Fluorescence spectroscopic investigation of the interaction of citrinin with native and chemically modified cyclodextrins

Poór, Miklós; Matisz, Gergely; Kunsági‐Máté, Sándor; Derdák, Diána; Szente, Lajos; Lemli, Beáta

doi:10.1016/j.jlumin.2015.11.011

Cited by 22 publications

(28 citation statements)

References 22 publications

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“…When the guest molecule enters into the CD cavity, the interaction (at least partly) destroys the solvation shell of the host and weakens the CD-solvent interaction. Similarly to our earlier findings [32], when the solvent molecules leave the host's cavity, reorganization of the more ordered BCD-water structure results in a higher entropy change vs. the less ordered RAMEB-water system.…”

Section: Driving Forces Of the Smt-cd Complex Formationssupporting

confidence: 88%

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Thermodynamic Characterization of the Interaction between the Antimicrobial Drug Sulfamethazine and Two Selected Cyclodextrins

et al. 2019

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Sulfamethazine is a representative member of the sulfonamide antibiotic drugs; it is still used in human and veterinary therapy. The protonation state of this drug affects its aqueous solubility, which can be controlled by its inclusion complexes with native or chemically-modified cyclodextrins. In this work, the temperature-dependent (298-313 K) interaction of sulfamethazine with native and randomly methylated β-cyclodextrins have been investigated at acidic and neutral pH. Surprisingly, the interaction between the neutral and anionic forms of the guest molecule and cyclodextrins with electron rich cavity are thermodynamically more favorable compared to the cationic guest. This property probably due to the enhanced formation of zwitterionic form of sulfamethazine in the hydrophobic cavities of cyclodextrins. Spectroscopic measurements and molecular modeling studies indicated the possible driving forces (hydrophobic interaction, hydrogen bonding, and electrostatic interaction) of the complex formation, and highlighted the importance of the reorganization of the solvent molecules during the entering of the guest molecule into the host's cavity.Molecules 2019, 24, 4565 2 of 12 tissues [13,14]. Furthermore, sulfonamides can appear as contaminants in various foods, which may cause adverse health effects [15][16][17]. The host-guest type complex formation of these antibiotics with CDs is an extensively studied field [18][19][20][21][22][23][24]. Zoppi et al. focus on the increased water solubility of sulfonamide drugs in the presence of native and methylated β-CD [23,24]. In the case of sulfamethazine (SMT), their nuclear magnetic resonance (NMR) and molecular modeling results demonstrate that SMT included the substituted pyrimidine ring into the β-CD cavity. Contradictory, NMR and quantum chemical results of Bani-Yaseen and Mo'ala revealed that complex formation is favorable with inclusion of the aniline moiety through the β-CD cavity [18].Several studies have been performed to get an insight into the factors which affect the thermodynamic and kinetic stability or selectivity of host-guest complexes [25,26], because the deeper understanding of these interactions has high importance. The pH-responsive host-guest encapsulation is also a highly studied field in material sciences [27] and in pharmacology [28,29]. Therefore, besides the complex stability and stoichiometry of SMT -β-CD complex and along the contradictory description of the related structures [18,23,24], the investigation of the pH dependence interaction of SMT with CDs is also reasonable.In our recent study [30], we demonstrated the importance of pH-dependent dipole moment of SMT molecule, which phenomenon can affect the complex geometry formed with β-CD (BCD) and randomly methylated β-CD (RAMEB) (Figure 1). Now we focus on the thermodynamic properties of the formation of inclusion complexes at different pH values. Our aim is to analyze the weak interactions between the pH dependent ionic and neutral forms of SMT and native or methylated CDs at molecular l...

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Section: Driving Forces Of the Smt-cd Complex Formationssupporting

confidence: 88%

“…The association constants of CD complexes generally decrease with the elevation of the temperature [19,31]. However, one of our earlier work showed an opposite example [32]. The thermodynamic parameters have been also determined to analyze further the related processes.…”

Section: Introductionmentioning

confidence: 99%

Thermodynamic Characterization of the Interaction between the Antimicrobial Drug Sulfamethazine and Two Selected Cyclodextrins

et al. 2019

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“…Chemically modified CDs are also commonly used, because the stability and selectivity of host-guest complexes are strongly influenced by these modifications [ 18 , 19 ]. Previous studies have reported that several mycotoxins, including aflatoxins, citrinin, ochratoxin A, and ZEN, form stable complexes with native and chemically modified β-CDs [ 5 , 20 , 21 , 22 ]. Complex formation of ZEN with β-CDs has been characterized in multiple studies, showing that complex formation leads to substantial increase in the fluorescence signal of ZEN [ 5 , 23 , 24 ].…”

