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    InvivoChem Cat #: V0406
    CAS #: 154-42-7Purity ≥98%

    Description: Thioguanine (also known as AAN, USAN, 6-Thioguanine; 2-Amino-6-purinethiol and 6-TG) is a purine antimetabolite and an anti-leukemia and immunosuppressant agent that potently inhibits DNMT1 activity through ubiquitin-targeted degradation, it has been used in the treatment of acute lymphoblastic leukemia, autoimmune disorders (e.g., Crohn's disease, rheumatoid arthritis) and organ transplant recipients. However, thioguanine has been used less frequently in recent years because of safety concerns. However, it is becoming more widely used for treating ulcerative colitis and some autoimmune diseases. 

    ReferencesFASEB J. 2000 Nov;14(14):2339-44; Cancer Res. 2010 Aug 1;70(15):6268-76.

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    Name: Thioguanine
    CAS#: 154-42-7
    Chemical Formula: C5H5N5S
    Exact Mass: 167.02657
    Molecular Weight: 167.19
    Elemental Analysis: C, 35.92; H, 3.01; N, 41.89; S, 19.18
    Storage-20℃ for 3 years in powder form
    -80℃ for 2 years in solvent
    Technical InformationSynonym: 2-Amino-6-purinethiol; Tabloid brand thioguanine; Thioguanine;Tabloid; Tioguanine. Foreign brand names: Lanvis; Tioguanin. Abbreviations: 6TG; TG. Code names: BW 5071; Wellcome U3B; WR1141; X 27.
    Chemical Name: 2-amino-1H-purine-6(7H)-thione
    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)
    SMILES Code: S=C1NC(N)=NC2=C1NC=N2

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    In Vitro

    In vitro activity: Thioguanine incorporation alters the DNA cleavage induced by topoisomerase II in the presence and absence of etoposide. 6-Thioguanine alters the structure and lowers the thermal stability of duplex DNA, but duplex DNA can be formed in the presence of 6SG. 6-Thioguanine induced apopotosis is similarly observed in both mismatch repair-proficient and -deficient HCT116 and HeLa cells. Thioguanine integrates into DNA and unlike the canonical DNA bases, it is a strong UVA chromophore with an absorbance maximum at 342 nm. 6-Thioguanine is a photosensitizer and a source of reactive oxygen species. In canine lymphoma cells, Thioguanine significantly decreases DNMT1 protein and global DNA methylation.

    Cell Assay: Treatments consists of 3 thiopurines (azathioprine, 6-mercaptopurine, and 6-Thioguanine (Thioguanine)) at each of 6 concentrations (0.468, 0.937, 1.875, 3.750, 7.500, and 15.000 μM). Each thiopurinee is dissolved in DMSO solution to achieve a concentration of 10 mg/mL. Sterile filtered maintenance medium is used to further dilute each thiopurine solution to each of the 6 treatment concentrations. Twenty-four hours after the hepatocytes are plated on 96-well culture

    In VivoThioguanine is as efficient as a PARP inhibitor in selectively killing BRCA2-defective tumors in a xenograft model. 6-Thioguanine efficiently kills such BRCA1-defective PARP inhibitor-resistant tumors. 6-Thioguanine could kill cells and tumors that have gained resistance to PARP inhibitors or cisplatin through genetic reversion of the BRCA2 gene
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    FASEB J. 2000 Nov;14(14):2339-44; Cancer Res. 2010 Aug 1;70(15):6268-76.

    These protocols are for reference only. InvivoChem does not independently validate these methods.


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