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. 1974 Apr;1(4):531–547. doi: 10.1093/nar/1.4.531

Synthesis of 1,N6-etheno-2-aza-adenosine (2-aza-ε-adenosine): a new cytotoxic fluorescent nucleoside

KC Tsou 1, KF Yip 1, EE Miller 1, KW Lo 1
PMCID: PMC343355  PMID: 10793738

Abstract

1,N6-Etheno-2-aza-adenosine was synthesized by treating 1,N6-etheno-adenosine with alkali, followed by nitrosation. The mechanism of formation of this novel nucleoside was elucidated using adenosine tritiated at C-8 and C-2, and was found to deformylate exclusively at C-2. This new 2-aza nucleoside fluoresces at 494 nm when excited at 358 nm. Toxicity study showed the compound is active in a rat mammary tumor tissue culture line, but inactive in HeLa and Glioma 26 tissue culture lines. It was also found to selectively inhibit the thymidine incorporation into DNA in a rat mammary tumor, but exhibits no ill effect on normal proliferative tissue. The reactive intermediate 3-β-D-ribofuranosyl-4-amino-5-(imidazol-2-yl) imidazole was identified and was found to be an active agent in tissue culture.

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Selected References

These references are in PubMed. This may not be the complete list of references from this article.

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