Accéder au contenu
Merck
Toutes les photos(2)

Key Documents

View All Documentation

A9809

Sigma-Aldrich

Amsacrine hydrochloride

≥98% (TLC), powder

Synonyme(s) :

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

Se connecterpour consulter vos tarifs contractuels et ceux de votre entreprise/organisme
Toutes les photos(2)

About This Item

Formule empirique (notation de Hill):
C21H19N3O3S · HCl
Numéro CAS:
54301-15-4
Poids moléculaire :
429.92
Numéro MDL:
MFCD07799963
Code UNSPSC :
51111800
ID de substance PubChem :
24278248
Nomenclature NACRES :
NA.77

Niveau de qualité

200

Pureté

≥98% (TLC)

Forme

powder

Couleur

red to brown

Pf

197-199 °C (lit.)

Solubilité

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

Température de stockage

room temp

Chaîne 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

Clé InChI

WDISRLXRMMTXEV-UHFFFAOYSA-N

Informations sur le gène

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

Actions biochimiques/physiologiques

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.

Pictogrammes

Skull and crossbonesHealth hazard
GHS06,GHS08

Mention d'avertissement

Danger

Mentions de danger

H301,H317,H341,H351,H361d

Classification des risques

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

Code de la classe de stockage

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

Classe de danger pour l'eau (WGK)

WGK 3

Équipement de protection individuelle

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

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

Déjà en possession de ce produit ?

Retrouvez la documentation relative aux produits que vous avez récemment achetés dans la Bibliothèque de documents.

Consulter la Bibliothèque de documents

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
Afficher tous les articles scientifiques apparentés

Notre équipe de scientifiques dispose d'une expérience dans tous les secteurs de la recherche, notamment en sciences de la vie, science des matériaux, synthèse chimique, chromatographie, analyse et dans de nombreux autres domaines..

Contacter notre Service technique