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Molecules 2017, 22(10), 1709; doi:10.3390/molecules22101709

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

1
Department of Chemical Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences, Palackeho 1, Brno 61242, Czech Republic
2
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Comenius University, Odbojarov 10, Bratislava 83232, Slovakia
3
Department of Environmental Ecology, Faculty of Natural Sciences, Comenius University, Ilkovicova 6, Bratislava 84215, Slovakia
4
Central Laboratories, Faculty of Chemical and Food Technology, Slovak University of Technology in Bratislava, Radlinskeho 9, Bratislava 81237, Slovakia
5
Global Change Research Institute CAS, Belidla 986/4a, 60300 Brno, Czech Republic
6
Institute of Chemistry, Faculty of Natural Sciences, Comenius University, Ilkovicova 6, Bratislava 84215, Slovakia
Preliminary results were presented at the 46th EuroCongress on Drug Synthesis and Analysis, Bratislava, Slovakia, 5–8 September 2017 (paper P-61).
*
Authors to whom correspondence should be addressed.
Received: 21 September 2017 / Accepted: 9 October 2017 / Published: 12 October 2017
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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 (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. View Full-Text
Keywords: hydroxynaphthalene-carboxamides; photosynthetic electron transport (PET) inhibition; spinach chloroplasts; structure-activity relationships hydroxynaphthalene-carboxamides; photosynthetic electron transport (PET) inhibition; spinach chloroplasts; structure-activity relationships
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MDPI and ACS Style

Gonec, T.; Kos, J.; Pesko, M.; Dohanosova, J.; Oravec, M.; Liptaj, T.; Kralova, K.; Jampilek, J. Halogenated 1-Hydroxynaphthalene-2-Carboxanilides Affecting Photosynthetic Electron Transport in Photosystem II. Molecules 2017, 22, 1709.

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