| Size | Price | Stock | Qty |
|---|---|---|---|
| 250mg |
|
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| Other Sizes |
| Targets |
PEGs
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, BocNH-PEG5-CH2CH2Br 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 Boc-protected amine provides an orthogonal protecting group that can be removed under acidic conditions (e.g., with TFA) to reveal a free primary amine. This free amine can then be conjugated to a carboxylic acid-containing ligand via amide bond formation using EDC/NHS coupling. The orthogonal protecting groups enable stepwise conjugation to two different ligands. The PEG5 spacer provides flexibility and water solubility, facilitating the formation of productive ternary complexes. |
| 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 ≥97%. The Boc protecting group can be characterized by its characteristic chemical shifts in NMR spectroscopy (e.g., a singlet around 1.4-1.5 ppm for the tert-butyl group). The bromide group can be characterized by mass spectrometry. The IUPAC name is tert-butyl (17-bromo-3,6,9,12,15-pentaoxaheptadecyl)carbamate.
|
| 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 two-step synthesis, the bromide group is first displaced by a nucleophile (e.g., a thiol-containing target protein ligand) in the presence of a base such as K2CO3. The Boc group is then removed using TFA, and the resulting free amine is conjugated to a carboxylic acid-containing E3 ligase ligand via amide bond formation using EDC and NHS. The resulting PROTAC is then tested in cells for target degradation activity. The PEG5 spacer improves the water solubility of the reactants, facilitating the reactions in aqueous or mixed solvent systems.
|
| 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 PEG5 spacer may improve the pharmacokinetic properties of the conjugate by enhancing water solubility and reducing aggregation.
|
| ADME/Pharmacokinetics |
This compound has a molecular weight of 444.36, a molecular formula of C17H34BrNO7, and a standard purity of ≥97%. The IUPAC name is tert-butyl (17-bromo-3,6,9,12,15-pentaoxaheptadecyl)carbamate. For storage, it should be kept as a solid at -20degC for up to 3 years, sealed, away from moisture. It is soluble in DMSO and other organic solvents. The product should be stored under nitrogen to prevent moisture absorption. The Boc-protected amine is stable under neutral and basic conditions but is acid-labile, so exposure to strong acids should be avoided.
|
| 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 bromide group is reactive and should be handled with care to avoid premature reactions. The product should be stored in a sealed and protected environment (e.g., under nitrogen) to avoid moisture absorption. 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
|
| Additional Infomation |
The orthogonal combination of a bromide leaving group and a Boc-protected amine on a PEG5 spacer provides a versatile platform for constructing heterobifunctional PROTACs. The bromide group can be displaced by a wide range of nucleophiles, including thiols, amines, and carboxylates, enabling the attachment of diverse ligands. The Boc-protected amine provides a protected handle for subsequent conjugation after acidic deprotection. The PEG5 spacer provides a balance of hydrophilicity and flexibility, making it suitable for a wide range of PROTAC applications. This linker is also known as t-boc-N-amido-PEG5-bromide and is a valuable building block for bioconjugation and PROTAC development.
|
| Molecular Formula |
C17H34BRNO7
|
|---|---|
| Molecular Weight |
444.358365535736
|
| Exact Mass |
443.151
|
| CAS # |
1392499-33-0
|
| PubChem CID |
137346995
|
| Appearance |
Colorless to light yellow liquid（Density：1.212±0.06 g/cm3）
|
| LogP |
1
|
| Hydrogen Bond Donor Count |
1
|
| Hydrogen Bond Acceptor Count |
7
|
| Rotatable Bond Count |
19
|
| Heavy Atom Count |
26
|
| Complexity |
327
|
| Defined Atom Stereocenter Count |
0
|
| SMILES |
BrCCOCCOCCOCCOCCOCCNC(=O)OC(C)(C)C
|
| InChi Key |
NQPCGFYLHACMDX-UHFFFAOYSA-N
|
| InChi Code |
InChI=1S/C17H34BrNO7/c1-17(2,3)26-16(20)19-5-7-22-9-11-24-13-15-25-14-12-23-10-8-21-6-4-18/h4-15H2,1-3H3,(H,19,20)
|
| Chemical Name |
tert-butyl N-[2-[2-[2-[2-[2-(2-bromoethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethyl]carbamate
|
| 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) |
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
|
|---|---|
| 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 | 2.2504 mL | 11.2521 mL | 22.5043 mL | |
| 5 mM | 0.4501 mL | 2.2504 mL | 4.5009 mL | |
| 10 mM | 0.2250 mL | 1.1252 mL | 2.2504 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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