BCN-endo-PEG2-maleimide - CAS 2675364-08-4

BCN-endo-PEG2-maleimide - CAS 2675364-08-4 Catalog number: BADC-01805

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BCN-endo-PEG2-maleimide is an ADC linker containing 4 PEG units.

Category
ADCs Linker
Product Name
BCN-endo-PEG2-maleimide
CAS
2675364-08-4
Catalog Number
BADC-01805
Molecular Formula
C24H33N3O7
Molecular Weight
475.53

Ordering Information

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Description
BCN-endo-PEG2-maleimide is an ADC linker containing 4 PEG units.
Synonyms
BCN-exo-PEG2-maleimide
IUPAC Name
[(1R,8S)-9-bicyclo[6.1.0]non-4-ynyl]methyl N-[2-[2-[2-[3-(2,5-dioxopyrrol-1-yl)propanoylamino]ethoxy]ethoxy]ethyl]carbamate
Canonical SMILES
C1CC2C(C2COC(=O)NCCOCCOCCNC(=O)CCN3C(=O)C=CC3=O)CCC#C1
InChI
InChI=1S/C24H33N3O7/c28-21(9-12-27-22(29)7-8-23(27)30)25-10-13-32-15-16-33-14-11-26-24(31)34-17-20-18-5-3-1-2-4-6-19(18)20/h7-8,18-20H,3-6,9-17H2,(H,25,28)(H,26,31)/t18-,19+,20?
InChIKey
WOCRQFMPRIJWEQ-YOFSQIOKSA-N

BCN-endo-PEG2-maleimide, a bifunctional molecule, exhibits several critical applications in biochemical and pharmaceutical research. One of its key applications is in the site-specific conjugation of proteins and peptides. The combination of BCN and maleimide functionalities allows for selective and efficient conjugation workflows. The BCN group reacts with azides through copper-free click chemistry, which is especially advantageous in biological settings due to its bioorthogonality and speed. Meanwhile, the maleimide group reacts specifically with thiol groups on cysteine residues, enabling selective attachment to proteins or peptides containing these groups. This dual reactivity makes BCN-endo-PEG2-maleimide a powerful tool in creating antibody-drug conjugates (ADCs), labeling proteins for imaging, or crosslinking proteins to study complex interactions.

Another prominent application of BCN-endo-PEG2-maleimide is in drug delivery systems. The PEG2 spacer in the molecule offers improved solubility and reduced immunogenicity, which are critical factors in pharmaceutical formulations. By attaching therapeutic agents to the maleimide end and targeting ligands to the BCN end, researchers can develop sophisticated drug delivery vehicles that ensure the precise delivery of drugs to specific cellular targets. This versatility in conjugation allows for the construction of nanoparticles, liposomes, and other carrier systems that can navigate the complex biological environments found in the human body. The PEGylation not only enhances the stability of these drug delivery systems but also prolongs their circulation time in the bloodstream, thereby reducing the frequency of dosing and potentially improving patient compliance.

BCN-endo-PEG2-maleimide also plays a crucial role in the development of diagnostic tools. Its ability to conjugate with a wide range of biomolecules makes it an invaluable reagent in the creation of probes for imaging techniques such as fluorescence microscopy and magnetic resonance imaging (MRI). For instance, by linking imaging agents to biomolecules using BCN-endo-PEG2-maleimide, researchers can develop highly specific and sensitive diagnostic probes that target molecular markers associated with diseases such as cancer. These probes can help visualize the distribution and dynamics of the biomarkers within living organisms, providing detailed insights into disease progression and response to treatment. The specificity and stability afforded by the PEG linkage ensure that these diagnostic tools provide accurate and reliable results, paving the way for earlier and more precise disease detection.

Finally, BCN-endo-PEG2-maleimide is instrumental in the field of surface modification and biomaterials. Its bifunctional nature allows it to act as a linker between biomolecules and a variety of surfaces, including metals, polymers, and nanoparticles. This facilitates the creation of biofunctionalized surfaces for applications such as biosensors, where the immobilization of enzymes or antibodies on sensor surfaces is critical for their function. Moreover, the PEG2 spacer reduces nonspecific binding and increases the biocompatibility of the modified surfaces, making them suitable for use in medical devices and implants. By tethering proteins, peptides, or other bioactive molecules to surfaces via BCN-endo-PEG2-maleimide, researchers can design interfaces that interact predictably and efficiently with biological systems, enhancing the performance and reliability of these applications.

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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