Specific binding capacity of beta-cyclodextrin with cis and trans enalapril: physicochemical characterization and structural studies by molecular modeling.
The main objective of this work was to study an inclusion complex between enalapril (ENA), and beta-cyclodextrin (beta-CD). From nuclear magnetic resonance (NMR) we determined that the complex showed a 1:1 stoichiometry, with an apparent formation constant (K(C)) of 439 and 290 M(-1) for the cis and trans isomers, respectively. The molecular modeling and NMR techniques demonstrated that the aromatic moiety of ENA was inserted into the hydrophobic cavity of beta-CD. When studying the chemical stability of ENA complexed to beta-CD, a clear stabilizing effect was observed in both the aqueous solution and solid state.
Zoppi
Ariana
A
Departamento de Farmacia, Facultad de Ciencias Químicas, Universidad Nacional de Córdoba, Ciudad Universitaria, 5000 Córdoba, Argentina.
Quevedo
Mario A
MA
Longhi
Marcela R
MR
D000465:Algorithms; D000806:Angiotensin-Converting Enzyme Inhibitors / Q000737:chemistry* / Q000494:pharmacology; D000959:Antihypertensive Agents / Q000737:chemistry* / Q000494:pharmacology; D001665:Binding Sites; D002152:Calorimetry, Differential Scanning; D003198:Computer Simulation; D004656:Enalapril / Q000737:chemistry* / Q000494:pharmacology; D057927:Hydrophobic and Hydrophilic Interactions; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D012996:Solutions / Q000737:chemistry; D017550:Spectroscopy, Fourier Transform Infrared; D013237:Stereoisomerism; D014867:Water / Q000737:chemistry; D047392:beta-Cyclodextrins / Q000737:chemistry* / Q000378:metabolism
D000806:Angiotensin-Converting Enzyme Inhibitors; D000959:Antihypertensive Agents; D012996:Solutions; D047392:beta-Cyclodextrins; D014867:Water; D004656:Enalapril