5,11-ジメチル-6H-ピリド[4,3-b]カルバゾール
エリプチシン · 5,11-ジメチル-6H-ピリド[4,3-b]カルバゾール · エリプティシン溶液 · エリプティシン · K00071 · LP00531 · CS-1794 · icig770
![5,11-ジメチル-6H-ピリド[4,3-b]カルバゾール の分子構造式](/img/chemical/3213.png)
識別子と物理属性
| CAS No. | 519-23-3 |
|---|---|
| 分子式 | C17H14N2 |
| 平均分子量 | 246.31 g/mol |
| 単同位体質量 | 246.11569845 g/mol |
| SMILES | Cc1c2ccncc2c(C)c2c1[nH]c1ccccc12 |
| InChIKey | CTSPAMFJBXKSOY-UHFFFAOYSA-N |
| PubChem CID | 3213 |
| ChEMBL | CHEMBL123 |
| ChEBI | CHEBI:4776 |
| EC No. | 208-264-0 |
| DTXSID | DTXSID30199855 |
| 現地名 | 5,11-ジメチル-6H-ピリド[4,3-b]カルバゾール |
化学・物理的性質
| XLogP | 4.8 |
|---|---|
| 極性表面積 | 28.7 |
| 水素結合供与体数 | 1 |
| 水素結合受容体数 | 1 |
| 回転可能結合数 | 0 |
| 重原子数 | 19 |
| 形式電荷 | 0 |
| 複雑度 | 342 |
| LogP（分配係数） | 4.8 |
| 融点 | 316-318°C |
| 沸点 | 379.31°C (rough estimate) |
| 密度 | 1.257±0.06 g/cm3 (20 ºC 760 Torr) |
| 屈折率 | 1.5794 (estimate) |
| 貯蔵条件 | Keep in dark place,Sealed in dry,2-8°C |
| 溶解度 | DMSO：可溶 |
| 外観・状態 | 明るい黄色の固体 |
| pKa（酸解離定数） | 16.59±0.40(Predicted) |
| 色 | Light yellow to yellow |
| Merck | 13,3581 |
| InChI | 1S/C17H14N2/c1-10-14-9-18-8-7-12(14)11(2)17-16(10)13-5-3-4-6-15(13)19-17/h3-9,19H,1-2H3 |
| InChIKey | CTSPAMFJBXKSOY-UHFFFAOYSA-N |
| SMILES | [nH]1c2c(c4c1cccc4)c(c3c(c2C)ccnc3)C |
| LogP（分配係数） | 4.800 |
| CAS データベース | 519-23-3(CAS DataBase Reference) |
安全性と法規制
| GHS 分類 | DangerH301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 38 reports by companies from 1 notifications to the ECHA C&L Inventory. |
|---|---|
| Hazard Classes and Categories | Acute Tox. 3 (100%) |
| 水環境危害等級（WGK） | 3 |
| RTECS 番号 | UU8825000 |
| 輸送番号（UN） | UN 3462 6.1/PG 3 |
| 毒性 | LD50 in mice (mg/kg): 19.5-22.4 i.v.178-204 orally (Rakieten) |
| 危険文句（R） | 25 |
| 危険表示 | T |
| 安全措置（S） | 45 |
| 危険等級 | 6.1(b)Acute Tox. 3 Oral |
| 包装等級 | III |
| 貯蔵分類 | 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects |
用途
説明
Ellipticine is an alkaloid isolated from Apocyanaceae plants that exhibits antitumor activities by intercalating into DNA and/or inhibiting DNA topoisomerase II. It forms covalent adducts in DNA after being enzymatically activated with cytochrome P450 isoforms (e.g., CYP3A4, CYP1A1, or CYP1A2) or by peroxidases in target tissues. Ellipticine has been shown to inhibit the proliferation of human breast adenocarcinoma MCF-7 cells, leukemia HL-60 and CCRF-CEM cells, neuroblastoma IMR-32, UKF-NB-3, and UKF-NB-4 cells, and U87MG glioblastoma cells with IC50 values ranging from 0.27-4.7 μM.
一般的な説明
A topoisomerase II inhibitor. Acts as an intercalative alkaloid that stimulates topoisomerase II-mediated DNA breakage. Is also capable of uncoupling mitochondrial oxidative phosphorylation.
製法・合成法
純化方法
This DNA intercalator is purified by recrystallisation from CHCl3 or MeOH and is dried in vacuo. The UV max values in aqueous EtOH/HCl are at 241, 249, 307, 335 and 426nm. [Marini-Bettolo & Schmutz Helv Chim Acta 42 2146 1959.] The methiodide has m 360o(dec), with UV (EtOH/KOH) at 223, 242, 251, 311, 362 and 432nm. [Goodwin et al. J Am max Chem Soc 81 1903 1959, Beilstein 23/9 V 417.]