Quinones and quinone imines are highly
reactive metabolites (RMs)
able to induce dangerous effects in vivo. They are responsible for
all kinds of toxicity, for example, cytotoxicity, immunotoxicity,
and carcinogenesis. Furthermore, hepatotoxicity of chemicals/drugs
in particular can be induced by quinone and quinone imine metabolites.
According to their reactivity, quinones and quinone imines react as
Michael’s acceptors with cell proteins or DNA and, in this
way, cause damage to the cells. Quinones and quinone imines also have
high redox potential and, due to their semiquinone radicals, are capable
of redox cycling and forming reactive oxygen species (ROS). However,
the presence of quinones and quinone imines structures in compounds
is not always responsible for a toxic effect. The main question, therefore,
is what are the main factors responsible for the toxicity of the chemicals
and drugs that form RMs. For this reason, the presence of structural
alerts and evidence for the formation of reactive quinones and quinone
imines metabolites and their mechanisms of toxicity through cellular
effects are discussed in this review, together with examples.