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M4002

Sigma-Aldrich

6-Methylmercaptopurine riboside

≥99% (HPLC)

Synonym(s):

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

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1 G
$372.00

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1 G
$372.00

About This Item

Empirical Formula (Hill Notation):
C11H14N4O4S
CAS Number:
342-69-8
Molecular Weight:
298.32
EC Number:
206-442-2
UNSPSC Code:
41106305
PubChem Substance ID:
24896894
NACRES:
NA.51

$372.00

In StockDetails

biological source

synthetic (organic)

Quality Level

200

assay

≥99% (HPLC)

form

powder

solubility

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

storage temp.

−20°C

SMILES string

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

InChI key

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) [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.

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.[4] 6MMPR is an analog of purine and an inhibitor of nerve growth factor-activated protein kinase N.[2]

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
0000377446
0000339055
0000334010
0000334010
0000339055

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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
Alexander Teml et al.
Scandinavian journal of gastroenterology, 40(10), 1205-1213 (2005-11-04)
6-thioguanine (6-TG) has emerged as a promising therapeutic alternative in patients with Crohn's disease intolerant or resistant to azathioprine (AZA) and/or 6-mercaptopurine (6-MP). The aim of the present study was to evaluate the safety and efficacy of 6-TG in patients
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
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
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