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BCN, also known as bicyclonon-4-yne, is a copper-free click chemistry probe that enables highly efficient and completely orthogonal bioconjugation to complex macromolecules including peptides, nucleic acids and proteins, including monoclonal antibodies. The most recent and powerful application of this technology has been in the field of antibody-drug conjugates which results in targeted cancer therapeutics that have an improved therapeutic index, meaning they are more effective and better tolerated. BCN is well-suited for aqueous bioconjugations due to its high reactivity with its azide counterpart and its high hydrophilicity, relative to other metal-free click chemistry probes.

References

1. Dommerholt; et al. (November 2014). "Highly accelerated inverse electron-demand cycloaddition of electron-deficient azides with aliphatic cyclooctynes". Nature Communications. 5: 5378. Bibcode:2014NatCo...5.5378D. doi:10.1038/ncomms6378. hdl:2066/135700. PMID 25382411.
2. van Geel; et al. (June 2015). "Chemoenzymatic conjugation of toxic payloads to the globally conserved N-glycan of native mAbs provides homogeneous and highly efficacious antibody-drug conjugates". Bioconjugate Chemistry. 26 (11): 2233–42. doi:10.1021/acs.bioconjchem.5b00224. PMID 26061183.
3. Debets; et al. (September 2011). "Bioconjugation with strained alkenes and alkynes". Acc Chem Res. 44 (9): 805–15. doi:10.1021/ar200059z. hdl:2066/91597. PMID 21766804.

• Bicyclic compounds
• Cyclopropanes