Sildenafil/cyclodextrin complexation: stability constants, thermodynamics, and guest-host interactions probed by 1H NMR and molecular modeling studies

Journal of Pharmaceutical and Biomedical Analysis
Mahmoud M Al OmariAdnan A Badwan

Abstract

Guest-host interactions of sildenafil (Sild) with cyclodextrins (CyDs) have been investigated using several techniques including phase solubility diagrams (PSD), differential scanning calorimetry (DSC), X-ray powder diffractometry (XRPD), proton nuclear magnetic resonance (1H NMR) and molecular mechanical modeling (MM+). Estimates of the complex formation constant (K11) show that the tendency of Sild to complex with CyDs follows the order: beta-CyD>HP-beta-CyD>gamma-CyD, alpha-CyD, where K11 values at pH 8.7 and 30 degrees C were 150, 68 and 46, 43 M-1, respectively. Ionization of Sild reduces its tendency to complex with beta-CyD, where protonated (at pH 3.6) and anionic Sild (at pH 12.1) species have K11 values of 17 and 42 M-1, respectively, compared with 150 M-1 for neutral Sild (at pH 8.7). The hydrophobic character of Sild was found to provide 39% of the driving force for complex stability, while other factors including specific interactions contribute -7.9 kJ/mol. Complex formation of Sild with beta-CyD (DeltaG degrees=-22.9 kJ/mol) is largely driven by enthalpy (DeltaH degrees=-19.8 kJ/mol) and slight entropy (DeltaS degrees=10.3 J/molK) changes. 1H NMR and MM+ studies indicate formation of two isomeric 1:1 complexes: o...Continue Reading

Citations

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