53053-08-0

Basic information

• Product Name: N-HYDROXYSUCCINIMIDYL-4-AZIDOBENZOATE
• Synonyms: HSAB;4-AZIDOBENZOIC ACID N-HYDROXYSUCCINIMIDE ESTER;N-HYDROXYSUCCINIMIDYL-4-AZIDOBENZOATE;hydroxysuccinimidyl-4-azidobenzoate;4-AZIDOBENZOIC ACID N-HYDROXY- &;4-azidobenzoic acid N-hydroxysuccinimide;Nsc329704;HSAB(N-HydroxysulfosucciniMidyl-4-azidobenzoate
• CAS NO: 53053-08-0
• Molecular Formula: C₁₁H₈N₄O₄
• Molecular Weight: 260.21
• Product Categories: Heterobifunctional Crosslinker;photoazide
• Mol File: 53053-08-0.mol
• Article Data: 24

Chemical Properties

• Melting Point: 171-172°C
• Appearance: /powder
• Storage Temp.: −20°C
• Solubility: chloroform: 50 mg/mL
• CAS DataBase Reference: N-HYDROXYSUCCINIMIDYL-4-AZIDOBENZOATE(CAS DataBase Reference)
• NIST Chemistry Reference: N-HYDROXYSUCCINIMIDYL-4-AZIDOBENZOATE(53053-08-0)
• EPA Substance Registry System: N-HYDROXYSUCCINIMIDYL-4-AZIDOBENZOATE(53053-08-0)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 53053-08-0(Hazardous Substances Data)

Usage

Description

N-HYDROXYSUCCINIMIDYL-4-AZIDOBENZOATE, also known as an aryl azide-based crosslinker, is a chemical compound that possesses both amine-reactive and photoreactive properties. It is primarily used for covalent bonding and immobilization of biomolecules, such as proteins and peptides, onto various surfaces. Its unique reactivity allows for the formation of stable and specific bonds under controlled conditions, making it a valuable tool in the fields of biochemistry, molecular biology, and materials science.

Uses

Used in Biochemistry and Molecular Biology:
N-HYDROXYSUCCINIMIDYL-4-AZIDOBENZOATE is used as a crosslinking agent for the covalent attachment of biomolecules, such as proteins and peptides, to surfaces or other molecules. This application is crucial for various research and diagnostic techniques, including enzyme immobilization, protein microarray fabrication, and the study of protein-protein interactions.
Used in Materials Science:
In the field of materials science, N-HYDROXYSUCCINIMIDYL-4-AZIDOBENZOATE is used as a coupling agent to facilitate the attachment of biological molecules to various surfaces, such as polymers, nanoparticles, and other materials. This enables the development of novel biomaterials and devices with specific biological functions, such as biosensors, drug delivery systems, and tissue engineering scaffolds.
Used in Drug Delivery Systems:
N-HYDROXYSUCCINIMIDYL-4-AZIDOBENZOATE is employed as a key component in the design and synthesis of targeted drug delivery systems. By covalently attaching therapeutic molecules to drug carriers, such as nanoparticles or liposomes, this crosslinker ensures the stable and specific attachment of the drug to the carrier, improving the overall efficacy and targeting of the therapeutic agent.
Used in Diagnostic Applications:
In the diagnostic industry, N-HYDROXYSUCCINIMIDYL-4-AZIDOBENZOATE is used as a labeling agent for the conjugation of detection molecules, such as fluorescent dyes or enzymes, to biomolecules of interest. This allows for the development of highly sensitive and specific diagnostic assays, such as immunoassays and nucleic acid detection methods.
Used in Research and Development:
N-HYDROXYSUCCINIMIDYL-4-AZIDOBENZOATE is utilized as a versatile tool in the research and development of new biological and medical applications. Its unique reactivity enables the creation of novel bioconjugates, probes, and materials with tailored properties and functions, contributing to the advancement of scientific knowledge and the development of innovative technologies.

