1820717-35-8

Basic information

• Product Name: Azido-PEG1-CH2CO2tBu
• Synonyms: Azido-PEG1-CH2CO2tBu;Azido-PEG1-CH2CO2-t-butyl ester;tert-Butyl 2-(2-azidoethoxy)acetate;Azido-PEG1-t-butyl acetate
• CAS NO: 1820717-35-8
• Molecular Formula: C8H15N3O3
• Molecular Weight: 201.223
• Mol File: 1820717-35-8.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• Solubility: Soluble in DCM, DMF
• CAS DataBase Reference: Azido-PEG1-CH2CO2tBu(CAS DataBase Reference)
• NIST Chemistry Reference: Azido-PEG1-CH2CO2tBu(1820717-35-8)
• EPA Substance Registry System: Azido-PEG1-CH2CO2tBu(1820717-35-8)

Safety Data

• Hazardous Substances Data: 1820717-35-8(Hazardous Substances Data)

Usage

Description

Azido-PEG1-CH2CO2tBu is a functionalized polyethylene glycol (PEG) molecule that incorporates an azide group and a t-butyl protected carboxyl group. The azide group enables the molecule to participate in Click Chemistry reactions with alkynes, BCN, and DBCO, resulting in the formation of a stable triazole linkage. The t-butyl protected carboxyl group can be selectively removed under acidic conditions, providing versatility in the molecule's reactivity and potential applications.

Uses

Used in Bioconjugation Applications:
Azido-PEG1-CH2CO2tBu is used as a bioconjugation agent for the covalent attachment of biomolecules to various surfaces or other molecules. The azide group allows for efficient and site-specific coupling through Click Chemistry, while the t-butyl protected carboxyl group provides a means to control the reactivity and timing of the deprotection process.
Used in Drug Delivery Systems:
In the pharmaceutical industry, Azido-PEG1-CH2CO2tBu is used as a component in drug delivery systems to improve the solubility, stability, and bioavailability of therapeutic agents. The PEGylation of drugs can reduce immunogenicity and increase circulation time, while the azide group facilitates the attachment of drug molecules or targeting ligands through Click Chemistry.
Used in Materials Science:
Azido-PEG1-CH2CO2tBu is utilized in the development of functional materials, such as hydrogels, nanoparticles, and surfaces, for various applications in tissue engineering, diagnostics, and sensors. The combination of PEG's biocompatibility and the azide group's reactivity allows for the creation of stimuli-responsive materials and the incorporation of multiple functionalities.
Used in Chemical Synthesis:
In organic synthesis, Azido-PEG1-CH2CO2tBu serves as a versatile building block for the synthesis of complex molecules and macromolecules. The azide group can be used for various transformations, such as the Staudinger ligation or the reduction to amines, while the t-butyl protected carboxyl group can be selectively deprotected to introduce new functional groups or enable further reactions.

Upstream product

• 1517-05-1 2-azidoethanol 
• 5292-43-3 bromoacetic acid tert-butyl ester 
• 1309451-06-6 2-(2-(benzyloxy)ethoxy)acetic acid tert-butyl ester 
• 287174-32-7 (2-hydroxyethoxy)acetic acid tert-butyl ester 
• 1643957-24-7 tert-butyl 2-(2-[[(4-methylbenzene)sulfonyl]oxy]ethoxy)acetate 

Downstream Products

• 1155811-37-2 tert-butyl 2-(2-aminoethoxy)acetate 

Relevant articles and documents

Development of small-molecule BRD4 degraders based on pyrrolopyridone derivative

Bromodomain-containing protein 4 (BRD4) plays a crucial role in the epigenetic regulation of gene transcription and some BRD4 inhibitors have been advanced to clinical trials. Nevertheless, the clinical application of BRD4 inhibitors could be limited by drug resistance. As an alternative strategy, the emerging Proteolysis Targeting Chimeras (PROTACs) technology has the potential to overcome the drug resistance of traditional small-molecule drugs. Based on PROTACs approaches, several BRD4 degraders were developed and have been proved to degrade BRD4 protein and inhibit tumor growth. Herein, we present the design, synthesis, and biological evaluation of pyrrolopyridone derivative-based BRD4 degraders. Four synthesized compounds displayed comparative potence against BRD4 BD1 with IC50 at low nanomolar concentrations. Anti-proliferative activity of 32a against BxPC3 cell line (IC50 = 0.165 μM) was improved by about 7-fold as compared to the BRD4 inhibitor ABBV-075. Furthermore, degrader 32a potently induced the degradation of BRD4 and inhibited the expression of c-Myc in BxPC3 cell line in a time-dependent manner. The exploration of intracellular antitumor mechanism showed 32a induced cell cycle arrest and apoptosis effectively. All the results demonstrated that compound 32a could be considered as a potential BRD4 degrader for further investigation.

Identification of New Small-Molecule Inducers of Estrogen-related Receptor α (ERRα) Degradation

A series of (E)-3-(4-((2,4-bis(trifluoromethyl)benzyl)oxy)-3-methoxyphenyl)-2-cyanoacrylamide derivatives were designed and synthesized as new estrogen-related receptor α (ERRα) degraders based on the proteolysis targeting chimera (PROTAC) concept. One of the representative compounds 6c is capable of specifically degrading ERRα protein by >80% at a relatively low concentration of 30 nM, becoming one of the most potent and selective ERRα degraders to date. Compound 6c could be utilized as a new powerful research tool for further biological investigation of ERRα.

Pyrrolopyridone bifunctional molecular compound based on VHL ligand-induced BET degradation

The invention relates to a novel kind of pyrrolopyridone bifunctional molecule and its pharmaceutically acceptable salt, hydrate and prodrug and a pharmaceutical composition using the compounds as active ingredients, and application in the preparation of these compounds and their pharmaceutical composition and in the treatment or prevention of tumors, inflammation, diseases related immunity, etc.The bifunctional molecule involved in the invention is a proteolytic targeting chimera (PROTAC). A small molecule inhibitor of BET protein and a Von Hippel-Lindau (VHL) protein ligand in E3 ubiquitinligase complex are linked by a connecting arm to obtain the bifunctional molecule. The obtained compound can selectively induce the degradation of BET protein, and has significant anti-tumor effect.