Global InformationBicyclononyne information
 | This article's factual accuracy is disputed. (August 2022) |
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| IUPAC name
bicyclo[6.1.0]non-4-yne
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3D model (JSmol)
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Chemical formula
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C9H12 |
| Molar mass | 120.195 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
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BCN, also known as bicyclo[6.1.0]non-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.[1] 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.[2] 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.[3]
- ^ 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.
- ^ 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.
- ^ 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.