TY - JOUR A1 - Castiglione, Franca A1 - Ganazzoli, Fabio A1 - Malpezzi, Luciana A1 - Mele, Andrea A1 - Panzeri, Walter A1 - Raffaini, Giuseppina T1 - Inclusion complexes of β-cyclodextrin with tricyclic drugs: an X-ray diffraction, NMR and molecular dynamics study JF - Beilstein Journal of Organic Chemistry PY - 2017/// VL - 13 SP - 714 EP - 719 SN - 1860-5397 DO - 10.3762/bjoc.13.70 PB - Beilstein-Institut JA - Beilstein J. Org. Chem. UR - https://doi.org/10.3762/bjoc.13.70 KW - amitriptyline KW - β-cyclodextrin KW - crystal structure KW - cyclobenzaprine KW - molecular dynamics simulations KW - NOE N2 - Tricyclic fused-ring cyclobenzaprine (1) and amitriptyline (2) form 1:1 inclusion complexes with β-cyclodextrin (β-CD) in the solid state and in water solution. Rotating frame NOE experiments (ROESY) showed the same geometry of inclusion for both 1/β-CD and 2/β-CD complexes, with the aromatic ring system entering the cavity from the large rim of the cyclodextrin and the alkylammonium chain protruding out of the cavity and facing the secondary OH rim. These features matched those found in the molecular dynamics (MD) simulations in solution and in the solid state from single-crystal X-ray diffraction of 1/β-CD and 2/β-CD complexes. The latter complex was found in a single conformation in the solid state, whilst the MD simulations in explicit water reproduced the conformational transitions observed experimentally for the free molecule. ER -