3H-Purin-6-amine, 3-methyl- (9CI)
3-methyl-3H-adenine
CAS: 5142-23-4
Molecular Formula: C6H7N5
3H-Purin-6-amine, 3-methyl- (9CI) - Names and Identifiers
| Name | 3-methyl-3H-adenine |
| Synonyms | NSC 66389 BRN 0146087 3-METHYLADENINE 3-methyl-adenin 3-Methyladenine Adenine, 3-methyl- 3-methyl-3H-adenine 3-Methyl-3H-adenine 6-AMINO-3-METHYLPURINE 3-methyl-3h-purin-6-amin 3-methyl-3H-purin-6-amine 3-Methyl-3H-purin-6-amine 3H-Purin-6-amine, 3-methyl- 3H-Purin-6-amine, 3-methyl- (9CI) 5-26-17-00151 (Beilstein Handbook Reference) |
| CAS | 5142-23-4 |
| EINECS | 225-908-6 |
| InChI | InChI=1/C6H7N5/c1-11-3-10-5(7)4-6(11)9-2-8-4/h2-3H,7H2,1H3 |
3H-Purin-6-amine, 3-methyl- (9CI) - Physico-chemical Properties
| Molecular Formula | C6H7N5 |
| Molar Mass | 149.15 |
| Density | 1.60 |
| Melting Point | ~300°C (dec.)(lit.) |
| Boling Point | 240℃ |
| Flash Point | 99℃ |
| Solubility | DMF: 9.80-10.20 mg/mL |
| Vapor Presure | 0.0387mmHg at 25°C |
| Appearance | White to light yellow or light pink crystalline powder |
| Color | White |
| BRN | 146087 |
| pKa | 6.77±0.20(Predicted) |
| Storage Condition | Keep in dark place,Sealed in dry,Room Temperature |
| 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. |
| Refractive Index | 1.8070 (estimate) |
| MDL | MFCD00010531 |
| Physical and Chemical Properties | White to light yellow or light pink crystalline powder |
| In vitro study | The slight bias of 3-MA to Vps34 may be due to the fact that a specific hydrophobic ring structure in Vps34 can surround the 3-methyl group of 3-MA. It has been reported that 3-MA can cause cell death for both normal cultured and starvation treated cancer cells. 3-MA may also inhibit cell migration and invasion without inhibiting autophagy, suggesting that 3-MA has other biological functions besides inhibiting autophagy. 3-MA can cause caspase-dependent cell death, a function that has nothing to do with its inhibition of autophagy. Treatment of glucose-starved Hela cells with 5mm 3-MA reduced the proportion of gfp-lc3-positive cells to 23%. LC3-I levels rose and LC3-II levels fell within 12 to 48 hours of 3-MA treatment. The conversion of LC3-I to LC3-II was inhibited by 3-MA. Treatment of HeLa cells with 2.5 mM or 5 mM 3-MA for one day did not affect cell viability, whereas treatment with 10 mM 3-MA for one day caused a 25.0 percent decrease in cell viability. Treatment of cells with 2.5, 5, or 10 mM 3-MA for two days decreased cell viability by 11.5, 38.0, and 79.4 percent, respectively. 3-MA The effect of reducing cell viability has a time-and dose-dependent character. 3-MA significantly shortened the pre-metaphase blocking time induced by nocodazole. 3-MA inhibits su11274-induced cell death by inhibiting autophagy. Prolonged 3-MA treatment time (up to 9 H) in wild-type MEF cells clearly resulted in LC3 I to II conversion. Extending the 3-MA treatment time significantly increased GFP-LC3 aggregation whereas wortmannin did not have this feature. 3-MA-mediated LC3 turnover and free GFP release are ATG7 dependent. 3-ma treatment resulted in a significant increase in p62 protein levels. Even in Atg5 −/− MEF cells, 3-MA increased p62 levels, as in cells with DOX-mediated ATG5 deletion. 3-MA inhibits type I and Type III PI3K in different ways. 3-MA induced LC3 I to LC3 II in Tsc2 −/− cells compared with wild-type cells The conversion process has dropped significantly. 3-MA disrupts the antagonistic autophagy function of mTOR complex 1. |
| In vivo study | 3-Methyladenine (3-MA) can block autophagy by acting on phosphoinositide 3-phosphate kinase (PI3K), the activity of PI3K is necessary for the nucleation and assembly of the early membrane pool of autophagosome formation. 3-MA did not change the extent of bleeding compared to the SAH-treated group. Neurological symptoms were significantly aggravated after pretreatment with 3-ma compared with the SAH control group. 3-MA treatment reduced autophagy. In contrast, expression of cleaved caspases was significantly up-regulated in the SAH 3-MA group, consistent with the SAH control group, the number of in situ end-labeled positive cells in the right cerebral cortex was significantly increased in the SAH 3-MA group. |
