Interactions of di- and trihydroxybenzenes with transition metals and their biological consequences

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11160%2F25%3A10507721" target="_blank" >RIV/00216208:11160/25:10507721 - isvavai.cz</a>

Výsledek na webu

<a href="https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=gdcH_IJ0R0" target="_blank" >https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=gdcH_IJ0R0</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1080/10715762.2025.2598763" target="_blank" >10.1080/10715762.2025.2598763</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Interactions of di- and trihydroxybenzenes with transition metals and their biological consequences

Popis výsledku v původním jazyce

Small dihydroxy- and trihydroxybenzenes are polyphenolic compounds found in plant-based materials and formed by the human gut microbiota from other dietary phenolics. This study aimed to explore how 5 structurally related hydroxybenzenes interact with the biologically relevant metals iron and copper under various (patho)physiological pH conditions, focusing on their chelating and reducing abilities, influence on the metal-driven Fenton reactions, and their role in copper-induced hemolysis. Only compounds with hydroxyl groups in an ortho-position, specifically pyrogallol and 4-methylcatechol, were able to strongly chelate Fe2+ at neutral pH and exhibited the largest capacity to reduce Fe3+ and Cu2+. However, the ability to chelate metals did not translate into inhibition of the Fenton reaction. Only 2,4-dihydroxyacetophenone and resorcinol, compounds with hydroxyl groups in a meta-position that lack chelating capability, were effective in suppressing hydroxyl radical formation triggered by the Fe2+-driven Fenton reaction. Interestingly, pyrogallol, despite its strong pro-oxidant properties, was the only compound that protected human erythrocytes from Cu-induced lysis. In conclusion, solely pyrogallol seems to have a protective effect against copper-induced toxicity under biologically relevant conditions.

Název v anglickém jazyce

Interactions of di- and trihydroxybenzenes with transition metals and their biological consequences

Popis výsledku anglicky

Small dihydroxy- and trihydroxybenzenes are polyphenolic compounds found in plant-based materials and formed by the human gut microbiota from other dietary phenolics. This study aimed to explore how 5 structurally related hydroxybenzenes interact with the biologically relevant metals iron and copper under various (patho)physiological pH conditions, focusing on their chelating and reducing abilities, influence on the metal-driven Fenton reactions, and their role in copper-induced hemolysis. Only compounds with hydroxyl groups in an ortho-position, specifically pyrogallol and 4-methylcatechol, were able to strongly chelate Fe2+ at neutral pH and exhibited the largest capacity to reduce Fe3+ and Cu2+. However, the ability to chelate metals did not translate into inhibition of the Fenton reaction. Only 2,4-dihydroxyacetophenone and resorcinol, compounds with hydroxyl groups in a meta-position that lack chelating capability, were effective in suppressing hydroxyl radical formation triggered by the Fe2+-driven Fenton reaction. Interestingly, pyrogallol, despite its strong pro-oxidant properties, was the only compound that protected human erythrocytes from Cu-induced lysis. In conclusion, solely pyrogallol seems to have a protective effect against copper-induced toxicity under biologically relevant conditions.

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<br>I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2025

Kód důvěrnosti údajů

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

Název periodika

Free Radical Research

ISSN

1071-5762

e-ISSN

1029-2470

Svazek periodika

59

Číslo periodika v rámci svazku

10-12

Stát vydavatele periodika

GB - Spojené království Velké Británie a Severního Irska

Počet stran výsledku

16

Strana od-do

824-839

Kód UT WoS článku

001640227700001

EID výsledku v databázi Scopus

2-s2.0-105025048944