A mutagenic nitrative guanine derivative
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8-Nitroguanine

Item No. 89295

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-amino-1,9-dihydro-8-nitro-6H-purin-6-one
CAS Number
168701-80-2
Molecular Formula
C5H4N6O3
Formula Weight
196.1
Purity
≥95%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
1 M NaOH: 50 mg/ml
λmax
397 nm
SMILES
O=C1C2=C(N=C([N+]([O-])=O)N2)N=C(N)N1
InChi Code
InChI=1S/C5H4N6O3/c6-4-8-2-1(3(12)10-4)7-5(9-2)11(13)14/h(H4,6,7,8,9,10,12)
InChi Key
IYHJRKNFFYAOGE-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $134

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    5 mg

    $530

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    Cayman Chemical
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    Product Description

    8-Nitroguanine is a nitrative guanine derivative formed by oxidative damage to the guanine base in DNA by reactive nitrogen species (RNS) during inflammation and in vitro by reaction of DNA with peroxynitrite and other RNS reagents.1,2,3 It is mutagenic and induces G:C to T:A transversion in DNA. Incorporation of 8-nitroguanine as an 8-nitroG:anti-G base pair into a primer template stalls human DNA polymerase β and induces a 2:1 preference for deoxyadenosine (dA) insertion over deoxycytosine (dC).3 8-Nitroguanine levels are increased in the lung tissue of mice with conditional expression of mutant K-Ras(G12V) that developed lung adenocarcinoma and in the lung tissue and peripheral lymphocyte DNA of cigarette smoke-exposed rats.4,5 It is also increased in the lung tissue of influenza- or Sendai virus-infected mice and the colon epithelial cells of mice in an inflammatory bowel disease (IBD) model.6,7

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Hiraku, Y. Formation of 8-nitroguanine, a nitrative DNA lesion, in inflammation-related carcinogenesis and its significance. Environ. Health Prev. Med. 15(2), 63-72 (2010).

    2. Ohshima, H., Sawa, T., and Akaike, T. 8-nitroguanine, a product of nitrative DNA damage caused by reactive nitrogen species: Formation, occurrence, and implications in inflammation and carcinogenesis. Antioxid. Redox Signal. 8(5-6), 1033-1045 (2006).

    3. Bhamra, I., Compagnone-Post, P., O'Neil, I.A., et al. Base-pairing preferences, physicochemical properties and mutational behaviour of the DNA lesion 8-nitroguanine. Nucleic Acids Res. 40(21), 11126-11138 (2012).

    4. Ohnishi, S., Saito, H., Suzuki, N., et al. Nitrative and oxidative DNA damage caused by K-ras mutation in mice. Biochem. Biophys. Res. Commun. 413(2), 236-240 (2011).

    5. Hsieh, Y.-S., Chen, B.-C., Shiow, S.-J., et al. Formation of 8-nitroguanine in tobacco cigarette smokers and in tobacco smoke-exposed Wistar rats. Chem. Biol. Interact. 140(1), 67-80 (2002).

    6. Akaike, T., Okamoto, S., Sawa, T., et al. 8-nitroguanosine formation in viral pneumonia and its implication for pathogenesis. Proc. Natl. Acad. Sci. USA 100(2), 685-690 (2003).

    7. Ding, X., Hiraku, Y., Ma, N., et al. Inducible nitric oxide synthase-dependent DNA damage in mouse model of inflammatory bowel disease. Cancer Sci. 96(3), 157-163 (2005).