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Complexation of tropane alkaloids by cyclodextrins
Monika Asztemborska1, Magdalena Ceborska1, Mariusz Pietrzak1
1Institute of Physical Chemistry of the Polish Academy of Sciences, Kasprzaka 44/52, 01-224, Warsaw, Poland.
Carbohydrate Polymers
|February 9, 2019
Summary
Tropane alkaloids like atropine form stable complexes with cyclodextrins, particularly β-cyclodextrin. These complexes exhibit specific binding interactions and conformational changes, impacting drug delivery potential.
Area of Science:
- Pharmaceutical Chemistry
- Supramolecular Chemistry
- Analytical Chemistry
Background:
- Tropane alkaloids are crucial pharmaceutical compounds.
- Cyclodextrins are widely used as complexing agents.
- Understanding host-guest interactions is vital for drug formulation.
Purpose of the Study:
- To investigate the complexation of tropane alkaloids with cyclodextrins.
- To determine the stoichiometry and stability of these complexes.
- To elucidate the structural basis of tropane alkaloid-cyclodextrin interactions.
Main Methods:
- Nuclear Magnetic Resonance (NMR) spectroscopy
- Capillary Electrophoresis (CE)
- X-ray crystallography
- Density Functional Theory (DFT) calculations
Main Results:
- Tropane alkaloids form 1:1 complexes with β- and γ-cyclodextrins.
- β-cyclodextrin forms significantly more stable complexes than γ-cyclodextrin.
- Complexation involves interactions with both aliphatic and aromatic parts of the alkaloids.
- Crystal structure reveals specific binding modes of (-)-hyoscyamine within β-cyclodextrin dimers.
- Conformational changes of alkaloids upon complexation were observed.
Conclusions:
- β-cyclodextrin demonstrates superior complexation ability with tropane alkaloids compared to γ-cyclodextrin.
- The binding is driven by specific interactions within the cyclodextrin cavity.
- Complexation induces conformational adaptations in tropane alkaloids, relevant for their pharmaceutical applications.
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