Merck
All Photos(5)

A4882

Sigma-Aldrich

6-Thioguanine

≥98%

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

Quality Level

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

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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

Packaging

100, 250, 500 mg in glass bottle
1, 5 g in glass bottle

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

Signal Word

Danger

Hazard Statements

Precautionary Statements

Hazard Classifications

Acute Tox. 3 Oral

Storage Class Code

6.1D - Non-combustible, acute toxic Cat.3 / toxic hazardous materials or hazardous materials 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

Certificate of Analysis

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Certificate of Origin

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