Perturbations of the 1H NMR spectrum of the free base of Adriamycin in DMF solution were found when MCl2(DMF)2 (M = Pd or Pt) was added to the Adriamycin solutions. These perturbations were greatest for the 3' proton on the sugar ring and the effect decreased as the distance from this site increased. No changes were observed in the NMR spectrum of the rest of the molecule nor was there any color change when the metal solutions were added. This is interpreted as evidence that Adriamycin binds to these metals at the 3 ' amino group in DMF solution and that there is no reaction at the chromophore. The complexes were found to be in the fast exchange regime on the NMR time scale. As well, some products were isolated from reactions of Adriamycin with MCl2(DMF)2 in 20% MeOH/CH2Cl2 and MCl2 in DMF solution. They were characterized by their elemental analyses, as well as by 1H NMR and infrared spectroscopies.
ASJC Scopus subject areas
- Inorganic Chemistry