Thioguanine

Catalog No.S1774

Thioguanine Chemical Structure

Molecular Weight(MW): 167.19

Thioguanine, 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.

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Choose Selective DNA Methyltransferase Inhibitors

Biological Activity

Description Thioguanine, 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 17 mg/mL (101.68 mM)
Water Insoluble
Ethanol Insoluble

* 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
Synonyms N/A

Bio Calculators

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Clinical Trial Information

NCT Number Recruitment Conditions Sponsor/Collaborators Start Date Phases
NCT03007147 Not yet recruiting B Acute Lymphoblastic Leukemia With t(9;22)(q34.1;q11.2); BCR-ABL1|BCR-ABL1 Fusion Protein Expression|Minimal Residual Disease|Philadelphia Chromosome Positive|T Acute Lymphoblastic Leukemia|Untreated Adult Acute Lymphoblastic Leukemia|Untreated Childhood Acute Lymphoblastic Leukemia Childrens Oncology Group|National Cancer Institute (NCI) July 2017 Phase 3
NCT02828358 Not yet recruiting Acute Leukemia of Ambiguous Lineage|Childhood B Acute Lymphoblastic Leukemia|Mixed Phenotype Acute Leukemia National Cancer Institute (NCI) December 2016 --
NCT02912676 Recruiting Acute Lymphoblastic Leukemia Kjeld Schmiegelow|Danish Child Cancer Foundation|Nordic Society for Pediatric Hematology and Oncology|Rigshospitalet, Denmark October 2016 Phase 1|Phase 2
NCT02723994 Recruiting B-cell Acute Lymphoblastic Leukemia Incyte Corporation|Childrens Oncology Group August 2016 Phase 2
NCT02419469 Recruiting Leukemia|Precursor-B Acute Lymphoblastic Leukemia|Lymphoblastic Lymphoma|Lymphoma M.D. Anderson Cancer Center|Jazz Pharmaceuticals November 2015 Phase 2
NCT02521493 Recruiting Childhood Acute Myeloid Leukemia|Childhood Myelodysplastic Syndrome|Cytopenia|Down Syndrome|Myeloid Leukemia Associated With Down Syndrome|Myeloproliferative Neoplasm Childrens Oncology Group|National Cancer Institute (NCI) November 2015 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.

Handling Instructions

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Related Antibodies

DNA Methyltransferase Signaling Pathway Map

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Cell Lines Assay Type Concentration Incubation Time Formulation Activity Description PMID