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M4002

Sigma-Aldrich

6-Methylmercaptopurine riboside

≥99% (HPLC)

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C11H14N4O4S
Numéro CAS:
342-69-8
Poids moléculaire :
298.32
Numéro CE :
206-442-2
Code UNSPSC :
41106305
ID de substance PubChem :
24896894
Nomenclature NACRES :
NA.51

Source biologique

synthetic (organic)

Pureté

≥99% (HPLC)

Forme

powder

Solubilité

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

Température de stockage

−20°C

Chaîne 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

Clé InChI

ZDRFDHHANOYUTE-UHFFFAOYSA-N

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Application

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) , 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, as a metabolite of 6-methylmercaptopurine to determine its levels in human plasma by high-performance liquid chromatography (HPLC) method .
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.

Actions biochimiques/physiologiques

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

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

Certificats d'analyse (COA)

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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
Jennifer Hauser Kunz et al.
Inflammatory bowel diseases, 16(6), 939-946 (2009-12-10)
This study compared youth and parent-proxy reports of health-related quality of life (HRQoL) among youth with inflammatory bowel disease (IBD) to published comparison group data and examined concordance between youth and parent-proxy reports of HRQoL. One hundred thirty-six youth and
Wuxian Shi et al.
The Journal of biological chemistry, 279(18), 18103-18106 (2004-02-26)
Purine nucleoside phosphorylase from Plasmodium falciparum (PfPNP) is an anti-malarial target based on the activity of Immucillins. The crystal structure of PfPNP.Immucillin-H (ImmH).SO(4) reveals a homohexamer with ImmH and SO(4) bound at each catalytic site. A solvent-filled cavity close to
J A Koutcher et al.
International journal of radiation oncology, biology, physics, 39(5), 1145-1152 (1997-12-10)
To evaluate the effects of biochemical modulation by N-(phosphonacetyl)-L-aspartate (PALA), 6-methylmercaptopurine riboside (MMPR), and 6-aminonicotinamide (6AN), (PALA + MMPR + 6AN is referred to as PMA) on tumor radiosensitivity, and evaluate the efficacy of the addition of 5-FU to the
Rong Guan et al.
Biochemistry, 50(7), 1247-1254 (2011-01-05)
The PA3004 gene of Pseudomonas aeruginosa PAO1 was originally annotated as a 5'-methylthioadenosine phosphorylase (MTAP). However, the PA3004 encoded protein uses 5'-methylthioinosine (MTI) as a preferred substrate and represents the only known example of a specific MTI phosphorylase (MTIP). MTIP
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