Section: Introductionmentioning

confidence: 99%

Interaction of α- and β-zearalenols with β-cyclodextrins

et al. 2017

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Zearalenone (ZEN) is a mycotoxin produced by Fusarium fungi. ZEN primarily contaminates different cereals, and exerts a strong xenoestrogenic effect in animals and humans. ZEN is a fluorescent mycotoxin, although molecular interactions and microenvironmental changes significantly modify its spectral properties. During biotransformation, ZEN is converted into α-zearalenol (α-ZOL) and β-zearalenol (β-ZOL), the toxic metabolites of ZEN, which mimick the effect of estrogen. Cyclodextrins (CDs) are host molecules, and have been studied extensively; they can form stable complexes with several mycotoxins, including ZEN. However, information is limited regarding the interactions of CDs with ZOLs. Therefore, we studied the interactions of α- and β-ZOLs with native and six chemically modified β-CDs by fluorescence spectroscopy. Fluorescence enhancement during complex formation, as well as binding constants, were determined. To understand ZOL-CD interactions better, molecular modeling studies were also carried out. Both mycotoxin derivatives formed the most stable complexes with methylated and sulfobutylated CD-derivatives; however, the CD complexes of α-ZOL were significantly stronger than those of β-ZOL. The data presented here indicate which of the chemically modified β-CDs appear more suitable as fluorescence enhancers or as potential mycotoxin binders.

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“…Fluorescence spectroscopic investigation of DHC in the absence and presence of HSA First, the fluorescence excitation and emission spectra of DHC were recorded in PBS (pH 7.4). Despite the parent compound (CIT) does not express fluorescence at physiological pH (Poór et al, 2016), conversion of CIT to DHC leads to significant spectral changes. As Fig.…”

Section: Resultsmentioning

confidence: 99%

“…In vitro cellular toxicity and genotoxicity of DHC is significantly lower compared to the parent compound (Dunn et al, 1983;Föllmann et al, 2014). Under acidic conditions, CIT expresses strong fluorescence (λex = 330 nm; λem = 505 nm); however, fluorescence signal of CIT strongly decreases with the elevation of the pH and disappears approximately at pH 5, due to the deprotonation of the molecule (Poór et al, 2016).…”

Section: Introductionmentioning

confidence: 94%

Interaction of the mycotoxin metabolite dihydrocitrinone with serum albumin

et al. 2018

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Citrinin (CIT) is a nephrotoxic mycotoxin produced by Penicillium, Monascus, and Aspergillus species. CIT appears as a contaminant in cereals, cereal-based products, fruits, nuts, and spices. During the biotransformation of CIT, its major urinary metabolite dihydrocitrinone (DHC) is formed. Albumin interacts with several compounds (including mycotoxins) affecting their tissue distribution and elimination. CIT-albumin interaction is known; however, the complex formation of DHC with albumin has not been reported previously. In this study, we aimed to investigate the interaction of DHC with albumin, employing fluorescence spectroscopy, circular dichroism, and molecular modeling studies. Furthermore, species differences and thermodynamics of the interaction, as well as the effects of albumin on the acute in vitro toxicity of DHC and CIT were also tested. Our main observations/conclusions are as follows: (1) Fluorescence signal of DHC is strongly enhanced by albumin. (2) Formation of DHC-albumin complexes are supported by both fluorescence spectroscopic and circular dichroism studies. (3) DHC forms similarly stable complexes with human albumin (K ~ 10 5 L/mol) as CIT. (4) DHC-albumin interaction did not show significant species differences (tested with human, bovine, porcine, and rat albumins). (5) Based on modeling studies and investigations with site markers, DHC occupies the Heme binding site (subdomain IB) on human albumin. (6) The presence of albumin significantly decreased the acute in vitro cytotoxic effects of both DHC and CIT on MDCK cell line.

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Fluorescence spectroscopic investigation of the interaction of citrinin with native and chemically modified cyclodextrins

Cited by 22 publications

References 22 publications

Thermodynamic Characterization of the Interaction between the Antimicrobial Drug Sulfamethazine and Two Selected Cyclodextrins

Thermodynamic Characterization of the Interaction between the Antimicrobial Drug Sulfamethazine and Two Selected Cyclodextrins

Interaction of α- and β-zearalenols with β-cyclodextrins

Interaction of the mycotoxin metabolite dihydrocitrinone with serum albumin

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