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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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L R Ferguson et al.
Environmental and molecular mutagenesis, 27(4), 255-262 (1996-01-01)
Amsacrine (4'-(9-acridinylamino)methanesulphon-m-anisidide) is an antileukemic drug which inhibits topoisomerase II (topo II) enzymes. We studied effects of two concentrations of amsacrine on the GM10115A cell line. This is a Chinese hamster line containing a single human chromosome 4, which can
Toshiyuki Kozuki et al.
Nucleic acids research, 45(10), 5995-6010 (2017-05-05)
Topoisomerase (topo) IIα and IIβ maintain genome stability and are targets for anti-tumor drugs. In this study, we demonstrate that the decatenation checkpoint is regulated, not only by topo IIα, as previously reported, but also by topo IIβ. The decatenation
Michael Jahnz et al.
Chembiochem : a European journal of chemical biology, 6(5), 920-926 (2005-04-07)
Topoisomerase II is the only enzyme able to cleave and religate double-stranded DNA; this makes it essential for many vital functions during normal cell growth. Increased expression of topoisomerase II is a common occurrence in neoplasia, and different topoisomerase II
José Carlos Páez-Franco et al.
Journal of cellular biochemistry, 118(5), 1164-1173 (2016-09-30)
9-[(3-chloro)phenylamine]-2-[3-(diethylamine)propylamine]thiazolo[5,4-b]quinolone (D3ClP) is a bioisostere of N-(4-(acridin-9-ylamino)-3-methoxyphenyl)methanesulfonamide (m-AMSA) a DNA topoisomerase II inhibitor with proven cytotoxic activity and known to induce DNA damage and apoptotic cell death in K562 cells. However, recent evidence is not consistent with DNA topoisomerase II
Adam C Ketron et al.
Biochemistry, 51(8), 1730-1739 (2012-02-07)
Amsacrine (m-AMSA) is an anticancer agent that displays activity against refractory acute leukemias as well as Hodgkin's and non-Hodgkin's lymphomas. The drug is comprised of an intercalative acridine moiety coupled to a 4'-amino-methanesulfon-m-anisidide headgroup. m-AMSA is historically significant in that
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