Name: 3-azidopropanoate-N-hydroxysuccinimide ester
Brand: BOC Sciences
Rating: 5 (1 reviews)

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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.

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