Мақола

Resveratrol–Maltol and Resveratrol–Thiophene Hybrids as Cholinesterase Inhibitors and Antioxidants: Synthesis, Biometal Chelating Capability and Crystal Structure

Milena MlakićDepartment of Organic Chemistry, Faculty of Chemical Engineering and Technology, University of Zagreb, Marulićev trg 19, HR-10000 Zagreb, CroatiaLajos FodorDepartment of General and Inorganic Chemistry, Institute of Chemistry, Faculty of Engineering, University of Pannonia, P.O. Box 158, H-8201 Veszprém, HungaryIlijana OdakDepartment of Chemistry, Faculty of Science and Education, University of Mostar, Matice hrvatske bb, 88000 Mostar, Bosnia and HerzegovinaOttó HorváthDepartment of General and Inorganic Chemistry, Institute of Chemistry, Faculty of Engineering, University of Pannonia, P.O. Box 158, H-8201 Veszprém, HungaryMarija Jelena Lovrić ŠtefičekGroup for Computational Life Sciences, Division of Physical Chemistry, Ruđer Bošković Institute, Bijenička cesta 54, HR-10000 Zagreb, CroatiaDanijela BarićGroup for Computational Life Sciences, Division of Physical Chemistry, Ruđer Bošković Institute, Bijenička cesta 54, HR-10000 Zagreb, CroatiaValentina MilašinovićDivision of Physical Chemistry, Rudjer Bošković Institute, Bijenička cesta 54, HR-10000 Zagreb, CroatiaKrešimir MolčanovDivision of Physical Chemistry, Rudjer Bošković Institute, Bijenička cesta 54, HR-10000 Zagreb, CroatiaŽeljko MarinićNMR Center, Rudjer Bošković Institute, Bijenička cesta 54, HR-10000 Zagreb, CroatiaZlata LasićTeva api Analytical R&D, Pliva, Prilaz Baruna Filipovića 25, HR-10000 Zagreb, CroatiaIrena ŠkorićDepartment of Organic Chemistry, Faculty of Chemical Engineering and Technology, University of Zagreb, Marulićev trg 19, HR-10000 Zagreb, Croatia

2022en

ABI

Аннотация

New resveratrol–thiophene and resveratrol–maltol hybrids were synthesized as cholinesterase inhibitors and antioxidants. As with photostability experiments, biological tests also found remarkable differences in the properties and behavior of thiophene and maltol hybrids. While resveratrol–thiophene hybrids have excellent inhibitory and antioxidant properties (similar to the activity of reference drug galantamine), maltols have been proven to be weaker inhibitors and antioxidants. The molecular docking of selected active ligands gave insight into the structures of docked enzymes. It enabled the identification of interactions between the ligand and the active site of both cholinesterases. The maltols that proved to be active cholinesterase inhibitors were able to coordinate Fe3+ ion, forming complexes of 1:1 composition. Their formation constants, determined by spectrophotometry, are very similar, lgK = 11.6–12.6, suggesting that Fe3+ binds to the common hydroxy-pyranone moiety and is hardly affected by the other aromatic part of the ligand. Accordingly, the characteristic bands in their individual absorption spectra are uniformly red-shifted relative to those of the free ligands. The crystal structures of two new resveratrol–maltol hybrids were recorded, giving additional information on the molecules’ intermolecular hydrogen bonds and packing. In this way, several functionalities of these new resveratrol hybrids were examined as a necessary approach to finding more effective drugs for complicated neurodegenerative diseases.

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Идентификаторлар

DOI: 10.3390/molecules27196379

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