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A9546

Sigma-Aldrich

2-Amino-6-methylmercaptopurine

≥95%

Sinonimo/i:

2-Amino-6-methylthiopurine

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About This Item

Formula empirica (notazione di Hill):
C6H7N5S
Numero CAS:
1198-47-6
Peso molecolare:
181.22
Numero CE:
214-833-4
Numero MDL:
MFCD00044701
Codice UNSPSC:
41106305
ID PubChem:
24891471
NACRES:
NA.51

Saggio

≥95%

Forma fisica

solid

Stringa SMILE

[H]n1cnc2c(SC)nc(N)nc12

InChI

1S/C6H7N5S/c1-12-5-3-4(9-2-8-3)10-6(7)11-5/h2H,1H3,(H3,7,8,9,10,11)
YEGKYFQLKYGHAR-UHFFFAOYSA-N

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Applicazioni

2-Amino-6-methylmercaptopurine (6-MTG) has been used as a supplement in Dulbecco′s modified Eagles medium (DMEM) medium for the selection of gpt-expressing recombinant virus mCMVhMIEPE-gpt.lacZ (cytomegalovirus major immediate-early promotor-enhancer complex-gpt.lacz). It has also been used as a standard in high performance liquid chromatography (HPLC) to assess the activity of thiopurine methyltransferase (TPMT) enzyme.
2-Amino-6-methylmercaptopurine is a 2-amino-6-alkyldithiopurine that has been used with other 6-position carbon analogues to study brain specific diazepam binding.

Azioni biochim/fisiol

2-Amino-6-methylmercaptopurine is synthesized from 6-mercaptopurine by the S methylation activity of thiopurine methyl transferase (TMPT) enzyme.

Pittogrammi

CorrosionExclamation mark
GHS05,GHS07

Avvertenze

Danger

Indicazioni di pericolo

H302,H315,H318,H335

Classi di pericolo

Acute Tox. 4 Oral - Eye Dam. 1 - Skin Irrit. 2 - STOT SE 3

Organi bersaglio

Respiratory system

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

dust mask type N95 (US), Eyeshields, Gloves

Certificati d'analisi (COA)

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Pharmacogenetics of drug metabolizing enzyme: thiopurine methyl transferase phenotypes and multidrug resistance 1 gene polymorphism in inflammatory bowel disease
Bahrehmand F, et al.
Cellular and Molecular Biology, 62(7), 102-109 (2016)
Loretta T Ford et al.
Annals of clinical biochemistry, 41(Pt 4), 303-308 (2004-08-10)
Although widely used, thiopurine drugs have a narrow therapeutic index and treatment can result in life-threatening toxicity, the basis being pharmacogenetic variation in thiopurine metabolism by thiopurine S-methyltransferase (TPMT). We recently developed a modified phenotyping assay to determine TPMT activity
Bifeng Yuan et al.
ACS chemical biology, 5(11), 1021-1027 (2010-09-03)
Thiopurines are effective immunosuppressants and anticancer agents. However, the long-term use of thiopurines was found to be associated with a significantly increased risk of various types of cancer. To date, the specific mechanism(s) underlying the carcinogenicity associated with thiopurine treatment
Hongxia Wang et al.
Analytical chemistry, 82(13), 5797-5803 (2010-06-17)
Thiopurines, including mercaptopurine (MP), 6-thioguanine ((S)G) and azathioprine, are widely used for the treatment of many human diseases including acute lymphoblastic leukemia (ALL). To exert their cytotoxic effect, these prodrugs need to be metabolically activated to (S)G nucleotides and incorporated
G R Erdmann et al.
Journal of chromatography, 571(1-2), 149-156 (1991-11-15)
A reversed-phase high-performance liquid chromatographic (HPLC) procedure was developed to quantify intracellular lymphocyte 6-thioguanine, methylmercaptopurine and methylthioguanine. The free base of each metabolite was obtained by acid hydrolysis, which allowed for a total determination of thiopurine metabolites. 6-Thioguanine was analyzed
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