title: Host-guest interaction between new nitrooxoisoaporphine and β-cyclodextrins: synthesis, electrochemical, electron spin resonance and molecular modeling studies.
abstract: A new nitrooxoisoaporphine derivative was synthetized and characterized by cyclic voltammetry and electron spin resonance. Its aqueous solubility was improved by complexes formation with β-cyclodextrin, heptakis(2,6-di-O-methyl)-β-cyclodextrin and (2-hydroxypropyl)-β-cyclodextrin. In order to assess the inclusion degree reached by nitrooxoisoaporphine in cyclodextris cavity, the stability constants of formation of the complexes were determined by phase-solubility measurements obtaining in all cases a type-A(L) diagram. Moreover, electrochemical studies were carried out, where the observed change in the EPC value indicated a lower feasibility of the nitro group reduction. Additionally, a detailed spatial configuration is proposed for inclusion of derivate within the cyclodextrins cavity by 2D NMR techniques. Finally, these results are further interpreted by means of molecular modeling studies. Thus, theoretical results are in complete agreement with the experimental data.
authors.affiliation: Department of Inorganic and Analytical Chemistry, Faculty of Chemical and Pharmaceutical Sciences, University of Chile, Sergio Livingstone 1007, Santiago, Chile.
authors.forename: Fernanda
authors.initials: F
authors.lastname: Pérez-Cruz
authors.forename: Benjamín
authors.initials: B
authors.lastname: Aguilera-Venegas
authors.forename: Michel
authors.initials: M
authors.lastname: Lapier
authors.forename: Eduardo
authors.initials: E
authors.lastname: Sobarzo-Sánchez
authors.forename: Eugenio
authors.initials: E
authors.lastname: Uriarte Villares
authors.forename: Claudio
authors.initials: C
authors.lastname: Olea-Azar
mesh_terms: D000073738:2-Hydroxypropyl-beta-cyclodextrin; D001060:Aporphines / Q000138:chemical synthesis / Q000737:chemistry*; D055664:Electrochemical Techniques; D004578:Electron Spin Resonance Spectroscopy; D009682:Magnetic Resonance Spectroscopy; D029583:Menispermaceae / Q000737:chemistry; D008958:Models, Molecular; D012995:Solubility; D047392:beta-Cyclodextrins / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D001060:Aporphines; D047392:beta-Cyclodextrins; D000073738:2-Hydroxypropyl-beta-cyclodextrin; C038119:heptakis(2,6-O-dimethyl)beta-cyclodextrin; C031215:betadex