(1S,2R,5R)-5-(4-氨基-1H-咪唑并[4,5-C]吡啶-1-基)-3-羟甲基-3-环戊烯-1,2-二醇
| 中文名称 | (1S,2R,5R)-5-(4-氨基-1H-咪唑并[4,5-C]吡啶-1-基)-3-羟甲基-3-环戊烯-1,2-二醇 |
|---|---|
| 中文同义词 | (1S,2R,5R)-5-(4-氨基-1H-咪唑并[4,5-C]吡啶-1-基)-3-羟甲基-3-环戊烯-1,2-二醇;3-去氮腺嘌呤;(1S,2R,5R)-5-(4-氨基-1H-咪唑并[4,5-C]吡啶-1-基)-3-羟甲基-3-环戊烯-1,2-二醇 1级;INSOLUTION EZH2 INHIBITOR, DZNEP CALBIOCHEM;(1S,2R,5R)-5-(4-氨基-1H-咪唑并[4,5-C]吡啶-1-基)-3-(羟甲基)环戊-3-烯-1,2-二醇;3-脱氮胸腺素A |
| 英文名称 | 3-deazaneplanocin |
| 英文同义词 | 3-deazaneplanocin;NSC 617989 3-deazaneplanocin(DzNep);3-Cyclopentene-1,2-diol,5-(4-amino-1H-imidazo[4,5-c]pyridin-1-yl)-3-(hydroxymethyl)-, (1S,2R,5R)-;(1R,4R,5S)-4-(5-amino-4,7,9-triazabicyclo[4.3.0]nona-2,4,7,10-tetraen-9-yl)-2-(hydroxymethyl)cyclopent-2-ene-1,5-diol;(1S,2R,5R)-5-(4-Amino-1H-imidazo[4,5-c]pyridin-1-yl)-3-(hydroxymethyl)-3-cyclopentene-1,2-diol;3-Deazaneplanocin A (DZNeP);3-deazaneplanocin(DzNep);NSC 617989 |
| CAS号 | 102052-95-9 |
| 分子式 | C12H14N4O3 |
| 分子量 | 262.26 |
| EINECS号 | |
| 相关类别 | 小分子抑制剂，天然产物;Inhibitors;Epigenetics;Other APIs |
| Mol文件 | 102052-95-9.mol |
| 结构式 | ![(1S,2R,5R)-5-(4-氨基-1H-咪唑并[4,5-C]吡啶-1-基)-3-羟甲基-3-环戊烯-1,2-二醇 结构式](CAS/GIF/102052-95-9.gif) |
(1S,2R,5R)-5-(4-氨基-1H-咪唑并[4,5-C]吡啶-1-基)-3-羟甲基-3-环戊烯-1,2-二醇 性质
| 沸点 | 624.1±65.0 °C(Predicted) |
|---|---|
| 密度 | 1.75 |
| 储存条件 | = -70C |
| 溶解度 | 可溶于 DMSO（高达 20 mg/ml） |
| 形态 | 液体 |
| 酸度系数(pKa) | 13.52±0.70(Predicted) |
| 颜色 | 米色 |
| 水溶解性 | Soluble in Water |
| 稳定性 | 可在-20°C下的DMSO溶液保存长达1个月。 |
EZH2
3-Deazaneplanocin A is a potent histone methyltransferase EZH2 inhibitor. Treatment of OCI-AML3 cells with 3-Deazaneplanocin A (1.0 μM) results in a significant increase in accumulation of cells in the G 0 /G 1 phase (58.5%) with a concomitant decrease in the number of cells in S phase (35.2%) and G 2 /M phases (6.3%) of the cell cycle (P<0.05). Treatment with 3-Deazaneplanocin A (200 nM to 2.0 μM) for 48 hours, dose dependently, inhibits colony growth of OCI-AML3 and HL-60 cells. 3-Deazaneplanocin A reduces the expression of EZH2, especially after 72 hours (e.g. 48%, 32% and 36% reduction of EZH2 in PANC-1, MIA-PaCa-2 and LPc006 cells, respectively). 3-Deazaneplanocin A shows minimal growth inhibition in PANC-1 cells. More than 50% of these cells are still growing after exposure at the highest concentration (20 μM). MIA-PaCa-2 and LPc006 cells are much more sensitive, with IC 0 values of 1±0.3 and 0.1±0.03 μM, respectively. 3-Deazaneplanocin A causes dose-dependent inhibition of cell proliferation of NSCLC cell lines, and the IC 0 values range from 0.08 to 0.24 μM.
The survival of NOD/SCID mice with acute myeloid leukemia (AML) due to HL-60 cells is significantly higher, if treated with 3-Deazaneplanocin A and Panobinostat (PS) compare to treatment with PS, 3-Deazaneplanocin A, or vehicle alone (P<0.05). Median survival is as follows: control, 36 days; PS, 42 days; 3-Deazaneplanocin A, 43 days; and 3-Deazaneplanocin A plus PS, 52 days. There is a progressive increase in weight of rats treated with physiological saline in a time-dependent manner (the mean growth rate=3.19% per day). Administration of 20 mg/kg 3-Deazaneplanocin A not only markedly reduces the relative weight of the rats compare to the initial weight (−2.0%, −4.9% and −1.2%) in the first three days post-treatment, but also suppresses the weight growth rate to 2.6% per day from the fourth day onwards post-dose.