Complexation of the potassium cation with enniatin B: an experimental and theoretical study

Makrlík, Emanuel; Böhm, Stanislav; Vaňura, Petr

doi:10.1007/s00706-016-1792-9

Cited by 3 publications

(1 citation statement)

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“…Quantum computational studies of mycotoxins provide information on the relationship between structure and properties and are employed in predicting the electronic structure characteristics of these compounds [ 6 , 7 , 8 , 9 , 10 ]. DFT has been used in recent times to study the reactivity of OH groups in emodin, complexation of potassium and ammonium cations with enniatin B [ 11 , 12 ], tautomerism of tenuazonic acid [ 13 ], and in photophysical properties studies of zearalenone [ 14 ].…”

Section: Introductionmentioning

confidence: 99%

Investigation on electronic structure, vibrational spectra, NBO analysis, and molecular docking studies of aflatoxins and selected emerging mycotoxins against wild-type androgen receptor

Agwupuye

Neji

Louis

et al. 2021

Heliyon

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The geometry, frontier molecular orbitals (FMOs), vibrational, NBO analysis, and molecular docking simulations of aflatoxins (B1, B2, M1, M2, G1, G2), zearalenone (ZEA) emodin (EMO), alternariol (AOH), alternariol monoethyl ether (AMME), and tenuazonic acid (TeA) mycotoxins have been extensively theoretically studied and discussed based on quantum density functional theory calculations using Gaussian 16 software package. The theoretical computation for the geometry optimization, NBOs, and the molecular docking interaction was conducted using Density Functional Theory with B3LYP/6-31+G(d,p), NBO program, and AutoDock Vina tools respectively. Charge delocalization patterns and second-order perturbation energies of the most interacting natural bond orbitals (NBOs) of these mycotoxins have also been computed and predicted. Interestingly, among the mycotoxins investigated, aflatoxin G1 is seen to give the strongest stabilization energy while Zearalenone shows the highest tendency to accept electron(s) and emodin, an emerging mycotoxin gave the best binding pose within the androgen receptor pocket with a mean binding affinity of -7.40 kcal/mol.

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Section: Introductionmentioning

confidence: 99%

Investigation on electronic structure, vibrational spectra, NBO analysis, and molecular docking studies of aflatoxins and selected emerging mycotoxins against wild-type androgen receptor

Agwupuye

Neji

Louis

et al. 2021

Heliyon

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Cyclic Peptoids as Mycotoxin Mimics: An Exploration of Their Structural and Biological Properties

D’Amato¹,

Volpe²,

Vaccaro³

et al. 2017

J. Org. Chem.

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Cyclic peptoids have recently emerged as important examples of peptidomimetics for their interesting complexing properties and innate ability to permeate biological barriers. In the present contribution, experimental and theoretical data evidence the intricate conformational and stereochemical properties of five novel hexameric peptoids decorated with N-isopropyl, N-isobutyl, and N-benzyl substituents. Complexation studies by NMR, in the presence of sodium tetrakis[3,5-bis(trifluoromethyl)phenyl]borate (NaTFPB), theoretical calculations, and single-crystal X-ray analyses indicate that the conformationally stable host/guest metal adducts display architectural ordering comparable to that of the enniatins and beauvericin mycotoxins. Similarly to the natural depsipeptides, the synthetic oligolactam analogues show a correlation between ion transport abilities in artificial liposomes and cytotoxic activity on human cancer cell lines. The reported results demonstrate that the versatile cyclic peptoid scaffold, for its remarkable conformational and complexing properties, can morphologically mimic related natural products and elicit powerful biological activities.

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Protonation of enniatin B: Experimental and theoretical study

Vaňura,

Böhm

2024

Preprint

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On the basis of extraction experiments, the exchange extraction constant corresponding to the equilibrium H3O+(aq) + 1.Na+(nb) 1.H3O+(nb) + Na+(aq) occurring in the two–phase water–nitrobenzene system (1 = enniatin B; aq = aqueous phase, nb = nitrobenzene phase) was evaluated as log Kex (H3O+, 1.Na+) = 0.9 ± 0.1. Further, the stability constant of the 1.H3O+ complex in nitrobenzene saturated with water was calculated for a temperature of 25 oC: log βnb (1.H3O+) = 6.4 ± 0.2. Finally, by using quantum mechanical DFT calculations, the most probable structure of the cationic complex species 1.H3O+ was derived. In the resulting complex, the “central” cation H3O+ is bound by three relatively strong hydrogen bonds to the corresponding three carbonyl oxygens of the parent enniatin B ligand. The interaction energy, E(int), of the considered complex 1.H3O+ was found to be -424.8 kJ/mol, confirming also the formation of this investigated complex.

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Complexation of the potassium cation with enniatin B: an experimental and theoretical study

Cited by 3 publications

References 37 publications

Investigation on electronic structure, vibrational spectra, NBO analysis, and molecular docking studies of aflatoxins and selected emerging mycotoxins against wild-type androgen receptor

Investigation on electronic structure, vibrational spectra, NBO analysis, and molecular docking studies of aflatoxins and selected emerging mycotoxins against wild-type androgen receptor

Cyclic Peptoids as Mycotoxin Mimics: An Exploration of Their Structural and Biological Properties

Protonation of enniatin B: Experimental and theoretical study

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