Ring-substituted 8-hydroxyquinoline-2-carboxanilides as photosystem II inhibitors
Language English Country England, Great Britain Media print-electronic
Document type Journal Article
PubMed
27432762
DOI
10.1016/j.bmcl.2016.07.021
PII: S0960-894X(16)30723-5
Knihovny.cz E-resources
- Keywords
- 8-Hydroxyquinolines, Hill reaction, Photosystem II, Structure–activity relationships,
- MeSH
- Anilides chemical synthesis chemistry metabolism MeSH
- Chlorophyll A MeSH
- Chlorophyll chemistry MeSH
- Chloroplasts metabolism MeSH
- Spectrometry, Fluorescence MeSH
- Photosynthesis MeSH
- Photosystem II Protein Complex antagonists & inhibitors metabolism MeSH
- Oxyquinoline chemistry MeSH
- Spinacia oleracea metabolism MeSH
- Electron Transport MeSH
- Protein Binding MeSH
- Structure-Activity Relationship MeSH
- Publication type
- Journal Article MeSH
- Names of Substances
- Anilides MeSH
- Chlorophyll A MeSH
- Chlorophyll MeSH
- Photosystem II Protein Complex MeSH
- Oxyquinoline MeSH
Ring-substituted 8-hydroxyquinoline-2-carboxanilides inhibited photosynthetic electron transport (PET) through photosystem (PS) II. Their inhibitory efficiency depended on the compound lipophilicity, the electronic properties of the substituent R and the position of the substituent R on the benzene ring. The most effective inhibitors showing IC50 values in the range 2.3-3.6μM were substituted in C'(3) by F, CH3, Cl and Br. The dependence of the PET-inhibiting activity on the lipophilicity of the compounds was quasi-parabolic for 3-substituted derivatives, while for C'(2) ones a slight increase and for C'(4) derivatives a sharp decrease of the activity were observed with increasing lipophilicity. In addition, the dependence of PET-inhibiting activity on electronic Hammett's σ parameter of the substituent R was observed with optimum σ value 0.06 for C'(4) and 0.34 for C'(3) substituted derivatives, while the value of σ parameter did not significantly influence the PET-inhibiting activity of C'(2) substituted compounds. Interactions of the studied compounds with chlorophyll a and aromatic amino acids present in the pigment-protein complexes mainly in PS II were documented by fluorescence spectroscopy. The section between P680 and plastoquinone QB occurring on the acceptor side of PS II can be suggested as the site of action of the compounds.
References provided by Crossref.org
Photosynthesis-Inhibiting Activity of N-(Disubstituted-phenyl)-3-hydroxynaphthalene-2-carboxamides
Synthesis and Spectrum of Biological Activities of Novel N-arylcinnamamides
