Chemical properties of catechols and their molecular modes of toxic action in cells, from microorganisms to mammals

Abstract

SummaryCatechols can undergo a variety of chemical reactions. In this review, we particularly focus on complex formations and the redox chemistry of catechols, which play an inportant role in the toxicity of catechols. In the presence of heavy metals, such as iron or copper, stable complexes can be formed. In the presence of oxidizing agents, catechols can be oxidized to semiquinone radicals and in a next step to o-benzoquinones. Heavy metals may catalyse redox reactions in which catechols are involved. Further chemical properties like the acidity constant and the lipophilicity of different catechols are shortly described as well. As a consequence of the chemical properties and the chemical reactions of catechols, many different reactions can occur with biomolecules such as DNA, proteins and membranes, ultimately leading to non-repairable damage. Reactions with nucleic acids such as adduct formation and strand breaks are discussed among others. Interactions with proteins causing protein and enzyme inactivation are described. The membrane±catechol interactions discussed here are lipid peroxidation and uncoupling. The deleterious effect of the interactions between catechols and the different biomolecules is discussed in the context of the observed toxicities, caused by catechols.

Naphthalene metabolism and growth inhibition by naphthalene in Polaromonas naphthalenivorans strain CJ2

“…Alteration of membrane structure can disrupt energy transduction and the activity of membrane-associated proteins (Sikkema et al, 1995). Additionally, metabolites of aromatic compounds, such as catechols and quinones, can be more toxic than the parent compound due to an increase in solubility, production of reactive oxygen species, or adduct formation with DNA and proteins (Penning et al, 1999;Schweigert et al, 2001).…”

Detoxifying Polyhalogenated Catechols through a Copper‐Chelating Agent by Forming Stable and Redox‐Inactive Hydrogen‐Bonded Complexes with an Unusual Perpendicular Structure

“…Therefore, our findings may have interesting biological and environmental implications because these polyhalogenated catecholic compounds are the reactive and toxic metabolites, or degradation products for many widely used polyhalogenated aromatic compounds (such as pentachlorophenol, Agent Orange, and hexachlorobenzene), which are considered probable human carcinogens and have also been detected in discharges from pulp and paper mills. [26][27][28] Polyphenolic compounds, which are found in large amounts in fruits and vegetables, have been reported to exhibit beneficial antioxidant and anticancer activities. [29,30] However, they could also exert deleterious effects by generating reactive phenoxyl or semiquinone radicals.…”

Stable Expression of the Chlorocatechol Dioxygenase Gene fromRalstonia eutrophaNH9 in Hybrid Poplar Cells

“…In animal and microbial cells, catechol alone undergoes chemical reactions with many macromolecules and has toxic effects. 9) Although the ability of plant cells to take up and metabolize chlorochatechols has not been investigated, 3-chlorocatechol might be accumulated in non-transgenic cells and reacted with macromolecules including DNA and proteins. It was noted that after 8 h of incubation in 3-chlorocatechol, the non-transgenic poplar calli turned dark brown and the transgenic calli retained a yellow-white color (data not shown).…”