Reaction of Malonaldehyde with Nucleic Acid. III. Studies of the Fluorescent Substances Released by Enzymatic Digestion of Nucleic Acids Modified with Malonaldehyde(Biological)

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Malonaldehyde (MA), a product of lipid peroxidation, is mutagenic in Salmonella typhimurium. It can produce interstrand cross-links in deoxyribonucleic acid (DNA), resulting in the formation of fluorescent structures. In order to elucidate the chemical interaction between MA and nucleic acid, cross-linked nucleic acid was digested enzymatically, fluorescent substances were isolated and some of their chemical properties were investigated, The fluorescent substances were formed preferentially in the reaction of MA with polyguanylic acid or polycytidylic acid rather than polyadenyiic acid or polyuridylic acid. No correlation was observed between the fluorescence intensities and 2-thiobarbituric acid (TBA) values of the modified nucleic acids. Modified ribonucleic acid (RNA) was digested with Penicillium nuclease P_1, followed by chromatography on an octadecylsilane column. The major fluorescent substances isolated by high performance liquid chromatography exhibited similar fluorescence spectra, which corresponded to that of the MA-modified RNA. The substances, which did not contain nucleic acid components, were labile fluorophores, though they were stable when incorporated into nucleic acid. The results suggest that the fluorophores bind preferentially to guanine and cytosine bases in the form of covalently linked adducts and are released by enzymatic digestion.
公益社団法人日本薬学会の論文
1986-12-25