Name: Maleimide-NH-PEG10-CH2CH2COONHS Ester
Brand: BOC Sciences
Rating: 5 (1 reviews)

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Synonyms

Alpha-Maleimidopropionyl-Omega-succinimidyl-10(ethylene glycol) ; (2,5-dioxopyrrolidin-1-yl) 3-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[3-(2,5-dioxopyrrol-1-yl)propanoylamino]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]propanoate

IUPAC Name

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

Canonical SMILES

C1CC(=O)N(C1=O)OC(=O)CCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCNC(=O)CCN2C(=O)C=CC2=O

InChI

InChI=1S/C34H55N3O17/c38-29(5-8-36-30(39)1-2-31(36)40)35-7-10-45-12-14-47-16-18-49-20-22-51-24-26-53-28-27-52-25-23-50-21-19-48-17-15-46-13-11-44-9-6-34(43)54-37-32(41)3-4-33(37)42/h1-2H,3-28H2,(H,35,38)

InChIKey

DUKFGPQZJAPKMG-UHFFFAOYSA-N

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Soild powder

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Room temperature

Maleimide-NH-PEG10-CH2CH2COONHS Ester, a versatile chemical reagent, finds wide applications in bioconjugation and surface modification.

Protein Conjugation: Maleimide-NH-PEG10-CH2CH2COONHS Ester plays a crucial role in conjugating proteins, peptides, or antibodies with various molecules or interfaces. The maleimide group selectively reacts with thiol groups on cysteine residues, forming robust thioether linkages.

Polymer Surface Modification: Delving into materials science, this compound is pivotal in altering polymer surface properties to enhance their compatibility with biological systems. The inclusion of the PEG moiety confers hydrophilicity and diminishes protein adsorption, making it ideal for coating medical devices like stents or catheters. This modification aids in reducing immune responses and optimizing device functionality.

Drug Delivery Systems: Embark on the realm of pharmaceuticals with Maleimide-NH-PEG10-CH2CH2COONHS Ester being utilized in crafting targeted drug delivery systems by affixing therapeutic agents to carrier molecules. The ester linkage facilitates drug attachment to nanocarriers, such as liposomes or nanoparticles, enabling precise and controlled drug release. This strategy amplifies drug efficacy while minimizing off-target effects.

Biomolecule Immobilization: In the domain of biosensor technology, Maleimide-NH-PEG10-CH2CH2COONHS Ester emerges as a key player in immobilizing biomolecules onto sensor surfaces. The NHS ester group engages with amines, ensuring stable attachment of proteins, enzymes, or DNA to sensor platforms. This process guarantees sensitive and reliable detection in diverse analytical and diagnostic scenarios, underscoring its significance in advancing biotechnology.

1. Fast-Acting Antibacterial, Self-Deactivating Polyionene Esters

Christian Krumm, Lena Benski, Joerg C Tiller, Manfred Köller, Franziska Oberhaus, Jens Wilken, Sylvia Trump ACS Appl Mater Interfaces . 2020 May 13;12(19):21201-21209. doi: 10.1021/acsami.9b19313.

Biocidal compounds that quickly kill bacterial cells and are then deactivated in the surrounding without causing environmental problems are of great current interest. Here, we present new biodegradable antibacterial polymers based on polyionenes with inserted ester functions (PBI esters). The polymers are prepared by polycondensation reaction of 1,4-dibromobutene and different tertiary diaminodiesters. The resulting PBI esters are antibacterially active against a wide range of bacterial strains and were found to quickly kill these cells within 1 to 10 min. Because of hydrolysis of the ester groups, the PBI esters are degraded and deactivated in aqueous media. The degradation rate depends on the backbone structure and the pH. The structure of the polymers also controls the deactivation mechanism. While the more hydrophilic polymers require hydrolyses of only 19 to 30% of the ester groups to become practically inactive, the more hydrophobic PBI esters require up to 85% hydrolysis to achieve the same result. Thus, depending on the environmental conditions and the chemical nature, the PBI esters can be active for only 20 min or for at least one week.

2. α-Imino Esters in Organic Synthesis: Recent Advances

Bagher Eftekhari-Sis, Maryam Zirak Chem Rev . 2017 Jun 28;117(12):8326-8419. doi: 10.1021/acs.chemrev.7b00064.

α-Imino esters are useful precursors for the synthesis of a variety of types of natural and unnatural α-amino acid derivatives, with a wide range of biological activities. Due to the adjacent ester group, α-imino esters are more reactive relative to other types of imines and undergo different kinds of reactions, including organometallics addition, metal catalyzed vinylation and alkynylation, aza-Henry, aza-Morita-Baylis-Hillman, imino-ene, Mannich-type, and cycloaddition reactions, as well as hydrogenation and reduction. This review discusses the mechanism, scope, and applications of the reactions of α-imino esters and related compounds in organic synthesis, covering the literature from the last 12 years.

3. Catalytic antibodies

A Tramontano, R A Lerner, K D Janda Science . 1986 Dec 19;234(4783):1566-70. doi: 10.1126/science.3787261.

Monoclonal antibodies elicited to haptens that are analogs of the transition state for hydrolysis of carboxylic esters behaved as enzymic catalysts with the appropriate substrates. These substrates are distinguished by the structural congruence of both hydrolysis products with haptenic fragments. The haptens were potent inhibitors of this esterolytic activity, in agreement with their classification as transition state analogs. Mechanisms are proposed to account for the different chemical behavior of these antibodies with two types of ester substrates. The generation of an artificial enzyme through transition state stabilization by antibodies was thus demonstrated. These studies indicate a potentially general approach to catalyst design.

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