endo-BCN-PEG3-NHS ester | 2101206-94-2

Endo-BCN-PEG3-NHS ester is a chemical compound widely utilized in the field of bioconjugation. It is composed of three key components: an endo-bicyclo[6.1.0]nonyne (BCN) group, a triethylene glycol (PEG3) spacer, and an N-hydroxysuccinimide (NHS) ester. The BCN group features a strained alkyne, which facilitates rapid and selective reactions with azides through copper-free click chemistry. The PEG3 spacer enhances its solubility and provides a flexible linker that reduces steric hindrance. The NHS ester is highly reactive towards primary amines, making it an efficient means for labeling or conjugating biomolecules such as proteins and peptides. This combination of chemical features enables endo-BCN-PEG3-NHS ester to play a crucial role in various biochemical applications.

One of the key applications of endo-BCN-PEG3-NHS ester is in the development of antibody-drug conjugates (ADCs). ADCs are hybrid molecules that combine the targeting ability of monoclonal antibodies with the cytotoxicity of small molecule drugs. By using the NHS ester for conjugation, researchers can attach ADCs to target-specific antibodies, ensuring that the drug is delivered directly to cancer cells. This precision reduces off-target effects and enhances the therapeutic index of cancer treatments. The strained BCN group allows for efficient linkage with azide-tagged drugs or imaging agents, further assisting in the targeted delivery of therapeutic payloads.

Another significant application lies in the field of protein labeling and functionalization. The endo-BCN-PEG3-NHS ester enables the labeling of proteins with fluorescent dyes or biotin, allowing researchers to study protein dynamics, localization, and interaction within cells. Moreover, it facilitates the immobilization of proteins onto various surfaces for applications in biosensors or diagnostic assays. The PEG3 spacer minimizes non-specific interactions and steric hindrance, preserving the native conformation and biological activity of the proteins after conjugation.

Additionally, this compound is crucial in the development of imaging probes for biomedical research. By conjugating endo-BCN-PEG3-NHS ester to imaging agents, scientists can produce probes that are highly specific for particular biomolecules or cellular structures. These probes are beneficial in non-invasive imaging techniques like PET or MRI, offering enhanced spatial resolution and the ability to track biological processes in real-time. The BCN-azide click reaction ensures strong covalent attachment, bolstering probe stability under physiological conditions.

Lastly, endo-BCN-PEG3-NHS ester is utilized in the creation of biomaterials with tailored properties. By modifying the surfaces of polymers, hydrogels, or nanoparticles using this compound, researchers can impart specific functionalities, such as increased hydrophilicity, biocompatibility, or cell-targeting capabilities. This is particularly useful in tissue engineering and regenerative medicine, where such materials can support cell growth, differentiation, and integration within the body. The robust chemistry facilitated by the endo-BCN-PEG3-NHS ester ensures durable and stable modification of biomaterial surfaces.