3-Methyladenine

Modify Date: 2024-01-02 17:50:37

3-Methyladenine Structure
3-Methyladenine structure
 Common Name 3-Methyladenine
CAS Number 5142-23-4 Molecular Weight 149.153
Density 1.6±0.1 g/cm3 Boiling Point 240.1±50.0 °C at 760 mmHg
Molecular Formula C6H7N5 Melting Point -300ºC (dec.)(lit.)
MSDS Chinese USA Flash Point 99.0±30.1 °C

 Use of 3-Methyladenine


3-Methyladenine is a PI3K inhibitor. 3-Methyladenine is a widely used inhibitor of autophagy via its inhibitory effect on class III PI3K.

 Names

Name 3-methyladenine
Synonym More Synonyms

 3-Methyladenine Biological Activity

Description 3-Methyladenine is a PI3K inhibitor. 3-Methyladenine is a widely used inhibitor of autophagy via its inhibitory effect on class III PI3K.
Related Catalog
Target

PtdIns3Kγ:60 μM (IC50, Cell Assay)

Vps34:25 μM (IC50, Cell Assay)

Human Endogenous Metabolite

Autophagy

Mitophagy

In Vitro 3-Methyladenine shows slight preference to binds to Vps34 in vitro, with an IC50 of 25 µM for Vps34 as compared with 60 µM for PtdIns3Kγ, and 3-Methyladenine (10 mM) can inhibit all PtdIns3Ks[1]. 3-Methyladenine (3-MA, 5 mM) suppresses autophagy in HeLa cells under both glucose-free conditions and normal conditions. 3-Methyladenine (2.5, 5 or 10 mM) induces caspase-dependent cell death in HeLa cells, and the death occurs independently of the inhibition of autophagy. Moreover, 3-Methyladenine (3-MA, 1 mM) significantly shortens the duration of nocodazole-induced-prometaphase arrest[2].
In Vivo 3-Methyladenine (1.5 mg/100 g, i.p.) treatment alleviates sodium taurocholate-induced severe acute pancreatitis (SAP) in rats at both 12 and 24 h. 3-Methyladenine inhibits autophagy of pancreatic acinar cells in sodium taurocholate-tnduced SAP. 3-Methyladenine also shows inhibitory effects on PI3K/Akt signaling pathway and NF-κB signaling pathway in sodium taurocholate-tnduced SAP[3].
Cell Assay Cell viability is determined by a trypan blue exclusion assay. Cells are cultured in the medium with 3-Methyladenine. Both adherent and floating cells are collected and suspended in phosphate buffered saline (PBS, pH 7.4) at a final density of 1-2×106/mL. An equal volume of 0.4% trypan blue solution (w/v, in PBS) is added to the cell suspension and mixed thoroughly. After incubation at room temperature for 3 min, cell counting is performed using a hemacytometer.
Animal Admin All rats are fasted for 12 h with free access to water prior to operation. After anesthesia by intraperitoneal (i.p.) injection of 2% sodium pentobarbital (0.25 mL/100 g), they are laid and fixed on the table, routinely shaven, disinfected, and draped. The rat SAP model is induced by 0.1 mL/min speed uniformly retrograde infusion of a freshly prepared 3.5% sodium taurocholate solution (0.1 mL/100 g) into the biliopancreatic duct after laparotomy. Equivalent volume of normal saline solution is substituted for 3.5% sodium taurocholate solution in the sham-operation (SO) control group. The incision is closed with a continuous 3-0-silk suture, and 2 mL/100 g of saline is injected into the back subcutaneously to compensate for the fluid loss. 180 rats are randomly divided into four groups: (1) Acanthopanax treatment group (Aca group, n = 45) where the rats are injected with 0.2% Acanthopanax injection at a dose of 3.5 mg/100 g 3 h after successful modeling via the vena caudalis once, knowing that this dosage is effective; (2) 3-Methyladenine treatment group (3-methyladenine group, n = 45) where the rats are injected with 100 nmol/μL 3-methyladenine solution at a dose of 1.5 mg/100 g 3 h after successful modeling via the intraperitoneal route once, knowing that this dosage is effective; (3) SAP model group (SAP group, n = 45) where these rats receive an equivalent volume of the normal saline instead of Acanthopanax injection 3 h after successful modeling via the vena caudalis once; (4) SO group (control, n = 45) where these rats receive an equivalent volume of the normal saline instead of Acanthopanax injection 3 h after successful sham-operation via the vena caudalis once. The 45 animals in each of the four groups are equally randomized into 3, 12, and 24 h subgroups for postoperative observations[3].
References

[1]. Miller S, et al. Finding a fitting shoe for Cinderella: searching for an autophagy inhibitor. Autophagy. 2010 Aug;6(6):805-807.

[2]. Hou H, et al. Inhibitors of phosphatidylinositol 3'-kinases promote mitotic cell death in HeLa cells. PLoS One. 2012;7(4):e35665.

[3]. Wang X, et al. Acanthopanax versus 3-Methyladenine Ameliorates Sodium Taurocholate-Induced Severe Acute Pancreatitis by Inhibiting the Autophagic Pathway in Rats. Mediators Inflamm. 2016;2016:8369704.

[4]. Meng Li, et al. Alda-1 Ameliorates Liver Ischemia-Reperfusion Injury by Activating Aldehyde Dehydrogenase 2 and Enhancing Autophagy in Mice. J Immunol Res. 7 August 2018.

 Chemical & Physical Properties

Density 1.6±0.1 g/cm3
Boiling Point 240.1±50.0 °C at 760 mmHg
Melting Point -300ºC (dec.)(lit.)
Molecular Formula C6H7N5
Molecular Weight 149.153
Flash Point 99.0±30.1 °C
Exact Mass 149.070145
PSA 69.62000
LogP -2.36
Appearance of Characters Powder | White
Vapour Pressure 0.0±0.5 mmHg at 25°C
Index of Refraction 1.807
Storage condition Store at +4°C

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
AU6520000
CHEMICAL NAME :
Adenine, 3-methyl-
CAS REGISTRY NUMBER :
5142-23-4
BEILSTEIN REFERENCE NO. :
0146087
LAST UPDATED :
199712
DATA ITEMS CITED :
1
MOLECULAR FORMULA :
C6-H7-N5
MOLECULAR WEIGHT :
149.18

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
280 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
FATOAO Farmakologiya i Toksikologiya (Moscow). For English translation, see PHTXA6 and RPTOAN. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.2- 1939- Volume(issue)/page/year: 46(5),104,1983

 Safety Information

Hazard Codes Xn
Risk Phrases 22
Safety Phrases 24/25
RIDADR NONH for all modes of transport
WGK Germany 3
RTECS AU6520000
HS Code 2933990090

 Synthetic Route

 Customs

HS Code 2933990090
Summary 2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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 Synonyms

3-Methyl-3H-purin-6-amine
EINECS 225-908-6
methyladenine
N(3)-methyladenine
3-methyl-3H-adenine
3-MA,6-Amino-3-methylpurine
3-methylpurin-6-amine
MFCD00010531
3H-Purin-6-amine, 3-methyl-
6-Amino-3-methylpurine
3-Methyladenine
3-MA
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