Effect of side groups of phenanthridines on their hetero¬association with antibiotic daunomycin and the competitive binding with a DNA oligomer.
Abstract
500 MHz 'H NMR spectroscopy has been used to study the hetero-association of phenanthndine dyes, containing different side groups in the chromophore, with anthracycline antibiotic daunomycin (DAU) and the competitive binding of aromatic dye/drug molecules with a DNA oligomer 5'-d(TpGpCpA ). The magnitudes of the hetero- association parameters of Ethidium Bromide (EB) and its azido-denvatives, 8-azido-Ethidium Bromide (EMB) and 3,8-Diazido-Ethidium Chloride (EDC) with DAU show a successive decrease with mono and di-substitution ot the 3,8-amino groups of EB due to less probability of the formation of an intermolecular hydrogen bond between the amino groups of EB and the 9 MeCO group of DAU. Analysis has shown that the equilibrium balance of self- association, hetero-association and dye/drug-DNA binding depends on solution conditions. In order to elucidate the molecular complexation processes in multi-component equilibria occurring in mixed solution (including mutagen, aromatic antibiotic and DNA), it is necessary to take into account not only the hetero-association of the aromatic molecules but also the competition between drug and mutagen for the oligonucleotide binding sitesю.
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