Amsacrine hydrochloride

Product NameAmsacrine hydrochloride
CAS54301-15-4
MFC21H20ClN3O3S
MW429.92
EINECS637-255-8
MOL File54301-15-4.mol

Chemical Properties

Melting point	197-199 °C(lit.)
storage temp.	Refrigerator
solubility	DMSO: 10 mg/mL with heat and sonication
form	powder
color	red to brown
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
InChIKey	WDISRLXRMMTXEV-UHFFFAOYSA-N
SMILES	Cl.COc1cc(NS(C)(=O)=O)ccc1Nc2c3ccccc3nc4ccccc24

Safety Information

Hazard Codes	T
Risk Statements	25-36/37/38
Safety Statements	26-45
RIDADR	UN 2811 6.1/PG 3
WGK Germany	3
RTECS	PB1081000
HS Code	2933.99.8290
HazardClass	6.1(b)
PackingGroup	III
Storage Class	6.1C - Combustible acute toxic Cat.3 toxic compounds or compounds which causing chronic effects
Hazard Classifications	Acute Tox. 3 Oral Carc. 2 Muta. 2 Repr. 2 Skin Sens. 1

Usage And Synthesis

Uses

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

Biological Activity

amsacrine hydrochloride (amsidine, m-amsa) is an inhibitor of topoisomerase 2 [1].amsacrine hydrochloride is a chemotherapy drug of antineoplastic, used to treat some types of lymphoma and acute leukaemia. in addition, amsacrine hydrochloride has shown the sensitivities to the cancer cell lines with the ic50 values of 190.2±27.4ng/ml, 46.1±3.9ng/ml,22.6±3.1ng/ml, 11.8±2.0ng/ml, 5.0±0.4ng/ml, and 11.7±1.5ng/ml for three bladder cancer cell lines (ht1376,rt112, rt4) and three testis cancer cell lines(833k, susa, gh), respectively. and it has been found that the testis tumor cell lines are more sensitive to inhibiting by amsacrine hydrochloride than the bladder cell lines [1].

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.

in vivo

In animals treated with different doses of amsacrine (0.5-12 mg/kg), the frequencies of micronucleated polychromatic erythrocytes increase significantly after treatment with 9 and 12 mg/kg. Furthermore, the present study demonstrates for the first time that Amsacrine (mAMSA) has high incidences of clastogenicity and low incidences of aneugenicity whereas Nocodazole has high incidences of aneugenicity and low incidences of clastogenicity during mitotic phases in vivo^[2].

IC 50

Topoisomerase II

References

[1] nelson em, tewey km, liu lf. mechanism of antitumor drug action: poisoning of mammalian dna topoisomerase ii on dna by 4'-(9-acridinylamino)-methanesulfon-m-anisidide. proc natl acad sci u s a. 1984 mar;81(5):1361-5.

Amsacrine hydrochloride

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