Possible Involvement of Dihydrofructosazine in the DNA Breaking Activity of D-Glucosamine
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概要
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Dehydrochlorination of D-glucosamine (2-amino-2-deoxy-D-glucose) hydrochloride with an anion exchange resin made its DNA breaking activity in plasmid pBR322 much higher, especially in the presence of Cu^<2+>. The sample of anion exchanger-treated D-glucosamine hydrochloride, i.e., HCl-free D-glucosamine sample, showed an absorption maximum at 274 nm on the UV absorption spectrum in water as seen in the case of fructosazine [2,5-bis (D-arabino-tetrahydroxybutyl) pyrazine], one of the dimers of D-glucosamine. On a positive-ion fast atom bombardment (FAB) mass spectrum, the sample showed an ion peak at m/z 323 as a base peak, corresponding to dihydrofructosazine [2,5-bis (D-arabino-tetrahydroxybutyl) dihydropyrazine], which was a precursor of fructosazine, as well as those of D-glucosamine itself (m/z 180) and fructosazine (m/z 321). The DNA strand breaking activity of HCl-free D-glucosamine sample was directly proportional to the peak intensity of m/z 323 ion, while the DNA breaking activity of fructosazine was much weaker than that of HCl-free D-glucosamine sample. 2,5-Dihydro-3,6-dimethylpyrazine and 2,3-dihydro-5,6-dimethylpyrazine having a dihydropyrazine skeleton the same as dihydrofructosazine showed the same extent of DNA strand breaking activity as did the HCl-free D-glucosamine sample. These results indicated that dihydrofructosazine produced during the dehydrochlorination is closely involved in the DNA breaking activity of HCl-free D-glucosamine sample.
- 社団法人日本薬学会の論文
- 1995-05-15
著者
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見明 史雄
福岡大学薬学部
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鹿志毛 信広
Faculty of Pharmaceutical Sciences, Fukuoka University
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山口 忠敏
Department of Hygiene, Miyazaki Medical College
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三代 典子
Department of Hygiene, Miyazaki Medical College
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花園 弘志
Faculty of Pharmaceutical Sciences, Fukuoka University
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見明 史雄
Faculty of Pharmaceutical Sciences, Fukuoka University
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渡辺 健治
Faculty of Pharmaceutical Sciences, Fukuoka University
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鹿志毛 信広
Faculty Of Pharmaceutical Sciences Fukuoka University
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山口 忠敏
Department Of Hygiene Miyazaki Medical College
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三代 典子
Department Of Hygiene Miyazaki Medical College
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渡辺 健治
Faculty Of Pharmaceutical Sciences Fukuoka University
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Miake Fumio
Faculty Of Pharmaceutical Sciences Fukuoka University
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花園 弘志
Faculty Of Pharmaceutical Sciences Fukuoka University
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