Interaction of Dihydrocitrinone with Native and Chemically Modified Cyclodextrins

Faisal, Zelma; Kunsági‐Máté, Sándor; Lemli, Beáta; Szente, Lajos; Bergmann, Dominik; Humpf, Hans‐Ulrich; Poór, Miklós

doi:10.3390/molecules24071328

Cited by 11 publications

(9 citation statements)

References 32 publications

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“…Cyclodextrins have been widely used to increase the performance and sensitivity of analytical techniques, including mycotoxin analysis [32,33,46]. Previous studies demonstrated that the fluorescence intensity of fluorescent mycotoxins can be strongly increased as a result of the formation of mycotoxin–CD host–guest type complexes [29,33,42,47]. It can be explained by the fact that water molecules can significantly quench the fluorescence of aromatic fluorophores [48].…”

Section: Discussionmentioning

confidence: 99%

“…Molecular modeling studies have been performed at semi-empirical AM1 level using HyperChem 8 code [41,42]. After geometry optimization at AM1 level, the vibrational-rotational analyses were performed in harmonic approximation.…”

Section: Methodsmentioning

confidence: 99%

“…To consider the overall effect of the entropy changes, the different terms of the entropy contents of all species were calculated applying the Boltzmann-statistics. For example, after calculating the vibrational frequencies using the harmonic approximation, the entropy was determined on the common way using the following HyperChem code [41,42]:Svib=R∑i{hvi/kTe(hvikT)−1−ln[1−e(−hvikT)]} where ν i is the frequency of vibration and T is the temperature (298.16 K). The stability constants were determined from the Gibbs free energy changes associated to the complex formation at 298 K. A neutral aqueous environment was considered by the TIP3P solvation model implemented in HyperChem code (HyperChem, Hypercube Inc. 2007).…”

Section: Methodsmentioning

confidence: 99%

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Interactions of Mycotoxin Alternariol with Cyclodextrins and Its Removal from Aqueous Solution by Beta-Cyclodextrin Bead Polymer

et al. 2019

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Alternariol is an Alternaria mycotoxin that appears in fruits, tomatoes, oilseeds, and corresponding products. Chronic exposure to it can induce carcinogenic and xenoestrogenic effects. Cyclodextrins (CDs) are ring-shaped molecules built up by glucose units, which form host–guest type complexes with some mycotoxins. Furthermore, insoluble CD polymers seem suitable for the extraction/removal of mycotoxins from aqueous solutions. In this study, the interactions of alternariol with β- and γ-CDs were tested by employing fluorescence spectroscopic and modeling studies. Moreover, the removal of alternariol from aqueous solutions by insoluble β-CD bead polymer (BBP) was examined. Our major observations/conclusions are the following: (1) CDs strongly increased the fluorescence of alternariol, the strongest enhancement was induced by the native γ-CD at pH 7.4. (2) Alternariol formed the most stable complexes with the native γ-CD (logK = 3.2) and the quaternary ammonium derivatives (logK = 3.4–3.6) at acidic/physiological pH and at pH 10.0, respectively. (3) BBP effectively removed alternariol from aqueous solution. (4) The alternariol-binding ability of β-CD polymers was significantly higher than was expected based on their β-CD content. (5) CD technology seems a promising tool to improve the fluorescence detection of alternariol and/or to develop new mycotoxin binders to decrease alternariol exposure.

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Section: Discussionmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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Interactions of Mycotoxin Alternariol with Cyclodextrins and Its Removal from Aqueous Solution by Beta-Cyclodextrin Bead Polymer

et al. 2019

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“…Ether type oxygen and polar hydrogen groups (C3 and C5) are present inside the trunk of the CDs. While the external hydroxyls are responsible for the relative solubility of CDs in water and micro-heterogeneous environments, the glycosidic oxygen bridges and, consequently, their pairs of non-binding electrons facing the interior of the cavity give this region, in addition to its Lewis basic character, hydrophobicity [18,19], making it capable of complexing nonpolar molecules [20]. The chirality caused by the five chiral carbons of the D-glucose unit associated with the rigidity of the macrocycle due to the intramolecular hydrogen interactions between the 2-and 3-hydroxyl groups are fundamental characteristics of the chemistry of CDs.…”

Section: General Characteristics Of Cyclodextrinsmentioning

confidence: 99%

The Role of β-Cyclodextrin in the Textile Industry—Review

Bezerra

Arias²,

Firmino

et al. 2020

Molecules

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β-Cyclodextrin (β-CD) is an oligosaccharide composed of seven units of D-(+)-glucopyranose joined by α-1,4 bonds, which is obtained from starch. Its singular trunk conical shape organization, with a well-defined cavity, provides an adequate environment for several types of molecules to be included. Complexation changes the properties of the guest molecules and can increase their stability and bioavailability, protecting against degradation, and reducing their volatility. Thanks to its versatility, biocompatibility, and biodegradability, β-CD is widespread in many research and industrial applications. In this review, we summarize the role of β-CD and its derivatives in the textile industry. First, we present some general physicochemical characteristics, followed by its application in the areas of dyeing, finishing, and wastewater treatment. The review covers the role of β-CD as an auxiliary agent in dyeing, and as a matrix for dye adsorption until chemical modifications are applied as a finishing agent. Finally, new perspectives about its use in textiles, such as in smart materials for microbial control, are presented.

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“…After 10 ps MD simulation to equilibrate the system at room-temperature at MM+ level, the calculations for the complexes and the separated species interacted were performed at MINDO/3 level. To reduce the huge computational time, the random-methylated CD derivative (RAMEB, which have electron-rich cavity) was considered as negatively charged species of the native BCD [48,49].…”

Section: Modeling Studiesmentioning

confidence: 99%

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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Interaction of Dihydrocitrinone with Native and Chemically Modified Cyclodextrins

Cited by 11 publications

References 32 publications

Interactions of Mycotoxin Alternariol with Cyclodextrins and Its Removal from Aqueous Solution by Beta-Cyclodextrin Bead Polymer

Interactions of Mycotoxin Alternariol with Cyclodextrins and Its Removal from Aqueous Solution by Beta-Cyclodextrin Bead Polymer

The Role of β-Cyclodextrin in the Textile Industry—Review

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

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