| Size | Price | Stock | Qty |
|---|---|---|---|
| 250mg |
|
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| Other Sizes |
| Targets |
PEGs
Bromide acts as a leaving group for nucleophilic substitution; Cbz protects an amine (after conversion) and can be removed by hydrogenolysis. |
|---|---|
| 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].
The bromide group is a good leaving group for SN2 reactions with thiols, amines, or alcohols to form thioether, amine, or ether bonds. The PEG2 spacer (2 ethylene glycol units) provides a short, hydrophilic linker (length ~0.6 nm). The Cbz group is a common protecting group for amines; it is stable under basic and mildly acidic conditions but removed by catalytic hydrogenation (H2, Pd/C). The compound does not have biological activity; it is a chemical linker. |
| ln Vivo |
In vitro, the compound is used to alkylate thiol-containing molecules (e.g., cysteine residues in peptides) or amines. The reaction is typically performed in DMF or DMSO with a base (e.g., DIEA, K2CO3). After conjugation, the Cbz group can be removed to reveal a free amine for further derivatization. No direct in vivo activity.
|
| Enzyme Assay |
Cbz-PEG2-bromide (1-10 mM) is incubated with a thiol-containing model compound (e.g., cysteine, 1-5 mM) in DMF with DIEA (2 equiv) for 2-12 hours at room temperature. Reaction progress is monitored by TLC or LC-MS. Yield is typically 60-90%. Cbz removal is tested by hydrogenation (H2, Pd/C) in methanol for 2 hours, confirmed by disappearance of Cbz UV signal.
|
| Cell Assay |
Cells are not typically treated with this linker alone as it is reactive and potentially cytotoxic. For cellular studies, the linker is first conjugated to a targeting ligand (e.g., a PROTAC warhead or E3 ligase ligand). The resulting conjugate is purified and tested in cells (1-1000 nM) for desired activity (e.g., protein degradation). The linker alone may cause non-specific alkylation and toxicity at high concentrations.
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| Animal Protocol |
In vivo, the linker is not administered alone. It is used to synthesize PROTACs or ADC linkers. The final conjugate is dosed in animals. The PEG2 spacer may improve solubility and reduce aggregation compared to alkyl-only linkers. The Cbz group is removed before final conjugation if a free amine is needed. Animal studies are performed with the final product.
|
| ADME/Pharmacokinetics |
Molecular weight: approximately 358 g/mol. The PEG2 chain (MW ~88) provides modest water solubility. The bromide is reactive; store at -20degC, protected from light and moisture. The Cbz group absorbs UV at 254-280 nm. The compound is soluble in DMSO, DMF, and dichloromethane. Hydrolysis of bromide occurs slowly in aqueous buffer.
|
| Toxicity/Toxicokinetics |
The compound may be irritating due to the reactive bromide. Cbz is not highly toxic. Acute toxicity: estimated LD50 > 1000 mg/kg in rodents. However, the alkylating nature means it should be handled as a potential mutagen (although bromide is a good leaving group, it is less reactive than iodides). Standard precautions: fume hood, gloves. Not for human use.
|
| References | |
| Additional Infomation |
This compound is a chemical linker for bioconjugation and PROTAC synthesis. PEG2 bromide is a versatile alkylating agent. The Cbz protecting group allows orthogonal protection of an amine that can be introduced after alkylation (e.g., by converting bromide to azide then reduction, or by direct reaction with amine-containing nucleophiles). The Cbz group is removed by hydrogenation without affecting other functional groups. No clinical status.
|
| Molecular Formula |
C14H20BRNO4
|
|---|---|
| Molecular Weight |
346.216903686523
|
| Exact Mass |
345.057
|
| CAS # |
2100283-00-7
|
| PubChem CID |
150338890
|
| Appearance |
Colorless to light yellow liquid
|
| LogP |
1.9
|
| Hydrogen Bond Donor Count |
1
|
| Hydrogen Bond Acceptor Count |
4
|
| Rotatable Bond Count |
11
|
| Heavy Atom Count |
20
|
| Complexity |
247
|
| Defined Atom Stereocenter Count |
0
|
| SMILES |
BrCCOCCOCCNC(=O)OCC1C=CC=CC=1
|
| InChi Key |
GRGPUJRSMCXZNT-UHFFFAOYSA-N
|
| InChi Code |
InChI=1S/C14H20BrNO4/c15-6-8-18-10-11-19-9-7-16-14(17)20-12-13-4-2-1-3-5-13/h1-5H,6-12H2,(H,16,17)
|
| Chemical Name |
benzyl N-[2-[2-(2-bromoethoxy)ethoxy]ethyl]carbamate
|
| 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
|
|---|---|
| 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 | 2.8883 mL | 14.4417 mL | 28.8834 mL | |
| 5 mM | 0.5777 mL | 2.8883 mL | 5.7767 mL | |
| 10 mM | 0.2888 mL | 1.4442 mL | 2.8883 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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