Key result
Doxorubicin exhibits enhanced 1:1 complexation with Fe3+ compared to daunorubicin due to the presence of an additional hydroxyl group, resulting in a different binding mode.
The structural difference between doxorubicin and daunorubicin alters their iron-binding properties, which may have implications for their mechanisms of action or toxicity.
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May influence anthracycline cardiotoxicity via iron binding; leaves open mechanistic confirmation in patients.
We have investigated the stability of doxorubicin and daunorubicin complexes with Fe(3+) 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 Fe(3+) 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 Fe(3+). Our data indicate that the binding mode of iron in the complex is different for doxorubicin and daunorubicin.
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Nawara et al. (2013) studied this question. Doxorubicin vs. Daunorubicin was evaluated on Stability and binding mode of complexes with Fe3+. Doxorubicin exhibits enhanced 1:1 complexation with Fe3+ compared to daunorubicin due to the presence of an additional hydroxyl group, resulting in a different binding mode.
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