Synthesis, theoretical studies, and effect on the photosynthetic electron transport of trifluoromethyl arylamides

Teixeira, Róbson Ricardo; Barros, Marcus Vinícius de Andrade; Bressan, Gustavo Costa; Siqueira, Raoni Pais; Santos, Fabíola S. dos; Bertazzini, Michele; Kiralj, Rudolf; Ferreira, Márcia M. C.; Forlani, Giuseppe

doi:10.1002/ps.4623

Cited by 8 publications

(11 citation statements)

References 40 publications

(71 reference statements)

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“…Strictly speaking, herbicides that target PSII and inhibit PET compete with the electron acceptor PQ for binding at the Q A site in the subunit D1 in order to block the electron transfer from Q A to Q B [39,40]. The most potent PET inhibitors contain an amide and/or carbamate fragment that can be substituted with mutual displacement of Q B from the binding pocket in the D1 subunit; therefore, the effects of differently substituted amides/carbamates as anti-invasive agents that reveal the herbicidal properties are being investigated thoroughly [41,42,43]. Obviously, the clarification of the specific herbicide–amino acid residue interactions is crucial for the proper understanding of the molecular mechanism of inhibition.…”

Section: Introductionmentioning

confidence: 99%

SAR-mediated Similarity Assessment of the Property Profile for New, Silicon-Based AChE/BChE Inhibitors

Bąk

Pizova

Kozik

et al. 2019

IJMS

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A set of 25 novel, silicon-based carbamate derivatives as potential acetyl- and butyrylcholinesterase (AChE/BChE) inhibitors was synthesized and characterized by their in vitro inhibition profiles and the selectivity indexes (SIs). The prepared compounds were also tested for their inhibition potential on photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts. In fact, some of the newly prepared molecules revealed comparable or even better inhibitory activities compared to the marketed drugs (rivastigmine or galanthamine) and commercially applied pesticide Diuron®, respectively. Generally, most compounds exhibited better inhibition potency towards AChE; however, a wider activity span was observed for BChE. Notably, benzyl N-[(1S)-2-[(tert-butyldimethylsilyl)oxy]-1-[(2-hydroxyphenyl)carbamoyl]ethyl]-carbamate (2) and benzyl N-[(1S)-2-[(tert-butyldimethylsilyl)oxy]-1-[(3-hydroxyphenyl)carbamoyl]ethyl]-carbamate (3) were characterized by fairly high selective indexes. Specifically, compound 2 was prescribed with the lowest IC50 value that corresponds quite well with galanthamine inhibition activity, while the inhibitory profiles of molecules 3 and benzyl-N-[(1S)-2-[(tert-butyldimethylsilyl)oxy]-1-[(4-hydroxyphenyl)carbamoyl]ethyl]carbamate (4) are in line with rivastigmine activity. Moreover, a structure–activity relationship (SAR)-driven similarity evaluation of the physicochemical properties for the carbamates examined appeared to have foreseen the activity cliffs using a similarity–activity landscape index for BChE inhibitory response values. The ‘indirect’ ligand-based and ‘direct’ protein-mediated in silico approaches were applied to specify electronic/steric/lipophilic factors that are potentially valid for quantitative (Q)SAR modeling of the carbamate analogues. The stochastic model validation was used to generate an ‘average’ 3D-QSAR pharmacophore pattern. Finally, the target-oriented molecular docking was employed to (re)arrange the spatial distribution of the ligand property space for BChE and photosystem II (PSII).

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Section: Introductionmentioning

confidence: 99%

SAR-mediated Similarity Assessment of the Property Profile for New, Silicon-Based AChE/BChE Inhibitors

Bąk

Pizova

Kozik

et al. 2019

IJMS

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“…The presence of an amide (-CONH-) group in the structure of compounds enables interaction with various enzymatic systems [1][2][3][4] and is also characteristic for a number of herbicides acting as inhibitors of photosynthesis [5][6][7][8][9]. Although at present approximately 20 modes of action of herbicides are known [10], over 50% of commercially available herbicides act by reversible binding to photosystem II (PS II) [11], and due to this interaction, the photosynthetic electron transport (PET) is interrupted [12][13][14][15][16].…”

Section: Introductionmentioning

confidence: 99%

Preparation and Photosynthesis-Inhibiting Activity of Novel Dihalogenated 3-Hydroxynaphthalene-2-carboxanilides

