5142-23-4 Usage
Description
Autophagy 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 Properties
White powder
Uses
Different sources of media describe the Uses of 5142-23-4 differently. You can refer to the following data:
1. 3-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.
2. A multi-use inhibitor that protects cerebellar granule cells from apoptosis.
3. A synthetic intermediate and a cell-permeable autophagic sequestration blocker that protects cerebellar granule cells from apoptosis post serum/potassium deprivation
Definition
ChEBI: A methyladenine that is adenine substituted with a methyl group at position N-3.
General Description
A 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 Actions
3-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).
References
1) 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
Check Digit Verification of cas no
The CAS Registry Mumber 5142-23-4 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 5,1,4 and 2 respectively; the second part has 2 digits, 2 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 5142-23:
(6*5)+(5*1)+(4*4)+(3*2)+(2*2)+(1*3)=64
64 % 10 = 4
So 5142-23-4 is a valid CAS Registry Number.
InChI:InChI=1/C6H7N5/c1-11-3-10-5(7)4-6(11)9-2-8-4/h2-3H,7H2,1H3
5142-23-4Relevant articles and documents
A versatile methodology for the regioselective C8-metalation of purine bases
Brackemeyer, Dirk,Hervé, Alexandre,Schulte To Brinke, Christian,Jahnke, Mareike C.,Hahn, F. Ekkehardt
, p. 7841 - 7844 (2014)
Purine nucleobases are excellent ligands for metal ions, forming normally coordinative Werner-type bonds by utilizing the N donor atoms of the nucleobase skeleton. Here we show that purines such as 8-chlorocaffeine and 8-bromo-9-methyladenine react with [Pt(PPh3)4] under oxidative addition of the C8-halogen bond to the metal center. The resulting PtII complexes feature a C8-bound ylidene ligand. Protonation of the ylidene at the N7/9-atom yields complexes bearing a protic N-heterocyclic carbene ligand derived from the purine base with an NMe,NH-substitution pattern.
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Saito,Fujii
, p. 135 (1979)
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SYNTHESIS OF ADENINE 7-OXIDE FROM ADENINE: UTILIZATION OF A BENZYL GROUP AS A CONTROL SYNTHON AT THE 3-POSITION
Fujii, Tozo,Ogawa, Kazuo,Saito, Tohru,Kobayashi, Keiko,Itaya, Taisuke
, p. 477 - 480 (2007/10/02)
The first unequivocal synthetic route to adenine 7-oxide (7) has been established.The route started with peroxycarboxylic acid oxidation of 3-benzyladenine (5), readily obtainable from adenine (2) by benzylation, 8nd proceeded through nonreductive debenzylation of the resulting 3-benzyladenine 7-oxide (6).
