Chemical modification of oxanosine. I. Synthesis and biological properties of 2'-deoxyoxanosine.
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Biomedical subjects
Publications and source records attributed to N Yagisawa.
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Oxanosine, a novel nucleoside, inhibits the growth of Escherichia coli K-12 on peptone agar, but not on Nutrient agar. This antibiotic activity was found to be bacteriostatic and was antagonized by guanine, guanosine, and guanylic acid. The growth of leukemia L 1210 cell was also inhibited by oxanosine, and the inhibition was reversed by guanylic acid. Oxanosine was confirmed to be a competitive inhibitor of GMP synthetase (E.C. 6.3.5.2) and the Ki value was 7.4 X 10(-4) M.
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Oxanosine, a novel nucleoside, has been isolated from the culture filtrate of a strain of Streptomyces. The structure was determined to be 5-amino-3-beta-D-ribofuranosyl-3H-imidazo [4,5-d] [1,3]oxazin-7-one by X-ray crystallographic analysis and chemical studies. Oxanosine showed weak antibacterial activity on peptone agar; for example, Escherichia coli K-12 (MIC 12.5 mcg/ml). The antibacterial activity was antagonized by addition of guanine, guanosine and 5'-guanylic acid. Oxanosine inhibited the growth of HeLa cells in vitro (IC50 32 mcg/ml) and suppressed the growth of L-1210 leukemia in mice. The primary action of oxanosine appears to be inhibition of GMP-synthetase. Intravenous injection of 4 mg of oxanosine to mice does not show any toxic sign.
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