Combined in Silico and in Vitro Approaches To Uncover the Oxidation and Schiff Base Reaction of Baicalein as an Inhibitor of Amyloid Protein Aggregation.
Schiff bases
autoxidation
computational chemistry
quinones
transition states
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
19 Feb 2022
19 Feb 2022
Historique:
received:
26
11
2021
pubmed:
7
1
2022
medline:
24
2
2022
entrez:
6
1
2022
Statut:
ppublish
Résumé
The oxidized form of baicalein (BA) leads to covalent binding with human amyloid proteins. Such adducts hamper the aggregation and deposition of fibrils. A novel reaction of BA with pentylamine (PA) as a model for the lysine side chain is described. This is the first study addressing the atomistic details of a Schiff base reaction with the trihydroxylated moiety of BA. Nuclear magnetic resonance and mass spectrometry approaches clearly indicate the formation of dehydrobaicalein in solution as well as its condensation with PA under aerobic conditions, yielding regioselectively C6-substituted products. The combined results suggest initial ion pair formation between BA and PA, followed by a redox chain reaction: the initiation by oxygen/air; an o-quinone-based chain involving oxidation and reduction steps; and extra off-chain formation of a doubly oxidized product. These mechanistic details support the anti-amyloid activity of BA and endorse its trihydroxyphenyl moiety as a pharmacophore for drug-design studies.
Identifiants
pubmed: 34989442
doi: 10.1002/chem.202104240
doi:
Substances chimiques
Amyloidogenic Proteins
0
Flavanones
0
Protein Aggregates
0
Schiff Bases
0
baicalein
49QAH60606
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202104240Subventions
Organisme : Fundação para a Ciência e a Tecnologia
ID : UIDB/50006/2020
Organisme : Fundação para a Ciência e a Tecnologia
ID : CEECIND/02017/2018
Informations de copyright
© 2022 Wiley-VCH GmbH.
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