Name: Maleimide-NH-PEG3-CH2CH2COOPFP Ester
Brand: BOC Sciences
Rating: 5 (1 reviews)

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Synonyms

perfluorophenyl 15-(2,5-dioxo-2H-pyrrol-1(5H)-yl)-13-oxo-3,6,9-trioxa-12-azapentadecan-1-oate

IUPAC Name

(2,3,4,5,6-pentafluorophenyl) 2-[2-[2-[2-[3-(2,5-dioxopyrrol-1-yl)propanoylamino]ethoxy]ethoxy]ethoxy]acetate

SMILES

C1=CC(=O)N(C1=O)CCC(=O)NCCOCCOCCOCC(=O)OC2=C(C(=C(C(=C2F)F)F)F)F

InChI

InChI=1S/C21H21F5N2O8/c22-16-17(23)19(25)21(20(26)18(16)24)36-15(32)11-35-10-9-34-8-7-33-6-4-27-12(29)3-5-28-13(30)1-2-14(28)31/h1-2H,3-11H2,(H,27,29)

InChIKey

ZBIQVRXGRCZPMF-UHFFFAOYSA-N

Appearance

Soild powder

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-20°C (International: -20°C)

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-20°C

Maleimide-NH-PEG3-CH2CH2COOPFP Ester, a versatile chemical reagent with widespread utility in bioconjugation and surface modification across scientific and industrial domains, is explored through four key applications:

Protein Conjugation: Serving as a pivotal player in protein modification and labeling, Maleimide-NH-PEG3-CH2CH2COOPFP Ester engages in thiol-specific conjugation processes, enabling precise attachment of polymers, dyes, or biomolecules at specific protein sites through interaction with free thiols.

Surface Functionalization: This versatile ester plays a critical role in surface modification by endowing surfaces with PEGylated chains to enhance biocompatibility and curtail nonspecific binding in biosensors and medical devices. By introducing a PEG spacer, the compound establishes a hydrophilic shield that deters fouling and enhances instrument performance, ultimately advancing biomaterials and medical device technology.

Drug Delivery Systems: Maleimide-NH-PEG3-CH2CH2COOPFP Ester emerges as a linchpin in designing targeted drug delivery systems by facilitating attachment of targeting ligands or therapeutic agents to nanoparticles and liposomes. This precision-driven mechanism heightens drug efficacy, diminishes adverse effects, and holds promising implications in cancer treatment and personalized medicine, offering finely honed strategies for potent therapeutic outcomes.

Polymer Synthesis: Within polymer chemistry, this compound assumes a central role in synthesizing functionalized PEG polymers for diverse applications. By introducing reactive ester groups, researchers fashion block copolymers and hydrogels with tailored properties suitable for applications like tissue engineering and regenerative medicine. This versatility enables fine-tuning of physical and biochemical attributes of polymer-based materials, fostering the creation of bespoke materials for specific applications.

1. 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.

2. 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.

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.