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Azido-PEG2-PFP ester

  CAS No.: 1393330-37-4   Cat No.: BADC-00408   Purity: ≥98% 4.5  

Azido-PEG2-PFP ester is a mixture of azide-functionalized polyethylene glycol (PEG) derivatives interleaved with pentafluorophenyl (PFP) ester moieties. This special compound is widely used as a coupling agent in the field of bioconjugation chemistry and shows unparalleled potential in efficient biomolecule modification. Whether proteins or peptides, azido-PEG2-PFP esters open up many possibilities for revolutionary applications, including drug delivery systems, targeted therapies, and transformative diagnostics.

Azido-PEG2-PFP ester

Structure of 1393330-37-4

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Category
ADC Linker
Molecular Formula
C13H12F5N3O4
Molecular Weight
369.24
Shipping
Room temperature
Storage
-20 °C

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Popular Publications Citing BOC Sciences Products
Synonyms
perfluorophenyl 3-(2-(2-azidoethoxy)ethoxy)propanoate;
IUPAC Name
(2,3,4,5,6-pentafluorophenyl) 3-[2-(2-azidoethoxy)ethoxy]propanoate
Canonical SMILES
C(COCCOCCN=[N+]=[N-])C(=O)OC1=C(C(=C(C(=C1F)F)F)F)F
InChI
InChI=1S/C13H12F5N3O4/c14-8-9(15)11(17)13(12(18)10(8)16)25-7(22)1-3-23-5-6-24-4-2-20-21-19/h1-6H2
InChIKey
FEXHEMGARNABFF-UHFFFAOYSA-N
Solubility
DMF, DCM
Appearance
Soild powder
Shipping
Room temperature
Storage
-20 °C

Azido-PEG2-PFP ester is a heterobifunctional ADC linker designed for bioorthogonal conjugation strategies. It contains an azide functional group for click chemistry and a pentafluorophenyl (PFP) ester for efficient reaction with antibody amines. The PEG2 spacer enhances solubility and reduces steric interference between the antibody and ADC cytotoxin.

In ADC linker design, the azide-PFP combination enables site-specific payload attachment and controlled drug-to-antibody ratios (DAR). The PEG2 segment provides flexibility, supporting efficient payload conjugation while maintaining antibody-antigen binding and ADC stability.

Azido-PEG2-PFP ester is compatible with a variety of cytotoxic payloads, including auristatins and maytansinoids. Its chemical stability under physiological conditions ensures that ADC payloads remain attached until reaching the target tumor environment.

This linker is commonly applied in ADC research for constructing conjugates with predictable pharmacokinetics, controlled payload release, and reliable antibody conjugation. Its combination of bioorthogonal reactivity and PEG2 flexibility supports diverse ADC design strategies.

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. 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.
3. 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.

What is Azido-PEG2-PFP ester and its purpose in ADC synthesis?

Azido-PEG2-PFP ester is a pentafluorophenyl ester-functionalized PEG linker with an azide group, used for selective conjugation to antibodies or payloads. The PFP ester improves reactivity with amines, and the azide enables SPAAC click chemistry.

15/9/2020

Dear BOC Sciences, how does Azido-PEG2-PFP ester enable site-specific ADC conjugation?

The azide group reacts with cyclooctyne-functionalized molecules via strain-promoted azide-alkyne cycloaddition, allowing copper-free, site-specific conjugation, while the PFP ester reacts efficiently with primary amines to attach payloads.

7/12/2018

Dear BOC Sciences, which types of payloads can be conjugated using this linker?

Azido-PEG2-PFP ester can conjugate cytotoxins, peptides, and imaging probes. Its PEG2 spacer increases hydrophilicity, flexibility, and reduces steric hindrance, improving ADC pharmacokinetics and solubility.

9/10/2016

Good afternoon! Could you kindly share the recommended storage conditions for Azido-PEG2-PFP ester?

Store the compound in anhydrous solvents at low temperature (-20°C), protected from light and moisture, to maintain ester reactivity and prevent azide decomposition prior to conjugation.

23/4/2022

Dear BOC Sciences, what is the recommended handling procedure for Azido-PEG2-PFP ester to ensure safe usage?

Azido-PEG2-PFP ester should be handled in a well-ventilated laboratory with appropriate personal protective equipment. Avoid contact with heat and open flames. Storage in a cool, dry, and dark environment is advised, and the compound should be used promptly after opening to prevent hydrolysis or degradation.

1/8/2022

— Dr. Jonathan White, Medicinal Chemist (UK)

Azido-PEG2-PFP ester enabled highly efficient click chemistry conjugation in our ADC research.

9/10/2016

— Ms. Clara Hoffmann, Biochemist (Germany)

Excellent batch-to-batch reproducibility allowed seamless integration of Azido-PEG2-PFP ester into our workflow.

1/8/2022

— Dr. William Parker, Senior Scientist (USA)

Solubility and reactivity were outstanding, facilitating multi-step conjugation reactions.

23/4/2022

— Prof. Olivia Martinez, Bioconjugation Scientist (USA)

Azido-PEG2-PFP ester enabled rapid bioconjugation reactions with high efficiency. The product consistency was excellent.

15/9/2020

— Mr. Noah Brown, Bioconjugation Specialist (Canada)

QC documentation provided by BOC Sciences supported regulatory compliance and smooth ADC development.

— Dr. Richard Evans, Bioconjugation Scientist (USA)

The Azido-PEG2-PFP ester arrived with comprehensive quality documentation. Its high reactivity facilitated rapid bioconjugation in our workflow without side reactions.

7/12/2018

The molarity calculator equation

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

The dilution calculator equation

Concentration (start) × Volume (start) = Concentration (final) × Volume (final)

This equation is commonly abbreviated as: C1V1 = C2V2

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