581066-04-8

Basic information

• Product Name: N3-PEG4-tBu
• Synonyms: N3-PEG4-tBu;N3-PEG4-CH2CH2COOtBu;15-Azido-4,7,10,13-tetraoxapentadecanoic acid 1,1-dimethylethyl ester;Azido-PEG5-t-butyl ester;N3-PEG4-CH2CH2COOtBu
• CAS NO: 581066-04-8
• Molecular Formula: C15H29N3O6
• Molecular Weight: 347.40726
• Mol File: 581066-04-8.mol

Chemical Properties

• Appearance: /
• Refractive Index: 1.449 (589.3 nm 23℃)
• CAS DataBase Reference: N3-PEG4-tBu(CAS DataBase Reference)
• NIST Chemistry Reference: N3-PEG4-tBu(581066-04-8)
• EPA Substance Registry System: N3-PEG4-tBu(581066-04-8)

Safety Data

• Hazardous Substances Data: 581066-04-8(Hazardous Substances Data)

Usage

Uses

Used in Bioconjugation:
N3-PEG4-tBu is used as a bioconjugation agent for the selective and efficient attachment of biomolecules, such as proteins, peptides, and nucleic acids, to other molecules or surfaces. The azide group's reactivity in click chemistry enables the formation of stable and covalent bonds with alkyne-containing molecules, facilitating the development of novel bioconjugates for research and therapeutic applications.
Used in Drug Delivery Systems:
In the pharmaceutical industry, N3-PEG4-tBu is used as a component in the design and synthesis of drug delivery systems. The hydrophilic PEG spacer and the reactive azide group allow for the conjugation of drugs or drug carriers to the linker, improving the solubility, stability, and targeted delivery of therapeutic agents. This can lead to enhanced bioavailability, reduced side effects, and increased efficacy of the drugs.
Used in Materials Science:
N3-PEG4-tBu is used as a building block in the development of novel materials with tailored properties. The click chemistry functionality enables the formation of complex architectures and networks, such as hydrogels, micelles, and nanoparticles, for various applications, including drug delivery, tissue engineering, and sensing.
Used in Chemical Synthesis:
In organic synthesis, N3-PEG4-tBu serves as a versatile intermediate for the synthesis of a wide range of PEGylated compounds. The t-butyl protected carboxyl group can be deprotected under acidic conditions, allowing for further functionalization and the introduction of various functional groups, such as amines, alcohols, and thiols, to the PEG chain. This enables the creation of diverse PEGylated molecules with specific properties and applications in various fields, including pharmaceuticals, diagnostics, and materials science.

Upstream product

• 870487-48-2 tert-butyl 1-(methanesulfonyloxy)-3,6,9,12-tetraoxapentadecan-15-oate 
• 1663-39-4 tert-Butyl acrylate 
• 86770-67-4 2-[2-[2-(2-azidoethoxy)ethoxy]ethoxy]ethanol 
• 77544-60-6 p-toluenesulfonic acid 2-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]ethyl ester 
• 581065-94-3 tert-butyl 3-[2-(2-{2-[2-(toluene-4-sulfonyloxy)-ethoxy]ethoxy}ethoxy)ethoxy]propionate 
• 518044-32-1 tert-butyl 3-(2-{2-[2-(2-hydroxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)propanoate 
• 112-60-7 Tetraethylene glycol 

Downstream Products

• 581065-95-4 tert-butyl 3-[2-[2-[2-(2-aminoethoxy)ethoxy]ethoxy]ethoxy]propanoate 
• 1537170-85-6 1-(4-{2-azatricyclo[10.4.0.0^4,9]hexadeca-1⁽¹²⁾,4⁽⁹⁾,5,7,13,15-hexane-10-yn-2-yl}-4-oxobutanamido)-3,6,9,12-tetraoxapentadecan-15-oic acid 
• 1427004-19-0 2,5-dioxopyrrolidin-1-yl 1-(4-{2-azatricyclo[10.4.0.0^4,9]hexadeca-1⁽¹²⁾,4⁽⁹⁾,5,7,13,15-hexane-10-yn-2-yl}-4-oxobutanamido)-3,6,9,12-tetraoxapentadecan-15-oate 
• 663921-15-1 3-[2-(2-{2-[2-(2-aminoethoxy)ethoxy]ethoxy}ethoxy)ethoxy]propanoic acid 
• 1257063-35-6 3-[2-[2-[2-(2-azidoethoxy)ethoxy]ethoxy]ethoxy]propanoic acid 

Relevant articles and documents

Synthesis of carboxy-polyethylene glycol-amine (CA (PEG)n) and [1-14C]-CA (PEG)n via oxa-Michael addition of amino-polyethylene glycols to propiolates vs to acrylates

Synthesis of carboxy-polyethylene glycol-amine (CA (PEG)n) via oxa-Michael addition of amino-polyethylene glycols to either acrylates or propiolates was investigated. Compared with the oxa-Michael addition to acrylates, the corresponding addition to propiolates was found to proceed under mild reaction conditions and afford the adducts in high yields from a broad scope of substrates. A two-step efficient and convenient synthesis of benzyl [1-14C]-propiolate from 14CO2 was therefore developed and utilized as a common synthon to afford practical and high yielding access to [1-14C]-CA (PEG)n.

