M4002
6-Methylmercaptopurine riboside
≥99% (HPLC), synthetic (organic), powder
Synonym(s):
6MMPr, 6-(Methylthio)-9-β-D-ribofuranosyl-9H-purine
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About This Item
Empirical Formula (Hill Notation):
C11H14N4O4S
CAS Number:
Molecular Weight:
298.32
UNSPSC Code:
41106305
PubChem Substance ID:
NACRES:
NA.51
EC Number:
206-442-2
Assay:
≥99% (HPLC)
Biological source:
synthetic (organic)
Form:
powder
Solubility:
methanol: 50 mg/mL, clear to slightly hazy, colorless to faintly yellow
Storage temp.:
−20°C
Product Name
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
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.
Storage Class
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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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)
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
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
Human cytomegalovirus can procure deoxyribonucleotides for viral DNA replication in the absence of retinoblastoma protein phosphorylation
Kuny C V and Kalejta R F
Journal of Virology, 90(19), 8634-8643 (2016)
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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