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Controlling the Size, Shape and Stability of Supramolecular Polymers in Water
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Cyclodextrin binding constants as a function of pH for compounds with multiple pKa values.

Lisa Samuelsen1, René Holm2, Christian Schönbeck1

  • 1Department of Science and Environment, Roskilde University, Universitetsvej 1, DK 4000 Roskilde, Denmark.

International Journal of Pharmaceutics
|June 6, 2020
PubMed
Summary

This study presents a new theoretical model to predict how pH affects cyclodextrin complex stability with ionizable molecules. The model accurately predicts complex formation across various pH levels, aiding in drug formulation and delivery.

Keywords:
Distribution of speciesDrug DevelopmentGraphical User InterfaceHydrophobic interactionsIonizationMonte Carlo simulations

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Area of Science:

  • Supramolecular Chemistry
  • Physical Chemistry
  • Pharmaceutical Sciences

Background:

  • Cyclodextrin complexation with ionizable molecules is pH-dependent.
  • Neutral guest species generally exhibit higher affinity for cyclodextrins.
  • Existing models may not fully capture complex pH-dependent behavior for multi-pKa guests.

Purpose of the Study:

  • To develop a theoretical expression for the pH-dependent stability constant of cyclodextrin-ionizable guest complexes.
  • To account for guest molecules with multiple acid dissociation (pKa) values.
  • To provide a tool for predicting and understanding cyclodextrin complexation across different pH environments.

Main Methods:

  • Development of a theoretical expression relating stability constants to guest pKa values and pH.
  • Validation using empirical data sets from existing literature.
  • Utilizing Monte Carlo simulations to confirm the model's fit to experimental data.

Main Results:

  • A theoretical expression accurately predicts the pH-dependent stability constant for cyclodextrin-ionizable guest interactions.
  • The model demonstrates that the pH profile is influenced by the guest's acid-base properties and pKa values.
  • The expression shows good agreement with empirical data and simulation results.

Conclusions:

  • The developed theoretical expression provides a robust method for predicting cyclodextrin complex stability as a function of pH.
  • The findings are applicable to various ionizable guests, including polyprotic acids, bases, and amphoteric compounds.
  • An experimental protocol and a user-friendly graphical interface are provided to facilitate practical application of the model.