title: Supramolecular structures based on regioisomers of cinnamyl-α-cyclodextrins - new media for capillary separation techniques.
abstract: This work focuses on the preparation and application of supramolecular structures based on mono-cinnamyl-α-cyclodextrins (Cin-α-CD). Pure regioisomers of Cin-α-CD having the cinnamyl moiety at the 2-O- or at the 3-O-position, respectively, were prepared, characterized and applied in capillary electrophoresis as additives to the background electrolyte. These new monomer units with a potential to self-organize into supramolecular structures were synthesized via a straightforward one-step synthetic procedure and purified using preparative reversed-phase chromatography allowing a large scale separation of the regioisomers. The ability of the monomers to self-assemble was proved by various methods including NMR spectroscopy and dynamic light scattering (DLS). The light scattering experiments showed that the monomer units have distinguishable ability to form supramolecular structures in different solvents and the size distribution of the aggregates in water can be easily modulated using different external stimuli, such as temperature or competitive guest molecules. The obtained results indicated that the two regioisomers of Cin-α-CD formed different supramolecular assemblies highlighting the fact that the position of the cinnamyl group plays an important role in the intermolecular complex formation.
authors.affiliation: Department of Organic Chemistry, Faculty of Science, Charles University in Prague, Hlavova 8, 128 43, Prague 2, Czech Republic; CycloLab, Cyclodextrin R&D Ltd, Budapest, H-1097 Illatos út 7, Hungary.
authors.forename: Gabor
authors.initials: G
authors.lastname: Benkovics
authors.affiliation: Department of Analytical Chemistry, Faculty of Science, Charles University in Prague, Hlavova 8, 128 43, Prague 2, Czech Republic.
authors.forename: Ondrej
authors.initials: O
authors.lastname: Hodek
authors.affiliation: Department of Analytical Chemistry, Faculty of Science, Charles University in Prague, Hlavova 8, 128 43, Prague 2, Czech Republic.
authors.forename: Martina
authors.initials: M
authors.lastname: Havlikova
authors.affiliation: Department of Analytical Chemistry, Faculty of Science, Charles University in Prague, Hlavova 8, 128 43, Prague 2, Czech Republic.
authors.forename: Zuzana
authors.initials: Z
authors.lastname: Bosakova
authors.affiliation: Department of Analytical Chemistry, Faculty of Science, Charles University in Prague, Hlavova 8, 128 43, Prague 2, Czech Republic.
authors.forename: Pavel
authors.initials: P
authors.lastname: Coufal
authors.affiliation: CycloLab, Cyclodextrin R&D Ltd, Budapest, H-1097 Illatos út 7, Hungary.
authors.forename: Milo
authors.initials: M
authors.lastname: Malanga
authors.affiliation: CycloLab, Cyclodextrin R&D Ltd, Budapest, H-1097 Illatos út 7, Hungary.
authors.forename: Eva
authors.initials: E
authors.lastname: Fenyvesi
authors.affiliation: Department of Pharmacognosy, Semmelweis University, Budapest, H-1085 Üllői út 26, Hungary.
authors.forename: Andras
authors.initials: A
authors.lastname: Darcsi
authors.affiliation: Department of Pharmacognosy, Semmelweis University, Budapest, H-1085 Üllői út 26, Hungary.
authors.forename: Szabolcs
authors.initials: S
authors.lastname: Beni
authors.affiliation: Department of Organic Chemistry, Faculty of Science, Charles University in Prague, Hlavova 8, 128 43, Prague 2, Czech Republic.
authors.forename: Jindrich
authors.initials: J
authors.lastname: Jindrich
keywords: capillary electrophoresis; cyclodextrin derivatives; mono-cinnamyl; regioisomers; supramolecular structures