title: Molecular and environmental factors governing non-covalent bonding interactions and conformations of phosphorous functionalized γ-cyclodextrin hydrate systems.
abstract: Recent strategies in molecular drugs-design shift efforts to nanomedicine. Large supra-molecular inclusion systems are implemented as therapeutics. The sophistication of design is based on major advances of cyclodextrins (CDs) as host molecules. They are friendly towards biological environment. CDs have good (bio)compatibility as well. CDs can form host-guest macromolecular systems incorporating small molecules with suitable shapes due to non-covalent interactions. Innovative strategies yield to polymeric nano-particles; micelles; linear polymers and/or CDs-functionalized dendrimeric nanostructures; nanofibers as well as hydrogels. Attractive are phosphorous containing (bio)matrerials, having high selectivity toward biological active molecules. The non-covalent interactions in aquatic CD-systems contribute to stability of host-guest systems under physiological conditions, determining conformational preferences of host-CD macromolecule and guest small molecular template. In this paper we have reported complementation application of mass spectrometric (MS) and quantum chemical analysis of phosphorous chemically substituted γ-cyclodextrin hydrates γ-CDPO/nH2O (n ∊ [0-14]), studying neutral and polynegatively charged molecules as an effort to describe realistic a representative scale of physiological conditions. The binding affinity and molecular conformations are discussed. The 250 neutral and charged systems (γ-CDPOHm/nH2O, n ∊ [10][0,14], m ∊ [0,15], γ-CDPOH-8/nH2O.8Na(+), and γ-CDPOH-16/nH2O.16Na(+)) in four main domains of non-covalent hydrogen bonding interactions are studied.
authors.affiliation: Lehrstuhl für Analytische Chemie, Institut für Umweltforschung, Fakultät für Chemie, Universität Dortmund, Otto-Hahn-Straße 6, 44227 Dortmund, Nordrhein-Westfalen, Germany. Electronic address: B.Ivanova@infu.uni-dortmund.de.
authors.forename: Bojidarka
authors.initials: B
authors.lastname: Ivanova
authors.affiliation: Lehrstuhl für Analytische Chemie, Institut für Umweltforschung, Fakultät für Chemie, Universität Dortmund, Otto-Hahn-Straße 6, 44227 Dortmund, Nordrhein-Westfalen, Germany.
authors.forename: Michael
authors.initials: M
authors.lastname: Spiteller
mesh_terms: D002236:Carbohydrate Conformation; D008958:Models, Molecular; D010758:Phosphorus / Q000737:chemistry*; D011789:Quantum Theory; D047408:gamma-Cyclodextrins / Q000737:chemistry*
chemical_list: D047408:gamma-Cyclodextrins; D010758:Phosphorus; C023792:gamma-cyclodextrin
keywords: Cyclodextrins; Mass spectrometry; Quantum chemistry; Solute–solvent interactions