Structure-Dependent Complexation of Fe3+ by Anthracyclines. 1. The Importance of Pendent Hydroxyl Functionality
2013
Nawara, Krzysztof | McCracken, John L. | Krysiński, Paweł | Blanchard, G. J.
We have investigated the stability of doxorubicin and daunorubicin complexes with Fe³⁺ in aqueous solution. Doxorubicin and daunorubicin are anthracycline chemotherapeutic agents that differ structurally by the presence of a hydroxymethylketone functionality in doxorubicin versus a methyl ketone moiety in daunorubicin. We demonstrate that the presence of the hydroxyl group in doxorubicin enhances its 1:1 complexation with Fe³⁺ relative to that seen for daunorubicin. We utilize UV–visible absorbance, circular dichroism, fluorescence and EPR spectroscopies, molecular dynamics, and semiempirical calculations to understand how the presence of an additional hydroxyl group affects the interactions of anthracyclines with Fe³⁺. Our data indicate that the binding mode of iron in the complex is different for doxorubicin and daunorubicin.
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