Bicyclononyne

Last updated
Bicyclononyne
Names
IUPAC name
bicyclo[6.1.0]non-4-yne
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • Key: QDNSAFCVPAMWCJ-UHFFFAOYSA-N
  • InChI=1S/C9H12/c1-2-4-6-9-7-8(9)5-3-1/h8-9H,3-7H2
  • C1CC2CC2CCC#C1
Properties
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).
BCN, with free hydroxymethyl group Bicyclenonyne.png
BCN, with free hydroxymethyl group

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]

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.
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