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

J 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

DOI

http://dx.doi.org/10.3390/molecules22101709

UT WoS

000414670600136

Keywords in English

hydroxynaphthalene-carboxamides; photosynthetic electron transport (PET) inhibition; spinach chloroplasts; structure-activity relationships

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.

Citovat

GONĚC, Tomáš, J KOS, M PESKO, J DOHANOSOVA, M ORAVEC, T LIPTAJ, K KRALOVA and J JAMPILEK. Halogenated 1-Hydroxynaphthalene-2-Carboxanilides Affecting Photosynthetic Electron Transport in Photosystem II. Molecules. BASEL: Mayer und Muller, 2017, vol. 22, No 10, 12 pp. ISSN 1420-3049. Available from: https://dx.doi.org/10.3390/molecules22101709.

@article{1727091,
   author = {Goněc, Tomáš and Kos, J and Pesko, M and Dohanosova, J and Oravec, M and Liptaj, T and Kralova, K and Jampilek, J},
   article_location = {BASEL},
   article_number = {10},
   doi = {http://dx.doi.org/10.3390/molecules22101709},
   keywords = {hydroxynaphthalene-carboxamides; photosynthetic electron transport (PET) inhibition; spinach chloroplasts; structure-activity relationships},
   language = {eng},
   issn = {1420-3049},
   journal = {Molecules},
   title = {Halogenated 1-Hydroxynaphthalene-2-Carboxanilides Affecting Photosynthetic Electron Transport in Photosystem II},
   volume = {22},
   year = {2017}
}

TY  - JOUR
ID  - 1727091
AU  - Goněc, Tomáš - Kos, J - Pesko, M - Dohanosova, J - Oravec, M - Liptaj, T - Kralova, K - Jampilek, J
PY  - 2017
TI  - Halogenated 1-Hydroxynaphthalene-2-Carboxanilides Affecting Photosynthetic Electron Transport in Photosystem II
JF  - Molecules
VL  - 22
IS  - 10
PB  - Mayer und Muller
SN  - 14203049
KW  - hydroxynaphthalene-carboxamides
KW  - photosynthetic electron transport (PET) inhibition
KW  - spinach chloroplasts
KW  - structure-activity relationships
N2  - 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.
ER  -

GONĚC, Tomáš, J KOS, M PESKO, J DOHANOSOVA, M ORAVEC, T LIPTAJ, K KRALOVA and J JAMPILEK. Halogenated 1-Hydroxynaphthalene-2-Carboxanilides Affecting Photosynthetic Electron Transport in Photosystem II. \textit{Molecules}. BASEL: Mayer und Muller, 2017, vol.~22, No~10, 12 pp. ISSN~1420-3049. Available from: https://dx.doi.org/10.3390/molecules22101709.

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