Use este identificador para citar ou linkar para este item: https://locus.ufv.br//handle/123456789/18273
Tipo: Artigo
Título: Tailoring natural abenquines to inhibit the photosynthetic electron transport through interaction with the D1 protein in photosystem II
Autor(es): Nain-Perez, Amalyn
Barbosa, Luiz C. A.
Maltha, Celia R. A.
Giberti, Samuele
Forlani, Giuseppe
Abstract: Abenquines are natural N-acetylaminobenzoquinones bearing amino acid residues, which act as weak inhibitors of the photosynthetic electron transport chain. Aiming to exploit the abenquine scaffold as a model for the synthesis of new herbicides targeting photosynthesis, 14 new analogues were prepared by replacing the amino acid residue with benzylamines and the acetyl with different acyl groups. The synthesis was accomplished in three steps with a 68−95% overall yield from readily available 2,5-dimethoxyaniline, acyl chlorides, and benzyl amines. Key steps include (i) acylation of the aniline, (ii) oxidation, and (iii) oxidative addition of the benzylamino moiety. The compounds were assayed for their activity as Hill inhibitors, under basal, uncoupled, or phosphorylating conditions, or excluding photosystem I. Four analogues showed high effectiveness (IC 50 = 0.1− 0.4 μM), comparable with the commercial herbicide diuron (IC 50 = 0.3 μM). The data suggest that this class of compounds interfere at the reducing side of photosystem II, having protein D1 as the most probable target. Molecular docking studies with the plastoquinone binding site of Spinacia oleracea further strengthened this proposal.
Palavras-chave: Abenquine analogues
Aminoquinones
Photosynthesis inhibitors
Photosynthetic electron transport
Herbicides
Editor: Journal of Agricultural and Food Chemistry
Tipo de Acesso: American Chemical Society
URI: https://doi.org/10.1021/acs.jafc.7b04624
http://www.locus.ufv.br/handle/123456789/18273
Data do documento: 1-Dez-2017
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