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| Targets |
As a chemical linker rather than a pharmacologically active agent, N-Boc-PEG3-bromide does not bind to biological targets such as receptors or enzymes. Its functional "targets" are the chemical groups on payload molecules, antibodies, and E3 ligase ligands to which it conjugates. In PROTAC applications, the linker connects an E3 ubiquitin ligase ligand to a target protein ligand, enabling the ubiquitin-proteasome system to selectively degrade target proteins. In ADC applications, the linker attaches cytotoxic drugs to monoclonal antibodies through stable covalent bonds. The bromide terminus reacts with nucleophiles (e.g., thiols, amines) via nucleophilic substitution, while the Boc-protected amine provides a handle for deprotection and subsequent amide bond formation. The PEG3 spacer contributes to improved solubility and reduced aggregation of bioconjugates.
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| ln Vitro |
Two distinct ligands, one for the E3 ubiquitin ligase and the other for the target protein, are present in PROTAC and are joined by a linker. PROTAC targets and selectively degrades target proteins by means of the intracellular ubiquitin-proteasome system. An ADC cytotoxin is connected to an antibody by use of an ADC linker to form an ADC.
N-Boc-PEG3-bromide itself does not exhibit pharmacological activity in cell-based assays because it is a synthetic linker molecule. Its in vitro utility is demonstrated through the successful synthesis and characterization of PROTAC or ADC constructs incorporating this linker. Researchers typically evaluate the linker's performance by assessing conjugation efficiency (via HPLC, LC-MS, or NMR), the stability of the resulting conjugates in cell culture media, and the biological activity of the final constructs in target cell lines. For PROTACs, target protein degradation is measured by Western blot analysis; for ADCs, cytotoxicity is assessed using cell viability assays such as MTT or CellTiter-Glo. The compound is soluble in DMSO at approximately 100 mg/mL (~280.70 mM), facilitating its use in standard bioconjugation workflows. |
| ln Vivo |
No intrinsic in vivo pharmacological activity is attributed to N-Boc-PEG3-bromide; its in vivo relevance is through the ADC or PROTAC constructs synthesized with this linker. For in vivo administration, conjugates containing this linker are formulated using sequential solvent addition: 10% DMSO + 40% PEG300 + 5% Tween-80 + 45% saline, or 10% DMSO + 90% (20% SBE-β-CD in saline), yielding clear solutions at ≥2.5 mg/mL. Typical preclinical studies involve administering the conjugate to rodent models (e.g., tumor xenografts) via intravenous injection. Efficacy endpoints include tumor volume reduction, survival prolongation, and target modulation in tissues. The linker's stability in circulation and its ability to release payloads at target sites are critical parameters evaluated through pharmacokinetic sampling.
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| Enzyme Assay |
In vitro enzyme/receptor binding assays are not applicable to N-Boc-PEG3-bromide as it is a chemical linker devoid of biological target affinity. Quality control and characterization are performed using standard analytical methods. Purity is assessed by HPLC (≥98%) and structural integrity is confirmed by ¹H NMR and mass spectrometry. The bromide content and functional group integrity are verified through elemental analysis and spectroscopic methods. For researchers using this linker in bioconjugation, reaction progress (bromide displacement by nucleophiles) is typically monitored by TLC, HPLC, or LC-MS. Boc deprotection efficiency is confirmed by NMR or LC-MS following acid treatment (e.g., TFA in DCM), indicated by the disappearance of tert-butyl proton signals. Solubility testing in various solvents (DMSO, DMF, ethanol) is performed to guide formulation development.
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| Cell Assay |
Cell-based assays are not performed directly on N-Boc-PEG3-bromide because the compound lacks biological activity. However, the biological activity of PROTAC or ADC constructs containing this linker is evaluated in relevant cell lines. For PROTAC evaluation, cells are treated with the construct for 4-24 hours, and target protein degradation is quantified by Western blot or ELISA. Cell viability, proliferation, and apoptosis are assessed using standard assays (MTT, CCK-8, flow cytometry). For ADC evaluation, cancer cell lines are treated with the conjugate, and cytotoxicity is measured over 48-72 hours. The linker's contribution to conjugate stability, solubility, and target engagement is inferred from comparative studies. DMSO stock solutions are prepared and diluted in culture media to achieve desired final concentrations. Control groups include vehicle-treated and unconjugated antibody or payload-treated cells.
