硫代秋水仙碱
| 中文名称 | 硫代秋水仙碱 |
|---|---|
| 中文同义词 | 硫代秋水仙碱;硫秋水仙碱;硫秋水仙素EP杂质B;硫秋水仙苷杂质B;硫代秋水仙碱,10 MM DMSO 溶液;(S)-N-(1,2,3-三甲氧基-10-(甲硫基)-9-氧代-5,6,7,9-四氢苯并[a]庚搭烯-7-基)乙酰胺 |
| 英文名称 | thiocolchicine |
| 英文同义词 | thiocolchicine;thiocholchicine;(S)-7-Acetylamino-6,7-dihydro-10-methylthio-1,2,3-trimethoxybenzo[a]heptalen-9(5H)-one;(S)-7α-Acetylamino-6,7-dihydro-10-(methylthio)-1,2,3-trimethoxybenzo[a]heptalene-9(5H)-one;10-Demethoxy-10-methylthiocolchicine;10-Thiocolchicine;N-[(S)-5,6,7,9-Tetrahydro-1,2,3-trimethoxy-10-methylthio-9-oxobenzo[a]heptalen-7-yl]acetamide;N-[(7S)-5,6,7,9-Tetrahydro-1,2,3-triMethoxy-10-(Methylthio)-9-oxobenzo[a]heptalen-7-yl]acetaMide |
| CAS号 | 2730-71-4 |
| 分子式 | C22H25NO5S |
| 分子量 | 415.5 |
| EINECS号 | 220-346-8 |
| 相关类别 | Intermediates & Fine Chemicals;Pharmaceuticals |
| Mol文件 | 2730-71-4.mol |
| 结构式 |  |
硫代秋水仙碱 性质
| 熔点 | 193℃ |
|---|---|
| 比旋光度 | D20 -221° |
| 沸点 | 729.1±60.0 °C(Predicted) |
| 密度 | 1.27±0.1 g/cm3(Predicted) |
| 储存条件 | -20°C |
| 溶解度 | DMSO：可溶10mg/mL，澄清 |
| 形态 | 粉末 |
| 酸度系数(pKa) | 14.75±0.40(Predicted) |
| 颜色 | 白色至米色 |
| InChI | 1S/C22H25NO5S/c1-12(24)23-16-8-6-13-10-18(26-2)21(27-3)22(28-4)20(13)14-7-9-19(29-5)17(25)11-15(14)16/h7,9-11,16H,6,8H2,1-5H3,(H,23,24)/t16-/m0/s1 |
| InChIKey | CMEGANPVAXDBPL-INIZCTEOSA-N |
| SMILES | S(C)c1[c](cc2c(cc1)c3c(cc(c(c3OC)OC)OC)CC[C@@H]2NC(=O)C)=O |
Thiocolchicine 是秋水仙碱 (HY-16569) 的衍生物，是一种有效的微管蛋白聚合 (tubulin polymerization) 抑制剂 (IC50=2.5 µM)，竞争性结合微管蛋白 (Ki=0.7 µM)。Thiocolchicine 可以作为 ADC 的毒素分子。
Thiocolchicine is against MCF-7, LoVo, LoVo/DX, A-549 and BALB/3T3 cells with IC 50 values of 0.01 μM, 0.021 μM, 0.398 μM, 0.011 μM and 0.114 μM, respectively.Thiocolchicine (1 nM-100 μM; 24-72 hours) shows a relationship between cell cycle blocking activity and growth inhibition in breast cancer cells. It inhibits cell proliferation of MDA-MB-231 and multidrug resistant (MDR) MCF-7 ADRr breast cancer cells with IC 50 s of 0.6 nM and 400 nM, respectively, as well as MDR CEM-VBL leukemia cells (IC 50 =50 nM).