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A4882

Sigma-Aldrich

6-Thioguanine

≥98%

Synonym(s):

2-Amino-6-mercaptopurine, 2-Amino-6-purinethiol

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About This Item

Empirical Formula (Hill Notation):
C5H5N5S
CAS Number:
154-42-7
Molecular Weight:
167.19
Beilstein:
157765
EC Number:
205-827-2
MDL number:
MFCD00233553
UNSPSC Code:
12352202
PubChem Substance ID:
24890748
NACRES:
NA.77

Assay

≥98%

form

powder

mp

≥300 °C (lit.)

SMILES string

NC1=Nc2nc[nH]c2C(=S)N1

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

Gene Information

human ... IMPDH1(3614) , IMPDH2(3615)

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General description

6-Thioguanine is a variant of guanine with hydrogen bonding at the N-7 of the purine ring. Its association with cytosine alters the dimension of the base stacking. 6-Thioguanine usage in treating inflammatory bowel disease (IBD) contributes to nodular regenerative hyperplasia (NRH) in the liver.

Application

6-Thioguanine has been used:
  • to induce autophagy and apoptosis in colorectal cancer cell lines HCT116
  • as a selection marker in the mutation and survival assay in chinese hamster lung fibroblasts culture V79
  • as a selection marker in clonogenic Lung metastasis assay of 4T1-luc cells

Biochem/physiol Actions

Ribosylated and phosphorylated by the same pathway as natural purine bases; as the nucleotide, inhibits a variety of cellular processes involved in nucleic acid synthesis. Has a long history as an effective treatment of leukemia.
Antimetabolite used in the treatment of leukemias. Competes with hypoxanthine and guanine for the enzyme hypoxanthine-guanine phosphoribosyltransferase, which catalzyes a critical step in the generation of purine nucleotides.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301

Precautionary Statements

P301 + P310

Hazard Classifications

Acute Tox. 3 Oral

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Interconnections between apoptotic and autophagic pathways during thiopurine-induced toxicity in cancer cells: the role of reactive oxygen species
Chaabane W and Appell ML
Testing, 7(46), 75616-75616 (2016)
Tumor-suppressor inactivation of GDF11 occurs by precursor sequestration in triple-negative breast cancer
Bajikar SS, et al.
Developmental Cell, 43(4), 418-435 (2017)
6-thioguanine can cause serious liver injury in inflammatory bowel disease patients
Dubinsky MC, et al.
Gastroenterology, 125(2), 298-303 (2003)
Crystal and molecular structure of 6-thioguanine
Bugg CE and Thewalt U
Journal of the American Chemical Society, 92(25), 7441-7445 (1970)
Delayed effects of accelerated heavy ions on the induction of HPRT mutations in V79 hamster cells
Blaha P, et al.
Mutation Research. Fundamental and Molecular Mechanisms of Mutagenesis, 803(46), 35-41 (2017)
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