1056024-94-2

Basic information

• Product Name: Azido-dPEG4-acid
• Synonyms: Azido-dPEG4-acid;N3-PEG3-CH2CH2COOH
• CAS NO: 1056024-94-2
• Molecular Formula: C₉H₁₇N₃O₅
• Molecular Weight: 247.25
• EINECS: -0
• Mol File: 1056024-94-2.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Azido-dPEG4-acid(CAS DataBase Reference)
• NIST Chemistry Reference: Azido-dPEG4-acid(1056024-94-2)
• EPA Substance Registry System: Azido-dPEG4-acid(1056024-94-2)

Safety Data

• Hazardous Substances Data: 1056024-94-2(Hazardous Substances Data)

Usage

Description

Azido-dPEG4-acid is a versatile crosslinker that features an azide (N3) group and a carboxylic acid (CO2H). The terminal carboxylic acid is capable of forming stable amide bonds with primary amine groups in the presence of suitable activators, such as EDC or HATU. The azide group allows for the application of Click Chemistry, a set of reactions that are highly efficient, specific, and tolerant of a wide range of conditions. Additionally, the hydrophilic PEG (polyethylene glycol) spacer enhances solubility in aqueous media, making Azido-dPEG4-acid a valuable component in various applications across different industries.

Uses

Used in Bioconjugation:
Azido-dPEG4-acid is used as a crosslinker for bioconjugation applications due to its ability to form stable amide bonds with primary amine groups. This makes it an ideal candidate for linking biological molecules, such as proteins, peptides, and nucleic acids, to create conjugates with specific functions and improved properties.
Used in Drug Delivery Systems:
In the pharmaceutical industry, Azido-dPEG4-acid is used as a component in the development of drug delivery systems. The hydrophilic PEG spacer and the ability to form stable bonds with drug molecules make it a suitable candidate for improving the solubility, stability, and targeted delivery of therapeutic agents.
Used in Materials Science:
Azido-dPEG4-acid is used as a building block in the synthesis of various materials, such as hydrogels and polymers, due to its ability to participate in Click Chemistry reactions. This allows for the creation of materials with tailored properties, such as controlled release systems, self-healing materials, and stimuli-responsive polymers.
Used in Diagnostics:
In the field of diagnostics, Azido-dPEG4-acid is used as a component in the development of detection systems. The azide group enables the attachment of detection moieties, such as fluorescent tags or enzymes, to biological molecules, allowing for the sensitive and specific detection of target analytes.
Used in Chemical Synthesis:
Azido-dPEG4-acid is used as an intermediate in the synthesis of various chemical compounds, taking advantage of its reactive carboxylic acid and azide groups. This allows for the creation of a wide range of molecules with diverse applications, from pharmaceuticals to specialty chemicals.

Upstream product

• 252881-73-5 tert-Butyl 3-(2-(2-(2-azidoethoxyl)ethoxy)ethoxy)propanoate 
• 1024602-74-1 tert-butyl 3-(2-{2-[2-(methanesulphonyloxy)ethoxy]ethoxy}ethoxy)propanoate 
• 186020-66-6 3-{2-[2-(2-hydroxy-ethoxy)-ethoxy]-ethoxy}-propionic acid tert-butyl ester 
• 217817-01-1 tert-butyl 3-[2-[2-[2-(4-methylphenyl)sulfonyloxyethoxy]ethoxy]ethoxy]propanoate 
• 112-27-6 2,2'-[1,2-ethanediylbis(oxy)]bisethanol 
• 784105-33-5 3-{2-[2-(2-aminoethoxy)ethoxy]ethoxy}propanoic acid 

