ZFIN ID: ZDB-PUB-210501-12
Caffeine-Cyclodextrin Complexes as Solids: Synthesis, Biological and Physicochemical Characterization
Szmeja, S., Gubica, T., Ostrowski, A., Zalewska, A., Szeleszczuk, Ł., Zawada, K., Zielińska-Pisklak, M., Skowronek, K., Wiweger, M.
Date: 2021
Source: International Journal of Molecular Sciences   22(8): (Journal)
Registered Authors: Wiweger, Malgorzata
Keywords: analytical methods, caffeine, cyclodextrins, mechanochemical synthesis, toxicity, zebrafish
MeSH Terms:
  • Animals
  • Caffeine/chemistry*
  • Caffeine/pharmacology
  • Calorimetry, Differential Scanning
  • Cyclodextrins/chemistry*
  • Cyclodextrins/pharmacology
  • Drug Synergism
  • Embryo, Nonmammalian/drug effects
  • Spectroscopy, Fourier Transform Infrared
  • Spectrum Analysis, Raman
  • X-Ray Diffraction
  • Zebrafish
PubMed: 33919556 Full text @ Int. J. Mol. Sci.
Mechanochemical and in-solution synthesis of caffeine complexes with α-, β-, and γ-cyclodextrins was optimized. It was found that short-duration, low-energy cogrinding, and evaporation (instead of freeze-drying) are effective methods for the formation and isolation of these complexes. The products obtained, their pure components, and their mixtures were examined by powder X-ray diffraction (PXRD), differential scanning calorimetry (DSC), FT-IR and Raman spectroscopy. Moreover, molecular modeling provided an improved understanding of the association process between the guest and host molecules in these complexes. The complexes were found to exhibit high toxicity in zebrafish (Danio rerio) embryos, in contrast to pure caffeine and cyclodextrins at the same molar concentrations. HPLC measurements of the caffeine levels in zebrafish embryos showed that the observed cytotoxicity is not caused by an increased caffeine concentration in the body of the organism, as the concentrations are similar regardless of the administered caffeine form. Therefore, the observed high toxicity could be the result of the synergistic effect of caffeine and cyclodextrins.