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A9809

Sigma-Aldrich

Amsacrine hydrochloride

≥98% (TLC), powder

Synonyma:

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

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About This Item

Empirický vzorec (Hillův zápis):
C21H19N3O3S · HCl
Číslo CAS:
54301-15-4
Molekulová hmotnost:
429.92
MDL number:
MFCD07799963
UNSPSC Code:
51111800
PubChem Substance ID:
24278248
NACRES:
NA.77

Quality Level

200

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

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

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.

pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

signalword

Danger

Hazard Classifications

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

Storage Class

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

wgk_germany

WGK 3

ppe

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

Osvědčení o analýze (COA)

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Navštívit knihovnu dokumentů

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
Wenge Wang et al.
Cancer biology & therapy, 4(8), 893-898 (2005-09-24)
CP-31398 activates wild-type p53 by a novel mechanism that does not involve phosphorylation of the amino-terminus of p53 and disassociation of MDM2. To identify more potent CP-31398-like p53 activators, we synthesized 4 acridine derivatives with a similar structure to CP-31398.
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
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
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
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