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

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Synonyms

perfluorophenyl 3-(2-(2-(2-azidoethoxy)ethoxy)ethoxy)propanoate;

IUPAC Name

(2,3,4,5,6-pentafluorophenyl) 3-[2-[2-(2-azidoethoxy)ethoxy]ethoxy]propanoate

Canonical SMILES

C(COCCOCCOCCN=[N+]=[N-])C(=O)OC1=C(C(=C(C(=C1F)F)F)F)F

InChI

InChI=1S/C15H16F5N3O5/c16-10-11(17)13(19)15(14(20)12(10)18)28-9(24)1-3-25-5-7-27-8-6-26-4-2-22-23-21/h1-8H2

InChIKey

ZBZNPFUVVAAJIK-UHFFFAOYSA-N

Solubility

DMSO, DCM, DMF

Appearance

Soild powder

Shipping

Room temperature

Storage

-20 °C

Azido-PEG3-PFP ester is a versatile reagent commonly used in bioconjugation and chemical biology. Here are some key applications of Azido-PEG3-PFP ester:

Click Chemistry: Azido-PEG3-PFP ester is a pivotal compound in click chemistry, enabling the formation of stable covalent bonds between biomolecules. It reacts with alkynes in the presence of a copper catalyst, facilitating the attachment of various functional groups to proteins, nucleic acids, or other molecules. This application is central to creating bioconjugates for imaging, diagnostics, and therapeutic purposes.

Protein Labeling: This reagent is used for site-specific labeling of proteins, allowing the introduction of azide groups into protein structures. The azide-functional group can later react with alkyne- or cyclooctyne-modified probes for detection or immobilization. This precise labeling technique is crucial for studying protein interactions, tracking protein dynamics, and developing biosensors.

Drug Delivery Systems: Azido-PEG3-PFP ester is instrumental in developing advanced drug delivery systems. It facilitates the attachment of therapeutic agents to PEGylated carriers, enhancing drug solubility, stability, and bioavailability. This strategy is employed to improve the pharmacokinetic profiles of drugs, targeting them more effectively to disease sites while reducing side effects.

Surface Modification: This ester can be used to modify the surface properties of various materials, including nanoparticles, hydrogels, and medical devices. By introducing azido groups onto surfaces, it provides reactive sites for further functionalization through click reactions. This capability is crucial for applications in tissue engineering, biosensing, and the development of biocompatible materials.

1. Lactose esters: synthesis and biotechnological applications

Maciej Guzik, Jakub Staroń, Janusz M Dąbrowski, Ewelina Cichoń Crit Rev Biotechnol . 2018 Mar;38(2):245-258. doi: 10.1080/07388551.2017.1332571.

Biodegradable nonionic sugar esters-based surfactants have been gaining more and more attention in recent years due to their chemical plasticity that enables the various applications of these molecules. In this review, various synthesis methods and biotechnological implications of lactose esters (LEs) uses are considered. Several chemical and enzymatic approaches are described for the synthesis of LEs, together with their applications, i.e. function in detergents formulation and as additives that not only stabilize food products but also protect food from undesired microbial contamination. Further, this article discusses medical applications of LEs in cancer treatment, especially their uses as biosensors, halogenated anticancer drugs, and photosensitizing agents for photodynamic therapy of cancer and photodynamic inactivation of microorganisms.

2. 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.

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.