TY - JOUR
TI - Molecular, crystal and solution structure of a beta-cyclodextrin complex
with the bromide salt of
2-(3-dimethylaminopropyl)tricyclo[3.3.1.1(3,7)]decan-2-ol, a potent
antimicrobial drug
AU - Perrakis, A
AU - Antoniadou-Vyza, E
AU - Tsitsa, P
AU - Lamzin, VS and
AU - Wilson, KS
AU - Hamodrakas, SJ
JO - Carbohydrate Research
PY - 1999
VL - 317
TODO - 1-4
SP - 19-28
PB - Elsevier Sci Ltd, Exeter, United Kingdom
SN - 0008-6215
TODO - 10.1016/S0008-6215(99)00021-X
TODO - beta-cyclodextrin; antimicrobial drug; X-ray crystallography; NMR; ab
initio structure solution; synchrotron radiation
TODO - The pharmacological properties of a cyclomaltoheptaose
(beta-cyclodextrin) series of adamantane-group-bearing compounds that
exhibit potent antibacterial activity have been studied, both isolated
and in complex with beta-cyclodextrins (beta CDs). In this work, the
structure of the bromide salt of
2-(3-dimethylaminopropyl)-tricyclo[3.3.1.1(3.7)]decan-2-ol (ADM-10)
complexed with beta CD and ten water molecules was studied in the solid
state by X-ray crystallography and in solution by NMR spectroscopy.
X-ray crystallographic studies of the complex were performed both at
room and cryogenic temperatures. The long aliphatic chain of ADM-10
adopts a single conformation at low temperature in contrast to what is
observed at room temperature, where two side chain conformations are
seen. Both NMR and X-ray crystallography studies indicate that the
adamantane moiety of ADM-10 is buried in the beta CB cavity. Chemical
shifts in NMR experiments can be explained on the basis of the crystal
structure of the complex. (C) 1999 Elsevier Science Ltd. All rights
reserved.
ER -