Protonation and β-cyclodextrin complex formation equilibria of fluconazole

Gábor Orgován, Hajnal Kelemen, B. Noszál

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

Fluconazole, the adequate antifungal agent in Candida infections was studied to quantify its acid-base and cyclodextrin-complex formation equilibria. 1H NMR-pH titrations revealed protonation steps in the highly basic region (log K1 = 11.96) and in the acidic region (log K2 = 1.48). The stability and structure of its complexes with β-cyclodextrin (2-hydroxy)propyl-β-cyclodextrin and sulfobutyl ether-β-cyclodextrin were investigated by 1D and 2D solution NMR spectroscopic techniques. The cyclodextrin complexes of fluconazole are of moderate stability (1 <log K <2). Peculiarly enough, two isomeric complexes of comparable stability are formed between the neutral fluconazole and β-cyclodextrin.

Original languageEnglish
Pages (from-to)189-196
Number of pages8
JournalJournal of Inclusion Phenomena
Volume84
Issue number3-4
DOIs
Publication statusPublished - Apr 1 2016

Fingerprint

fluconazole
cyclodextrins
Fluconazole
Protonation
Cyclodextrins
nuclear magnetic resonance
infectious diseases
titration
ethers
Nuclear magnetic resonance
acids
antifungal agents
candidiasis
Candida
Antifungal Agents
Titration
Ether
Acids
Infection

Keywords

  • Cyclodextrin
  • Fluconazole
  • NMR-pH
  • Stability constant

ASJC Scopus subject areas

  • Condensed Matter Physics
  • Food Science
  • Chemistry(all)

Cite this

Protonation and β-cyclodextrin complex formation equilibria of fluconazole. / Orgován, Gábor; Kelemen, Hajnal; Noszál, B.

In: Journal of Inclusion Phenomena, Vol. 84, No. 3-4, 01.04.2016, p. 189-196.

Research output: Contribution to journalArticle

Orgován, Gábor ; Kelemen, Hajnal ; Noszál, B. / Protonation and β-cyclodextrin complex formation equilibria of fluconazole. In: Journal of Inclusion Phenomena. 2016 ; Vol. 84, No. 3-4. pp. 189-196.
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