New resveratrol analogs as improved biologically active structures: Design, synthesis and computational modeling.

Antioxidative activity Cholinesterase inhibition Computational modeling Resveratrol analogs Synthesis

Journal

Bioorganic chemistry
ISSN: 1090-2120
Titre abrégé: Bioorg Chem
Pays: United States
ID NLM: 1303703

Informations de publication

Date de publication:
30 Nov 2023
Historique:
received: 09 10 2023
revised: 07 11 2023
accepted: 10 11 2023
medline: 9 12 2023
pubmed: 9 12 2023
entrez: 8 12 2023
Statut: aheadofprint

Résumé

New analogs of the well-known bioactive trihydroxy-stilbene resveratrol were synthesized to investigate their potential biological activity. The focus was on assessing their ability to inhibit cholinesterase enzymes (ChEs) and their antioxidative properties, which were thoroughly examined. New resveratrol analogs were synthesized through Wittig or McMurry reaction in moderate-to-good yields. In all synthetic pathways, mixtures of cis- and trans-isomers were obtained, then separated by chromatography, and trans-isomers were isolated as targeted structures. The stilbene derivatives underwent evaluation for antioxidant activity (AOA) using DPPH and CUPRAC assay, and their potential to inhibit acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) was also measured. The biological tests have shown that the same compounds exhibited significant antioxidative and butyrylcholinesterase inhibitory potential, as evidenced by lower IC

Identifiants

pubmed: 38064804
pii: S0045-2068(23)00626-0
doi: 10.1016/j.bioorg.2023.106965
pii:
doi:

Types de publication

Journal Article

Langues

eng

Sous-ensembles de citation

IM

Pagination

106965

Informations de copyright

Copyright © 2023 Elsevier Inc. All rights reserved.

Déclaration de conflit d'intérêts

Declaration of Competing Interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.

Auteurs

Milena Mlakić (M)

Department of Organic Chemistry, Faculty of Chemical Engineering and Technology, University of Zagreb, Marulićev trg 19, HR-10 000 Zagreb, Croatia.

Ilijana Odak (I)

Department of Chemistry, Faculty of Science and Education, University of Mostar, Matice hrvatske bb, 88 000 Mostar, Bosnia and Herzegovina. Electronic address: ilijana.odak@fpmoz.sum.ba.

Danijela Barić (D)

Group for Computational Life Sciences, Division of Physical Chemistry, Ruđer Bošković Institute, Bijenička cesta 54, HR-10 000 Zagreb, Croatia.

Stanislava Talić (S)

Department of Chemistry, Faculty of Science and Education, University of Mostar, Matice hrvatske bb, 88 000 Mostar, Bosnia and Herzegovina.

Ivana Šagud (I)

Croatian Agency for Medicinal Products and Medical Devices, Ksaverska Cesta 4, HR-10 000 Zagreb, Croatia.

Zoran Štefanić (Z)

Division of Physical Chemistry, Rudjer Bošković Institute, Bijenička cesta 54, HR-10 000 Zagreb, Croatia.

Krešimir Molčanov (K)

Division of Physical Chemistry, Rudjer Bošković Institute, Bijenička cesta 54, HR-10 000 Zagreb, Croatia.

Zlata Lasić (Z)

Teva api Analytical R&D, Pliva, Prilaz Baruna Filipovića 25, HR-10 000 Zagreb, Croatia.

Borislav Kovačević (B)

Group for Computational Life Sciences, Division of Physical Chemistry, Ruđer Bošković Institute, Bijenička cesta 54, HR-10 000 Zagreb, Croatia. Electronic address: Borislav.Kovacevic@irb.hr.

Irena Škorić (I)

Department of Organic Chemistry, Faculty of Chemical Engineering and Technology, University of Zagreb, Marulićev trg 19, HR-10 000 Zagreb, Croatia.

Classifications MeSH