An isomer of guanine
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Isomer(s)
34248Guanine
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Isoguanine

Item No. 21703

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
6-amino-3,7-dihydro-2H-purin-2-one
CAS Number
3373-53-3
Synonyms
  • Crotonoside
  • 2-hydroxy-6-Aminopurine
  • 2-Hydroxyadenine
  • NSC 241501
  • 2-Oxoadenine
Molecular Formula
C5H5N5O
Formula Weight
151.1
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
1 M NaOH: 50 mg/ml
λmax
240, 292 nm
SMILES
NC1=NC(NC2=C1NC=N2)=O
InChi Code
InChI=1S/C5H5N5O/c6-3-2-4(8-1-7-2)10-5(11)9-3/h1H,(H4,6,7,8,9,10,11)
InChi Key
DRAVOWXCEBXPTN-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    10 mg

    $36

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    50 mg

    $103

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    100 mg

    $153

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    250 mg

    $336

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    Product Description

    Isoguanine is a natural isomer of guanine originally isolated from Croton seed but is also a product of oxidative damage to the adenine base in DNA.1,2 It can be formed through oxidative damage to deoxyadenosine and deoxyadenosine-ATP (d-ATP) as well as single- and double-stranded DNA and induces a parallel-stranded DNA structure when incorporated into DNA.2,3 It is mutagenic to S. tymphimurium in the Ames test and induces sister chromatid exchange, a measure of mutagenicity, in isolated human peripheral blood lymphocytes.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Cherbuliez, E., and Bernhard, K. Croton seed. I. Crotonoside (2-hydroxy-6-aminopurine-d-riboside). Helv. Chim. Acta 15, 464-471 (1932).

    2. Cheng, Q., Gu, J., Compaan, K.R., et al. Isoguanine formation from adenine. Chemistry 18(16), 4877-4886 (2012).

    3. Kamiya, H., and Kasai, H. 2-Hydroxyadenine (isoguanine) as oxidative DNA damage: Its formation and mutation inducibility. Nucleic Acids Symp. Ser. (34), 233-234 (1995).

    4. Arashidani, K., Iwamoto-Tanaka, N., Muraoka, M., et al. Genotoxicity of ribo- and deoxyribonucleosides of 8-hydroxyguanine, 5-hydroxycytosine, and 2-hydroxyadenine: Induction of SCE in human lymphocytes and mutagenicity in Salmonella typhimurium TA 100. Mutat. Res. 403(1-2), 223-227 (1998).