Chemical properties of catechols and their molecular modes of toxic action in cells, from microorganisms to mammals.
Catechols 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.
Schweigert
N
N
Swiss Federal Institute for Environmental Science and Technology, EAWAG, Dübendorf.
Zehnder
A J
AJ
Eggen
R I
RI
D000818:Animals; D002396:Catechols / Q000737:chemistry* / Q000633:toxicity*; D002462:Cell Membrane / Q000187:drug effects; D004249:DNA Damage / Q000187:drug effects; D015227:Lipid Peroxidation / Q000187:drug effects; D008322:Mammals; D008564:Membrane Potentials / Q000187:drug effects; D010084:Oxidation-Reduction; D011506:Proteins / Q000187:drug effects / Q000378:metabolism; D017382:Reactive Oxygen Species / Q000378:metabolism
D002396:Catechols; D011506:Proteins; D017382:Reactive Oxygen Species