1198-47-6

Basic information

• Product Name: 2-AMINO-6-METHYLMERCAPTOPURINE
• Synonyms: 1H-Purin-2-amine, 6-(methylthio)-;2-Amino-6-methylthiopurine;6-(Methylsulfanyl)-1H-purin-2-amine;6-Methylthioguanine;TIMTEC-BB SBB000228;6-(METHYLSULFANYL)-7H-PURIN-2-YLAMINE;2-AMINO-6-METHYLMERCAPTOPURINE;6-(methylthio)-1H-purin-2-amine
• CAS NO: 1198-47-6
• Molecular Formula: C₆H₇N₅S
• Molecular Weight: 181.22
• EINECS: 214-833-4
• Product Categories: Bases & Related Reagents;Heterocycles;Metabolites & Impurities;Mutagenesis Research Chemicals;Nucleotides;Sulfur & Selenium Compounds;Heterocycles, Metabolites & Impurities, Nucleotides, Bases & Related Reagents, Mutagenesis Research Chemicals, Sulfur & Selenium Compounds
• Mol File: 1198-47-6.mol
• Article Data: 3

Chemical Properties

• Melting Point: 235.5°C
• Boiling Point: 622.1 °C at 760 mmHg
• Flash Point: 330 °C
• Appearance: /solid
• Density: 1.403 (estimate)
• Vapor Pressure: 6.74E-05mmHg at 25°C
• Refractive Index: 1.4606 (estimate)
• Storage Temp.: -20°C Freezer
• Solubility: DMSO (Slightly), Methanol (Slightly, Sonicated)
• CAS DataBase Reference: 2-AMINO-6-METHYLMERCAPTOPURINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-AMINO-6-METHYLMERCAPTOPURINE(1198-47-6)
• EPA Substance Registry System: 2-AMINO-6-METHYLMERCAPTOPURINE(1198-47-6)

Safety Data

• Hazard Codes: Xn
• Statements: 22-37/38-41
• Safety Statements: 24/25-39-26
• WGK Germany: 3
• Hazardous Substances Data: 1198-47-6(Hazardous Substances Data)

Usage

Description

2-AMINO-6-METHYLMERCAPTOPURINE, also known as 6-Methylthioguanine, is a 2-amino-6-alkyldithiopurine derivative that serves as a metabolite of 2’-Deoxy-6-thio Guanosine (D281650) and 6-Thioguanine. It is an off-white crystalline powder with significant applications in the medical field due to its immunosuppressive and anticancer properties.

Uses

Used in Pharmaceutical Industry:
2-AMINO-6-METHYLMERCAPTOPURINE is used as an immunosuppressant and anticancer agent for its effectiveness in treating various types of cancer and suppressing the immune system. However,

Biochem/physiol Actions

2-Amino-6-methylmercaptopurine is synthesized from 6-mercaptopurine by the S methylation activity of thiopurine methyl transferase (TMPT) enzyme.

InChI:InChI=1/C6H7N5S/c1-12-5-3-4(9-2-8-3)10-6(7)11-5/h2-3H,1H3,(H2,7,8,9,10)

Upstream product

• 154-42-7 thioguanin 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 
• 154985-75-8 6-thioguanine 
• 10310-21-1 2-Amino-6-chloropurin 
• 5188-07-8 sodium thiomethoxide 

Downstream Products

• 59856-85-8 N⁶-phenethyl-7⁽⁹⁾H-purine-2,6-diyldiamine 
• 5437-49-0 2-Amino-6-dimethyl-amino-purin 
• 5437-50-3 N⁶-butyl-7(9)H-purine-2,6-diyldiamine 
• 4421-04-9 N⁶-methyl-2,6-diaminopurine 
• 4014-90-8 N⁶-benzyl-7⁽⁹⁾H-purine-2,6-diyldiamine 
• 5446-90-2 2-Amino-6-hydrazino-7H-purine 
• 578-76-7 7-methylguanine 
• 4914-73-2 (2R,3R,4S,5R)-2-[2-amino-6-(methylthio)-9H-purin-9-yl]-5-(hydroxymethyl)tetrahydrofuran-3,4-diol 
• 22247-87-6 7-(2-chloroethyl)guanine 
• 37113-42-1 2'-deoxy-6-methylthioguanosine 
• 14666-87-6 9-Butyl-2-amino-6-methylmercapto-9H-purin 
• 152965-58-7 2-amino-9-(2-deoxy-3,5-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)-6-(methylthio)purine 
• 2879-78-9 2-Amino-6-methylmercapto-9-(2-chlorethyl)-purin 

Relevant articles and documents

6-Substituted 2-Aminopurine-2′-deoxyribonucleoside 5′-Triphosphates that Trace Cytosine Methylation

Gene expression is extensively regulated by the occurrence and distribution of the epigenetic marker 2′-deoxy 5-methylcytosine (5mC) in genomic DNA. Because of its effects on tumorigenesis there is an important link to human health. In addition, detection of 5mC can serve as an outstanding biomarker for diagnostics as well as for disease therapy. Our previous studies have already shown that, by processing O6-alkylated 2′-deoxyguanosine triphosphate (dGTP) analogues, DNA polymerases are able to sense the presence of a single 5mC unit in a template. Here we present the synthesis and evaluation of an extended toolbox of 6-substituted 2-aminopurine-2′-deoxyribonucleoside 5′-triphosphates modified at position 6 with various functionalities. We found that sensing of 5-methylation by this class of nucleotides is more general, not being restricted to O6-alkyl modification of dGTP but also applying to other functionalities.

Methylation of mercaptopurine, thioguanine, and their nucleotide metabolites by heterologously expressed human thiopurine S-methyltransferase

Thiopurine S-methyltransferase (TPMT), a cytosolic enzyme that exhibits genetic polymorphism, catalyzes S-methylation of mercaptopurine (MP) and thioguanine (TG), yielding S-methylated nucleobases that are inactive, whereas S-methylated nucleotides of these thiopurines are cytotoxic. A yeast- based heterologous expression system was therefore used to characterize human TPMT-catalyzed methylation of MP, TG, and their principal nucleotide metabolites [thioinosine monophosphate (TIMP) and thioguanosine monophosphate (TGMP), respectively]. MP, TG, TIMP, and TGMP were all substrates for human TPMT, exhibiting similar Michaelis-Menten kinetic parameters (K(m), 10.6- 27.1 μM; V(max), 31-59 nmol/min/mg of TPMT). Consistent with these kinetic parameters, human leukemia cells (CEM) incubated for 24 hr with 10 μM MP or TG accumulated significantly higher (2.3-fold, p = 0.01) concentrations of methyl-TIMP after MP incubation than methyl-TGMP after TG incubation, due to the 2.7-fold higher concentration of TIMP after MP incubation, compared with TG nucleotides (TGN) after TG incubation. Moreover, intracellular accumulation of TGN was 2.5-fold greater after TG incubation than after MP incubation (p = 0.01). These data establish that MP, TG, and their principal nucleotide metabolites are comparable substrates for polymorphic TPMT, and they demonstrate significant differences in the accumulation of active TGN and methylated nucleotides when leukemia cells are treated with MP versus TG.