Ring-substituted 8-hydroxyquinoline-2-carboxanilides as photosystem II inhibitors

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F62157124%3A16370%2F16%3A43874575" target="_blank" >RIV/62157124:16370/16:43874575 - isvavai.cz</a>

Result on the web

<a href="http://dx.doi.org/10.1016/j.bmcl.2016.07.021" target="_blank" >http://dx.doi.org/10.1016/j.bmcl.2016.07.021</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1016/j.bmcl.2016.07.021" target="_blank" >10.1016/j.bmcl.2016.07.021</a>

Result language

angličtina

Original language name

Ring-substituted 8-hydroxyquinoline-2-carboxanilides as photosystem II inhibitors

Original language description

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 2.3-3.6 ?M 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 ? parameter of the substituent R was observed with optimum r value 0.06 for C'(4) and 0.34 for C'(3) substituted derivatives, while the value of ? 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.

Czech name

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Czech description

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Type

J_x - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)

CEP classification

FR - Pharmacology and apothecary chemistry

OECD FORD branch

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Project

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Continuities

S - Specificky vyzkum na vysokych skolach

Publication year

2016

Confidentiality

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Name of the periodical

Bioorganic and Medicinal Chemistry Letters

ISSN

0960-894X

e-ISSN

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Volume of the periodical

26

Issue of the periodical within the volume

16

Country of publishing house

NL - THE KINGDOM OF THE NETHERLANDS

Number of pages

4

Pages from-to

3862-3865

UT code for WoS article

000380574400006

EID of the result in the Scopus database

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