Azido-PEG8-NHS ester

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Azido-PEG8-NHS ester

Azido-PEG8-NHS ester | 1204834-00-3

Catalog Number R14-0316
Category Azides
Molecular Formula C23H40N4O12
Molecular Weight 564.58
Catalog Number Size Price Quantity
R14-0316 -- $--

Product Introduction

Azido-PEG8-NHS ester is a cleavable 8 unit PEG ADC linker used in the synthesis of antibody-drug conjugates (ADCs). Azido-PEG8-NHS ester is also a PEG- and Alkyl/ether-based PROTAC linker that can be used in the synthesis of PROTACs.

Chemical Information

Related CAS 1108750-59-9 (polymer)
Synonyms Azido-PEG8-CH2CO2-NHS; N3-PEG8-C2-NHS ester; N3-PEG8-CH2CH2COONHS Ester; 1-[(1-Azido-27-oxo-3,6,9,12,15,18,21,24-octaoxaheptacosan-27-yl)oxy]-2,5-pyrrolidinedione; 2,5-Pyrrolidinedione, 1-[(27-azido-1-oxo-4,7,10,13,16,19,22,25-octaoxaheptacos-1-yl)oxy]-; 1-Azido-3,6,9,12,15,18,21,24-octaoxaheptacosan-27-oic acid succinimidyl ester
Purity ≥95%
Shelf Life 0-4°C for short term (days to weeks), or -20°C for long term (months).
IUPAC Name (2,5-dioxopyrrolidin-1-yl) 3-[2-[2-[2-[2-[2-[2-[2-(2-azidoethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]propanoate
Canonical SMILES C1CC(=O)N(C1=O)OC(=O)CCOCCOCCOCCOCCOCCOCCOCCOCCN=[N+]=[N-]
InChI InChI=1S/C23H40N4O12/c24-26-25-4-6-32-8-10-34-12-14-36-16-18-38-20-19-37-17-15-35-13-11-33-9-7-31-5-3-23(30)39-27-21(28)1-2-22(27)29/h1-20H2
InChI Key AZXJVYAMFTUKFC-UHFFFAOYSA-N
Solubility Soluble in DMSO (10 mm)
Appearance Pale Yellow or Colorless Oily Liquid
  • Product Specification
  • Application
Storage Store at 2-8°C

Bioconjugation in Drug Development: Azido-PEG8-NHS ester is widely utilized in bioconjugation strategies for drug development, particularly in the synthesis of antibody-drug conjugates (ADCs). Its azide group allows for selective and efficient coupling with various biomolecules, such as proteins, peptides, or small molecules, through click chemistry methods, like the Staudinger or Cu-catalyzed azide-alkyne cycloaddition (AAC). This application is crucial for creating targeted therapies that can deliver cytotoxic agents directly to cancer cells, thereby minimizing off-target effects and enhancing therapeutic efficacy. Researchers are increasingly using Azido-PEG8-NHS ester to develop novel ADCs that improve treatment outcomes for various cancers while reducing systemic toxicity.

Enhancing Solubility and Bioavailability: The incorporation of polyethylene glycol (PEG) moieties, such as those present in Azido-PEG8-NHS ester, significantly enhances the solubility and bioavailability of therapeutic agents. By attaching this PEG linker to drugs or biologics, researchers can increase their solubility in aqueous environments, which is essential for effective delivery in vivo. This application is particularly beneficial for poorly soluble compounds, where enhancing solubility can lead to improved absorption and distribution within the body. Additionally, PEGylation can extend the circulation time of drugs in the bloodstream, allowing for prolonged therapeutic effects and reduced dosing frequency, ultimately improving patient compliance.

Protein Modification for Biomedical Applications: Azido-PEG8-NHS ester is also used for modifying proteins, enabling the introduction of new functional groups or labels for various biomedical applications. This modification can facilitate the study of protein interactions, localization, and dynamics in live cells. By attaching fluorescent dyes or biotin tags through the azide group, researchers can visualize proteins within cellular contexts or isolate them for further analysis. This application is vital for understanding the roles of specific proteins in cellular processes and disease mechanisms. The ability to modify proteins selectively and efficiently opens new avenues for research in proteomics and molecular biology.

Development of Diagnostic Tools: In addition to therapeutic applications, Azido-PEG8-NHS ester plays a significant role in the development of diagnostic tools. Its unique chemistry allows for the functionalization of biomolecules used in biosensors and imaging agents. For example, researchers can conjugate the ester to antibodies or aptamers that specifically recognize disease markers, enhancing the sensitivity and specificity of diagnostic assays. This application is critical in developing rapid and accurate tests for diseases, including cancer and infectious diseases. By integrating Azido-PEG8-NHS ester into diagnostic platforms, scientists can improve detection methods, leading to better patient outcomes through timely diagnosis and treatment.

Computed Properties

XLogP3 -1.1
Hydrogen Bond Donor Count 0
Hydrogen Bond Acceptor Count 14
Rotatable Bond Count 29
Exact Mass 564.26427272 g/mol
Monoisotopic Mass 564.26427272 g/mol
Topological Polar Surface Area 152Ų
Heavy Atom Count 39
Formal Charge 0
Complexity 693
Isotope Atom Count 0
Defined Atom Stereocenter Count 0
Undefined Atom Stereocenter Count 0
Defined Bond Stereocenter Count 0
Undefined Bond Stereocenter Count 0
Covalently-Bonded Unit Count 1
Compound Is Canonicalized Yes

Patents

Publication NumberTitlePriority Date
EP-3619216-A1 Rapamycin analogs as mtor inhibitors 2017-05-02
WO-2018204416-A1 Rapamycin analogs as mtor inhibitors 2017-05-02
US-2021094975-A1 Rapamycin analogs as mtor inhibitors 2017-05-02
AU-2018249559-A1 Trifunctional constructs with tunable pharmacokinetics useful in imaging and anti-tumor therapies 2017-04-05
CN-110612126-A Trifunctional constructs with tunable pharmacokinetics for imaging and antitumor therapy 2017-04-05
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