Antimycobacterial N-alkoxyphenylhydroxy-naphthalenecarboxamides affecting photosystem II.

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F62157124%3A16370%2F17%3A43876062" target="_blank" >RIV/62157124:16370/17:43876062 - isvavai.cz</a>

Result on the web

<a href="http://dx.doi.org/10.1016/j.bmcl.2017.03.050" target="_blank" >http://dx.doi.org/10.1016/j.bmcl.2017.03.050</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1016/j.bmcl.2017.03.050" target="_blank" >10.1016/j.bmcl.2017.03.050</a>

Result language

angličtina

Original language name

Antimycobacterial N-alkoxyphenylhydroxy-naphthalenecarboxamides affecting photosystem II.

Original language description

N-(Alkoxyphenyl)-2-hydroxynaphthalene-1-carboxamides (series A) and N-(alkoxyphenyI)-1-hydroxy-naphthalene-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 42.5 mu M, respectively) and 1-hydroxy-N-(3-propoxyphenyl)naphthalene-2-carboxamide and 1-hydroxy-N-(3-ethoxyphenyl)-naphthalene-2-carboxamide (IC50= 2.0 and 3.1 mu M, respectively) within series B. The inhibitory activity of C&apos;(3) or C&apos;(4) alkoxy substituted compounds of series B was considerably higher than that of C&apos;(2) ones within series A. The PET-inhibiting activities of both series were compared with the PET inhibition of isomeric N-alkoxypheny1-3-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 P(68)0 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.

Czech name

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Czech description

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Type

J_imp - Article in a specialist periodical, which is included in the Web of Science database

CEP classification

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OECD FORD branch

30104 - Pharmacology and pharmacy

Project

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Continuities

S - Specificky vyzkum na vysokych skolach

Publication year

2017

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

27

Issue of the periodical within the volume

9

Country of publishing house

NL - THE KINGDOM OF THE NETHERLANDS

Number of pages

5

Pages from-to

1881-1885

UT code for WoS article

000399862800001

EID of the result in the Scopus database

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