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| Animal Protocol |
In vivo animal studies are conducted with ADC or PROTAC constructs incorporating N-Boc-PEG3-bromide, not with the linker alone. Typical protocols utilize immunocompromised mice bearing tumor xenografts. The conjugate is administered via intravenous, intraperitoneal, or subcutaneous injection at doses determined by the payload's maximum tolerated dose. For in vivo formulation, the conjugate is prepared in 10% DMSO + 40% PEG300 + 5% Tween-80 + 45% saline or 10% DMSO + 90% (20% SBE-β-CD in saline) at ≥2.5 mg/mL. Efficacy is assessed by caliper measurement of tumor volumes every 2-3 days, body weight monitoring, and survival analysis. Pharmacodynamic endpoints include target protein degradation (PROTACs) or tumor growth inhibition (ADCs). Plasma samples are collected for pharmacokinetic analysis of conjugate stability and payload release.
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| ADME/Pharmacokinetics |
As a chemical linker, N-Boc-PEG3-bromide does not have a conventional pharmacokinetic profile. However, the pharmacokinetic properties of bioconjugates incorporating this linker are evaluated in preclinical studies. Following intravenous administration in rodents, key parameters such as half-life (t₁/₂), clearance (CL), volume of distribution (Vd), and area under the curve (AUC) are determined from plasma concentration-time data. The PEG3 spacer contributes to enhanced aqueous solubility, reduced protein binding, and prolonged circulation time of the conjugate. Linker stability in plasma is assessed by measuring free payload release over time using LC-MS/MS. The Boc-protected amine is stable at physiological pH (7.4) and is only deprotected under acidic conditions. Formulation studies indicate solubility ≥2.5 mg/mL in standard in vivo vehicles. The compound itself is not administered systemically; therefore, its absorption, distribution, metabolism, and excretion are not characterized.
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| Toxicity/Toxicokinetics |
Toxicological data for N-Boc-PEG3-bromide are limited because it is a research-grade reagent not intended for human use. As a bromoalkyl compound, it may cause skin and eye irritation upon contact. The reactive bromide group can act as an alkylating agent, necessitating standard laboratory safety precautions: use of personal protective equipment (gloves, safety goggles, lab coat) and handling in a well-ventilated fume hood. The compound should be stored at -20°C for long-term stability (up to 3 years) and at 4°C for short-term storage (up to 2 years). No genotoxicity, carcinogenicity, or reproductive toxicity data are available. Researchers should consult the safety data sheet (SDS) before handling. The compound is not classified as a hazardous drug but should be treated with care due to the presence of the alkyl bromide moiety.
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| References | |
| Additional Infomation |
Additional information for N-Boc-PEG3-bromide: The compound has a CAS number of 1076199-21-7 and a molecular formula of C₁₃H₂₆BrNO₅. Its molecular weight is 356.26 g/mol. The compound appears as a colorless to light yellow liquid. Purity is typically ≥95% to ≥98%. The Boc-protected amine can be deprotected under mild acidic conditions (e.g., TFA) to yield the free amine. The bromide group enables efficient nucleophilic substitution reactions. The hydrophilic PEG spacer increases the aqueous solubility of resulting compounds. This product is for research use only and is not approved for clinical, diagnostic, or therapeutic applications. No clinical trials or regulatory approvals exist for this compound as it is a synthetic building block. Related CAS numbers include various salt forms and derivatives of similar PEG linkers.
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| Molecular Formula |
C13H26BRNO5
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|---|---|
| Molecular Weight |
356.2532
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| Exact Mass |
355.099
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| CAS # |
1076199-21-7
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| PubChem CID |
29974540
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| Appearance |
Colorless to light yellow liquid
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| Boiling Point |
422.1±35.0°C at 3 mmHg
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| LogP |
2.16
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
5
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| Rotatable Bond Count |
13
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| Heavy Atom Count |
20
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| Complexity |
245
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| Defined Atom Stereocenter Count |
0
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| SMILES |
BrC([H])([H])C([H])([H])OC([H])([H])C([H])([H])OC([H])([H])C([H])([H])OC([H])([H])C([H])([H])N([H])C(=O)OC(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H]
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| InChi Key |
GNDQONYTPMGMTM-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C13H26BrNO5/c1-13(2,3)20-12(16)15-5-7-18-9-11-19-10-8-17-6-4-14/h4-11H2,1-3H3,(H,15,16)
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| Chemical Name |
tert-butyl N-[2-[2-[2-(2-bromoethoxy)ethoxy]ethoxy]ethyl]carbamate
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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 : ~100 mg/mL (~280.70 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (7.02 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (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 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 (7.02 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (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 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (7.02 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.8070 mL | 14.0351 mL | 28.0702 mL | |
| 5 mM | 0.5614 mL | 2.8070 mL | 5.6140 mL | |
| 10 mM | 0.2807 mL | 1.4035 mL | 2.8070 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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