3-Methyladenine
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MedKoo CAT#: 406971

CAS#: 5142-23-4

Description: 3-Methyladenine, aslo known as NSC 66389, is an Autophagy inhibitor. 3-methyladenine enhances the sensitivity of nasopharyngeal carcinoma cells to chemotherapy and radiotherapy. 3-Methyladenine can depress drug efflux transporters via blocking the PI3K-AKT-mTOR pathway thus sensitizing MDR cancer to chemotherapy. 3-methyladenine potentiates apoptosis induced by dietary tocotrienols in breast cancer cells.


Price and Availability

Size
Price

100mg
USD 190
1g
USD 1150
Size
Price

200mg
USD 350
2g
USD 1950
Size
Price

500mg
USD 650
5g
Ask price

3-Methyladenine, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 406971
Name: 3-Methyladenine
CAS#: 5142-23-4
Chemical Formula: C6H7N5
Exact Mass: 149.0701
Molecular Weight: 149.157
Elemental Analysis: C, 48.32; H, 4.73; N, 46.95


Synonym: 3-Methyladenine, NSC 66389; NSC-66389; NSC66389.

IUPAC/Chemical Name: 3-methyl-3H-purin-6-amine

InChi Key: FSASIHFSFGAIJM-UHFFFAOYSA-N

InChi Code: InChI=1S/C6H7N5/c1-11-3-10-5(7)4-6(11)9-2-8-4/h2-3H,7H2,1H3

SMILES Code: NC(N=CN1C)=C2C1=NC=N2


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
293490


References

1: Zheng XY, Li LJ, Li W, Jiang PF, Shen HQ, Chen YH, Chen X. Low concentrations of chloroquine and 3-methyladenine suppress the viability of retinoblastoma cells synergistically with vincristine independent of autophagy inhibition. Graefes Arch Clin Exp Ophthalmol. 2015 Dec;253(12):2309-15. doi: 10.1007/s00417-015-3157-1. PubMed PMID: 26335535.

2: Song L, Ma L, Chen G, Huang Y, Sun X, Jiang C, Liu H. [Autophagy inhibitor 3-methyladenine enhances the sensitivity of nasopharyngeal carcinoma cells to chemotherapy and radiotherapy]. Zhong Nan Da Xue Xue Bao Yi Xue Ban. 2016 Jan;41(1):9-18. doi: 10.11817/j.issn.1672-7347.2016.01.002. Chinese. PubMed PMID: 26819419.

3: Hermann R, Vélez DE, Rusiecki TM, Fernández Pazos Mde L, Mestre Cordero VE, Marina Prendes MG, Perazzo Rossini JC, Savino EA, Varela A. Effects of 3-methyladenine on isolated left atria subjected to simulated ischaemia-reperfusion. Clin Exp Pharmacol Physiol. 2015 Jan;42(1):41-51. doi: 10.1111/1440-1681.12323. PubMed PMID: 25311855.

4: Zou Z, Zhang J, Zhang H, Liu H, Li Z, Cheng D, Chen J, Liu L, Ni M, Zhang Y, Yao J, Zhou J, Fu J, Liang Y. 3-Methyladenine can depress drug efflux transporters via blocking the PI3K-AKT-mTOR pathway thus sensitizing MDR cancer to chemotherapy. J Drug Target. 2014 Nov;22(9):839-48. doi: 10.3109/1061186X.2014.936870. PubMed PMID: 25019701.

5: Zhang R, Wang R, Chen Q, Chang H. Inhibition of autophagy using 3-methyladenine increases cisplatin-induced apoptosis by increasing endoplasmic reticulum stress in U251 human glioma cells. Mol Med Rep. 2015 Aug;12(2):1727-32. doi: 10.3892/mmr.2015.3588. PubMed PMID: 25846607; PubMed Central PMCID: PMC4464427.

6: Horwacik I, Gaik M, Durbas M, Boratyn E, Zając G, Szychowska K, Szczodrak M, Kołoczek H, Rokita H. Inhibition of autophagy by 3-methyladenine potentiates sulforaphane-induced cell death of BE(2)-C human neuroblastoma cells. Mol Med Rep. 2015 Jul;12(1):535-42. doi: 10.3892/mmr.2015.3377. PubMed PMID: 25695841.

7: Pickard RD, Spencer BH, McFarland AJ, Bernaitis N, Davey AK, Perkins AV, Chess-Williams R, McDermott CM, Forbes A, Christie D, Anoopkumar-Dukie S. Paradoxical effects of the autophagy inhibitor 3-methyladenine on docetaxel-induced toxicity in PC-3 and LNCaP prostate cancer cells. Naunyn Schmiedebergs Arch Pharmacol. 2015 Jul;388(7):793-9. doi: 10.1007/s00210-015-1104-7. PubMed PMID: 25708950.

