Host–guest interactions in tetramethyl-cucurbit[6]uril with anti-tuberculosis drug isoniazid

•Our studies represent an important strategy to manipulate physicochemical properties of pharmaceutical agents by host-guest interactions.•A supramolecular strategy was used to chemically investigate the binding behaviours of the host TMeQ[6] with the guest INH.•The first example of structurally characterized cucurbit[n]uril-isoniazid host-guest complexes.

A novel supramolecular host–guest complex of anti-tuberculosis drug isoniazid (INH) with symmetrical α,α′,δ,δ′-tetramethyl-cucurbit[6]uril (TMeQ[6]) has been investigated using 1H NMR spectroscopy methods, mass spectrometer and single-crystal X-ray diffraction analysis. The result revealed that the INH guest is located the portal of the TMeQ[6] host in both the solutions and the solid state. The driving forces for the association between the guest INH and the host TMeQ[6] are made by a balance between hydrogen bonding interactions and ion-dipole interactions.

Graphical abstractA novel supramolecular host–guest complex of anti-tuberculosis drug isoniazid (INH) with symmetrical α,α′,δ,δ′-tetramethyl-cucurbit[6]uril (TMeQ[6]) has been investigated using 1H NMR spectroscopy methods, mass spectrometer and single-crystal X-ray diffraction analysis. The result revealed that the INH guest is located the portal of the TMeQ[6] host in both the solutions and the solid state.Figure optionsDownload full-size imageDownload as PowerPoint slide