Acyclic cucurbituril congener binds to local anaesthetics

Da Ma, Raymond Glassenberg, Soumyadip Ghosh, Peter Y. Zavalij, Lyle Isaacs*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

17 Scopus citations

Abstract

The recognition properties of acyclic cucurbit[n]uril (CB[n]) congener 1 towards seven local anaesthetic drugs (2-8) are reported. Job plots constructed from 1H NMR experiments confirm the 1:1 host:guest nature of these complexes, whereas the changes in chemical shift observed upon complex formation ( values) provide information about the geometry of the host-guest complexes. For complexes between host 1 and guests 2-5 and 8, a single geometry was preferred, whereas for guests 6 and 7 a mixture of two diastereomeric complexes was indicated. The K a values for complexes between 1 and 2-8 fall in the range of 10 3-10 8M 1 as determined by UV-vis and 1H NMR competition experiments. The results further establish that acyclic CB[n]-type receptor 1 is preorganised into the C-shape required for binding and that its aromatic o-xylylene walls endow it with a potency towards aromatic ammonium ions. The K a values reported in this paper constitute a blind data-set used in the SAMPL3 challenge aimed at testing computational methods relevant to proteinligand systems. The work thus highlights the great potential of CB[n] receptors as model systems to promote synergy between the supramolecular and computational chemistry communities.

Original languageEnglish (US)
Pages (from-to)325-332
Number of pages8
JournalSupramolecular Chemistry
Volume24
Issue number5
DOIs
StatePublished - May 1 2012

Keywords

  • cucurbituril
  • host-guest complexation
  • local anaesthetic
  • molecular container

ASJC Scopus subject areas

  • Chemistry(all)

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