8: Alam MJ, Ahmad S. Quantum chemical and spectroscopic investigations of 3-methyladenine. Spectrochim Acta A Mol Biomol Spectrosc. 2014 Jul 15;128:653-64. doi: 10.1016/j.saa.2014.02.170. PubMed PMID: 24704482.

9: Liu J, Hao G, Yi L, Sun TS. [Protective effects of 3-methyladenine on acute lung injury caused by multiple trauma in rats]. Zhongguo Gu Shang. 2015 Apr;28(4):350-3. Chinese. PubMed PMID: 26072619.

10: Tran AT, Ramalinga M, Kedir H, Clarke R, Kumar D. Autophagy inhibitor 3-methyladenine potentiates apoptosis induced by dietary tocotrienols in breast cancer cells. Eur J Nutr. 2015 Mar;54(2):265-72. doi: 10.1007/s00394-014-0707-y. PubMed PMID: 24830781; PubMed Central PMCID: PMC4233202.

11: Zhu B, Yang C, Ding LC, Liu N. 3-methyladenine, an autophagic inhibitor, attenuates therapeutic effects of sirolimus on scopolamine-induced cognitive dysfunction in a rat model. Int J Clin Exp Med. 2014 Oct 15;7(10):3327-32. PubMed PMID: 25419365; PubMed Central PMCID: PMC4238551.

12: McFarland AJ, Grant GD, Perkins AV, Flegg C, Davey AK, Allsopp TJ, Renshaw G, Kavanagh J, McDermott CM, Anoopkumar-Dukie S. Paradoxical role of 3-methyladenine in pyocyanin-induced toxicity in 1321N1 astrocytoma and SH-SY5Y neuroblastoma cells. Int J Toxicol. 2013 May-Jun;32(3):209-18. doi: 10.1177/1091581813482146. PubMed PMID: 23525265.

13: Liu M, He Y, Zhang J. [Effect of autophagy inhibitor 3-methyladenine on proliferation and activation of hepatic stellate cells]. Xi Bao Yu Fen Zi Mian Yi Xue Za Zhi. 2013 Aug;29(8):809-12. Chinese. PubMed PMID: 23948405.

14: Sheng Y, Sun B, Guo WT, Zhang YH, Liu X, Xing Y, Dong DL. 3-Methyladenine induces cell death and its interaction with chemotherapeutic drugs is independent of autophagy. Biochem Biophys Res Commun. 2013 Mar 1;432(1):5-9. doi: 10.1016/j.bbrc.2013.01.106. PubMed PMID: 23395679.

15: Heckmann BL, Yang X, Zhang X, Liu J. The autophagic inhibitor 3-methyladenine potently stimulates PKA-dependent lipolysis in adipocytes. Br J Pharmacol. 2013 Jan;168(1):163-71. doi: 10.1111/j.1476-5381.2012.02110.x. PubMed PMID: 22817685; PubMed Central PMCID: PMC3570012.

16: Lei FR, Li XQ, Liu H, Zhu RD, Meng QY, Rong JJ. Rapamycin and 3-methyladenine regulate apoptosis and autophagy in bone-derived endothelial progenitor cells. Chin Med J (Engl). 2012 Nov;125(22):4076-82. PubMed PMID: 23158146.

17: Pliyev BK, Menshikov M. Differential effects of the autophagy inhibitors 3-methyladenine and chloroquine on spontaneous and TNF-α-induced neutrophil apoptosis. Apoptosis. 2012 Oct;17(10):1050-65. doi: 10.1007/s10495-012-0738-x. PubMed PMID: 22638980.

18: Liu L, Huang C, He ZG. A TetR family transcriptional factor directly regulates the expression of a 3-methyladenine DNA glycosylase and physically interacts with the enzyme to stimulate its base excision activity in Mycobacterium bovis BCG. J Biol Chem. 2014 Mar 28;289(13):9065-75. doi: 10.1074/jbc.M113.528919. PubMed PMID: 24509852; PubMed Central PMCID: PMC3979383.

19: Lin YC, Kuo HC, Wang JS, Lin WW. Regulation of inflammatory response by 3-methyladenine involves the coordinative actions on Akt and glycogen synthase kinase 3β rather than autophagy. J Immunol. 2012 Oct 15;189(8):4154-64. doi: 10.4049/jimmunol.1102739. PubMed PMID: 22972931.

20: Zhu X, Yan X, Carter LG, Liu H, Graham S, Coote PJ, Naismith J. A model for 3-methyladenine recognition by 3-methyladenine DNA glycosylase I (TAG) from Staphylococcus aureus. Acta Crystallogr Sect F Struct Biol Cryst Commun. 2012 Jun 1;68(Pt 6):610-5. doi: 10.1107/S1744309112016363. PubMed PMID: 22684054; PubMed Central PMCID: PMC3370894.