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Paclitaxel/β-Cyclodextrin interactions, a perspective from pulsed NMR spectroscopy experiments.

Natalia S Velázquez1, María Graciela Ferreyra1, Luciano N Mengatto1

  • 1Instituto de Desarrollo Tecnológico para la Industria Química (INTEC), Universidad Nacional del Litoral-Consejo Nacional de Investigaciones Científicas y Técnicas (UNL-CONICET), Centro Científico Tecnológico, Ruta Nacional 168, Paraje El Pozo, Santa Fe, Argentina.

Carbohydrate Research
|October 25, 2019
PubMed
Summary

Cyclodextrins enhance drug properties by forming inclusion complexes. Paclitaxel and randomly methylated-β-cyclodextrin (RAMEβ-CD) form optimal complexes at a 1:20 ratio, improving solubility and stability.

Keywords:
Inclusion complexesMethylated-β-cyclodextrinPaclitaxelPulsed nuclear magnetic resonance

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Area of Science:

  • Pharmaceutical Chemistry
  • Supramolecular Chemistry
  • Drug Delivery

Background:

  • Cyclodextrins are cyclic oligosaccharides capable of forming inclusion complexes with guest molecules.
  • These complexes can improve the solubility, stability, dissolution rate, and bioavailability of poorly soluble drugs.
  • Paclitaxel is a vital chemotherapeutic agent with limited water solubility.

Purpose of the Study:

  • To investigate the interaction between paclitaxel and randomly methylated-β-cyclodextrin (RAMEβ-CD) during inclusion complex formation.
  • To determine the optimal ratio for complexation and identify the preferred site of interaction.
  • To compare various analytical techniques for characterizing these inclusion complexes.

Main Methods:

  • Infrared Spectroscopy (IR)
  • Differential Scanning Calorimetry (DSC)
  • Nuclear Magnetic Resonance (NMR) Spectroscopy
  • Scanning Electron Microscopy (SEM)

Main Results:

  • Pulsed NMR spectroscopy identified a paclitaxel:RAMEβ-CD molar ratio of 1:20 as optimal for inclusion complex formation.
  • NMR analysis indicated that the aromatic ring at position 3' of the paclitaxel side chain is the preferred site for inclusion.
  • Comparative analysis of IR, DSC, NMR, and SEM provided comprehensive insights into the complexation process.

Conclusions:

  • The formation of paclitaxel-RAMEβ-CD inclusion complexes significantly enhances drug properties.
  • A 1:20 molar ratio of paclitaxel to RAMEβ-CD is ideal for maximizing complex formation.
  • The 3'-position aromatic ring of paclitaxel is the primary site of interaction within the RAMEβ-CD cavity.