64862-96-0

Basic information

• Product Name: Ametantrone
• Synonyms: Ametantrone;1,4-Bis[[2-[(2-hydroxyethyl)amino]ethyl]amino]-9,10-anthraquinone;HAQ;NSC-287513;NSC 196473;NSC 290813;AMetantrone(NSC 196473);Ametantrone, >=98%
• CAS NO: 64862-96-0
• Molecular Formula: C22H28 N4 O4
• Molecular Weight: 412.54
• Mol File: 64862-96-0.mol
• Article Data: 6

Chemical Properties

• Melting Point: 156-158 °C
• Boiling Point: 531.92°C (rough estimate)
• Flash Point: 382.4°C
• Appearance: /
• Density: 1.2344 (rough estimate)
• Vapor Pressure: 4.4E-21mmHg at 25°C
• Refractive Index: 1.6500 (estimate)
• PKA: 14.47±0.10(Predicted)
• CAS DataBase Reference: Ametantrone(CAS DataBase Reference)
• NIST Chemistry Reference: Ametantrone(64862-96-0)
• EPA Substance Registry System: Ametantrone(64862-96-0)

Safety Data

• Hazardous Substances Data: 64862-96-0(Hazardous Substances Data)

Usage

Description

Ametantrone is an inhibitor of topoisomerase II, a DNA enzyme that plays a crucial role in DNA replication and transcription. It induces double-strand breaks in SV40 DNA in the presence of topoisomerase II and single-strand breaks in DNA in NCI H187 cells. Ametantrone also induces interstrand DNA cross-links in HeLa S3 cells at a minimum concentration of 4.1 μM. It exhibits cytotoxic effects on NCI H187 and HL-60 cells, with IC50s of 112 and 0.44 μM, respectively. However, its effects on tumor growth vary depending on the type of cancer, as it inhibits tumor growth in a Ridgway osteogenic sarcoma mouse model but increases tumor growth in mouse models of mammary adenocarcinoma and colon adenocarcoma 11a.

Uses

Used in Cancer Therapy:
Ametantrone is used as a chemotherapeutic agent for the treatment of various types of cancer. Its ability to inhibit topoisomerase II and induce DNA damage makes it a potential candidate for cancer treatment. It has been shown to inhibit tumor growth in a Ridgway osteogenic sarcoma mouse model when administered at a dose of 5 mg/kg. However, its effectiveness may vary depending on the type of cancer, as it has been observed to increase tumor growth in mouse models of mammary adenocarcinoma and colon adenocarcoma 11a.
Used in Cancer Research:
Ametantrone is used as a research tool to study the role of topoisomerase II in DNA replication, transcription, and cancer development. Its ability to induce double-strand breaks in SV40 DNA in the presence of topoisomerase II and single-strand breaks in DNA in NCI H187 cells makes it a valuable compound for investigating the mechanisms of DNA damage and repair. Additionally, its cytotoxic effects on NCI H187 and HL-60 cells provide insights into the development of novel anticancer therapies.
Used in Drug Development:
Ametantrone serves as a starting point for the development of new drugs targeting topoisomerase II and other DNA-related enzymes. Its unique properties, such as inducing DNA damage and inhibiting tumor growth in certain cancer models, can be leveraged to design more effective and targeted therapies. Researchers can use Ametantrone as a template to develop new compounds with improved efficacy, selectivity, and reduced side effects.

InChI:InChI=1/C22H28N4O4.2C2H4O2/c27-13-11-23-7-9-25-17-5-6-18(26-10-8-24-12-14-28)20-19(17)21(29)15-3-1-2-4-16(15)22(20)30;2*1-2(3)4/h1-6,23-28H,7-14H2;2*1H3,(H,3,4)

Upstream product

• 141-43-5 ethanolamine 
• 111228-28-5 1,4-bis<<2-<(p-toluenesulfonyl)oxy>ethyl>amino>anthracene-9,10-dione 
• 28736-42-7 1,4-difluoroanthracene-9,10-dione 
• 111-41-1 2-(2-Aminoethylamino)ethanol 
• 4471-41-4 1,4-bis-(2-hydroxyethylamino)anthraquinone 
• 17648-03-2 9,10-Dihydroxy-2,3-dihydro-anthracene-1,4-dione 

Relevant articles and documents

Ametantrone-based compounds as potential regulators of Tau pre-mRNA alternative splicing

Tau pre-mRNA contains a stem-loop structure involved in the regulation of the alternative splicing of tau protein. We describe here a new family of Tau RNA ligands selected by dynamic combinatorial chemistry based on the combination of ametantrone with small RNA-binding molecules. The most promising compound results from derivatization of one of the side chains of the anthraquinone ring with the small aminoglycoside neamine through a short spacer. This compound binds the RNA target with a high affinity in a preferred binding site, in which the heteroaromatic moiety intercalates in the bulged region of the stem-loop and its side chains and neamine interact with the major groove of the RNA. Importantly, binding of this compound to mutated RNA sequences involved in the onset of some tauopathies such as FTDP-17 restores their thermodynamic stability to a similar or even higher levels than that of the wild-type sequence, thereby revealing its potential as a modulator of Tau pre-mRNA splicing.

MEANS FOR DYEING AND/OR MATTING KERATINIC FIBRES CONTAINING NOVEL 1,4 DIAMINOANTHRAQUINONE DYES

Agents for coloring and/or matting keratinic fibers, in particular human hair, include in a cosmetic carrier at least one specific substituted 1,4-diaminoanthraquinone derivative of formula (I), wherein the residues (R2, R4) mutually independently denote a grouping of formula (II). The cosmetic method of using these agents can be for producing intense blue shades and for matting keratin fibers.

Synthesis and Antitumor Evaluations of Symmetrically and Unsymmetrically Substituted 1,4-Bisanthracene-9,10-diones and 1,4-Bis-5,8-dihydroxyanthracene-9,10-diones

The ipso bis displacements of fluoride from 1,4-difluoroanthracene-9,10-dione (3) and 1,4-difluoro-5,8-dihydroxyanthracene-9,10-dione (4) by excess of a diamine (or a monoamine) in pyridine at room temperature lead to the symmetrically substituted 1,4-bis-substituted analogues 5 and 6, respectively.The ipso monodisplacements of fluoride from 3 and 4 can be accomplished by treatment with less than 1 molar equiv of a diamine (or a monoamine) to yield 7 and 8, respectively.Treatment of 7 or 8 with a different diamine leads to the unsymmetrically substituted1,4-bisanthracene-9,10-diones 9 and 10, respectively.Many of the synthetic unsymmetrical analogues have been evaluated for their antitumor activity against L1210 in vitro and in vivo.Cross resistance of analogue 10a with mitoxantrone (2) and doxorubicin was evaluated against MDR lines in vitro against human colon carcinoma LOVO and its subline resistant to DOXO (LOVO/DOXO).Potential mechanisms for the observed cytotoxicity are presented and discussed.