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6-Methylmercaptopurine riboside

Name: 6-Methylmercaptopurine riboside
Brand: SIGMA

≥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:

342-69-8

Molecular Weight:

298.32

UNSPSC Code:

41106305

PubChem Substance ID:

24896894

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

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Properties

Product Name

6-Methylmercaptopurine riboside, ≥99% (HPLC)

biological source

synthetic (organic)

Quality Segment

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

Description

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[1], 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.[1]

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This Item	B7877	D5287	D5412
Sigma-Aldrich M4002 6-Methylmercaptopurine riboside	Sigma-Aldrich B7877 6-Bromo-2-naphthyl β-D-glucopyranoside	Sigma-Aldrich D5287 2′-Deoxyinosine	Sigma-Aldrich D5412 2′-Deoxyuridine
biological source synthetic (organic)	biological source -	biological source synthetic (organic)	biological source synthetic (organic)
Quality Level 200	Quality Level 200	Quality Level 200	Quality Level 300
assay ≥99% (HPLC)	assay ≥99% (TLC)	assay ≥98%	assay ≥98.5%
form powder	form powder	form powder	form powder
solubility methanol: 50 mg/mL, clear to slightly hazy, colorless to faintly yellow	solubility pyridine: 50 mg/mL, clear to slightly hazy, colorless to faintly yellow	solubility 1 M NH₄OH: 50 mg/mL, clear, colorless	solubility water: 50 mg/mL, clear to slightly hazy, colorless to faintly yellow
storage temp. −20°C	storage temp. −20°C	storage temp. −20°C	storage temp. -

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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