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Merck
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Principaux documents

A9809

Sigma-Aldrich

Amsacrine hydrochloride

≥98% (TLC), powder

Synonyme(s) :

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

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About This Item

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

Niveau de qualité

Essai

≥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

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

Mention d'avertissement

Danger

Mentions de danger

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


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Consulter la Bibliothèque de documents

E M Nelson et al.
Proceedings of the National Academy of Sciences of the United States of America, 81(5), 1361-1365 (1984-03-01)
The intercalative acridine derivative 4'-(9-acridinylamino)methanesulfon-m-anisidide (m-AMSA), but not its isomer o-AMSA, is a potent antitumor drug that in mammalian cells stimulates the formation of DNA strand breaks that are characterized by tightly bound proteins. Using purified mammalian DNA topoisomerases, we
C Negri et al.
Biochimie, 77(11), 893-899 (1995-01-01)
We have analyzed the interference of antitumoral drugs acting through the inhibition of DNA topoisomerase II on the human HeLa cell metabolism. Different compounds characterized by a diverse mechanism of action have been used, namely m-amsacrine, an intercalative drug, etoposide
Adrien Marchand et al.
Journal of the American Chemical Society, 140(39), 12553-12565 (2018-09-06)
Designing ligands targeting G-quadruplex nucleic acid structures and affecting cellular processes is complicated because there are multiple target sequences and some are polymorphic. Further, structure alone does not reveal the driving forces for ligand binding. To know why a ligand
Kotaro Yamamoto et al.
Scientific reports, 9(1), 19288-19288 (2019-12-19)
Treatments for refractory glaucoma include trabeculectomy, in which a filtering bleb is created to reduce aqueous pressure. Mitomycin C (MMC) is often used as an adjuvant to reduce post-trabeculectomy bleb scarring and consequent failure. However, scarring sometimes still occurs. Thus
R A Davey et al.
Cancer chemotherapy and pharmacology, 39(5), 424-430 (1997-01-01)
The effectiveness of N-[2-(dimethylamino)ethyl]acridine-4-carboxamide (DACA) relative to that of amsacrine, idarubicin, daunorubicin and paclitaxel against three different forms of multidrug resistance (MDR) was determined using two sublines of the CCRF-CEM human leukaemia cell line, the P-glyco-protein-expressing CEM/VLB100 subline and the

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