Interaction of dihydrocitrinone with native and chemically modified cyclodextrins

Zelma Faisal, S. Kunsági-Máté, Beáta Lemli, Lajos Szente, Dominik Bergmann, Hans Ulrich Humpf, Miklós Poór

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Citrinin (CIT) is a nephrotoxic mycotoxin produced by Aspergillus, Penicillium, and Monascus genera. It appears as a contaminant in grains, fruits, and spices. After oral exposure to CIT, its major urinary metabolite, dihydrocitrinone (DHC) is formed, which can be detected in human urine and blood samples. Cyclodextrins (CDs) are ring-shaped molecules built up from glucose units. CDs can form host-guest type complexes with several compounds, including mycotoxins. In this study, the complex formation of DHC with native and chemically modified beta- and gamma-cyclodextrins was tested at a wide pH range, employing steady-state fluorescence spectroscopic and modeling studies. The weakly acidic environment favors the formation of DHC-CD complexes. Among the CDs tested, the quaternary-ammonium-γ-cyclodextrin (QAGCD) formed the most stable complexes with DHC. However, the quaternary-ammonium-β-cyclodextrin (QABCD) induced the strongest enhancement in the fluorescence signal of DHC. Our results show that some of the chemically modified CDs are able to form stable complexes with DHC (logK = 3.2-3.4) and the complex formation can produce even a 20-fold increase in the fluorescence signal of DHC. Considering the above-listed observations, CD technology may be a promising tool to increase the sensitivity of the fluorescence detection of DHC.

Original languageEnglish
Article numbermolecules24071328
JournalMolecules
Volume24
Issue number7
DOIs
Publication statusPublished - Jan 1 2019

Fingerprint

Cyclodextrins
fluorescence
Citrinin
Fluorescence
interactions
Aspergillus
urine
fruits
Mycotoxins
metabolites
Ammonium Compounds
glucose
blood
contaminants
gamma-Cyclodextrins
Monascus
beta-Cyclodextrins
Spices
dihydrocitrinone
augmentation

Keywords

  • Citrinin
  • Cyclodextrin
  • Dihydrocitrinone
  • Fluorescence spectroscopy
  • Host-guest interaction

ASJC Scopus subject areas

  • Analytical Chemistry
  • Chemistry (miscellaneous)
  • Molecular Medicine
  • Pharmaceutical Science
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Faisal, Z., Kunsági-Máté, S., Lemli, B., Szente, L., Bergmann, D., Humpf, H. U., & Poór, M. (2019). Interaction of dihydrocitrinone with native and chemically modified cyclodextrins. Molecules, 24(7), [molecules24071328]. https://doi.org/10.3390/molecules24071328

Interaction of dihydrocitrinone with native and chemically modified cyclodextrins. / Faisal, Zelma; Kunsági-Máté, S.; Lemli, Beáta; Szente, Lajos; Bergmann, Dominik; Humpf, Hans Ulrich; Poór, Miklós.

In: Molecules, Vol. 24, No. 7, molecules24071328, 01.01.2019.

Research output: Contribution to journalArticle

Faisal, Z, Kunsági-Máté, S, Lemli, B, Szente, L, Bergmann, D, Humpf, HU & Poór, M 2019, 'Interaction of dihydrocitrinone with native and chemically modified cyclodextrins', Molecules, vol. 24, no. 7, molecules24071328. https://doi.org/10.3390/molecules24071328
Faisal, Zelma ; Kunsági-Máté, S. ; Lemli, Beáta ; Szente, Lajos ; Bergmann, Dominik ; Humpf, Hans Ulrich ; Poór, Miklós. / Interaction of dihydrocitrinone with native and chemically modified cyclodextrins. In: Molecules. 2019 ; Vol. 24, No. 7.
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