Ellipticine
K00071 · LP00531 · CS-1794 · icig770 · CP-3025 · CCG36483 · CCG 36483 · DB-052047
식별자 및 물리적 특성
| CAS No. | 519-23-3 |
|---|---|
| 분자식 | C17H14N2 |
| 평균 분자량 | 246.31 g/mol |
| 단동위원소 질량 | 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 |
화학 및 물리적 성질
| XLogP | 4.8 |
|---|---|
| 극성 표면적 | 28.7 |
| 수소 결합 공여자 수 | 1 |
| 수소 결합 수용자 수 | 1 |
| 회전 가능 결합 수 | 0 |
| 무거운 원자 수 | 19 |
| 형식 전하 | 0 |
| 복잡도 | 342 |
| LogP(분배 계수) | 4.8 |
| 녹는점 | 316-318°C |
| 끓는 점 | 379.31°C (rough estimate) |
| 밀도 | 1.257±0.06 g/cm3 (20 ºC 760 Torr) |
| 굴절률 | 1.5794 (estimate) |
| 저장 조건 | Keep in dark place,Sealed in dry,2-8°C |
| 용해도 | DMSO: 용해될 수 있다 |
| 물리적 상태 | 밝은 노란색 고체 |
| pKa(산도 계수) | 16.59±0.40(Predicted) |
| 색상 | 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(분배 계수) | 4.800 |
안전 및 규제
| GHS 분류 | 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%) |
| 수질 위해 등급(WGK) | 3 |
| RTECS 번호 | UU8825000 |
| 운송 번호(UN) | UN 3462 6.1/PG 3 |
| 독성 | LD50 in mice (mg/kg): 19.5-22.4 i.v.178-204 orally (Rakieten) |
| 위험 문구(R) | 25 |
| 위험 표시 | T |
| 안전 문구(S) | 45 |
| 포장분류 | III |
| 위험 등급 | 6.1(b)Acute Tox. 3 Oral |
| 저장 분류 | 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects |
용도
개요
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.
일반 설명
A topoisomerase II inhibitor. Acts as an intercalative alkaloid that stimulates topoisomerase II-mediated DNA breakage. Is also capable of uncoupling mitochondrial oxidative phosphorylation.