Host-guest interaction between new nitrooxoisoaporphine and beta-cyclodextrins: Synthesis, electrochemical, electron spin resonance and molecular modeling studies

Perez-Cruz, F; Aguilera-Venegas, B; Lapier, M.; Sobarzo-Sanchez, E; Villares, EU; Olea Azar C.

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 beta-cyclodextrin, heptakis(2,6-di-O-methyl)-beta-cydodextrin and (2-hydroxypropyl)-beta-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. (C) 2012 Elsevier B.V. All rights reserved.

Más información

Título según WOS: Host-guest interaction between new nitrooxoisoaporphine and beta-cyclodextrins: Synthesis, electrochemical, electron spin resonance and molecular modeling studies
Título según SCOPUS: Host-guest interaction between new nitrooxoisoaporphine and ?-cyclodextrins: Synthesis, electrochemical, electron spin resonance and molecular modeling studies
Título de la Revista: Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy
Volumen: 102
Editorial: PERGAMON-ELSEVIER SCIENCE LTD
Fecha de publicación: 2013
Página de inicio: 226
Página final: 234
Idioma: English
URL: http://linkinghub.elsevier.com/retrieve/pii/S1386142512009390
DOI:

10.1016/j.saa.2012.09.068

Notas: ISI, SCOPUS