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A9809

Sigma-Aldrich

Amsacrine hydrochloride

≥98% (TLC), powder

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C21H19N3O3S · HCl
Número de CAS:
54301-15-4
Peso molecular:
429.92
Número MDL:
MFCD07799963
Código UNSPSC:
51111800
ID de la sustancia en PubChem:
24278248
NACRES:
NA.77

Nivel de calidad

200

Ensayo

≥98% (TLC)

Formulario

powder

color

red to brown

mp

197-199 °C (lit.)

solubilidad

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

temp. de almacenamiento

room temp

cadena SMILES

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

Clave InChI

WDISRLXRMMTXEV-UHFFFAOYSA-N

Información sobre el gen

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

Aplicación

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

Acciones bioquímicas o fisiológicas

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.

Pictogramas

Skull and crossbonesHealth hazard
GHS06,GHS08

Palabra de señalización

Danger

Frases de peligro

H301,H317,H341,H351,H361d

Clasificaciones de peligro

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

Código de clase de almacenamiento

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

Clase de riesgo para el agua (WGK)

WGK 3

Equipo de protección personal

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

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Certificados de análisis (COA)

Lot/Batch Number
0000404427
0000404427
0000375877
0000360738
0000360738

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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
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
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
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
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
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