On Complex Formation between 5-Fluorouracil and β-Cyclodextrin in Solution and in the Solid State: IR Markers and Detection of Short-Lived Complexes by Diffusion NMR

Daria L. Melnikova, Zilya F. Badrieva, Mikhail A. Kostin, Corina Maller, Monika Stas, Aneta Buczek, Malgorzata A. Broda, Teobald Kupka*, Anne-Marie Kelterer, Peter M. Tolstoy*, Vladimir D. Skirda*

*Korrespondierende/r Autor/in für diese Arbeit

Publikation: Beitrag in einer FachzeitschriftArtikel

Abstract

In this work, the nuclear magnetic resonance (NMR) and IR spectroscopic markers of the complexation between 5-fluorouracil (5-FU) and β-cyclodextrin (β-CD) in solid state and in aqueous solution are investigated. In the attenuated total reflectance(ATR) spectra of 5-FU/β-CD products obtained by physical mixing, kneading and co-precipitation, we have identified the two most promising marker bands that could be used to detect complex formations: the C=O and C-F stretching bands of 5-FU that experience a blue shift by ca. 8 and 2 cm-1 upon complexation. The aqueous solutions were studied by NMR spectroscopy. As routine NMR spectra did not show any signs of complexation, we have analyzed the diffusion attenuation of spin-echo signals and the dependence of the population factor of slowly diffusing components on the diffusion time (diffusion NMR of pulsed-field gradient (PFG) NMR). The analysis has revealed that, at each moment, ~60% of 5-FU molecules form a complex with β-CD and its lifetime is ca. 13.5 ms. It is likely to be an inclusion complex, judging from the independence of the diffusion coefficient of β-CD on complexation. The obtained results could be important for future attempts of finding better methods of targeted anticancer drug delivery.

Originalspracheenglisch
Aufsatznummer5706
Seitenumfang18
FachzeitschriftMolecules
Jahrgang25
Ausgabenummer23
DOIs
PublikationsstatusVeröffentlicht - 3 Dez 2020

ASJC Scopus subject areas

  • !!Drug Discovery
  • Analytische Chemie
  • !!Chemistry (miscellaneous)
  • !!Molecular Medicine
  • !!Physical and Theoretical Chemistry
  • !!Pharmaceutical Science
  • Organische Chemie

Fields of Expertise

  • Advanced Materials Science

Treatment code (Nähere Zuordnung)

  • Basic - Fundamental (Grundlagenforschung)
  • Experimental
  • Theoretical

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