Downstream Products

• 1610796-02-5 2,5-dioxopyrrolidin-1-yl 3-(2-(2-(2-azidoethoxy)ethoxy)ethoxy)propanoate 
• 2341740-84-7 N-[2-(2,6-dioxopiperidin-3-yl)-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl]-3-{2-[2-(2-{[3-methoxy-4-({4-[(3-oxo-2,3-dihydro-1Hinden-4-yl)oxy]-5-(trifluoromethyl)pyrimidin-2-yl}amino)phenyl]-formamido}ethoxy)ethoxy]ethoxy}propanamide 
• 1056024-95-3 C₉₄H₁₄₅N₅O₁₃ 
• 1056025-05-8 C₆₇H₁₁₇N₅O₇ 
• 1056025-06-9 C₅₅H₈₀N₄O₁₈ 

Relevant articles and documents

Gold Nanoparticles Functionalized with RGD-Semipeptides: A Simple yet Highly Effective Targeting System for αVβ3 Integrins

Effective and selective targeting of the αVβ3 integrin subtype is of high relevance in cancer research for the development of therapeutic systems with improved efficacy and of diagnostic imaging probes. We report here a new class of highly selective, αVβ3-targeted gold nanoparticles (AuNPs), which carry cyclic 4-aminoproline-RGD semipeptides (cAmpRGD) as the targeting moiety immobilized at low surface density on the poly(ethylene glycol) (PEG)-based nanoparticle coating. We show that these nanoparticles are potent inhibitors of the integrin-mediated melanoma tumor cell adhesion to vitronectin and are selectively internalized via receptor-mediated endocytosis. Furthermore, we have developed bifunctional cAmpRGD-functionalized AuNPs by conjugation of a fluorophore (FAM or TAMRA) to a separate set of reactive groups on the PEG-based coating. These bifunctional AuNPs not only recapitulate the binding properties of cAmpRGD-AuNPs but also can be visualized via confocal laser microscopy, allowing direct observation of nanoparticle internalization. The peculiar molecular design of these nanoparticles and their precisely defined architecture at the molecular level accounts for their selective integrin binding with very low nonspecific background.

Nanoscale biomolecular structures on self-assembled monolayers generated from modular pegylated disulfides

A solid-phase synthetic strategy was developed that uses modular building blocks to prepare symmetric oligo(ethylene glycol)-terminated disulfides with a variety of lengths and terminal functionalities. The modular disulfides, composed of alkyl amino groups linked by an amide group to oligoethylene chains were used to generate self-assembled monolayers (SAMs), which were characterised to determine their applicability for biomolecular applications. X-ray photoelectron spectroscopy (XPS) of the SAMs obtained from these molecules demonstrated improved stability towards displacement by 16-hexadecanethiol, while surface plasmon resonance (SPR) analyses of SAMs prepared with the hydroxy-terminated oligoethylene disulfide showed equal resistance to non-specific protein adsorption in comparison to 11-mercaptoundecyl tri(ethylene glycol). SAMs made from these adsorbates were amenable to nanoscale patterning by scanning near-field photolithography (SNP), facilitating the fabrication of nanopatterned, protein-functionalised surfaces. Such SAMs may be further developed for bionanotechnology applications such as the fabrication of nanoscale biological arrays and sensor devices. Play it again SAM! A synthetically expedient method for the assembly of functionalised pegylated alkyldisulfides employing an alternative solid-phase synthetic strategy was successfully demonstrated. Self-assembled monolayers (SAMs) of the synthesised disulfides were characterised and shown to possess a number of desirable properties that were relevant for biological applications and amenable to near-field photolithography.

CROSS-LINKED PYRROLOBENZODIAZEPINE DIMER (PBD) DERIVATIVE AND ITS CONJUGATES

A novel cross-linked cytotoxic agents, pyrrolobenzo-diazepine dimer (PBD) derivatives, and their conjugates to a cell-binding molecule, a method for preparation of the conjugates and the therapeutic use of the conjugates.

CONJUGATION OF A CYTOTOXIC DRUG WITH BIS-LINKAGE

What provided is the conjugation of cytotoxic to a cell-binding molecule with a bis-linker(dual-linker) as shown in Formula (I). It provides bis-linkage methods of making a conjugate of a cytotoxic drug molecule to a cell-binding agent in a specific manner. It also relates to application of the conjugates for the treatment of a cancer, or an autoimmune disease, or an infectious disease.