webinar
Oct. 27-28, 2025, Boston, MA, USA - Booth 114.
Read More

3-azidopropanoate-N-hydroxysuccinimide ester

  CAS No.: 850180-76-6   Cat No.: BADC-00412   Purity: ≥98% 4.5  

3-azidopropanoate-N-hydroxysuccinimide ester is a small molecule reagent. As a versatile reactive reagent, it has a significant impact on bioconjugation and cross-linking applications. It is deeply embedded in the synthetic mechanism of drug delivery systems, effectively achieving precise targeted release of therapeutic drugs.

3-azidopropanoate-N-hydroxysuccinimide ester

Structure of 850180-76-6

Quality
Assurance

Worldwide
Delivery

24/7 Customer
Support
Category
ADC Linker
Molecular Formula
C7H8N4O4
Molecular Weight
212.16
Shipping
Room temperature, or blue ice upon request.
Shipping
-20 °C

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

Size Price Stock Quantity
-- $-- In stock

Looking for different specifications? Click to request a custom quote!

Capabilities & Facilities

Popular Publications Citing BOC Sciences Products
Synonyms
3-Azidopropanoic acid NHS ester;Propanoic acid, 3-​azido-​, 2,​5-​dioxo-​1-​pyrrolidinyl ester ;
IUPAC Name
(2,5-dioxopyrrolidin-1-yl) 3-azidopropanoate
Canonical SMILES
C1CC(=O)N(C1=O)OC(=O)CCN=[N+]=[N-]
InChI
InChI=1S/C7H8N4O4/c8-10-9-4-3-7(14)15-11-5(12)1-2-6(11)13/h1-4H2
InChIKey
WATICTZQAVLEKN-UHFFFAOYSA-N
Solubility
DMSO, DCM, DMF
Appearance
Soild powder
Shipping
Room temperature, or blue ice upon request.
Storage
-20 °C

3-azidopropanoate-N-hydroxysuccinimide ester is a versatile chemical reagent with several important applications in bioconjugation and molecular biology. Here are some key applications of 3-azidopropanoate-N-hydroxysuccinimide ester:

Protein Labeling: 3-azidopropanoate-N-hydroxysuccinimide ester is commonly used to label proteins with azide groups. This allows for subsequent "click chemistry" reactions with alkyne-containing molecules, enabling the attachment of various probes such as fluorescent tags or biotin. This technique is essential for studying protein interactions, localization, and function.

Antibody Conjugation: This reagent can be used to conjugate antibodies to a variety of molecules, enhancing their functionality in detection and therapy. By attaching drugs, toxins, or imaging agents to antibodies, it’s possible to create targeted treatments for diseases such as cancer. This application is pivotal in the development of antibody-drug conjugates and diagnostic tools.

Immobilization of Biomolecules: 3-azidopropanoate-N-hydroxysuccinimide ester is employed to immobilize biomolecules like enzymes and DNA onto surfaces. By attaching these molecules to solid supports, scientists can create bioactive surfaces for use in biosensors, microarrays, and biochips. This facilitates the high-throughput analysis of biological samples and the development of diagnostic assays.

Synthetic Biology: In synthetic biology, this ester can be used to introduce azide groups into biomolecules, which can then undergo orthogonal chemical reactions. This enables the construction of complex bio-molecular architectures and the design of novel biological systems. These capabilities are crucial for the advancement of synthetic biology applications, including the creation of artificial cells and new metabolic pathways.

