Thioguanine (NSC 752)

For research use only.

Catalog No.S1774 Synonyms: 6-Thioguanine, 2-Amino-6-purinethiol

14 publications

Thioguanine (NSC 752) Chemical Structure

CAS No. 154-42-7

Thioguanine (NSC 752, 6-Thioguanine, 2-Amino-6-purinethiol), a purine antimetabolite, inhibits DNMT1 activity through ubiquitin-targeted degradation, used in the treatment of acute lymphoblastic leukemia, autoimmune disorders (e.g., Crohn's disease, rheumatoid arthritis) and organ transplant recipients.

Selleck's Thioguanine (NSC 752) has been cited by 14 publications

Purity & Quality Control

Choose Selective DNA Methyltransferase Inhibitors

Biological Activity

Description Thioguanine (NSC 752, 6-Thioguanine, 2-Amino-6-purinethiol), a purine antimetabolite, inhibits DNMT1 activity through ubiquitin-targeted degradation, used in the treatment of acute lymphoblastic leukemia, autoimmune disorders (e.g., Crohn's disease, rheumatoid arthritis) and organ transplant recipients.
Targets
DNMT1 [6]
()
In vitro

Thioguanine incorporation alters the DNA cleavage induced by topoisomerase II in the presence and absence of etoposide. [1] 6-Thioguanine alters the structure and lowers the thermal stability of duplex DNA, but duplex DNA can be formed in the presence of 6SG. [2] 6-Thioguanine induced apopotosis is similarly observed in both mismatch repair-proficient and -deficient HCT116 and HeLa cells. [3] 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. [4] In canine lymphoma cells, Thioguanine significantly decreases DNMT1 protein and global DNA methylation. [6]

In vivo

Thioguanine 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. [5]

Protocol

Solubility (25°C)

In vitro DMSO 9 mg/mL (53.83 mM)
Water Insoluble
Ethanol Insoluble
In vivo Add solvents to the product individually and in order(Data is from Selleck tests instead of citations):
2% DMSO+40% PEG 300+2% Tween 80+ddH2O
For best results, use promptly after mixing.
1mg/mL

* Please note that Selleck tests the solubility of all compounds in-house, and the actual solubility may differ slightly from published values. This is normal and is due to slight batch-to-batch variations.

Chemical Information

Molecular Weight 167.19
Formula

C5H5N5S

CAS No. 154-42-7
Storage powder
in solvent
Synonyms 6-Thioguanine, 2-Amino-6-purinethiol
Smiles C1=NC2=C(N1)C(=S)N=C(N2)N

In vivo Formulation Calculator (Clear solution)

Step 1: Enter information below (Recommended: An additional animal making an allowance for loss during the experiment)
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Step 2: Enter the in vivo formulation ()
% DMSO % % Tween 80 % ddH2O
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Clinical Trial Information

NCT Number Recruitment interventions Conditions Sponsor/Collaborators Start Date Phases
NCT03022747 Unknown status Drug: Allopurinol|Drug: Standard treatment Lymphoblastic Leukemia Acute Childhood Vastra Gotaland Region January 2017 Phase 2
NCT04304950 Recruiting Drug: Evening Group|Drug: Morning Group Inflammatory Bowel Diseases Rush University Medical Center April 25 2016 Phase 4
NCT00548431 Completed Drug: 6-mercaptopurine Leukemia Lymphocytic Acute Rigshospitalet Denmark December 2007 Phase 2
NCT00098111 Terminated Drug: azathioprine Crohn''s Disease Massachusetts General Hospital April 2005 Phase 3

Tech Support

Answers to questions you may have can be found in the inhibitor handling instructions. Topics include how to prepare stock solutions, how to store inhibitors, and issues that need special attention for cell-based assays and animal experiments.

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DNA Methyltransferase Signaling Pathway Map

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Cell Lines Assay Type Concentration Incubation Time Formulation Activity Description PMID