Syntheses of oxanosine and carbocyclic oxanosine derivatives as anti-HIV agents.

Oxanosine is a substrate of adenosine deaminase. Implications for the quest for a toxicological marker for nitrosation activity.

Oxanosine 3r, 5-amino-3-beta-(d-ribofuranosyl)-3H-imidazo[4,5-d][1,3]oxazine-7-one, was isolated as a novel nucleoside antibiotic in 1981 from Streptomyces capreolus MG265-CF3. Oxanosine became relevant in toxicology in 1996 with the discovery that it is formed in nitrosative guanosine deamination. As part of studies of the mechanism of oxanosine formation, the synthesis was attempted of [7- 18...

Induction by the guanosine analogue oxanosine of reversion toward the normal phenotype of K-ras-transformed rat kidney cells.

Oxanosine, a guanosine analogue antibiotic, altered the "transformed" morphology of rat kidney cells integrating a temperature-sensitive K-ras gene into "normal" morphology at 34 degrees C, a permissive temperature. Oxanosine also increased the cellular content of fibronectin to the normal level. The cells under these conditions had lower levels of guanine nucleotides and unstable and less palm...

Increased sensitivity to oxanosine, a novel nucleoside antibiotic, of rat kidney cells upon expression of the integrated viral src gene.

The mechanism of antitumor action of oxanosine was studied using a strain of rat kidney cells infected with a mutant Rous sarcoma virus, the src gene of which was temperature sensitive. Oxanosine inhibited cell growth in vitro, as well as nucleic acid synthesis in these cells, 10 times more strongly at a permissive temperature (33 degrees C) than at a non-permissive temperature (39 degrees C). ...

Cleavage of deoxyoxanosine-containing oligodeoxyribonucleotides by bacterial endonuclease V.

Oxanine (O) is a deamination product derived from guanine with the nitrogen at the N1 position substituted by oxygen. Cytosine, thymine, adenine, guanine as well as oxanine itself can be incorporated by Klenow Fragment to pair with oxanine in a DNA template with similar efficiency, indicating that oxanine in DNA may cause various mutations. As a nucleotide, deoxyoxanosine may substitute for deo...

Synthesis, purification, and characterization of the potent inhibitor of inosine monophosphate dehydrogenase: oxanosine monophosphate