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Merck

M4002

Sigma-Aldrich

6-Methylmercaptopurine riboside

≥99% (HPLC)

Sinónimos:

6MMPr, 6-(Methylthio)-9-β-D-ribofuranosyl-9H-purine

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About This Item

Fórmula empírica (notación de Hill):
C11H14N4O4S
Número de CAS:
Peso molecular:
298.32
Número CE:
Código UNSPSC:
41106305
ID de la sustancia en PubChem:
NACRES:
NA.51
En este momento no podemos mostrarle ni los precios ni la disponibilidad

origen biológico

synthetic (organic)

Nivel de calidad

Ensayo

≥99% (HPLC)

Formulario

powder

solubilidad

methanol: 50 mg/mL, clear to slightly hazy, colorless to faintly yellow

temp. de almacenamiento

−20°C

cadena SMILES

O[C@H]([C@@H](CO)O1)[C@@H](O)[C@@H]1N2C=NC3=C(SC)N=CN=C32

InChI

1S/C11H14N4O4S/c1-20-10-6-9(12-3-13-10)15(4-14-6)11-8(18)7(17)5(2-16)19-11/h3-5,7-8,11,16-18H,2H2,1H3

Clave InChI

ZDRFDHHANOYUTE-UHFFFAOYSA-N

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Aplicación

6-Methylmercaptopurine riboside (6MMPR) has been used as a phosphoribosyl pyrophosphate amidotransferase inhibitor to study its effects on DNA replication in a retinoblastoma (Rb) phosphorylation-independent manner in human cytomegalovirus (HCMV) [1], as a purine analog to determine its effects on angiogenesis of endothelial cells induced by fibroblast growth factor 2 (FGF2) in vitro and in vivo[2], as a metabolite of 6-methylmercaptopurine to determine its levels in human plasma by high-performance liquid chromatography (HPLC) method [3].
6-Methylmercaptopurine riboside (6MMPr) is used in studies on thiopurine metabolism by enzymes such as inosine-5′-monophosphate dehydrogenase and thiopurine methyltransferase. 6MMPr may also be used to study mechanisms of bovine viral diarrhea virus (BVDV) inhibition.

Acciones bioquímicas o fisiológicas

6-Methylmercaptopurine riboside (6MMPR) is a modified thiopurine nucleoside involved in the inhibition of purine synthesis. It exhibits anti-viral effects against various viruses.[4] 6MMPR is an analog of purine and an inhibitor of nerve growth factor-activated protein kinase N.[2]

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Equipo de protección personal

Eyeshields, Gloves, type N95 (US)


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Ulf Hindorf et al.
Journal of hepatology, 52(1), 106-111 (2009-11-13)
Corticosteroids alone or in conjunction with azathioprine (AZA) is the standard treatment in autoimmune hepatitis (AiH). Individual variations in thiopurine (TP) metabolism may affect both drug efficacy and toxicity. Our aim was to investigate the utility of thiopurine methyltransferase (TPMT)
P R Wielinga et al.
Molecular pharmacology, 62(6), 1321-1331 (2002-11-19)
Mercaptopurines have been used as anticancer agents for more than 40 years, and most acute lymphoblastic leukemias are treated with 6-mercaptopurine (6MP) or 6-thioguanine (TG). Overexpression of the two related multidrug resistance proteins MRP4 and MRP5 has been shown to
Pei-Yin Lim et al.
PloS one, 6(10), e26697-e26697 (2011-11-01)
Many viruses within the Flavivirus genus cause significant disease in humans; however, effective antivirals against these viruses are not currently available. We have previously shown that a thiopurine drug, 6-methylmercaptopurine riboside (6MMPr), inhibits replication of distantly related viruses within the
Assay of 6-mercaptopurine and its metabolites in patient plasma by high-performance liquid chromatography with diode-array detection
Su Y, et al.
Journal of Chromatography. B, Biomedical Sciences and Applications, 732(2), 459-468 (1999)
Li-Min Ting et al.
The Journal of biological chemistry, 280(10), 9547-9554 (2004-12-04)
Plasmodium falciparum is unable to synthesize purine bases and relies upon purine salvage and purine recycling to meet its purine needs. We report that purines formed as products of polyamine synthesis are recycled in a novel pathway in which 5'-methylthioinosine

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