Name: BCN-exo-PEG7-maleimide
Brand: BOC Sciences
Rating: 5 (1 reviews)

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Synonyms

5,8,11,14,17,20,23-Heptaoxa-2,26-diazanonacosanoic acid, 29-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)-27-oxo-, (1R,8S)-bicyclo[6.1.0]non-4-yn-9-ylmethyl ester, rel-

IUPAC Name

9-bicyclo[6.1.0]non-4-ynylmethyl N-[2-[2-[2-[2-[2-[2-[2-[2-[3-(2,5-dioxopyrrol-1-yl)propanoylamino]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethyl]carbamate

Canonical SMILES

C1CC2C(C2COC(=O)NCCOCCOCCOCCOCCOCCOCCOCCNC(=O)CCN3C(=O)C=CC3=O)CCC#C1

InChI

InChI=1S/C34H53N3O12/c38-31(9-12-37-32(39)7-8-33(37)40)35-10-13-42-15-17-44-19-21-46-23-25-48-26-24-47-22-20-45-18-16-43-14-11-36-34(41)49-27-30-28-5-3-1-2-4-6-29(28)30/h7-8,28-30H,3-6,9-27H2,(H,35,38)(H,36,41)

InChIKey

KLGLXRNSORBLCE-UHFFFAOYSA-N

Density

1.23±0.1 g/cm3

Boiling Point

821.1±65.0 °C at 760 mmHg

BCN-exo-PEG7-maleimide is widely used in the field of bioconjugation, where it serves as a crosslinker between biomolecules. Its maleimide group specifically reacts with thiol groups, typically found in cysteine residues of proteins or peptides. This reaction forms a stable thioether bond, ensuring that the conjugation is robust and durable. The BCN (bicyclo[6.1.0]nonyne) group can bind to azide-functionalized molecules through strain-promoted alkyne-azide cycloaddition (SPAAC), a copper-free “click” chemistry reaction. This dual reactivity makes BCN-exo-PEG7-maleimide a valuable tool for attaching diverse biomolecules in a controlled and efficient manner.

Another crucial application of BCN-exo-PEG7-maleimide is in the development of drug delivery systems. By attaching therapeutic agents to nanoparticles or other delivery vehicles using this linker, the drugs can be more effectively targeted to specific tissues or cells. The PEG (polyethylene glycol) spacer enhances the solubility and biocompatibility of the conjugate, reducing potential immunogenicity and increasing circulation time in the body. This can lead to improved therapeutic outcomes and reduced side effects, as the drug is delivered more precisely to its intended site.

BCN-exo-PEG7-maleimide is also instrumental in the field of diagnostics. It can be used to conjugate imaging agents or probes to targeting molecules, such as antibodies or peptides, that specifically bind to biomarkers of diseases. For instance, in cancer diagnostics, this linker can help create conjugates that selectively accumulate in tumor cells, allowing for enhanced imaging clarity and early detection. The biocompatibility and specificity provided by BCN-exo-PEG7-maleimide conjugation are crucial for developing accurate and reliable diagnostic tools.

Lastly, BCN-exo-PEG7-maleimide finds significant usage in the creation of bioactive surfaces and materials. By modifying surfaces of polymers, hydrogels, or other materials with bioactive molecules using this linker, researchers can generate functionalized surfaces with specific biological activities. These modified surfaces can promote cell adhesion, growth, and differentiation, making them invaluable in tissue engineering and regenerative medicine. The ability to precisely control the presentation and density of bioactive molecules on surfaces facilitates the development of sophisticated biomaterials that can mimic natural tissue environments.