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

Overview

Journal Molecules

Publisher MDPI

Specialty Biology

Date 2017 Oct 13

PMID 29023407

Citations 9

Authors

Tomas Gonec

Jiri Kos

Matus Pesko

Jana Dohanosova

Michal Oravec

Tibor Liptaj

Katarina Kralova

Josef Jampilek

Affiliations

Soon will be listed here.

Abstract

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 ( L.) chloroplasts. 1-Hydroxy--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 (IC = 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 and aromatic amino acids present in pigment-protein complexes mainly in PS II were documented by fluorescence spectroscopy. The section between P and plastoquinone Q 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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Consensus-Based Pharmacophore Mapping for New Set of -(disubstituted-phenyl)-3-hydroxyl-naphthalene-2-carboxamides.

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