InChI:InChI=1/C11H9N4O4/c12-14-13-8-3-1-7(2-4-8)11(18)19-15-9(16)5-6-10(15)17/h1-4,12H,5-6H2/q+1

Upstream product

• 6066-82-6 1-hydroxy-pyrrolidine-2,5-dione 
• 6427-66-3 4-azidobenzoic acid 
• 150-13-0 4-amino-benzoic acid 

Downstream Products

• 153695-19-3 N-(4-azidobenzoyl)-N-debenzoyltaxol 
• 58332-32-4 N-(4-azidobenzoyl)tyrosine 
• 85287-36-1 6-<(4-Azidobenzoyl)amino>hexanoic acid 
• 874163-06-1 3(R)-[(4(S)-((4-azidobenzoyl)amino)-1-(tert-butoxycarbonyl)-2(S)-pyrrolidinylcarbonyl)amino]-2-oxo-1-pyrrolidineacetamide 
• 874163-09-4 3(R)-[(4(R)-((4-azidobenzoyl)amino)-1-(tert-butoxycarbonyl)-2(S)-pyrrolidinylcarbonyl)amino]-2-oxo-1-pyrrolidineacetamide 
• 874163-20-9 3(R)-[(2(S)-1-(tert-butoxycarbonyl)pyrrolidinylcarbonyl)amino]-2-oxo-1-pyrrolidineacetamide N-(N'-(4-azidobenzoyl)amino)ethyl 
• 929681-74-3 N-(4-azidobenzoyl)-S-tritylglutathione 

Relevant articles and documents

Photoactive chelates for radiolabelling proteins

Photochemical reactions are an attractive foundation for the synthesis of radiolabelled antibodies, immunoglobulin fragments and other proteins/peptides. The synthesis, 68Ga-radiochemistry and photochemical reactivity of three macrocyclic chela

PHOTOAFFINITY PROBES FOR GIBBERELLIN-BINDING PROTEINS

A rational approach to the design, synthesis and radiolabelling, with either 3H or 125I, of gibberellin A4 (GA4) derivatives containing C-17-arylazido functionalities is described.The potential of these compounds as photoaffinity rea

Identification of Pyruvate Carboxylase as the Cellular Target of Natural Bibenzyls with Potent Anticancer Activity against Hepatocellular Carcinoma via Metabolic Reprogramming

Cancer cell proliferation in some organs often depends on conversion of pyruvate to oxaloacetate via pyruvate carboxylase (PC) for replenishing the tricarboxylic acid cycle to support biomass production. In this study, PC was identified as the cellular target of erianin using the photoaffinity labeling-click chemistry-based probe strategy. Erianin potently inhibited the enzymatic activity of PC, which mediated the anticancer effect of erianin in human hepatocellular carcinoma (HCC). Erianin modulated cancer-related gene expression and induced changes in metabolic intermediates. Moreover, erianin promotes mitochondrial oxidative stress and inhibits glycolysis, leading to insufficient energy required for cell proliferation. Analysis of 14 natural analogs of erianin showed that some compounds exhibited potent inhibitory effects on PC. These results suggest that PC is a cellular target of erianin and reveal the unrecognized function of PC in HCC tumorigenesis; erianin along with its analogs warrants further development as a novel therapeutic strategy for the treatment of HCC.

A Potent Halogen-Bonding Donor Motif for Anion Recognition and Anion Template Mechanical Bond Synthesis

The covalent attachment of electron deficient perfluoroaryl substituents to a bis-iodotriazole pyridinium group produces a remarkably potent halogen bonding donor motif for anion recognition in aqueous media. Such a motif also establishes halogen bonding anion templation as a highly efficient method for constructing a mechanically interlocked molecule in unprecedented near quantitative yield. The resulting bis-perfluoroaryl substituted iodotriazole pyridinium axle containing halogen bonding [2]rotaxane host exhibits exceptionally strong halide binding affinities in competitive 50 % water containing aqueous media, by a factor of at least three orders of magnitude greater in comparison to a hydrogen bonding rotaxane host analogue. These observations further champion and advance halogen bonding as a powerful tool for recognizing anions in aqueous media.