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A9809

Sigma-Aldrich

Amsacrine hydrochloride

≥98% (TLC), powder

Sinonimo/i:

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

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About This Item

Formula empirica (notazione di Hill):
C21H19N3O3S · HCl
Numero CAS:
54301-15-4
Peso molecolare:
429.92
Numero MDL:
MFCD07799963
Codice UNSPSC:
51111800
ID PubChem:
24278248
NACRES:
NA.77

Livello qualitativo

200

Saggio

≥98% (TLC)

Stato

powder

Colore

red to brown

Punto di fusione

197-199 °C (lit.)

Solubilità

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

Temperatura di conservazione

room temp

Stringa SMILE

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
WDISRLXRMMTXEV-UHFFFAOYSA-N

Informazioni sul gene

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

Applicazioni

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

Azioni biochim/fisiol

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.

Pittogrammi

Skull and crossbonesHealth hazard
GHS06,GHS08

Avvertenze

Danger

Indicazioni di pericolo

H301,H317,H341,H351,H361d

Classi di pericolo

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

Codice della classe di stoccaggio

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

Classe di pericolosità dell'acqua (WGK)

WGK 3

Dispositivi di protezione individuale

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

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Certificati d'analisi (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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