Name: Azido-PEG3-NHS ester
Brand: BOC Sciences
Rating: 5 (1 reviews)

Synonyms

Azido-PEG3-CH2CO2-NHS; N3-PEG3-C2-NHS ester; N3-PEG3-CH2CH2COONHS Ester; 1-[(3-{2-[2-(2-Azidoethoxy)ethoxy]ethoxy}propanoyl)oxy]-2,5-pyrrolidinedione; 2,5-Pyrrolidinedione, 1-[3-[2-[2-(2-azidoethoxy)ethoxy]ethoxy]-1-oxopropoxy]-; N3-PEG3-SPA; Propanoic acid, 3-[2-[2-(2-azidoethoxy)ethoxy]ethoxy]-, 2,5-dioxo-1-pyrrolidinyl ester

IUPAC Name

(2,5-dioxopyrrolidin-1-yl) 3-[2-[2-(2-azidoethoxy)ethoxy]ethoxy]propanoate

Canonical SMILES

C1CC(=O)N(C1=O)OC(=O)CCOCCOCCOCCN=[N+]=[N-]

InChI

InChI=1S/C13H20N4O7/c14-16-15-4-6-22-8-10-23-9-7-21-5-3-13(20)24-17-11(18)1-2-12(17)19/h1-10H2

InChIKey

BNLXVOZUEBSSRI-UHFFFAOYSA-N

Solubility

Soluble in DCM, DMF, DMSO, Water

Appearance

Pale Yellow or Colorless Oily Matter

Shelf Life

≥12 months if stored properly

Shipping

Room temperature

Storage

Store at 2-8°C

Azido-PEG3-NHS ester, a versatile reagent harnessed in bioconjugation and molecular biology, finds applications across diverse domains. Here are four key applications of Azido-PEG3-NHS ester articulated with a distinctive blend of perplexity and burstiness:

Click Chemistry: Integral to click chemistry, Azido-PEG3-NHS ester plays a pivotal role in bioconjugation. This reagent introduces an azide group to biomolecules, facilitating their efficient linkage to alkyne-containing molecules through a copper-catalyzed azide-alkyne cycloaddition reaction. This method is instrumental in crafting intricate biomolecular assemblies and tagging proteins or peptides with an array of probes.

Protein Labeling: Azido-PEG3-NHS ester emerges as a key player in labeling proteins with fluorescent dyes or other bioactive molecules. By engaging with primary amines on proteins, this reagent covalently affixes an azide group, which can subsequently be linked to a myriad of detection or functional tags. This application is paramount for investigating protein dynamics, interactions, and localization within biological systems.

Drug Delivery: Positioned at the forefront of targeted drug delivery systems, Azido-PEG3-NHS ester showcases its capabilities. The PEG linker confers solubility and diminishes immunogenicity, while the azide group facilitates the attachment of therapeutic agents or targeting moieties. This precision enables the targeted delivery of drugs to specific cells or tissues, augmenting therapeutic effectiveness while minimizing side effects.

Surface Modification: Aiding in the modification of surfaces of nanoparticles, biosensors, and other biomaterials, Azido-PEG3-NHS ester stands out for its versatility. By introducing azide groups onto surfaces, it enables the binding of various biofunctional molecules through click chemistry. This application is indispensable in creating biointerfaces with enhanced biocompatibility, specificity, and functionalization for diagnostic and therapeutic endeavors.

1. A Ketone Ester Drink Lowers Human Ghrelin and Appetite

Brianna J Stubbs, Pete J Cox, Malgorzata Cyranka, Rhys D Evans, Heidi de Wet, Kieran Clarke Obesity (Silver Spring) . 2018 Feb;26(2):269-273. doi: 10.1002/oby.22051.

Objective:The ketones d-β-hydroxybutyrate (BHB) and acetoacetate are elevated during prolonged fasting or during a "ketogenic" diet. Although weight loss on a ketogenic diet may be associated with decreased appetite and altered gut hormone levels, it is unknown whether such changes are caused by elevated blood ketones. This study investigated the effects of an exogenous ketone ester (KE) on appetite.Methods:Following an overnight fast, subjects with normal weight (n = 15) consumed 1.9 kcal/kg of KE, or isocaloric dextrose (DEXT), in drinks matched for volume, taste, tonicity, and color. Blood samples were analyzed for BHB, glucose, insulin, ghrelin, glucagon-like peptide 1 (GLP-1), and peptide tyrosine tyrosine (PYY), and a three-measure visual analogue scale was used to measure hunger, fullness, and desire to eat.Results:KE consumption increased blood BHB levels from 0.2 to 3.3 mM after 60 minutes. DEXT consumption increased plasma glucose levels between 30 and 60 minutes. Postprandial plasma insulin, ghrelin, GLP-1, and PYY levels were significantly lower 2 to 4 hours after KE consumption, compared with DEXT consumption. Temporally related to the observed suppression of ghrelin, reported hunger and desire to eat were also significantly suppressed 1.5 hours after consumption of KE, compared with consumption of DEXT.Conclusions:Increased blood ketone levels may directly suppress appetite, as KE drinks lowered plasma ghrelin levels, perceived hunger, and desire to eat.

2. Palladium-Catalyzed Tandem Ester Dance/Decarbonylative Coupling Reactions

Eisuke Ota, Naomi Inayama, Junichiro Yamaguchi, Masayuki Kubo Org Lett . 2022 Jun 3;24(21):3855-3860. doi: 10.1021/acs.orglett.2c01432.

"Dance reaction" on the aromatic ring is a powerful method in organic chemistry to translocate functional groups on arene scaffolds. Notably, dance reactions of halides and pseudohalides offer a unique platform for the divergent synthesis of substituted (hetero)aromatic compounds when combined with transition-metal-catalyzed coupling reactions. Herein, we report a tandem reaction of ester dance and decarbonylative coupling enabled by palladium catalysis. In this reaction, 1,2-translocation of the ester moiety on the aromatic ring is followed by decarbonylative coupling with nucleophiles to enable the installation of a variety of nucleophiles at the position adjacent to the ester in the starting material.

3. 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.