A9809
アムサクリン 塩酸塩
≥98% (TLC), DNA topoisomerase II inhibitor, powder
別名:
4-(9-アクリジニルアミノ)-N-(メタンスルホニル)-m-アニシジン 塩酸塩, m-AMSA
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この商品について
実験式（ヒル表記法）:
C21H19N3O3S · HCl
CAS番号:
分子量:
429.92
UNSPSC Code:
51111800
PubChem Substance ID:
NACRES:
NA.77
MDL number:
製品名
アムサクリン 塩酸塩, ≥98% (TLC), powder
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
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
Quality Level
Gene Information
human ... TOP2A(7153), TOP2B(7155)
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.
signalword
Danger
Hazard Classifications
Acute Tox. 3 Oral - Carc. 2 - Muta. 2 - Repr. 2 - Skin Sens. 1
保管分類
6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
wgk
WGK 3
ppe
Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
Emilia Komulainen et al.
ACS chemical biology, 14(6), 1110-1114 (2019-05-16)
Tyrosyl DNA phosphodiesterase 2 (TDP2) facilitates the repair of topoisomerase II (TOP2)-linked DNA double-strand breaks and, as a consequence, is required for cellular resistance to TOP2 "poisons". Recently, a deazaflavin series of compounds were identified as potent inhibitors of TDP2
Toshiyuki Kozuki et al.
Nucleic acids research, 45(10), 5995-6010 (2017-05-05)
Topoisomerase (topo) IIα and IIβ maintain genome stability and are targets for anti-tumor drugs. In this study, we demonstrate that the decatenation checkpoint is regulated, not only by topo IIα, as previously reported, but also by topo IIβ. The decatenation
Michael Jahnz et al.
Chembiochem : a European journal of chemical biology, 6(5), 920-926 (2005-04-07)
Topoisomerase II is the only enzyme able to cleave and religate double-stranded DNA; this makes it essential for many vital functions during normal cell growth. Increased expression of topoisomerase II is a common occurrence in neoplasia, and different topoisomerase II
Wenge Wang et al.
Cancer biology & therapy, 4(8), 893-898 (2005-09-24)
CP-31398 activates wild-type p53 by a novel mechanism that does not involve phosphorylation of the amino-terminus of p53 and disassociation of MDM2. To identify more potent CP-31398-like p53 activators, we synthesized 4 acridine derivatives with a similar structure to CP-31398.
L R Ferguson et al.
Environmental and molecular mutagenesis, 27(4), 255-262 (1996-01-01)
Amsacrine (4'-(9-acridinylamino)methanesulphon-m-anisidide) is an antileukemic drug which inhibits topoisomerase II (topo II) enzymes. We studied effects of two concentrations of amsacrine on the GM10115A cell line. This is a Chinese hamster line containing a single human chromosome 4, which can
ライフサイエンス、有機合成、材料科学、クロマトグラフィー、分析など、あらゆる分野の研究に経験のあるメンバーがおります。.
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