Name: perfluorophenyl 1-(1,3-dioxoisoindolin-2-yloxy)-3,6,9,12-tetraoxapentadecan-15-oate
Brand: BOC Sciences
Rating: 5 (1 reviews)

Synonyms

PFP-PEG4-1,3-dioxoisoindolin-2-yloxyisoindoline-1,3-dione;

Appearance

Soild powder

Perfluorophenyl 1-(1,3-dioxoisoindolin-2-yloxy)-3,6,9,12-tetraoxapentadecan-15-oate is a highly specialized ADC linker designed for the construction of advanced antibody-drug conjugates (ADCs) and targeted bioconjugation applications. As an efficient ADC linker, it enables precise conjugation between monoclonal antibodies and diverse ADC cytotoxins, facilitating controlled delivery of payloads to tumor cells. Its chemical structure features a perfluorophenyl ester for reactive conjugation and a phthalimide-protected tetraethylene glycol spacer, providing both aqueous solubility and flexibility in linker design. In ADC linker design, this compound allows modular bioconjugation strategies that maintain antibody functionality while supporting controlled intracellular release of ADC payloads in the tumor microenvironment.

In the context of ADC payload development, this linker shows compatibility with a broad range of cytotoxic agents, including microtubule inhibitors, DNA-targeting drugs, and other potent ADC payloads. The perfluorophenyl ester enables efficient and site-specific reaction with primary amine groups on antibodies, facilitating reproducible linker attachment and homogeneous ADC construction. Its tetraethylene glycol spacer provides optimal flexibility and reduces steric hindrance, supporting stable conjugation and improving pharmacokinetic properties. By using this ADC linker, researchers can achieve precise control over payload attachment, release kinetics, and antibody integrity, enhancing the overall performance of targeted therapies.

From an application perspective, this linker is widely utilized in oncology-focused ADC research, bioconjugation studies, and targeted drug delivery systems. Its chemical versatility allows the design of cleavable or non-cleavable ADC linker strategies tailored to therapeutic objectives. The linker’s predictable reactivity and solubility enable efficient conjugation under mild conditions, maintaining antibody functionality and ensuring efficient intracellular payload release. The combination of site-specific reactivity, aqueous compatibility, and structural flexibility makes this linker a valuable tool for constructing next-generation antibody-drug conjugates with high tumor specificity and optimized therapeutic outcomes.

1. Dynamic light scattering as an efficient tool to study glyconanoparticle-lectin interactions

Olof Ramström, Mingdi Yan, Xin Wang Analyst . 2011 Oct 21;136(20):4174-8. doi: 10.1039/c1an15469a.

Glyconanomaterials, an emerging class of bio-functional nanomaterials, have shown promise in detecting, imaging and targeting proteins, bacteria, and cells. In this article, we report that dynamic light scattering (DLS) can be used as an efficient tool to study glyconanoparticle (GNP)--lectin interactions. Silica and Au nanoparticles (NPs) conjugated with D-mannose (Man) and D-galactose (Gal) were treated with the lectins Concanavalin A (Con A) and Ricinus communis agglutinin (RCA(120)), and the hydrodynamic volumes of the resulting aggregates were measured by DLS. The results showed that the particle size grew with increasing lectin concentration. The limit of detection (LOD) was determined to be 2.9 nM for Con A with Man-conjugated and 6.6 nM for RCA(120) with Gal-conjugated silica NPs (35 nm), respectively. The binding affinity was also determined by DLS and the results showed 3-4 orders of magnitude higher affinity of GNPs than the free ligands with lectins. The assay sensitivity and affinity were particle size dependent and decreased with increasing particle diameter. Because the method relies on the particle size growth, it is therefore general and can be applied to nanomaterials of different compositions.

2. Fluorinated indazoles as novel selective inhibitors of nitric oxide synthase (NOS): synthesis and biological evaluation

Marta Pérez-Torralba, Carlos Pérez-Medina, Germaine Escames, Rosa M Claramunt, Concepción López, José Elguero, Darío Acuña-Castroviejo Bioorg Med Chem . 2009 Sep 1;17(17):6180-7. doi: 10.1016/j.bmc.2009.07.067.

In order to find new compounds with neuroprotective activity and NOS-I/NOS-II selectivity, we have designed, synthesized, and characterized 14 new NOS inhibitors with an indazole structure. The first group corresponds to 4,5,6,7-tetrahydroindazoles (4-8), the second to the N-methyl derivatives (9-12) of 7-nitro-1H-indazole (1) and 3-bromo-7-nitro-1H-indazole (2), and the latter to 4,5,6,7-tetrafluoroindazoles (13-17). Compound 13 (4,5,6,7-tetrafluoro-3-methyl-1H-indazole) inhibited NOS-I by 63% and NOS-II by 83%. Interestingly, compound 16 (4,5,6,7-tetrafluoro-3-perfluorophenyl-1H-indazole) inhibited NOS-II activity by 80%, but it did not affect to NOS-I activity. Structural comparison between these new indazoles further supports the importance of the aromatic indazole skeleton for NOS inhibition and indicate that bulky groups or N-methylation of 1 and 2 diminish their effect on NOS activity. The fluorination of the aromatic ring increased the inhibitory potency and NOS-II selectivity, suggesting that this is a promising strategy for NOS selective inhibitors.

3. Room temperature amine sensors enabled by sidewall functionalization of single-walled carbon nanotubes

Timothy M Swager, Fabio Di Francesco, Andrea Pucci, Maggie He, Matteo Mannini, Bernardo Melai, Brunetto Cortigiani, Francesca G Bellagambi, Pietro Salvo, Clara Paoletti, Nicola Calisi RSC Adv . 2018;8(10):5578-5585. doi: 10.1039/C7RA13304A.