3H-Purin-6-amine, 3-methyl- (9CI) - Risk and Safety
| Hazard Symbols | Xn - Harmful |
| Risk Codes | 22 - Harmful if swallowed |
| Safety Description | 24/25 - Avoid contact with skin and eyes. |
| WGK Germany | 3 |
| RTECS | AU6520000 |
| HS Code | 29335990 |
3H-Purin-6-amine, 3-methyl- (9CI) - Reference
| Reference Show more | 1. Rao Chunmei Cheng fine renting sun Yanbo Peng Xia Huang Zhengde. Effect of Jiawei Danshen decoction containing serum on expression of autophagy-related protein LC3 Ⅱ and Beclin1 in hypoxia/reoxygenation H9C2 cardiomyocytes [J]. Journal of Traditional Chinese Medicine, 2017, 58(12):1043-1048. 2. Rao Chunmei Cheng fine renting sun Yanbo Peng Xia Huang Zhengde. Effect of Jiawei Danshen decoction containing serum pretreatment on mRNA expression of autophagy related genes Atg5 and Beclin1 in hypoxia/reoxygenation H9C2 cardiomyocytes [J]. Chinese Journal of Gerontology, 2017, 37(08):1821-1824. 3. Jiang Tao, Ling cuitumin, Chen Qingzhen, Yang Bingxuan, Lin Yanping, Shao min. Icariin promotes osteoblast differentiation by enhancing autophagy to prevent and treat osteoporosis [J]. Chinese Journal of Tissue Engineering Research, 2021,25(17):2643-2649. 4. Gu Chao, Wang Kaichun, Xu Qinfen, Liu Wei, Hu morality. Kaempferol regulates PI3K/Akt/mTOR pathway to induce autophagy in human colorectal cancer RKO cells [J]. Central South pharmacy, 2020,18(10):1668-1673. 5. Zhang, Duanyang, et al. "Autophagy can alleviate severe burn-induced damage to the intestinal tract in mice." Surgery 162.2 (2017): 408-417.https:// doi.org/10.1016/j. Surg.4/003 7/2017 6. Zhang, Duan Y. MS; Qiu, Wei MS; Jin, PeiS MD; Wang, Peng MS; Sun, Yong MD Role of autophagy and its molecular mechanisms in mice intestinal tract after severe burn, Journal of Trauma and Acute Care Surgery: October 2017 - Volume 83 - Issue 4 - p 716-724do 7. [IF=3.476] Duanyang Zhang et al."Autophagy can alleviate severe burn-induced damage to the intestinal tract in mice."Surgery. 2017 Aug;162:408 8. [IF=5.546] Cuijie Li et al."Long noncoding RNA H19 act as a competing endogenous RNA of Let‐7g to facilitate IEC‐6 cell migration and proliferation via regulating EGF."J Cell Physiol. 2021 Apr;236(4):2881-2892 9. [IF=4.486] Cuijie Li et al."Epidermal growth factor regulation by autophagy‐mediated lncRNA H19 in murine intestinal tract after severe burn."J Cell Mol Med. 2020 May;24(10):5878-5887 |
3H-Purin-6-amine, 3-methyl- (9CI) - Introduction
3-Methyladenine is a selective PI3K inhibitor for Vps34 and PI3Kγ with IC50 of 25 μM and 60 μM; blocks class I PI3K consistently, whereas suppression of class III PI3K is transient, and also blocks autophagosome formation.
Last Update：2022-10-16 17:25:45
3H-Purin-6-amine, 3-methyl- (9CI) - Reference Information
| biological activity | 3-Methyladenine (3-MA, NSC 66389) is a selective PI3K inhibitor that acts on Vps34 and PI3Kγ, and IC50 in HeLa cells is 25 μM and 60 μM respectively; Permanent inhibition of type I PI3K, but the inhibition of type III PI3K is transient, which also blocks the formation of autophagosomes. 3-Methyladenine (3-MA) can be successfully applied to inhibit mitochondrial autophagy. Now ready for use (heating to help dissolve). |
| Target | Value |
| Vps34 (HeLa cells) | 25 μM |
| PI3Kγ (HeLa cells) | 60 μM |
| uses | spectroscopic determination of metals and common ligands for spectral analysis of CO2 reduction. Used for Cu(II)-catalyzed crosslinking reaction of organic boric acid |
Last Update：2024-04-09 20:52:54
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Multiple SpecificationsSpot supply
Product Name: 3-Methyladenine Visit Supplier Webpage Request for quotationCAS: 5142-23-4
Tel: 18301782025
Email: 3008007409@qq.com
Mobile: 18021002903
QQ: 3008007409
Wechat: 18301782025
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