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Merck

A4882

6-Thioguanine

≥98%, Guanine antimetabolite, powder

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
NACRES:
NA.77
PubChem Substance ID:
24890748
UNSPSC Code:
12352202
EC Number:
205-827-2
MDL number:
MFCD00233553
Beilstein/REAXYS Number:
157765

Key Documents

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Product Name

6-Thioguanine, ≥98%

InChI key

WYWHKKSPHMUBEB-UHFFFAOYSA-N

InChI

1S/C5H5N5S/c6-5-9-3-2(4(11)10-5)7-1-8-3/h1H,(H4,6,7,8,9,10,11)

SMILES string

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

biological source

synthetic (organic)

assay

≥98%

form

powder

mp

≥300 °C (lit.)

solubility

1 M NaOH: 50 mg/mL, clear to hazy, colorless to light greenish-yellow

storage temp.

room temp

Quality Level

200

Gene Information

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

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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

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.
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.

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.

pictograms

Skull and crossbones
GHS06

signalword

Danger

hcodes

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class

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

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
0000508054
0000508054
0000506241
0000506241
0000498507

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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)
Crystal and molecular structure of 6-thioguanine
Bugg CE and Thewalt U
Journal of the American Chemical Society, 92(25), 7441-7445 (1970)
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)
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
View All Related Papers

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Product Information Sheet - A4882

Product Information Sheet

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