1. [Evaluation of the Oral Absorption of Ester-type Prodrugs]
Kayoko Ohura Yakugaku Zasshi . 2020;140(3):369-376. doi: 10.1248/yakushi.19-00225.
The first-pass hydrolysis of oral ester-type prodrugs in the liver and intestine is mediated mainly by hCE1 and hCE2 of the respective predominant carboxylesterase (CES) isozymes. In order to provide high blood concentrations of the parent drugs, it is preferable that prodrugs are absorbed as an intact ester in the intestine, then rapidly converted to active parent drugs by hCE1 in the liver. In the present study, we designed a prodrug of fexofenadine (FXD) as a model parent drug that is resistant to hCE2 but hydrolyzed by hCE1, utilizing the differences in catalytic characteristics of hCE1 and hCE2. In order to precisely predict the intestinal absorption of an FXD prodrug candidate, we developed a novel high-throughput system by modifying Caco-2 cells. Further, we evaluated species differences and aging effects in the intestinal and hepatic hydrolysis of prodrugs to improve the estimation of in vivo first-pass hydrolysis of ester-type prodrugs. Consequently, it was possible to design a hepatotropic prodrug utilizing the differences in tissue distribution and substrate specificity of CESs. In addition, we successfully established three useful in vitro systems for predicting the intestinal absorption of hCE1 substrate using Caco-2 cells. However, some factors involved in estimating the bioavailability of prodrugs in human, such as changes in recognition of drug transporters by esterification, and species differences of the first-pass hydrolysis, should be comprehensively considered in prodrug development.
2. Microbial esterases and ester prodrugs: An unlikely marriage for combating antibiotic resistance
Erik M Larsen, R Jeremy Johnson Drug Dev Res . 2019 Feb;80(1):33-47. doi: 10.1002/ddr.21468.
The rise of antibiotic resistance necessitates the search for new platforms for drug development. Prodrugs are common tools for overcoming drawbacks typically associated with drug formulation and delivery, with ester prodrugs providing a classic strategy for masking polar alcohol and carboxylic acid functionalities and improving cell permeability. Ester prodrugs are normally designed to have simple ester groups, as they are expected to be cleaved and reactivated by a wide spectrum of cellular esterases. However, a number of pathogenic and commensal microbial esterases have been found to possess significant substrate specificity and can play an unexpected role in drug metabolism. Ester protection can also introduce antimicrobial properties into previously nontoxic drugs through alterations in cell permeability or solubility. Finally, mutation to microbial esterases is a novel mechanism for the development of antibiotic resistance. In this review, we highlight the important pathogenic and xenobiotic functions of microbial esterases and discuss the development and application of ester prodrugs for targeting microbial infections and combating antibiotic resistance. Esterases are often overlooked as therapeutic targets. Yet, with the growing need to develop new antibiotics, a thorough understanding of the specificity and function of microbial esterases and their combined action with ester prodrug antibiotics will support the design of future therapeutics.
3. Molecular Reaction Mechanism for the Formation of 3-Chloropropanediol Esters in Oils and Fats
Shuo Wang, Changmo Li, Yunping Yao, Ruizhi Cao, Wentao Liu, Hang Zhou J Agric Food Chem . 2019 Mar 6;67(9):2700-2708. doi: 10.1021/acs.jafc.8b06632.
3-Chloro-1,2-propanediol fatty acid esters (3-MCPD esters) are a group of process-induced contaminants that form during the refining and heating of fats and oils. In this study, a combined method of simulated deodorization and computational simulation was used to explore the precursor substance and the generation path of 3-MCPD esters. From the results, 3-MCPD esters reached a content level of 2.268 mg/kg when the diacylglyceride (DAG) content was 4% and temperature was 220 °C. A good correlation was observed between DAG and 3-MCPD ester contents ( y = 0.0612 x2- 1.6376 x + 10.558 [ R2= 0.958]). There were three pathways for the formation of 3-MCPD esters: (A) a direct nucleophilic substitution reaction, (B) an indirect nucleophilic substitution reaction, and (C) a mechanism of an intermediate (glycidyl ester) from the calculation of Gaussian software at the B3LYP/6-31+g** level. The data showed that the ester-based direct nucleophilic substitution reaction was the most likely reaction pathway. The energy barriers for the formation of the 3-MCPD esters dipalmitin, diolein, and dilinolein were 74.261, 66.017, and 59.856 kJ/mol, respectively, indicating that the formation process of 3-MCPD esters is a high-temperature endothermic process. Therefore, by controlling the introduction of precursor (DAG) and reducing the temperature, 3-MCPD ester formation was prevented.

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

Related Products

Contact our experts today for pricing and comprehensive details on our ADC offerings.

You May Also Be Interested In

From cytotoxin synthesis to linker design, discover our specialized services that complement your ADC projects.

ADC Linker Development Enzyme Cleavable Linker Cathepsin B Cleavable Linker/Peptide Linker Phosphatase Cleavable Linker β-Glucuronide Linker β-Galactosidase Cleavable Linker Sulfatase Cleavable Linker Chemically Cleavable Linker Non-Cleavable Linker Services Acid Cleavable Linker/Hydrazone Linker

Unlock Deeper ADC Insights

Learn more about payload design, linker strategies, and integrated CDMO support through our curated ADC content.

Linkers - A Crucial Factor in Antibody–Drug Conjugates In-Depth Review of ADC Linkers: Types, Mechanisms, and Research Progress New Structural Insights Solve Instability Issues of Maleimide Linkers in ADCs PEG Linkers in Antibody-Drug Conjugates Peptide Linkers in Antibody-Drug Conjugates Disulfide Linkers in Antibody-Drug Conjugates Biotinylation Reagents in Antibody-Drug Conjugates Maleimide Linkers in Antibody-Drug Conjugates Current ADC Linker Chemistry SPDB Linkers in Antibody-Drug Conjugates

Explore More ADC Products

Find exactly what your project needs from our expanded range of ADCs, offering flexible options to fit your timelines and goals.

ADC Cytotoxin

Powerful Targeted Cancer Solutions

ADC  Cytotoxin with Linker

Enhanced Stability And Efficacy

ADC Linker

Precise Conjugation For Success

Antibody-Drug  Conjugates (ADCs)

Maximized Therapeutic Performance

Auristatins

Next-Level Tubulin Inhibition

Calicheamicins

High-Impact DNA Targeting

Camptothecins

Advanced Topoisomerase Inhibition

Daunorubicins / Doxorubicins

Trusted Anthracycline Payloads

Duocarmycins

Potent DNA Alkylation Agents

Maytansinoids

Superior Microtubule Disruption

Pyrrolobenzodiazepines

Ultra-Potent DNA Crosslinkers

Traditional Cytotoxic Agents

Proven Chemotherapy Solutions

Cleavable Linker

Precise Intracellular Drug Release

Non-Cleavable Linker

Exceptional Long-Term Stability

Historical Records: Biotin-PEG4-PFP ester | Zilovertamab vedotin | CL2A-Chimmitecan | Fmoc-N-amido-PEG2-propionic acid | MC-VC-PABC-MMAE | Fmoc-N-amido-PEG3-propionic acid | MMAF | SMCC | INNO-206 | D8-MMAD | 3-Azido-D-alanine hydrochloride
Send Inquiry
Verification code
Inquiry Basket