The Boc-protected amine provides an orthogonal protecting group that can be removed under acidic conditions (TFA) to reveal a free amine for amide bond formation. The short C2 spacer provides a minimal, rigid connection. |
| ln Vivo |
No specific in vivo activity has been reported for this linker alone; its activity is derived from the final PROTAC molecule after conjugation with appropriate ligands. The in vivo efficacy of a complete PROTAC is determined in animal models.
|
| Enzyme Assay |
N/A; this compound is not assessed in isolated enzyme/receptor binding assays. As a synthetic intermediate, its quality is typically confirmed by analytical methods such as HPLC and NMR, with a standard purity of ≥95%. The azide group can be characterized by its characteristic IR absorption at around 2100 cm-1. The Boc group can be characterized by its singlet around 1.4-1.5 ppm in 1H NMR. The bromide group can be identified by mass spectrometry.
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| Cell Assay |
N/A; this linker is not tested alone in cell-based assays. It is used as a building block for constructing PROTACs. In a typical synthesis, the azide group is reacted with an alkyne-containing ligand via CuAAc or SPAAC. The bromide group is displaced by a nucleophile from another ligand. The Boc group is removed with TFA, and the resulting free amine is conjugated to a carboxylic acid-containing ligand. The resulting PROTAC is then tested in cells for target degradation activity. The short C2 spacer may be optimal for target-E3 ligase pairs requiring a minimal distance.
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| Animal Protocol |
N/A; no animal studies are performed with the linker alone. For a complete PROTAC conjugate, in vivo studies are conducted following institutional guidelines. The compound is typically formulated using a vehicle containing DMSO, PEG300, Tween-80, and saline and administered via intraperitoneal (IP) or intravenous (IV) injection. The short C2 spacer may improve the cellular permeability of the final PROTAC.
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| ADME/Pharmacokinetics |
This compound has a molecular weight of 265.11, a molecular formula of C7H13BrN4O2, and a standard purity of ≥95%. The IUPAC name is tert-butyl (2-bromoethyl)(2-azidoethyl)carbamate? Or similar. Based on typical nomenclature, it is likely tert-butyl (2-azidoethyl)(2-bromoethyl)carbamate. For storage, it should be kept at -20degC for up to 3 years, sealed, away from moisture. It is soluble in DMSO and other organic solvents. The product should be protected from light. CAS: 1120364-53-5.
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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 observed during handling. The azide group should be handled with care as it can be potentially explosive. The bromide group is reactive. PROTAC is a registered trademark of Arvinas Operations, Inc., and is used under license. This compound is not an approved drug and has not been cleared for clinical use.
|
| References |
[1]. An S, et al. Small-molecule PROTACs: An emerging and promising approach for the development of targeted therapy drugs. EBioMedicine. 2018 Oct;36:553-562
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| Additional Infomation |
Br-Boc-C2-azido is a compact, trifunctional linker containing three orthogonal reactive handles: a bromide (for nucleophilic substitution), an azide (for click chemistry), and a Boc-protected amine (for amide coupling after deprotection). This high degree of functionality allows for the construction of complex PROTACs with diverse conjugation strategies. The short C2 spacer provides a minimal, rigid connection that can be critical for target-E3 ligase pairs requiring a short distance for ternary complex formation. This linker is a valuable building block for advanced PROTAC development and for the synthesis of multifunctional probes.
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| Molecular Formula |
C6H10N3O2BR
|
|---|---|
| Molecular Weight |
236.066
|
| Exact Mass |
234.995
|
| CAS # |
1120364-53-5
|
| PubChem CID |
86650124
|
| Appearance |
Typically exists as solid at room temperature
|
| Flash Point |
>230 °F
|
| LogP |
2.4
|
| Hydrogen Bond Donor Count |
0
|
| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
5
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| Heavy Atom Count |
12
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| Complexity |
211
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| Defined Atom Stereocenter Count |
0
|
| SMILES |
BrC(C)(C)C(OCCN=[N+]=[N-])=O
|
| InChi Key |
OYSXPOJKJKBNSG-UHFFFAOYSA-N
|
| InChi Code |
InChI=1S/C6H10BrN3O2/c1-6(2,7)5(11)12-4-3-9-10-8/h3-4H2,1-2H3
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| Chemical Name |
2-azidoethyl 2-bromo-2-methylpropanoate
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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)
|
| 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.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 4.2360 mL | 21.1802 mL | 42.3603 mL | |
| 5 mM | 0.8472 mL | 4.2360 mL | 8.4721 mL | |
| 10 mM | 0.4236 mL | 2.1180 mL | 4.2360 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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