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Coordinate and redox interactions of epinephrine (Epi) with iron at physiological pH are essential for understanding two very different phenomena – the detrimental effects of chronic stress on the cardiovascular system and the cross-linking of catecholamine-rich biopolymers and frameworks. Here we show that Epi and Fe 3+  form stable high-spin complexes in the 1:1 or 3:1 stoichiometry, depending on the Epi/Fe 3+  concentration ratio (low or high). Oxygen atoms on the catechol ring represent the sites of coordinate bond formation within physiologically relevant bidentate 1:1 complex. Redox properties of Epi are slightly impacted by Fe 3+ . On the other hand, Epi and Fe 2+  form a complex that acts as a strong reducing agent, which leads to the production of hydrogen peroxide via O 2  reduction, and to a facilitated formation of the Epi–Fe 3+  complexes. Epi is not oxidized in this process,  i.e . Fe 2+  is not an electron shuttle, but the electron donor. Epi-catalyzed oxidation of Fe 2+  represents a plausible chemical basis of stress-related damage to heart cells. In addition, our results support the previous findings on the interactions of catecholamine moieties in polymers with iron and provide a novel strategy for improving the efficiency of cross-linking.

Coordinate and redox interactions of epinephrine with ferric and ferrous iron at physiological pH