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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 |
Aparece nas coleções: | Artigos |
Arquivos associados a este item:
Arquivo | Descrição | Tamanho | Formato | |
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artigo.pdf Until 2100-12-31 | Texto completo | 2,81 MB | Adobe PDF | Visualizar/Abrir ACESSO RESTRITO |
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