Host-guest interaction between tyrosine and β-cyclodextrin: Molecular modeling and nuclear studies

Bouhadiba, Abdelaziz; Belhocine, Youghourta; Rahim, Mohamed; Djilani, Imene; Leila, Nouar; Khatmi, Djameleddine

doi:10.1016/j.molliq.2017.03.029

Cited by 20 publications

(10 citation statements)

References 39 publications

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“…As previously mentioned, β-cyclodextrin has the tendency to form complexes with the hydrophobic molecules, especially with highly unsaturated structures such as benzene and its derivatives like benzocaine, as well as with amino acids such as tyrosine [18,33]. It has also been demonstrated that toxins containing ADDA are susceptible to form inclusion complexes with cyclodextrins driven by the hydrophobic interactions.…”

Section: Introductionmentioning

confidence: 95%

“…To better understand the differences in the adsorption mechanisms, the generated materials were characterized by Fourier-Transform Infrared Spectroscopy with Attenuated Total Reflectance (FTIR-ATR), X-ray Photoelectron Spectroscopy (XPS), Atomic Force Microscopy (AFM), and Thermogravimetric Analysis (TGA); while the adsorption capacity was measured by Quartz Crystal Microbalance with Dissipation monitoring (QCM-D). As previously mentioned, β-cyclodextrin has the tendency to form complexes with the hydrophobic molecules, especially with highly unsaturated structures such as benzene and its derivatives like benzocaine, as well as with amino acids such as tyrosine [18,33]. It has also been demonstrated that toxins containing ADDA are susceptible to form inclusion complexes with cyclodextrins driven by the hydrophobic interactions.…”

Section: Introductionmentioning

confidence: 95%

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Cellulose-Cyclodextrin Co-Polymer for the Removal of Cyanotoxins on Water Sources

et al. 2019

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With increasing global water temperatures and nutrient runoff in recent decades, the blooming season of algae lasts longer, resulting in toxin concentrations that exceed safe limits for human consumption and for recreational use. From the different toxins, microcystin-LR has been reported as the main cyanotoxin related to liver cancer, and consequently its abundance in water is constantly monitored. In this work, we report a methodology for decorating cellulose nanofibrils with β-cyclodextrin or with poly(β-cyclodextrin) which were tested for the recovery of microcystin from synthetic water. The adsorption was followed by Quartz Crystal Microbalance with Dissipation monitoring (QCM-D), allowing for real-time monitoring of the adsorption behavior. A maximum recovery of 196 mg/g was obtained with the modified by cyclodextrin. Characterization of the modified substrate was confirmed with Fourier Transform Infrared Spectroscopy (FT-IR), X-ray Photoelectron Spectroscopy (XPS), Thermogravimetric Analysis (TGA), and Atomic Force Microscopy (AFM).

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Section: Introductionmentioning

confidence: 95%

Section: Introductionmentioning

confidence: 95%

Cellulose-Cyclodextrin Co-Polymer for the Removal of Cyanotoxins on Water Sources

et al. 2019

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“…[23,24] We used the 6-31G++(d,p) basis set, since a family of 6-31G basis sets are often used for docking systems. [5,[25][26][27][28] We corrected the basis set superposition error by the counterpoise method. [29] In addition to the common functionals B3LYP, M06-2X, and M06L, we compared the reliability of CAM-B3LYP with long-range exchange correction[30] and B3LYP-GD3, M06-2X-GD3, M06L-GD3, and CAM-B3LYP-GD3 with Grimme's dispersion correction, [31] as shown in Table 1.…”

Section: Methodsmentioning

confidence: 99%

Importance of vdW and long-range exchange interactions to DFT-predicted docking energies between plumbagin and cyclodextrins

Ichibha¹,

Srihakulung²,

Guo³

et al. 2019

Preprint

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We calculated the docking energies between plumbagin and cyclodextrins, using density functional theory (DFT) with several functionals and some semi-empirical methods. Our DFT results revealed that GD3 dispersion force correction significantly improves the reliability of prediction. Also sufficient amount of long-range exchange is important to make it reliable further, agreeing with the previous work on argon dimer. In the semi-empirical methods, PM6 and PM7 qualitatively reproduce the stabilization by docking , yet under-and over-estimating the docking energies by ∼10 kcal/mol, respectively.

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“…In addition, β-cyclodextrin (β-CD) is a king of ring molecule connected by multiple D-β Pyran glucose units through α-1,4 glucosidic bond, with its conical cylindrical ring structure, showing typical internal hydrophobicity and external hydrophilicity. This inner hydrophobic cavity can be used as a perfect supermolecular host, allowing β-CD has excellent inclusion capacity for guest molecule [21][22]. By utilizing β-cyclodextrin polymer (β-CDP)/Reduced graphene oxide (rGO) hybrid system, an electrochemical sensor for PCBs sensitive detection was constructed in this sensing approach [23], the key point was that PCBs have more higher affinity towards β-CDP compared to Fc, which provided some ideas for our detection of PCB77 in a certain degree.…”

Section: Introductionmentioning

confidence: 99%

A Novel PCB77 Electrochemical Sensor Based on Nano-functionalized Electrode and Selected Aptamer

Yao¹,

Chen²,

Chen³

et al. 2020

JNMES

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3,3'4,4'-tetrachlorobiphenyl (PCB77) is a highly toxic substance that endanger ecological environment and human health. In our study, a novel PCB77 electrochemical sensor based on nano-functionalized electrode and selected aptamer was designed. β-cyclodextrin-Au nanoparticles (β-CD-AuNPs)/Nafion modified glassy carbon electrode (GCE) was used for amplify signal that enable sensitivity advanced, and the selected electroactive ferrocene (Fc) labed aptamer was assembled on the electrode surface via the host-guest recognition between β-CD and Fc. The detection was carried out according to the signal changed caused by transformation in the configuration of aptamer before and after the existence of PCB77. By this strategy, a detection limit down to 1.6×10-8 g/L was achieved. Moreover, it exhibited reliable selectivity against co-existing chemicals.

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Host-guest interaction between tyrosine and β-cyclodextrin: Molecular modeling and nuclear studies

Cited by 20 publications

References 39 publications

Cellulose-Cyclodextrin Co-Polymer for the Removal of Cyanotoxins on Water Sources

Cellulose-Cyclodextrin Co-Polymer for the Removal of Cyanotoxins on Water Sources

Importance of vdW and long-range exchange interactions to DFT-predicted docking energies between plumbagin and cyclodextrins

A Novel PCB77 Electrochemical Sensor Based on Nano-functionalized Electrode and Selected Aptamer

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