Kos

Goněc

Strhársky

et al. 2019

The 23rd International Electronic Conference on Synthetic Organic Chemistry

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In this study, a series of nine 3-hydroxynaphthalene-2-carboxanilides, disubstituted on the anilide ring by fluorine, chlorine and bromine in various positions, was prepared by microwave-assisted synthesis and characterized. The compounds were tested for their activity related to the inhibition of photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts. The PET-inhibiting activity of the compounds was within a wide range, but rather moderate; the highest activity within the series of the compounds was observed for N-(3,5-difluorophenyl)-3-hydroxynaphthalene-2-carboxamide (IC50 = 9.8 µM). The compounds were found to inhibit PET in photosystem II.

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“…Many QSAR studies of PS II inhibitors with diverse chemical structures have emphasized the hydrophobic nature of the binding domain, with lipophilicity being the dominant determinant of Hill inhibition activity [ 7 ], e.g., the review paper of Lambreva et al [ 8 ] presents a compendious overview of the recent improvements in the understanding of the structure and function of PS II donor side with a focus on the interactions of the plastoquinone cofactors with the surrounding environment and operational features. PET inhibitors in the functional dissection of the photosynthetic electron transport system were summarized in the review paper of Trebst [ 9 ], and a comprehensive overview of synthetic photosynthetic inhibitors and those based on natural products was published by Teixeira et al [ 10 ].…”

Section: Introductionmentioning

confidence: 99%

“…Both moieties can be substituted, and thus, their properties can be modified [ 14 , 15 ]. Amides are considered to be PS II inhibitors causing displacement of Q B from its binding pocket in the D 1 protein [ 16 ], and halogen substituents were found to contribute to enhanced PET-inhibiting activity [ 10 , 11 , 12 , 17 , 18 , 19 , 20 , 21 , 22 , 23 ]. Our team has investigated effects of various amides [ 11 , 16 , 18 , 19 , 20 , 21 , 22 , 24 , 25 , 26 , 27 , 28 ] or carbamates [ 29 , 30 , 31 , 32 , 33 , 34 ] on biological systems, in particular, as anti-invasive agents for, a long time.…”

Section: Introductionmentioning

confidence: 99%

Halogenated 1-Hydroxynaphthalene-2-Carboxanilides Affecting Photosynthetic Electron Transport in Photosystem II

et al. 2017

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Series of seventeen new multihalogenated 1-hydroxynaphthalene-2-carboxanilides was prepared and characterized. All the compounds were tested for their activity related to the inhibition of photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts. 1-Hydroxy-N-phenylnaphthalene-2-carboxamides substituted in the anilide part by 3,5-dichloro-, 4-bromo-3-chloro-, 2,5-dibromo- and 3,4,5-trichloro atoms were the most potent PET inhibitors (IC50 = 5.2, 6.7, 7.6 and 8.0 µM, respectively). The inhibitory activity of these compounds depends on the position and the type of halogen substituents, i.e., on lipophilicity and electronic properties of individual substituents of the anilide part of the molecule. Interactions of the studied compounds with chlorophyll a and aromatic amino acids present in pigment-protein complexes mainly in PS II were documented by fluorescence spectroscopy. The section between P680 and plastoquinone QB in the PET chain occurring on the acceptor side of PS II can be suggested as the site of action of the compounds. The structure-activity relationships are discussed.

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Synthesis, theoretical studies, and effect on the photosynthetic electron transport of trifluoromethyl arylamides

Abstract: Trifluoromethyl amides herein described, which were shown to act at the PSII level, may represent a novel scaffold to be exploited aiming at the development of new active ingredients for weed control. © 2017 Society of Chemical Industry.

Cited by 8 publications

References 40 publications

SAR-mediated Similarity Assessment of the Property Profile for New, Silicon-Based AChE/BChE Inhibitors

SAR-mediated Similarity Assessment of the Property Profile for New, Silicon-Based AChE/BChE Inhibitors

Preparation and Photosynthesis-Inhibiting Activity of Novel Dihalogenated 3-Hydroxynaphthalene-2-carboxanilides

Halogenated 1-Hydroxynaphthalene-2-Carboxanilides Affecting Photosynthetic Electron Transport in Photosystem II

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