title: Synthesis of uniform cyclodextrin thioethers to transport hydrophobic drugs.
abstract: Methyl and ethyl thioether groups were introduced at all primary positions of α-, β-, and γ-cyclodextrin by nucleophilic displacement reactions starting from the corresponding per-(6-deoxy-6-bromo)cyclodextrins. Further modification of all 2-OH positions by etherification with iodo terminated triethylene glycol monomethyl ether (and tetraethylene glycol monomethyl ether, respectively) furnished water-soluble hosts. Especially the β-cyclodextrin derivatives exhibit very high binding potentials towards the anaesthetic drugs sevoflurane and halothane. Since the resulting inclusion compounds are highly soluble in water at temperatures ≤37 °C they are good candidates for new aqueous dosage forms which would avoid inhalation anaesthesia.
authors.affiliation: Organic Macromolecular Chemistry, Saarland University, Campus C4.2, 66123 Saarbrücken, Germany.
authors.forename: Lisa F
authors.initials: LF
authors.lastname: Becker
authors.affiliation: Organic Macromolecular Chemistry, Saarland University, Campus C4.2, 66123 Saarbrücken, Germany.
authors.forename: Dennis H
authors.initials: DH
authors.lastname: Schwarz
authors.affiliation: Organic Macromolecular Chemistry, Saarland University, Campus C4.2, 66123 Saarbrücken, Germany.
authors.forename: Gerhard
authors.initials: G
authors.lastname: Wenz
keywords: active pharmaceutical ingredient; binding constant; cyclodextrin; derivatization; gas chromatography; sevoflurane; substitution pattern