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Merck

M4002

6-Methylmercaptopurine riboside

≥99% (HPLC), synthetic (organic), powder

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
UNSPSC Code:
41106305
PubChem Substance ID:
24896894
NACRES:
NA.51
EC Number:
206-442-2

Nom du produit

6-Methylmercaptopurine riboside, ≥99% (HPLC)

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

InChI key

ZDRFDHHANOYUTE-UHFFFAOYSA-N

SMILES string

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

biological source

synthetic (organic)

assay

≥99% (HPLC)

form

powder

solubility

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

storage temp.

−20°C

Quality Level

200

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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.

Biochem/physiol Actions

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.

Classe de stockage

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificats d'analyse (COA)

Lot/Batch Number
0000494914
0000494914
0000487407
0000487407
0000377446

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Consulter la Bibliothèque de documents

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)
M Presta et al.
Cancer research, 59(10), 2417-2424 (1999-05-27)
Angiogenesis has been identified as an important target for antineoplastic therapy. The use of purine analogue antimetabolites in combination chemotherapy of solid tumors has been proposed. To assess the possibility that selected purine analogues may affect tumor neovascularization, 6-methylmercaptopurine riboside
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
T Giverhaug et al.
Therapeutic drug monitoring, 19(6), 663-668 (1998-01-08)
Blood samples from 34 recipients of kidney transplants who were on multidrug therapy including azathioprine were analyzed using two methods in parallel for red blood cell (RBC) concentrations of methylated 6-mercaptopurine (6-MP) metabolites. Chemical hydrolysis with high-performance liquid chromatography (HPLC)
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