Optimization of IEDDA bioorthogonal system: Efficient process to improve trans-cyclooctene/tetrazine interaction

The antibody pretargeting approach for radioimmunotherapy (RIT) using inverse electron demand Diels-Alder cycloaddition (IEDDA) constitutes an emerging theranostic approach for solid cancers. However, IEDDA pretargeting has not reached clinical trial. The major limitation of the IEDDA strategy depends largely on trans-cyclooctene (TCO) stability. Indeed, TCO may isomerize into the more stable but unreactive cis-cyclooctene (CCO), leading to a drastic decrease of IEDDA efficiency. We have thus developed both efficient and reproducible synthetic pathways and analytical follow up for (PEGylated) TCO derivatives, providing high TCO isomeric purity for antibody modification. We have set up an original process to limit the isomerization of TCO to CCO before the mAbs’ functionalization to allow high TCO/tetrazine cycloaddition.

Expedient synthesis of trifunctional oligoethyleneglycol-amine linkers and their use in the preparation of PEG-based branched platforms

We designed a convergent synthesis pathway that provides access to trifunctional oligoethyleneglycol-amine (OEG-amine) linkers. By applying the reductive coupling of a primary azide to bifunctional OEG-azide precursors, the corresponding symmetrical dialkylamine bearing two homo-functional end chain groups and a central nitrogen was obtained. These building blocks bear minimal structural perturbation compared to the native OEG backbone which makes them attractive for biomedical applications. The NMR investigations of the mechanism process reveal the formation of nitrile and imine intermediates which can react with the reduced free amine form. Additionally, these trifunctional OEG-amine linkers were employed in a coupling reaction to afford branched multifunctional PEG dendrons which are molecularly defined. These discrete PEG-based dendrons (n = 16, 18 and 36) could be useful for numerous applications where multivalency is required.

STEROIDS AND PROTEIN-CONJUGATES THEREOF

Described herein protein steroid conjugates that are useful, for example, for the target-specific delivery of glucocorticoids (GCs) to cells.

OPTIMIZED TRANSGLUTAMINASE SITE-SPECIFIC ANTIBODY CONJUGATION

Provided herein are methods and compositions for site-specific conjugation of antibodies.

CRYPTOPHYCIN-BASED ANTIBODY-DRUG CONJUGATES WITH NOVEL SELF-IMMOLATIVE LINKERS

The present invention relates to antibody- or peptide-drug conjugate compounds where one or more cryptophycin derivatives (macrocyclic depsipeptide) are covalently attached by a self-immolative linker which binds to one or more tumor-associated antigens or cell-surface receptors. The linker contains a cleavage site for proteases and a dipeptide unit able to form a diketopiperazine. These compounds may be useful in methods of diagnosis or treatment of cancer, and other diseases and disorders, such as immune or infective diseases.

A new route for the synthesis of 1-amino-3,6,9,12-tetraoxapentadecan-15-oic acid

1-Amino-3,6,9,12-tetraoxapentadecan-15-oic acid 8 was synthesised from tetraethylene glycol through a 7 step sequence including esterification, mesylation, azide substitution with subsequent reduction followed by hydrolysis. The structure of product 8 was

Efficient synthesis of small-sized phosphonated dendrons: Potential organic coatings of iron oxide nanoparticles

We report herein the synthesis of biocompatible small-sized phosphonated monomers and dendrons used as functional coatings of metal oxide nanoparticles, more specifically superparamagnetic iron oxides (SPIOs) for magnetic resonance imaging (MRI) and therapy through hyperthermia. The molecules were engineered to modulate their size, their hydrophilic and/or biocompatible character (poly(amido)amine versus oligoethyleneglycol), the number of anchoring phosphonate groups (monophosphonate versus phosphonic tweezers) and the number of peripheral functional groups for further grafting of dyes or specific vectors. Such a library of hydrophilic phosphonic acids opens new possibilities for the investigation of dendronized nanohybrids as theranostics.

ANTI-CD70 ANTIBODY DRUG CONJUGATES

This invention relates to anti-CD70 antibodies and antibody drug conjugates comprising at least one non-naturally-encoded amino acid. Disclosed herein are αCD70 antibodies with one or more non-naturally encoded amino acids and further disclosed are antibody drug conjugates wherein the αCD70 antibodies of the invention are conjugated to one or more toxins. Further disclosed are methods for using such non-natural amino acid antibody drug conjugates, including therapeutic, diagnostic, and other biotechnology uses.

PROSTATE-SPECIFIC MEMBRANE ANTIGEN ANTIBODY DRUG CONJUGATES

This invention relates to prostate-specific membrane antigen (PSMA) antibodies and antibody drug conjugates comprising at least one non-naturally-encoded amino acid. Disclosed herein are αPSMA antibodies with one or more non-naturally encoded amino acids and further disclosed are antibody drug conjugates wherein the αPSMA antibodies of the invention are conjugated to one or more toxins. Also disclosed herein are non-natural amino acid dolastatin analogs that are further modified post-translationally, methods for effecting such modifications, and methods for purifying such dolastatin analogs. Typically, the modified dolastatin analogs include at least one oxime, carbonyl, dicarbonyl, and/or hydroxylamine group. Further disclosed are methods for using such non-natural amino acid antibody drug conjugates, dolastatin analogs, and modified non-natural amino acid dolastatin analogs, including therapeutic, diagnostic, and other biotechnology uses.