Name: Ald-PEG4-NHS ester
Brand: BOC Sciences
Rating: 5 (1 reviews)

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Synonyms

CHO-Ph-CONH-PEG4-NHS ester; Ald-Ph-PEG4-NHS ester; Ald-Ph-PEG4-NHS; DF-PEG4-NHS; Ald-Ph-amido-PEG4-C2-NHS ester; 2,5-dioxopyrrolidin-1-yl 1-[(4-formylphenyl)formamido]-3,6,9,12-tetraoxapentadecan-15-oate; 2,5-dioxopyrrolidin-1-yl 1-(4-formylphenyl)-1-oxo-5,8,11,14-tetraoxa-2-azaheptadecan-17-oate; Benzamide, N-[15-[(2,5-dioxo-1-pyrrolidinyl)oxy]-15-oxo-3,6,9,12-tetraoxapentadec-1-yl]-4-formyl-; N-{15-[(2,5-Dioxo-1-pyrrolidinyl)oxy]-15-oxo-3,6,9,12-tetraoxapentadec-1-yl}-4-formylbenzamide

IUPAC Name

(2,5-dioxopyrrolidin-1-yl) 3-[2-[2-[2-[2-[(4-formylbenzoyl)amino]ethoxy]ethoxy]ethoxy]ethoxy]propanoate

Canonical SMILES

C1CC(=O)N(C1=O)OC(=O)CCOCCOCCOCCOCCNC(=O)C2=CC=C(C=C2)C=O

InChI

InChI=1S/C23H30N2O10/c26-17-18-1-3-19(4-2-18)23(30)24-8-10-32-12-14-34-16-15-33-13-11-31-9-7-22(29)35-25-20(27)5-6-21(25)28/h1-4,17H,5-16H2,(H,24,30)

InChIKey

QUFDNMPGNAZKHD-UHFFFAOYSA-N

Density

1.3±0.1 g/cm3

Solubility

Soluble in DCM, DMF, DMSO, Water

Appearance

Pale Yellow or Colorless Oily Matter

Shipping

Room temperature, or blue ice upon request.

Storage

Store at 2-8°C

Ald-PEG4-NHS ester is a modified polyethylene glycol (PEG) linker with an N-hydroxysuccinimide (NHS) ester reactive group, widely used in bioconjugation applications. Here are some key applications of Ald-PEG4-NHS ester:

Bioconjugation: Ald-PEG4-NHS ester is extensively used in the bioconjugation of proteins, peptides, and antibodies. The NHS ester reacts efficiently with primary amines on biomolecules, forming stable amide bonds. This allows for the attachment of functional groups or labels, facilitating various biochemical assays and diagnostic applications.

Drug Delivery: In the field of drug delivery, Ald-PEG4-NHS ester can be used to modify the surface of nanoparticles and other carriers. The PEGylation process improves the pharmacokinetics and bio-distribution of therapeutic agents by enhancing their solubility and reducing immunogenicity. This leads to more effective and targeted drug delivery systems.

Surface Modification: Ald-PEG4-NHS ester is employed in the surface modification of biomaterials and medical devices. By attaching PEG chains to surfaces, it reduces non-specific protein adsorption and cellular adhesion, increasing biocompatibility and reducing potential for adverse reactions. This application is crucial in the development of implants, biosensors, and other medical devices.

Cross-Linking Reagents: As a cross-linking reagent, Ald-PEG4-NHS ester is used to create hydrogel networks and other polymeric structures. The PEG linkers provide flexibility and hydrophilicity, making them ideal for tissue engineering and regenerative medicine applications. These hydrogels can be tailored to support cell growth and tissue formation, enhancing their utility in biomedical research and therapy.

1. 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.

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. 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.