Antimycobacterial N-alkoxyphenylhydroxynaphthalenecarboxamides affecting photosystem II
Language English Country England, Great Britain Media print-electronic
Document type Journal Article, Research Support, Non-U.S. Gov't
PubMed
28363749
DOI
10.1016/j.bmcl.2017.03.050
PII: S0960-894X(17)30299-8
Knihovny.cz E-resources
- Keywords
- Hill reaction, Hydroxynaphthalenecarboxamides, Photosystem II, Structure–activity relationships,
- MeSH
- Anti-Bacterial Agents chemistry metabolism MeSH
- Photosystem II Protein Complex antagonists & inhibitors metabolism MeSH
- Naphthalenes chemistry metabolism MeSH
- Plant Proteins antagonists & inhibitors metabolism MeSH
- Spinacia oleracea drug effects metabolism MeSH
- Electron Transport drug effects MeSH
- Publication type
- Journal Article MeSH
- Research Support, Non-U.S. Gov't MeSH
- Names of Substances
- Anti-Bacterial Agents MeSH
- Photosystem II Protein Complex MeSH
- Naphthalenes MeSH
- Plant Proteins MeSH
N-(Alkoxyphenyl)-2-hydroxynaphthalene-1-carboxamides (series A) and N-(alkoxyphenyl)-1-hydroxynaphthalene-2-carboxamides (series B) affecting photosystem (PS) II inhibited photosynthetic electron transport (PET) in spinach chloroplasts. Their inhibitory activity depended on the compound lipophilicity as well as on the position of the alkoxy substituent. The most potent PET inhibitors were 2-hydroxy-N-phenylnaphthalene-1-carboxamide and N-[3-(but-2-yloxy)phenyl]-2-hydroxynaphthalene-1-carboxamide within series A (IC50=28.9 and 42.5µM, respectively) and 1-hydroxy-N-(3-propoxyphenyl)naphthalene-2-carboxamide and 1-hydroxy-N-(3-ethoxyphenyl)-naphthalene-2-carboxamide (IC50=2.0 and 3.1µM, respectively) within series B. The inhibitory activity of C'(3) or C'(4) alkoxy substituted compounds of series B was considerably higher than that of C'(2) ones within series A. The PET-inhibiting activities of both series were compared with the PET inhibition of isomeric N-alkoxyphenyl-3-hydroxynaphthalene-2-carboxamides (series C) reported recently. 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 PSII can be suggested as the site of action of the compounds.
References provided by Crossref.org
Insights into Antimalarial Activity of N-Phenyl-Substituted Cinnamanilides
Photosynthesis-Inhibiting Activity of N-(Disubstituted-phenyl)-3-hydroxynaphthalene-2-carboxamides
Synthesis and Spectrum of Biological Activities of Novel N-arylcinnamamides
Investigation of Hydro-Lipophilic Properties of N-Alkoxyphenylhydroxynaphthalenecarboxamides †
