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A9809

Sigma-Aldrich

Amsacrine hydrochloride

≥98% (TLC), powder

Sinônimo(s):

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

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About This Item

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

Nível de qualidade

200

Ensaio

≥98% (TLC)

Formulário

powder

cor

red to brown

pf

197-199 °C (lit.)

solubilidade

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

temperatura de armazenamento

room temp

cadeia de caracteres 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

chave InChI

WDISRLXRMMTXEV-UHFFFAOYSA-N

Informações sobre genes

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

Aplicação

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

Ações bioquímicas/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

Palavra indicadora

Danger

Classificações de perigo

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

Código de classe de armazenamento

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

Classe de risco de água (WGK)

WGK 3

Equipamento de proteção individual

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

Escolha uma das versões mais recentes:

Certificados de análise (COA)

Lot/Batch Number
095H4023
081K4137
058H4080
032K4605
011K4120

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Emilia Komulainen et al.
ACS chemical biology, 14(6), 1110-1114 (2019-05-16)
Tyrosyl DNA phosphodiesterase 2 (TDP2) facilitates the repair of topoisomerase II (TOP2)-linked DNA double-strand breaks and, as a consequence, is required for cellular resistance to TOP2 "poisons". Recently, a deazaflavin series of compounds were identified as potent inhibitors of TDP2
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
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.
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
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