A guanosine analog with diverse biological activities
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Isomer(s)
39018Xanthosine (hydrate)
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Oxanosine

Item No. 33503

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5-amino-3-β-D-ribofuranosyl-imidazo[4,5-d][1,3]oxazin-7(3H)-one
CAS Number
80394-72-5
Synonyms
  • NSC 359452
Molecular Formula
C10H12N4O6
Formula Weight
284.2
Purity
≥90%
Formulation (Request formulation change)
A solid
SMILES
O=C1C2=C(N=C(O1)N)N([C@@]3([H])[C@H](O)[C@H](O)[C@@H](CO)O3)C=N2
InChi Code
InChI=1S/C10H12N4O6/c11-10-13-7-4(9(18)20-10)12-2-14(7)8-6(17)5(16)3(1-15)19-8/h2-3,5-6,8,15-17H,1H2,(H2,11,13)/t3-,5-,6-,8-/m1/s1
InChi Key
PWVUOVPUCZNICU-ZIYNGMLESA-N
Origin
Bacterium/Streptomyces capreolus MG265-CF3
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $623

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    Product Description

    Oxanosine is an analog of guanosine (Item No. 27702) that has been found in S. capreolus and has diverse biological activities, including antibacterial, antiviral, and anticancer properties.1,2 It is active against a variety of bacteria, including S. flexneri, P. mirabilis, and E. coli (MICs = 6.25, 12.5, 25 µg/ml, respectively, on peptone, but not nutrient, agar). Oxanosine inhibits replication of the HIV-1 strain IIIb in infected CEM and U937, but not H9, cells (EC50s = 7, 27, and >500 µg/ml, respectively).1 It also inhibits the growth of HeLa human cervical cancer cells (IC50 = 32 µg/ml) and reduces tumor growth in a murine L1210 lymphocytic leukemia model.2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Saito, Y., Nakamura, M., Ohno, T., et al. Syntheses of oxanosine and carbocyclic oxanosine derivatives as anti-HIV agents. J. Antibiot. (Tokyo) 53(3), 309-313 (2000).

    2. Shimada, N., Yagisawa, N., Naganawa, H., et al. Oxanosine, a novel nucleoside from actinomycetes. J. Antibiot. (Tokyo) 34(9), 1216-1218 (1981).