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.Základní údaje
Originální název
Halogenated 1-Hydroxynaphthalene-2-Carboxanilides Affecting Photosynthetic Electron Transport in Photosystem II
Autoři
GONĚC, Tomáš, J KOS, M PESKO, J DOHANOSOVA, M ORAVEC, T LIPTAJ, K KRALOVA a J JAMPILEK
Vydání
Molecules, BASEL, Mayer und Muller, 2017, 1420-3049
Další údaje
Jazyk
angličtina
Typ výsledku
Článek v odborném periodiku
Utajení
není předmětem státního či obchodního tajemství
Impakt faktor
Impact factor: 3.098
UT WoS
000414670600136
Klíčová slova anglicky
hydroxynaphthalene-carboxamides; photosynthetic electron transport (PET) inhibition; spinach chloroplasts; structure-activity relationships
Příznaky
Mezinárodní význam, Recenzováno
Změněno: 10. 3. 2021 00:00, PharmDr. Tomáš Goněc, Ph.D.
Anotace
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.