3-METHYLADENINE

3-METHYLADENINE Basic information
Product Name:3-METHYLADENINE
Synonyms:3H-Purin-6-amine, 3-methyl-;3-methyl-3h-purin-6-amin;3-Methyl-3H-purin-6-amine;3-methyl-adenin;Adenine, 3-methyl-;3-METHYLADENINE;3-methyl-3H-adenine;6-AMINO-3-METHYLPURINE
CAS:5142-23-4
MF:C6H7N5
MW:149.15
EINECS:225-908-6
Product Categories:Akt;mTOR;Amines;Bases & Related Reagents;Heterocycles;PI3K;Inhibitors;Nucleotides
Mol File:5142-23-4.mol
3-METHYLADENINE Structure
3-METHYLADENINE Chemical Properties
Melting point ~300 °C (dec.)(lit.)
Boiling point 240℃
density 1.60
refractive index 1.8070 (estimate)
Fp 99℃
storage temp. Keep in dark place,Sealed in dry,Room Temperature
solubility Soluble in DMSO (up to 3 mg/ml), or in DMF (up to 10 mg/ml).
pka6.77±0.20(Predicted)
form Powder
color White
BRN 146087
Stability:Stable for 2 years from date of purchase as supplied. Solutions in DMSO or DMF may be stored at -20° for up to 3 months.
Safety Information
Hazard Codes Xn
Risk Statements 22
Safety Statements 24/25
WGK Germany 3
RTECS AU6520000
HS Code 29335990
MSDS Information
ProviderLanguage
SigmaAldrich English
ACROS English
3-METHYLADENINE Usage And Synthesis
DescriptionAutophagy is a multi-step process that involves the degradation and digestion of intracellular components by the lysosome. This process allows cells to efficiently mobilize and recycle cellular constituents, and also prevents the accumulation of damaged organelles, misfolded proteins, and invading microorganisms. mTOR, whose activation is controlled by phosphoinositide 3-kinase (PI3K), is a key regulator of autophagy. 3-Methyladenine (3-MA) is a specific inhibitor of PI3K activity and one of the most widely used inhibitors of the initial phase of the autophagic process: the sequestering of cytoplasmic material by the lysosome. At 5 mM, 3-MA inhibits protein degradation in rat hepatocytes by 65%. 3-MA has been shown to block class I, class II, and class III PI3Ks, including some downstream targets, and to suppress the invasion of highly metastatic human fibrosarcoma HT1080 cells at 10 mM.
Chemical PropertiesWhite powder
Uses3-Methyladenine (3-MA) inhibits autophagy by blocking autophagosome formation via the inhibition of type III Phosphatidylinositol 3-kinases (PI-3K). For use as an autophagy inhibitor, 3-MA is typically used at a concentration of 5 mM.
UsesA multi-use inhibitor that protects cerebellar granule cells from apoptosis.
UsesA synthetic intermediate and a cell-permeable autophagic sequestration blocker that protects cerebellar granule cells from apoptosis post serum/potassium deprivation
DefinitionChEBI: A methyladenine that is adenine substituted with a methyl group at position N-3.
General DescriptionA widely used cell-permeable autophagic sequestration blocker that effectly protects cerebellar granule cells from apoptosis following serum/potassium deprivation. Although a known class III PI3K inhibitor (IC50 = 4.5 mM in cell-free enzymatic assays), 3-MA exhibits quite distinct pharmacological properties from those of two other PI3K inhibitors, LY 294002 (Cat. Nos. 440202 and 440204) and Wortmannin (Cat. No. 681675)
Biochem/physiol Actions3-Methyladenine (3-MA) is used to inhibit and study the mechanism of autophagy (lysosomal self-degradation) and apoptosis under various conditions. 3-MA inhibits autophagy by blocking autophagosome formation via the inhibition of type III phosphatidylinositol 3-kinases (PI-3K).
storage+4°C
References1) Seglen and Gordon?et al.?(1982),?3-Methyladenine: specific inhibitor of autophagic/lysosomal protein degradation in isolated rat hepatocytes; Proc. Natl. Acad. Sci. USA,?79?1889 2) Blommaart?et al. (1997),?The phosphatidylinositol 3-kinase inhibitors wortmannin and LY294002 inhibit autophagy in isolated rat hepatocytes; Eur. J. Biochem.,?243?240 3) McFarland?et al. (2012),?Inhibition of autophagy by 3-methyladenine protects 1321N1 astrocytoma cells against pyocyanin- and 1-hydroxyphenazine-induced toxicity; Arch. Toxicol.,?86?275 4) Zhao?et al. (2014),?Inhibition of autophagy strengthens celastrol-induced apoptosis in human pancreatic cancer in vitro and in vivo models; Curr. Mol. Med.,?14?555
ZERENEX E/5047017 3-BENZYL-8-([2-(3-METHYLPHENOXY)ETHYL]THIO)-3H-PURIN-6-AMINE 3-ETHYL-D5-ADENINE 3-BENZYL-8-([2-(4-METHOXYPHENOXY)ETHYL]THIO)-3H-PURIN-6-AMINE 3-(6-AMINO-8-BROMO-3H-PURIN-3-YL)-1,2-PROPANEDIOL 3-BENZYL-8-([2-(2-FLUOROPHENOXY)ETHYL]THIO)-3H-PURIN-6-AMINE 3-METHYL-D3-ADENINE 3-BENZYL-8-([2-(4-METHYLPHENOXY)ETHYL]THIO)-3H-PURIN-6-AMINE 3-BENZYL-8-(BENZYLTHIO)-3H-PURIN-6-AMINE 3-BENZYL-8-(ISOPROPYLTHIO)-3H-PURIN-6-AMINE SPECS AB-323/25048538 3-(3-Methyl-2-butenyl)-3H-purin-6-amine ZERENEX E/5047015 3-METHYLADENINE 2-[(6-AMINO-3-BENZYL-3H-PURIN-8-YL)THIO]ETHANOL 6-BENZYLADENINE-3-BETA-D-GLUCOSIDE 3-BENZYL-8-(ETHYLTHIO)-3H-PURIN-6-AMINE ZERENEX EZX000209

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