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Host-guest kinetic interactions between HP-β-cyclodextrin and drugs for prediction of bitter taste masking.
Cyclodextrins (CD) are widely used bitter taste masking agents, for which the binding equilibrium constant (K) for the drug-CD complex is a conventional parameter for quantitating the taste masking effects. However, some exceptions have been reported to the expected relationship between K and bitterness reduction and the relationship between kinetic parameters of a drug-CD interaction, including association rate constant (Ka ) and disassociation rate constant (Kd ), and taste masking remains unexplored. In this study, based upon a database of kinetic parameters of drugs-HP-β-CD generated by Surface Plasmon Resonance Imaging for 485 drugs, the host-guest kinetic interactions between drugs and HP-β-CD for prediction of taste masking effects have been investigated. The taste masking effects of HP-β-CD for 13 bitter drugs were quantitatively determined using an electronic gustatory system (α-Astree e-Tongue). Statistical software was used to establish a model based on Euclidean distance measurements, Ka and Kd of the bitter drugs/HP-β-CD-complexes (R2 =0.96 and P<0.05). Optimized parameters, Ka 3 , Kd , Ka Kd , Kd 3 , Ka 2 and Ka /Kd with notable influence, were obtained by stepwise regression from 12 parameters derived from Ka , Kd and K (Ka /Kd ). 10-fold cross-validation was used to verify the reliability of the model (correlation coefficient of 0.84, P<0.05). The established model indicated a relationship between Ka , Kd , K and taste masking by HP-β-CD and was successful in predicting the extent of taste masking by HP-β-CD of 44 bitter drugs, which was in accordance with the literature reported. In conclusion, the relationship between kinetics of drug-CD interactions and taste masking was established and providing a new strategy for predicting the cyclodextrin mediated bitter taste masking.
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