Abstract
Fluorescence titration methods and equilibrium dialysis were used to study the thermodynamics of the interaction of doxorubicin, the β anomer of doxorubicin, daunorubicin, and hydroxyrubicin with DNA. All of these except hydroxyrubicin carry a net charge of +1 at neutral pH, arising from the protonation of the daunosamine moiety. Hydroxyrubicin is a synthetic anthracycline antibiotic in which the amine moiety has been replaced by a hydroxyl group, which is uncharged but polar at neutral pH. The comparative binding studies we describe offer a unique opportunity to evaluate the electrostatic contributions to the DNA binding free energy of these anthracycline antibiotics and to test specific predictions arising from current polyelectrolyte theory as applied to ligand-DNA interactions
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