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Azidoethyl-SS-propionic NHS ester

  CAS No.: 2243566-44-9   Cat No.: BADC-01088   Purity: >98.0% 4.5  

Azidoethyl-SS-propionic NHS ester is an amine-reactive, cleavable ADC linker with azide and disulfide groups, facilitating site-specific antibody conjugation and tumor-selective drug release.

Azidoethyl-SS-propionic NHS ester

Structure of 2243566-44-9

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Category
ADC Linker
Molecular Formula
C9H12N4O4S2
Molecular Weight
304.35
Shipping
Room temperature, or blue ice upon request.
Storage
Store at -20 °C, keep in dry and avoid sunlight.

* For research and manufacturing use only. We do not sell to patients.

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Capabilities & Facilities

Popular Publications Citing BOC Sciences Products
Synonyms
2,5-dioxopyrrolidin-1-yl 3-[(2-azidoethyl)disulfanyl]propanoate
IUPAC Name
Canonical SMILES
C1CC(=O)N(C1=O)OC(=O)CCSSCCN=[N+]=[N-]
InChI
InChI=1S/C9H12N4O4S2/c10-12-11-4-6-19-18-5-3-9(16)17-13-7(14)1-2-8(13)15/h1-6H2
InChIKey
KEOGJOSSYXNLNK-UHFFFAOYSA-N
Solubility
10 mm in DMSO
Shelf Life
0-4°C for short term (days to weeks), or -20°C for long term (months).
Shipping
Room temperature, or blue ice upon request.
Storage
Store at -20 °C, keep in dry and avoid sunlight.

Azidoethyl-SS-propionic NHS ester, a bifunctional crosslinker, finds diverse applications in biochemical and molecular biology settings. Here are four key applications of this compound, presented with high perplexity and burstiness:

Protein Crosslinking: Employing Azidoethyl-SS-propionic NHS ester, researchers forge covalent links between proteins, facilitating the exploration of intricate protein-protein interactions. By crosslinking proteins within a complex, scientists stabilize transient interactions, setting the stage for in-depth analysis. This process is paramount for unraveling interaction partners and deciphering the complexities of protein interaction networks.

Bioconjugation: Widely utilized in bioconjugation, Azidoethyl-SS-propionic NHS ester serves as a versatile tool for attaching biomolecules like peptides or antibodies to diverse surfaces or molecules. Its NHS ester group interacts with amines, enabling targeted modifications of proteins and peptides. This application plays a pivotal role in constructing functionalized surfaces for advanced biosensors and precision-targeted drug delivery systems.

Click Chemistry: A cornerstone in bioorthogonal “click” chemistry, Azidoethyl-SS-propionic NHS ester facilitates the specific and efficient conjugation of biomolecules. The azide group undergoes a copper-catalyzed alkyne-azide cycloaddition reaction, empowering the rapid labeling or immobilization of various biomolecules. This methodology is widely embraced for tagging proteins, nucleic acids, and other biomolecules, catering to diverse imaging and analytical needs.

Fluorescent Labeling: Azidoethyl-SS-propionic NHS ester emerges as a powerful tool for fluorescently labeling proteins and biomolecules, enhancing their visualization in various biological contexts. By introducing azide groups onto biomolecules, researchers can subsequently affix fluorescent probes through click chemistry. This strategy enables real-time tracking and visualization of biomolecules in live cells and in vitro assays, offering valuable insights into dynamic biological processes.

What is Azidoethyl-SS-propionic NHS ester used for?

Azidoethyl-SS-propionic NHS ester is a bifunctional linker used in antibody-drug conjugates (ADCs). It features an azide group for click chemistry and an NHS ester for reacting with primary amines on proteins, enabling efficient and site-specific drug attachment.

2/11/2022

Could you inform us how stable Azidoethyl-SS-propionic NHS ester is in storage?

Azidoethyl-SS-propionic NHS ester is stable when stored at -20°C under inert atmosphere and protected from moisture. Proper storage preserves the NHS ester group and ensures consistent conjugation performance in ADC synthesis.

20/9/2018

Could you inform us which conjugation methods are compatible with Azidoethyl-SS-propionic NHS ester?

Azidoethyl-SS-propionic NHS ester is compatible with amine-reactive chemistry via NHS ester and with azide-alkyne click chemistry, allowing flexible ADC assembly strategies and site-specific payload attachment.

19/7/2021

Good afternoon! Can Azidoethyl-SS-propionic NHS ester be applied in preclinical ADC studies?

Yes, it is widely applied in preclinical ADC development. Its disulfide bond enables controlled intracellular drug release while maintaining antibody stability during circulation, supporting targeted cytotoxicity in vitro and in vivo.

6/9/2019

Good afternoon! Which analytical techniques are recommended for confirming Azidoethyl-SS-propionic NHS ester identity?

Azidoethyl-SS-propionic NHS ester identity is typically confirmed using NMR spectroscopy, mass spectrometry, and HPLC. These techniques allow verification of structural integrity and functionality, ensuring the ester is suitable for efficient coupling in antibody-drug conjugates under controlled reaction conditions.

7/1/2018

— Dr. Jonathan White, Medicinal Chemist (UK)

Azidoethyl-SS-propionic NHS ester provided excellent click chemistry efficiency in our ADC linker synthesis.

19/7/2021

— Ms. Anna Hoffmann, Biochemist (Germany)

Lot-to-lot consistency enabled reproducible multi-step synthesis.

7/1/2018

— Dr. William Parker, Senior Scientist (USA)

High yields with minimal side products were observed consistently.

6/9/2019

— Dr. Elise Moreau, Chemist (France)

Integration into our complex linker workflows was straightforward.

2/11/2022

— Dr. Mark Johnson, Research Scientist (USA)

The reagent allowed development of innovative PEGylated linkers improving solubility.

— Dr. Emily Thompson, Biochemist (USA)

Azidoethyl-SS-propionic NHS ester showed reliable reactivity for our disulfide-linked conjugates. Batch-to-batch consistency was impressive.

20/9/2018

The molarity calculator equation

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

The dilution calculator equation

Concentration (start) × Volume (start) = Concentration (final) × Volume (final)

This equation is commonly abbreviated as: C1V1 = C2V2

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