A9809

Amsacrine hydrochloride

≥98% (TLC), powder

• Synonym(s): 4-(9-Acridinylamino)-N-(methanesulfonyl)-m-anisidine hydrochloride, m-AMSA
• Empirical Formula (Hill Notation): C₂₁H₁₉N₃O₃S · HCl
• CAS Number: 54301-15-4
• Molecular Weight: 429.92
• MDL number: MFCD07799963
• UNSPSC Code: 51111800
• PubChem Substance ID: 24278248
• NACRES: NA.77

Properties

• Quality Level: 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.

Safety Information

• Pictograms: GHS06,GHS08
• Signal Word: Danger
• Hazard Statements: H301,H317,H341,H351,H361d
• Precautionary Statements: P202 - P261 - P264 - P280 - P301 + P310 - P302 + P352
• Hazard Classifications: Acute Tox. 3 Oral - Carc. 2 - Muta. 2 - Repr. 2 - Skin Sens. 1
• Storage Class Code: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• WGK: WGK 3
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves