Antimycobacterial N-alkoxyphenylhydroxy-naphthalenecarboxamides affecting photosystem II.

Kód výsledku v 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>

Výsledek na webu

<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>

Jazyk výsledku

angličtina

Název v původním jazyce

Antimycobacterial N-alkoxyphenylhydroxy-naphthalenecarboxamides affecting photosystem II.

Popis výsledku v původním jazyce

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.

Název v anglickém jazyce

Antimycobacterial N-alkoxyphenylhydroxy-naphthalenecarboxamides affecting photosystem II.

Popis výsledku anglicky

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.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

30104 - Pharmacology and pharmacy

Projekt

—

Návaznosti

S - Specificky vyzkum na vysokych skolach

Rok uplatnění

2017

Kód důvěrnosti údajů

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

Název periodika

Bioorganic and Medicinal Chemistry Letters

ISSN

0960-894X

e-ISSN

—

Svazek periodika

27

Číslo periodika v rámci svazku

9

Stát vydavatele periodika

NL - Nizozemsko

Počet stran výsledku

5

Strana od-do

1881-1885

Kód UT WoS článku

000399862800001

EID výsledku v databázi Scopus

—