Amsacrine
Amsacrine is an anticancer chemotherapeutic acridine derivative that is clinically used to treat acute myelogenous leukemia (AML). Amsacrine acts as a DNA intercalator, binding AT base pairs; this inhibits the activity of topoisomerase II, preventing DNA repair. In leukemia cells, amsacrine decreases expression of matrix metalloproteinases 2 and 9 (MMP2/9), inhibiting cell invasion. This modulation of MMP2/9 expression is caused by increases in ROS and activation of p38 MAPK and JNK, which increases levels of protein phosphatase 2A (PP2A), a negative regulator of MMP activity. In vitro, amsacrine inhibits human Ether-a-go-go-Related Gene (hERG) K+ channels, causing potential prolongation of the QT interval.
References PubMed ID：:http://www.ncbi.nlm.nih.gov/pubmed/1883844
| Cas No. |
51264-14-3 |
|---|---|
| Purity |
≥98% |
| Formula |
C21H19N3O3S |
| Formula Wt. |
393.46 |
| IUPAC Name |
N-[4-(acridin-9-ylamino)-3-methoxyphenyl]methanesulfonamide |
| Synonym |
4-(9-Acridinylamino)-N-(methanesulfonyl)-m-anisidine hydrochloride, m-AMSA |
| Melting Point |
233-237°C |
| Appearance |
Salmon Crystalline powder |
Liu WH, Chen YJ, Chien JH, et al. Amsacrine suppresses matrix metalloproteinase-2 (MMP-2)/MMP-9 expression in human leukemia cells. J Cell Physiol. 2013 Oct 7. Epub ahead of print. PMID: 24122234.
Jangir DK, Dey SK, Kundu S, et al. Assessment of amsacrine binding with DNA using UV-visible, circular dichroism and Raman spectroscopic techniques. J Photochem Photobiol B. 2012 Sep 3;114:38-43. PMID: 22677564.
Thomas D, Hammerling BC, Wu K, et al. Inhibition of cardiac HERG currents by the DNA topoisomerase II inhibitor amsacrine: mode of action. Br J Pharmacol. 2004 Jun;142(3):485-94. PMID: 15148258.
Robinson MJ, Osheroff N. Stabilization of the topoisomerase II-DNA cleavage complex by antineoplastic drugs: inhibition of enzyme-mediated DNA religation by 4-(9-acridinylamino)methanesulfon-m-anisidide. Biochemistry. 1990 Mar 13;29(10):2511-5. PMID: 2159323.
