3-Methyladenine - CAS 5142-23-4
Catalog number: B0084-070159
Category: Inhibitor
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Molecular Formula:
C6H7N5
Molecular Weight:
149.157
COA:
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Targets:
PI3K
Description:
3-Methyladenine is an autophagy inhibitor that protects cerebellar granule cells (CGCs) from apoptosis following serum/potassium deprivation. 3-Methyladenine inhibits phosphoinositide 3-kinase (PI3K) activity, which plays a key role in autophagy process.
Ordering Information
Catalog Number Size Price Stock Quantity
B0084-070159 250 mg $168 In stock
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Brife Description:
PI3K inhibitor
Appearance:
White Solid
Synonyms:
3-Methyladenine, NSC 66389; NSC-66389; NSC66389. 3-Methyl-3H-purin-6-amine; 6-Amino-3-methylpurine; 3-MA; 3H-Purin-6-amine, 3-methyl-
MSDS:
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Melting Point:
>260°C (dec.)
InChIKey:
FSASIHFSFGAIJM-UHFFFAOYSA-N
InChI:
InChI=1S/C6H7N5/c1-11-3-10-5(7)4-6(11)9-2-8-4/h2-3H,7H2,1H3
Canonical SMILES:
CN1C=NC(=C2C1=NC=N2)N
1.Repair of alkylated DNA: recent advances.
Sedgwick B;Bates PA;Paik J;Jacobs SC;Lindahl T DNA Repair (Amst). 2007 Apr 1;6(4):429-42. Epub 2006 Nov 16.
Cytotoxic and mutagenic methylated bases in DNA can be generated by endogenous and environmental alkylating agents. Such damaged bases are removed by three distinct strategies. The abundant toxic lesion 3-methyladenine (3-alkyladenine) is excised by a specific DNA glycosylase that initiates a base excision-repair process. The toxic lesions 1-methyladenine and 3-methylcytosine are corrected by oxidative DNA demethylation catalyzed by DNA dioxygenases. These enzymes release the methyl moiety as formaldehyde, directly reversing the base damage. The third strategy involves the mutagenic and cytotoxic lesion O(6)-methylguanine which is also repaired by direct reversal but uses a different mechanism. Here, the methyl group is transferred from the lesion to a specific cysteine residue within the methyltransferase itself. In this review, we briefly describe endogenous alkylating agents and the extensively investigated DNA repair enzymes, mammalian 3-methyladenine-DNA glycosylase and O(6)-methylguanine-DNA methyltransferase. We provide a more detailed description of the structures and biochemical properties of the recently discovered DNA dioxygenases.
2.Resveratrol induces autophagic apoptosis via the lysosomal cathepsin D pathway in human drug-resistant K562/ADM leukemia cells.
Zhang Z;Liu Z;Chen J;Yi J;Cheng J;Dun W;Wei H Exp Ther Med. 2018 Mar;15(3):3012-3019. doi: 10.3892/etm.2018.5742. Epub 2018 Jan 12.
The aim of the present study was to investigate the crosstalk between resveratrol (Res)-induced autophagy and apoptosis, and the molecular pathway by which autophagy leads to apoptotic death in drug-resistant K562/ADM leukemia cells. The viability of K562/ADM cells was determined using the MTT assay. The formation of autophagic vacuoles was detected using transmission electron microscopy and monodansylcadaverine (MDC) staining. Cell apoptosis was evaluated using flow cytometry. The expression of apoptosis- or autophagy-associated proteins was measured using western blotting. The results indicated that treatment with Res inhibited cell viability in a concentration-dependent manner. Furthermore, the numbers of MDC-positive fluorescent points, autophagic vacuoles and autolysosome-engulfed cytoplasmic materials were markedly increased in Res-treated K562/ADM cells compared with untreated cells, as determined using fluorescence microscopy and transmission electron microscopy. Res-induced apoptosis was associated with increased cleaved caspase-3 and B-cell lymphoma 2 associated X protein, and decreased B-cell lymphoma 2 (Bcl-2) protein expression levels when compared with the control (P<0.
3.A model for 3-methyladenine recognition by 3-methyladenine DNA glycosylase I (TAG) from Staphylococcus aureus.
Zhu X;Yan X;Carter LG;Liu H;Graham S;Coote PJ;Naismith J Acta Crystallogr Sect F Struct Biol Cryst Commun. 2012 Jun 1;68(Pt 6):610-5. doi: 10.1107/S1744309112016363. Epub 2012 May 22.
The removal of chemically damaged DNA bases such as 3-methyladenine (3-MeA) is an essential process in all living organisms and is catalyzed by the enzyme 3-MeA DNA glycosylase I. A key question is how the enzyme selectively recognizes the alkylated 3-MeA over the much more abundant adenine. The crystal structures of native and Y16F-mutant 3-MeA DNA glycosylase I from Staphylococcus aureus in complex with 3-MeA are reported to 1.8 and 2.2 Å resolution, respectively. Isothermal titration calorimetry shows that protonation of 3-MeA decreases its binding affinity, confirming previous fluorescence studies that show that charge-charge recognition is not critical for the selection of 3-MeA over adenine. It is hypothesized that the hydrogen-bonding pattern of Glu38 and Tyr16 of 3-MeA DNA glycosylase I with a particular tautomer unique to 3-MeA contributes to recognition and selection.
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CAS 5142-23-4 3-Methyladenine

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