An intermediate in the pteridine pathway
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Isoxanthopterin

Item No. 17564

Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-amino-4,7(3H,8H)-pteridinedione
CAS Number
529-69-1
Synonyms
  • NSC 118090
  • NSC 614991
Molecular Formula
C6H5N5O2
Formula Weight
179.1
Purity
≥90%
Formulation (Request formulation change)
A crystalline solid
SMILES
O=C1C=NC(C(N=C(N)N2)=O)=C2N1
InChi Code
InChI=1S/C6H5N5O2/c7-6-10-4-3(5(13)11-6)8-1-2(12)9-4/h1H,(H4,7,9,10,11,12,13)
InChi Key
GLKCOBIIZKYKFN-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    10 mg

    $41

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    50 mg

    $119

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    100 mg

    $196

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    Product Description

    Isoxanthopterin is a natural intermediate in the pteridine pathway, which has roles in pigmentation and cell division.1 It can be produced naturally from 7-oxobiopterin or in vitro by the oxidation of pterin by xanthine oxidase.1,2 Isoxanthopterin is a guanine analog that interferes with RNA and DNA synthesis and can inhibit cell proliferation.3,4 Methylated derivatives of isoxanthopterin are fluorescent guanine analogs that are used to study DNA structure.3,5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Ziegler, I., McDonaldo, T., Hesslinger, C., et al. Development of the pteridine pathway in the zebrafish, Danio rerio. The Journal of Biological Chemisty 275(25), 18926-18932 (2000).

    2. Neubert, P., Besenfelder, E., and Koch, K. Enzymatic inhibition assay for fluorometric determination of allopurinol and oxipurinol in serum and urine. Arzneimittelforschung 30(11), 1857-1859 (1980).

    3. Lagowski, J.M., and Forrest, H.S. Interaction in vitro between isoxanthopterin and DNA. Proc. Natl. Acad. Sci. USA 58(4), 1541-1547 (1967).

    4. Ziegler, I., Hamm, U., and Berndt, J. Participation of pterins in the control of lymphocyte stimulation and lymphoblast proliferation. Cancer Res. 43(11), 5356-5359 (1983).

    5. Widom, J.R., Rappoport, D., Perdomo-Ortiz, A., et al. Electronic transition moments of 6-methyl isoxanthopterin--a fluorescent analogue of the nucleic acid base guanine. Nucleic Acids Res. 41(2), 995-1004 (2013).