A new series of sidewall modified single-walled carbon nanotubes (SWCNTs) with perfluorophenyl molecules bearing carboxylic acid or methyl ester moieties are herein reported. Pristine and functionalized SWCNTs (p-SWCNTs and f-SWCNTs, respectively) were characterized by X-ray photoelectron spectroscopy (XPS), Raman spectroscopy and scanning electron microscopy (SEM). The nitrene-based functionalization provided intact SWCNTs with methyl 4-azido-2,3,5,6-tetrafluorobenzoate (SWCNT-N-C6F4CO2CH3) and 4-azido-2,3,5,6-tetrafluorobenzoic acid (SWCNT-N-C6F4CO2H) attached every 213 and 109 carbon atoms, respectively. Notably, SWCNT-N-C6F4CO2H was sensitive in terms of the percentage of conductance variation from 5 to 40 ppm of ammonia (NH3) and trimethylamine (TMA) with a two-fold higher variation of conductance compared to p-SWCNTs at 40 ppm. The sensors are highly sensitive to NH3and TMA as they showed very low responses (0.1%) toward 200 ppm of volatile organic compounds (VOCs) containing various functional groups representative of different classes of analytes such as benzene, tetrahydrofurane (THF), hexane, ethyl acetate (AcOEt), ethanol, acetonitrile (CH3CN), acetone and chloroform (CHCl3). Our system is a promising candidate for the realization of single-use chemiresistive sensors for the detection of threshold crossing by low concentrations of gaseous NH3and TMA at room temperature.

Catalog	Product Name	CAS
BADC-00487	perfluorophenyl 3-(pyridin-2-yldisulfanyl)propanoate	160580-70-1
BADC-00426	Perfluorophenyl 2-(cyclooct-2-ynyloxy)acetate	886209-60-5
BADC-00468	perfluorophenyl 4-methyl-4-(pyridin-2-yldisulfanyl)pentanoate
BADC-00481	perfluorophenyl 4-(pyridin-2-yldisulfanyl)butanoate
BADC-00385	perfluorophenyl 3-(2-(2-(2-(1,3-dioxoisoindolin-2-yloxy)ethoxy)ethoxy)ethoxy)propanoate
BADC-00387	perfluorophenyl 3-(2-(2-(1,3-dioxoisoindolin-2-yloxy)ethoxy)ethoxy)propanoate
BADC-00400	perfluorophenyl 3-(2-(2-(4-formylbenzamido)ethoxy)ethoxy)propanoate
BADC-00402	perfluorophenyl 3-(2-(4-formylbenzamido)ethoxy)propanoate
BADC-00420	perfluorophenyl 1-(cyclooct-2-ynyloxy)-2-oxo-6,9,12,15-tetraoxa-3-azaoctadecan-18-oate
BADC-00422	perfluorophenyl 1-(cyclooct-2-ynyloxy)-2-oxo-6,9,12-trioxa-3-azapentadecan-15-oate

What is perfluorophenyl 1-(1,3-dioxoisoindolin-2-yloxy)-3,6,9,12-tetraoxapentadecan-15-oate and its function in ADC synthesis?

This bifunctional linker contains a perfluorophenyl ester and a phthalimide-protected amino group. It enables selective conjugation to amines on antibodies and provides a PEG-based spacer to improve solubility and flexibility of ADCs.

15/9/2021

Could you explain how this linker enhances ADC properties?

The PEG spacer reduces steric hindrance and aggregation, improving solubility and pharmacokinetics. The perfluorophenyl ester provides efficient amine coupling, allowing controlled payload attachment while preserving antibody function.

8/7/2019

We would like to know which payloads are compatible with this linker.

It can conjugate amine-containing cytotoxins, peptides, and fluorophores. The PEG-based structure maintains ADC solubility and facilitates site-specific payload attachment for improved therapeutic performance.

12/2/2020

Could you please advise the recommended conjugation conditions?

Conjugation is typically performed in slightly basic organic-aqueous solvents (pH 7–8.5) at mild temperatures to ensure perfluorophenyl ester reactivity while maintaining antibody and payload stability.

20/9/2021

Good afternoon! What are the recommended handling and storage procedures for perfluorophenyl 1-(1,3-dioxoisoindolin-2-yloxy)-3,6,9,12-tetraoxapentadecan-15-oate?

This product should be stored in a cool, dry environment, protected from light and moisture. Handling requires gloves and protective equipment to avoid hydrolysis or degradation. Inert gas or vacuum-sealed storage is recommended for long-term stability. Supporting documentation provides detailed guidelines.

5/7/2022

— Dr. Oliver Brown, Senior Scientist (UK)

This PFP ester showed excellent stability and reactivity for PEG-based linker conjugations.

12/2/2020

— Ms. Clara Weber, Biochemist (Germany)

High purity facilitated smooth integration into complex multi-step syntheses.

5/7/2022

— Dr. Ethan Parker, Medicinal Chemist (USA)

The reagent performed consistently, yielding reproducible results in all trials.

20/9/2021

— Dr. Sophie Moreau, Senior Scientist (France)

We observed minimal side reactions and high conjugation efficiency.

15/9/2021

— Dr. Liam Fischer, Chemist (UK)

The extended PEG chain allowed improved solubility and flexibility for our ADC constructs.

— Ms. Clara Müller, Medicinal Chemist (Germany)

This perfluorophenyl ester showed high purity and consistent performance in our conjugation experiments. BOC Sciences provided detailed handling instructions.

8/7/2019