Key result
Metal ions that form stable complexes with doxorubicin, such as Iron(III) and copper(II), catalyze its degradation into the inactive compound D, whereas Na(+), K(+), and Ca(2+) do not.
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The coordination of specific metal ions like Iron(III) and copper(II) to anthracyclines catalyzes their degradation into inactive products, which may explain loss of antitumor activity.
The influence of some metal ions on the degradation of anthracyclines was examined. One of the degradation products is the 7,8-dehydro-9,10-desacetyldoxorubicinone, D* ( yen), usually formed by hydrolysis at slightly basic pH. D* is a lipophilic compound with no cytostatic properties. Its formation could be responsible for the lack of antitumor activity of the parent compound. The coordination of metal ions to anthracycline derivatives is required to have degradation products. Cations such as Na(+), K(+), or Ca(2+) do not induce the D* formation however metals which can form stable complexes with doxorubicin afford D*. Iron(III) and copper(II) form appreciable amount of D* at slightly acidic pH. Terbium(III) forms D* but its complex is stable only at slightly basic pH. Palladium(II) which does not form D*. The influence of the coordination mode of metal ions to anthracycline on the D* formation is discussed.
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Fiallo et al. (1994) studied this question. Metal ions was evaluated on Formation of 7,8-dehydro-9,10-desacetyldoxorubicinone (D). Metal ions that form stable complexes with doxorubicin, such as Iron(III) and copper(II), catalyze its degradation into the inactive compound D, whereas Na(+), K(+), and Ca(2+) do not.
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