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BCN-PEG3-VC-PFP ester

  CAS No.: 2353409-45-5   Cat No.: BADC-01096   Purity: >98.0% 4.5  

BCN-PEG3-VC-PFP ester is a cleavable ADC linker with BCN for strain-promoted cycloaddition and Val-Cit dipeptide for enzymatic payload release, activated as PFP ester for amine coupling in ADC synthesis.

BCN-PEG3-VC-PFP ester

Structure of 2353409-45-5

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Category
ADC Linker
Molecular Formula
C37H50F5N5O10
Molecular Weight
819.81
Shipping
Room temperature
Storage
Store at -20 °C, keep in dry and avoid sunlight.

* For research and manufacturing use only. We do not sell to patients.

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Capabilities & Facilities

Popular Publications Citing BOC Sciences Products
IUPAC Name
Canonical SMILES
CC(C)C(C(=O)NC(CCCNC(=O)N)C(=O)OC1=C(C(=C(C(=C1F)F)F)F)F)NC(=O)CCOCCOCCOCCNC(=O)OCC2C3C2CCC#CCC3
InChI
InChI=1S/C37H50F5N5O10/c1-21(2)32(34(49)46-25(10-7-12-44-36(43)51)35(50)57-33-30(41)28(39)27(38)29(40)31(33)42)47-26(48)11-14-53-16-18-55-19-17-54-15-13-45-37(52)56-20-24-22-8-5-3-4-6-9-23(22)24/h21-25,32H,5-20H2,1-2H3,(H,45,52)(H,46,49)(H,47,48)(H3,43,44,51)/t22-,23+,24?,25-,32-/m0/s1
InChIKey
ODFSIYMVJDIAIS-COWKONOXSA-N
Solubility
10 mm in DMSO
Appearance
Solid
Shelf Life
-20°C 3 years powder; -80°C 2 years in solvent
Shipping
Room temperature
Storage
Store at -20 °C, keep in dry and avoid sunlight.
Form
Solid

BCN-PEG3-VC-PFP ester, a versatile chemical reagent, plays a pivotal role in bioconjugation and drug delivery applications. Here are four key applications of BCN-PEG3-VC-PFP ester presented with high perplexity and burstiness:

Drug Delivery Systems: In the realm of drug delivery, BCN-PEG3-VC-PFP ester serves as a cornerstone in crafting targeted delivery systems. By conjugating drugs with polyethylene glycol (PEG), the ester elevates drug solubility, stability, and half-life in the circulation. This augmentation enhances therapeutic agent efficacy while mitigating adverse effects, marking a paradigm shift in drug delivery precision.

Proteomics: Embarking on a journey through proteomics, BCN-PEG3-VC-PFP ester emerges as a critical tool for protein labeling and crosslinking. The PEG3 spacer, with its inherent flexibility, bridges and spaces linked proteins, facilitating intricate protein interaction investigations.

Biomaterials: Venturing into biomaterial modification, BCN-PEG3-VC-PFP ester plays a pivotal role in enhancing biocompatibility and functionality. By grafting PEG onto surfaces such as medical implants or tissue engineering scaffolds, the ester enhances hydrophilicity and reduces nonspecific protein binding. This transformative process fuels the development of next-generation biomaterials with bespoke properties tailored for diverse medical applications.

Chemical Biology: Diving into the depths of chemical biology, the BCN-PEG3-VC-PFP ester emerges as a catalyst for creating clickable bioconjugates through strain-promoted alkyne-azide cycloaddition (SPAAC). This bioorthogonal reaction paves the way for labeling biomolecules in live cells without disrupting native biochemical processes.

What is the key advantage of using the BCN-PEG3-VC-PFP ester linker?

The primary advantage of BCN-PEG3-VC-PFP ester lies in its azide-alkyne click chemistry capability. The BCN (Bicyclo[6.1.0]nonyne) group allows for a copper-free click reaction with an azide-modified antibody. This bioorthogonal conjugation method is highly efficient and selective, enabling precise control over the drug-to-antibody ratio (DAR) and facilitating the creation of homogeneous ADCs.

5/1/2017

Could you explain how the PFP ester functions in the conjugation process of BCN-PEG3-VC-PFP ester?

The pentafluorophenyl (PFP) ester in BCN-PEG3-VC-PFP ester is an activated ester designed to react with a primary amine. This allows for conjugation of the linker to an amine-containing payload or other molecule. The PFP ester's high reactivity ensures efficient and clean coupling under mild conditions, which is essential for maintaining the integrity of both the payload and the linker during the synthesis process.

27/9/2017

We are interested in what is the purpose of the VC-PFP ester component in the linker.

The valine-citrulline (VC) dipeptide, followed by the PFP ester, serves as a cleavable moiety in BCN-PEG3-VC-PFP ester. The VC dipeptide is a well-established substrate for lysosomal proteases like cathepsin B. This design ensures that after the ADC is internalized by the target cell, the linker is cleaved, releasing the drug payload. The PFP ester is for conjugation to the payload.

5/6/2019

Good morning! How does the PEG3 spacer in BCN-PEG3-VC-PFP ester contribute to ADC properties?

The PEG3 spacer in BCN-PEG3-VC-PFP ester is a short, hydrophilic chain that improves the solubility of the linker-payload conjugate. This hydrophilic nature helps to mitigate the aggregation often caused by the hydrophobic nature of many cytotoxic payloads. The PEG spacer thus contributes to the overall stability and pharmacokinetics of the final ADC product.

29/9/2017

Dear team, what are the recommended storage and handling conditions for BCN-PEG3-VC-PFP ester?

BCN-PEG3-VC-PFP ester should be stored at -20°C in a dry, inert atmosphere, shielded from light. Avoid repeated freeze-thaw cycles. Aliquoting is advised to maintain the active PFP ester functionality, ensuring consistent and efficient conjugation during antibody-drug conjugate preparation.

7/11/2019

— Dr. Emily Carter, Senior Scientist (USA)

BCN-PEG3-VC-PFP ester showed excellent reactivity and solubility, improving conjugation efficiency.

5/6/2019

— Prof. David Müller, Medicinal Chemist (Germany)

The PFP ester functionality in BCN-PEG3-VC-PFP ester enabled rapid and clean conjugation.

7/11/2019

— Dr. Anna Rossi, Bioconjugation Specialist (Italy)

BOC Sciences’ BCN-PEG3-VC-PFP ester was delivered on schedule with high analytical quality.

29/9/2017

— Mr. James Thompson, R&D Manager (UK)

Using BCN-PEG3-VC-PFP ester, we observed minimal side reactions and reproducible yields.

5/1/2017

— Dr. Laura Jensen, ADC Project Lead (Denmark)

Excellent solubility and batch consistency of BCN-PEG3-VC-PFP ester enabled smooth ADC screening.

— Ms. Sophie Martin, Senior Researcher (France)

The product facilitated high-throughput conjugation efficiently. Overall quality is outstanding.

27/9/2017

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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