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A9809

Amsacrine hydrochloride

Name: Amsacrine hydrochloride
Brand: SIGMA

≥98% (TLC), DNA topoisomerase II inhibitor, powder

Synonyme(s) :

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

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A propos de cet article

Formule empirique (notation de Hill) :

C₂₁H₁₉N₃O₃S · HCl

Numéro CAS:

54301-15-4

Poids moléculaire :

429.92

UNSPSC Code:

51111800

PubChem Substance ID:

24278248

NACRES:

NA.77

MDL number:

MFCD07799963

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Propriétés

Nom du produit

Amsacrine hydrochloride, ≥98% (TLC), powder

Quality Segment

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)

Description

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.

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Cet article	PZ0365	G3796	P7561
Sigma-Aldrich A9809 Amsacrine hydrochloride	Sigma-Aldrich PZ0365 CP-376395 hydrochloride	Sigma-Aldrich G3796 Granisetron hydrochloride	Sigma-Aldrich P7561 Phentolamine methanesulfonate salt
description ≥98% (TLC), powder	description ≥98% (HPLC)	description ≥98% (HPLC), solid	description ≥98% (TLC), powder
assay ≥98% (TLC)	assay ≥98% (HPLC)	assay ≥98% (HPLC)	assay ≥98% (TLC)
Gene Information human ... TOP2A(7153), TOP2B(7155)	Gene Information -	Gene Information -	Gene Information human ... ADRA1A(148), ADRA1B(147), ADRA1D(146), ADRA2A(150), ADRA2B(151), ADRA2C(152)
Quality Level 200	Quality Level 100	Quality Level 100	Quality Level 200
form powder	form powder	form solid	form powder
storage temp. room temp	storage temp. room temp	storage temp. room temp	storage temp. -
solubility 30% ethanol: 4 mg/mL, DMSO: 10 mg/mL (with heat and sonication)	solubility DMSO: 2 mg/mL, clear	solubility H₂O: >10 mg/mL	solubility H₂O: 50 mg/mL, ethanol: 26 mg/mL