Characterization, phase-solubility, and molecular modeling of inclusion complex of 5-nitroindazole derivative with cyclodextrins

The inclusion properties of 5-nitroindazole into native and (2,6-dimethyl)-β-cyclodextrin were evaluated using phase-solubility studies, electrochemistry, NMR and molecular modeling techniques. The slightly water-soluble 5-nitroindazole derivative (5-NI) and its inclusion with either β-cyclodextrin...

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Published in:Bioorganic & medicinal chemistry 2008-05, Vol.16 (9), p.5078-5084
Main Authors: Jullian, Carolina, Morales-Montecinos, Javier, Zapata-Torres, Gerald, Aguilera, Benjamín, Rodriguez, Jorge, Arán, Vicente, Olea-Azar, Claudio
Format: Article
Language:English
Subjects:
5-Nitroindazole
Biological and medical sciences
Computer Simulation
Cyclodextrin
Cyclodextrins - chemistry
Electrochemistry
General pharmacology
Health Science
Hälsovetenskap
Indazoles - chemistry
Magnetic Resonance Spectroscopy - methods
Magnetic Resonance Spectroscopy - standards
Medical sciences
Models, Molecular
Molecular modeling
Molecular Structure
NMR
Pharmacology. Drug treatments
Phase Transition
Physicochemical properties. Structure-activity relationships
Reference Standards
Solubility
Water - chemistry
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Summary:The inclusion properties of 5-nitroindazole into native and (2,6-dimethyl)-β-cyclodextrin were evaluated using phase-solubility studies, electrochemistry, NMR and molecular modeling techniques. The slightly water-soluble 5-nitroindazole derivative (5-NI) and its inclusion with either β-cyclodextrin (βCD) or Heptakis (2,6-di- O-methyl)-β-cyclodextrin (DMβCD) were investigated. The stoichiometric ratios and stability constants describing the extent of formation of the complexes were determined by phase-solubility measurements obtaining type-A L diagrams in both cases. According to the continuous variation method (Job’s plot) a 1:1 stoichiometry has been proposed for the complexes. Also electrochemical studies were carried out on both CDs complexes, where the observed change in the E PC value for DMβCD indicated a lower feasibility of the nitro group reduction. The detailed spatial configuration is proposed based on two-dimensional NMR methods. These results are further interpreted using molecular modeling studies. The latter results are in good agreement with the experimental data.
ISSN:0968-0896
1464-3391
1464-3391
DOI:10.1016/j.bmc.2008.03.026