A9809
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:
分子量:
429.92
UNSPSC Code:
51111800
PubChem Substance ID:
NACRES:
NA.77
MDL number:
产品名称
安丫啶 盐酸盐, ≥98% (TLC), powder
SMILES string
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
assay
≥98% (TLC)
form
powder
color
red to brown
mp
197-199 °C (lit.)
solubility
DMSO: 10 mg/mL (with heat and sonication), 30% ethanol: 4 mg/mL
storage temp.
room temp
Quality Level
Gene Information
human ... TOP2A(7153), TOP2B(7155)
Application
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
Biochem/physiol Actions
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.
signalword
Danger
Hazard Classifications
Acute Tox. 3 Oral - Carc. 2 - Muta. 2 - Repr. 2 - Skin Sens. 1
存储类别
6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
wgk
WGK 3
ppe
Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
法规信息
新产品
此项目有
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
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
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
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
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