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A4882

Sigma-Aldrich

6-Thioguanine

≥98%

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Synonym(s):
2-Amino-6-mercaptopurine, 2-Amino-6-purinethiol
Empirical Formula (Hill Notation):
C5H5N5S
CAS Number:
154-42-7
Molecular Weight:
167.19
Beilstein:
157765
EC Number:
205-827-2
MDL number:
MFCD00233553
PubChem Substance ID:
24890748
NACRES:
NA.77

Quality Level

200

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

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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)
Jen-Hwey Chiu et al.
Scientific reports, 10(1), 8060-8060 (2020-05-18)
Our previous study demonstrated that upregulation of multiple epidermal growth factor-like domains 11 (MEGF11) gene expression is involved in the mechanism by which recurrence of Triple Negative Breast Cancer (TNBC) occurs. Our aim was to elucidate the role of MEGF11
6-thioguanine can cause serious liver injury in inflammatory bowel disease patients
Dubinsky MC, et al.
Gastroenterology, 125(2), 298-303 (2003)
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)
Crystal and molecular structure of 6-thioguanine
Bugg CE and Thewalt U
Journal of the American Chemical Society, 92(25), 7441-7445 (1970)
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