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Merck
CN

A9809

Sigma-Aldrich

安丫啶 盐酸盐

≥98% (TLC), DNA topoisomerase II inhibitor, powder

别名:

4-(9-Acridinylamino)-N-(methanesulfonyl)-m-anisidine hydrochloride, m-AMSA

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关于此项目

经验公式（希尔记法）:
C21H19N3O3S · HCl
化学文摘社编号:
54301-15-4
分子量:
429.92
MDL编号:
MFCD07799963
UNSPSC代码:
51111800
PubChem化学物质编号:
24278248
NACRES:
NA.77

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产品名称

安丫啶 盐酸盐, ≥98% (TLC), powder

质量水平

200

方案

≥98% (TLC)

表单

powder

颜色

red to brown

mp

197-199 °C (lit.)

溶解性

DMSO: 10 mg/mL (with heat and sonication)
30% ethanol: 4 mg/mL

储存温度

room temp

SMILES字符串

Cl.COc1cc(NS(C)(=O)=O)ccc1Nc2c3ccccc3nc4ccccc24

InChI

1S/C21H19N3O3S.ClH/c1-27-20-13-14(24-28(2,25)26)11-12-19(20)23-21-15-7-3-5-9-17(15)22-18-10-6-4-8-16(18)21;/h3-13,24H,1-2H3,(H,22,23);1H

InChI key

WDISRLXRMMTXEV-UHFFFAOYSA-N

基因信息

human ... TOP2A(7153), TOP2B(7155)

相关类别

应用

Amsacrine hydrochloride has been used:
  • as a topoisomerase poison in bacteriophage T4 topoisomerase assay
  • as a topoisomerase inhibitor in Drosophila cell line, Kc167
  • as an antileukemia drug to test its effect on p53 transcriptional activity in tumor xenografts
  • as a topoisomerase II poison in dose-response assays in C elegans

生化/生理作用

Amsacrine (m-AMSA) is a derivative of acridine and an antileukemia drug. It is an anticancer drug with antineoplastic activity that targets topoisomerase II. AMSA is an apoptosis inducer and favors the accumulation of double-stranded breaks (DSBs). It also inhibits the expression of matrix metallopeptidase 2 (MMP-2) and MMP-9 expression in leukemia cells by generating reactive oxygen species (ROS). AMSA serves as an adjuvant in trabeculectomy surgery.
Amsacrine hydrochloride is a DNA topoisomerase II inhibitor.

象形图

Skull and crossbonesHealth hazard
GHS06,GHS08

警示用语：

Danger

危险分类

Acute Tox. 3 Oral - Carc. 2 - Muta. 2 - Repr. 2 - Skin Sens. 1

储存分类代码

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

个人防护装备

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

法规信息

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历史批次信息供参考:

分析证书(COA)

Lot/Batch Number
0000404427
0000404427
0000375877
0000360738
0000360738

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Kotaro Yamamoto et al.
Scientific reports, 9(1), 19288-19288 (2019-12-19)
Treatments for refractory glaucoma include trabeculectomy, in which a filtering bleb is created to reduce aqueous pressure. Mitomycin C (MMC) is often used as an adjuvant to reduce post-trabeculectomy bleb scarring and consequent failure. However, scarring sometimes still occurs. Thus
E M Nelson et al.
Proceedings of the National Academy of Sciences of the United States of America, 81(5), 1361-1365 (1984-03-01)
The intercalative acridine derivative 4'-(9-acridinylamino)methanesulfon-m-anisidide (m-AMSA), but not its isomer o-AMSA, is a potent antitumor drug that in mammalian cells stimulates the formation of DNA strand breaks that are characterized by tightly bound proteins. Using purified mammalian DNA topoisomerases, we
R A Davey et al.
Cancer chemotherapy and pharmacology, 39(5), 424-430 (1997-01-01)
The effectiveness of N-[2-(dimethylamino)ethyl]acridine-4-carboxamide (DACA) relative to that of amsacrine, idarubicin, daunorubicin and paclitaxel against three different forms of multidrug resistance (MDR) was determined using two sublines of the CCRF-CEM human leukaemia cell line, the P-glyco-protein-expressing CEM/VLB100 subline and the
Adrien Marchand et al.
Journal of the American Chemical Society, 140(39), 12553-12565 (2018-09-06)
Designing ligands targeting G-quadruplex nucleic acid structures and affecting cellular processes is complicated because there are multiple target sequences and some are polymorphic. Further, structure alone does not reveal the driving forces for ligand binding. To know why a ligand
C Negri et al.
Biochimie, 77(11), 893-899 (1995-01-01)
We have analyzed the interference of antitumoral drugs acting through the inhibition of DNA topoisomerase II on the human HeLa cell metabolism. Different compounds characterized by a diverse mechanism of action have been used, namely m-amsacrine, an intercalative drug, etoposide
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