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Hydroxymethylnitrofurazone:dimethyl-beta-cyclodextrin inclusion complex: a physical-chemistry characterization.

Renato Grillo1, Nathalie Ferreira Silva Melo, Carolina Morales Moraes

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Hydroxymethylnitrofurazone (NFOH) shows promise against Chagas disease but has solubility and toxicity issues. Complexing NFOH with dimethyl-beta-cyclodextrin (DM-beta-CD) improves its properties, offering a potential new therapeutic strategy.

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Area of Science:

  • Pharmaceutical Sciences
  • Medicinal Chemistry
  • Biophysical Chemistry

Background:

  • Hydroxymethylnitrofurazone (NFOH) exhibits activity against Trypanosoma cruzi, the causative agent of Chagas disease.
  • However, NFOH's poor solubility and high toxicity limit its therapeutic application.
  • Cyclodextrins, particularly modified beta-cyclodextrins like DM-beta-CD, are known drug carriers that can enhance drug bioavailability and reduce toxicity by forming inclusion complexes.

Purpose of the Study:

  • To characterize the inclusion complexes formed between NFOH and DM-beta-CD.
  • To evaluate the impact of DM-beta-CD complexation on NFOH's solubility, complexation/release kinetics, and molecular dynamics.
  • To explore the potential of these complexes as novel drug delivery systems for Chagas disease treatment.

Main Methods:

  • Complexation and release kinetics were studied using UV-visible spectrophotometry.
  • Solubility isotherms were determined to assess complex formation and solubility enhancement.
  • Nuclear Magnetic Resonance (NMR) spectroscopy, including T(1) relaxation times and Diffusion Ordered Spectroscopy (DOSY), was employed to probe molecular interactions and dynamics.

Main Results:

  • Complexation kinetics indicated stabilization of NFOH absorbance within 30 hours in the presence of DM-beta-CD.
  • Solubility isotherm studies demonstrated favorable complexation and a significant increase in NFOH solubility upon interaction with DM-beta-CD.
  • NMR data revealed decreased mobility of NFOH in solution with DM-beta-CD, confirming interaction within the cyclodextrin cavity, and altered release profiles.

Conclusions:

  • DM-beta-CD effectively forms inclusion complexes with NFOH, leading to enhanced solubility and altered release kinetics.
  • NMR studies confirm the interaction between NFOH and the DM-beta-CD cavity.
  • These findings support the development of NFOH-DM-beta-CD complexes as a promising drug delivery system for treating Chagas disease.