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

0479717 - ÚVGZ 2018 RIV CH eng J - Journal Article
Goněc, T. - Kos, J. - Pesko, M. - Dohanosová, J. - Oravec, Michal - Liptaj, T. - Králová, K. - Jampílek, J.
Halogenated 1-Hydroxynaphthalene-2-Carboxanilides Affecting Photosynthetic Electron Transport in Photosystem II.
Molecules. Roč. 22, č. 10 (2017), č. článku 1709. E-ISSN 1420-3049
R&D Projects: GA MŠMT(CZ) LO1415
Research Infrastructure: CzeCOS II - 90061
Institutional support: RVO:67179843
Keywords : hydroxynaphthalene-carboxamides * photosynthetic electron transport (PET) inhibition * spinach chloroplasts * structure-activity relationships
OECD category: Biochemistry and molecular biology
Impact factor: 3.098, year: 2017

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.
Permanent Link: http://hdl.handle.net/11104/0275673