Detailed Information on Publication Record
2017
Halogenated 1-Hydroxynaphthalene-2-Carboxanilides Affecting Photosynthetic Electron Transport in Photosystem II
GONĚC, Tomáš, J KOS, M PESKO, J DOHANOSOVA, M ORAVEC et. al.Basic information
Original name
Halogenated 1-Hydroxynaphthalene-2-Carboxanilides Affecting Photosynthetic Electron Transport in Photosystem II
Authors
GONĚC, Tomáš, J KOS, M PESKO, J DOHANOSOVA, M ORAVEC, T LIPTAJ, K KRALOVA and J JAMPILEK
Edition
Molecules, BASEL, Mayer und Muller, 2017, 1420-3049
Other information
Language
English
Type of outcome
Článek v odborném periodiku
Confidentiality degree
není předmětem státního či obchodního tajemství
Impact factor
Impact factor: 3.098
UT WoS
000414670600136
Keywords in English
hydroxynaphthalene-carboxamides; photosynthetic electron transport (PET) inhibition; spinach chloroplasts; structure-activity relationships
Tags
International impact, Reviewed
Změněno: 10/3/2021 00:00, PharmDr. Tomáš Goněc, Ph.D.
Abstract
V originále
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 mu M, 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 P-680 and plastoquinone Q(B) 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.