A thiopurine analog
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6-Thioguanine

Item No. 15774

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-amino-1,9-dihydro-6H-purine-6-thione
CAS Number
154-42-7
Synonyms
  • NSC 752
  • NSC 76504
  • 6-TG
Molecular Formula
C5H5N5S
Formula Weight
167.2
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
1 M NaOH: 50 mg/ml*
λmax
257, 347 nm
SMILES
NC1=NC(S)=C2C(NC=N2)=N1
InChi Code
InChI=1S/C5H5N5S/c6-5-9-3-2(4(11)10-5)7-1-8-3/h1H,(H4,6,7,8,9,10,11)
InChi Key
WYWHKKSPHMUBEB-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    250 mg

    $36

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    500 mg

    $53

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    1 g

    $75

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    5 g

    $262

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    Cayman Chemical
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    Product Description

    6-Thioguanine (6-TG) is a thio analog of the purine base guanine that incorporates into DNA during replication, inducing double-strand breaks that destabilize its structure and result in cytotoxicity.1,2 Upon incorporation into DNA, 6-TG has been shown to disrupt cytosine methylation by DNA methyltransferases, interfering with the epigenetic pathway of gene regulation.3,4 This compound has been used as a chemotherapeutic for acute leukemia and other types of cancer, including BRCA2-mutated tumors.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Bohon, J., and de los Santos, C.R. Effect of 6-thioguanine on the stability of duplex DNA. Nucleic Acids Res. 33(9), 2880-2886 (2005).

    2. LePage, G.A. Incorporation of 6-thioguanine into nucleic acids. Cancer Res. 20, 403-408 (1960).

    3. Wang, H., and Wang, Y. 6-Thioguanine perturbs cytosine methylation at the CpG dinucleotide site by DNA methyltransferases in vitro and acts as a DNA demethylating agent in vivo. Biochemistry 48(10), 2290-2299 (2009).

    4. Yuan, B., Zhang, J., Wang, H., et al. 6-Thioguanine reactivates epigenetically silenced genes in acute lymphoblastic leukemia cells by facilitating proteasome-mediated degradation of DNMT1. Cancer Res. 71(5), 1904-1911 (2011).

    5. Issaeva, N., Thomas, H.D., Djureinovic, T., et al. 6-thioguanine selectively kills BRCA2-defective tumors and overcomes PARP inhibitor resistance. Cancer Res. 70(15), 6268-6276 (2010).