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A4882

6-Thioguanine

Name: 6-Thioguanine
Brand: SIGMA

≥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

Assay:

≥98%

Biological source:

synthetic (organic)

Form:

powder

Solubility:

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

Storage temp.:

room temp

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Product Name

6-Thioguanine, ≥98%

biological source

synthetic (organic)

Quality Level

200

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

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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Related Categories

Bioactive Small Molecule Inhibitors

Bioactive Small Molecules

Biochemicals

Nucleosides and Nucleotides

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

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.

pictograms

GHS06

signalword

Danger

hcodes

H301

pcodes

P301 + P310

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

0000506241

0000498507

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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)

6-thioguanine can cause serious liver injury in inflammatory bowel disease patients

Dubinsky MC, et al.

Gastroenterology, 125(2), 298-303 (2003)

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

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)

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Global Trade Item Number

SKU	GTIN
A4882-500MG	04061833375075
A4882-100MG	04061833375051
A4882-5G	04061833375082
A4882-1G	04061826731680
A4882-250MG	04061833375068

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