1257063-35-6

Basic information

• Product Name: 15-Azido-4,7,10,13-tetraoxapentadecanoic acid
• Synonyms: 15-Azido-4,7,10,13-tetraoxapentadecanoic acid;N3-Peg(4)-cooh;3-[2-[2-[2-(2-Azidoethoxy)ethoxy]ethoxy]ethoxy]propanoic acid;Azido-PEG4-acid;Azido-PEG5-acid;N3-PEG4-CH2CH2COOH;Azido-PEG4-propionic acid;15-Azido-4,7,10,13-tetraoxapentadecanoic acid≥ 97% (NMR)
• CAS NO: 1257063-35-6
• Molecular Formula: C₁₁H₂₁N₃O₆
• Molecular Weight: 291.30094
• Mol File: 1257063-35-6.mol

Chemical Properties

• Appearance: Colorless to Pale Yellow/Liquid
• Storage Temp.: -20°C
• CAS DataBase Reference: 15-Azido-4,7,10,13-tetraoxapentadecanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 15-Azido-4,7,10,13-tetraoxapentadecanoic acid(1257063-35-6)
• EPA Substance Registry System: 15-Azido-4,7,10,13-tetraoxapentadecanoic acid(1257063-35-6)

Safety Data

• Hazardous Substances Data: 1257063-35-6(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
15-Azido-4,7,10,13-tetraoxapentadecanoic acid is used as an amineor phosphine-reactive building block for the derivatization of primary amines. This is achieved through the formation of a stable amide bond in the presence of activators such as EDC or HATU. The azide group can also react with alkyne, BCN, or DBCO via Click Chemistry, yielding a stable triazole linkage.
Used in Bioconjugation:
In the field of bioconjugation, 15-Azido-4,7,10,13-tetraoxapentadecanoic acid is used as a versatile linker for the ligation of alkyne-tagged molecules. The stable triazole linkage formed through Click Chemistry allows for the efficient and specific attachment of various biomolecules, such as proteins, peptides, or other ligands, for a wide range of applications, including drug development, diagnostics, and research.
Used in Drug Delivery Systems:
15-Azido-4,7,10,13-tetraoxapentadecanoic acid can be employed in the development of drug delivery systems, where its reactive groups can be utilized to attach drug molecules or targeting ligands to the carrier system. This can improve the solubility, stability, and targeted delivery of therapeutic agents, potentially enhancing their efficacy and reducing side effects.
Used in Material Science:
In material science, 15-Azido-4,7,10,13-tetraoxapentadecanoic acid can be used as a building block for the synthesis of functional polymers and materials with tailored properties. The azide and carboxylic acid groups can be exploited to create novel materials with specific interactions, such as self-assembly, stimuli-responsive behavior, or controlled release of encapsulated molecules.
Used in Diagnostics:
15-Azido-4,7,10,13-tetraoxapentadecanoic acid can be utilized in the development of diagnostic tools, where its reactive groups can be employed to attach detection agents or markers to various platforms, such as sensors or imaging agents. This can enhance the sensitivity and specificity of diagnostic assays, leading to improved disease detection and monitoring.

Upstream product

• 168640-82-2 11-azido-3,6,9-trioxa-undecanyl p-toluenesulfonate 
• 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 
• 112-60-7 Tetraethylene glycol 
• 581066-04-8 tert-butyl 1-azido-3,6,9,12-tetraoxapentadecan-15-oate 

Downstream Products

• 663921-15-1 3-[2-(2-{2-[2-(2-aminoethoxy)ethoxy]ethoxy}ethoxy)ethoxy]propanoic acid 
• 1604837-41-3 C₄₇H₅₈N₇O₇⁽¹⁺⁾ 
• 1320195-00-3 C₆₃H₉₀N₁₀O₁₈ 
• 1320194-99-7 benzyl 15-azido(4,7,10,13)tetraoxapentadecanoate 
• 1337909-86-0 C₃₅H₃₉N₆O₈P 
• 1337909-89-3 C₃₀H₃₇N₆O₇PS 

Relevant articles and documents

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.

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.