Ametantrone
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MedKoo CAT#: 200182

CAS#: 64862-96-0

Description: Ametantrone (AM) is a synthetic 9,10-anthracenedione bearing two (hydroxyethylamino)ethylamino residues at positions 1 and 4; along with other anthraquinones and anthracyclines, it shares a polycyclic intercalating moiety and charged side chains that stabilize DNA binding. Ametantrone is the second anthracene derivative to enter clinical trials.


Chemical Structure

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Ametantrone
CAS# 64862-96-0

Theoretical Analysis

MedKoo Cat#: 200182
Name: Ametantrone
CAS#: 64862-96-0
Chemical Formula: C22H28N4O4
Exact Mass: 412.21106
Molecular Weight: 412.48
Elemental Analysis: C, 64.06; H, 6.84; N, 13.58; O, 15.52

Price and Availability

Size Price Availability Quantity
5.0mg USD 315.0 2 Weeks
10.0mg USD 585.0 2 Weeks
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Synonym: CI881; NSC196473; NSC 287513; NSC-196473; NSC 287513; ametantrone diacetate.

IUPAC/Chemical Name: 1,4-bis((2-((2-hydroxyethyl)amino)ethyl)amino)anthracene-9,10-dione

InChi Key: FFGSXKJJVBXWCY-UHFFFAOYSA-N

InChi Code: InChI=1S/C22H28N4O4/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/h1-6,23-28H,7-14H2

SMILES Code: O=C1C2=C(C=CC=C2)C(C3=C(NCCNCCO)C=CC(NCCNCCO)=C13)=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >5 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Certificate of Analysis:

Safety Data Sheet (SDS):

Preparing Stock Solutions

The following data is based on the product molecular weight 412.48 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Gianoncelli A, Basili S, Scalabrin M, Sosic A, Moro S, Zagotto G, Palumbo M, Gresh N, Gatto B. Rational design, synthesis, and DNA binding properties of novel sequence-selective peptidyl congeners of ametantrone. ChemMedChem. 2010 Jul 5;5(7):1080-91. PubMed PMID: 20458714.

2: Shchekotikhin AE, Glazunova VA, Dezhenkova LG, Luzikov YN, Sinkevich YB, Kovalenko LV, Buyanov VN, Balzarini J, Huang FC, Lin JJ, Huang HS, Shtil AA, Preobrazhenskaya MN. Synthesis and cytotoxic properties of 4,11-bis[(aminoethyl)amino]anthra[2,3-b]thiophene-5,10-diones, novel analogues of antitumor anthracene-9,10-diones. Bioorg Med Chem. 2009 Mar 1;17(5):1861-9. Epub 2009 Jan 27. PubMed PMID: 19208482.

3: Hsin LW, Wang HP, Kao PH, Lee O, Chen WR, Chen HW, Guh JH, Chan YL, His CP, Yang MS, Li TK, Lee CH. Synthesis, DNA binding, and cytotoxicity of 1,4-bis(2-amino-ethylamino)anthraquinone-amino acid conjugates. Bioorg Med Chem. 2008 Jan 15;16(2):1006-14. Epub 2007 Oct 10. PubMed PMID: 17962028.

4: Morley JO, Furlong PJ. Synthesis and calculated properties of some 1,4-bis(amino)anthracene-9,10-diones. Org Biomol Chem. 2006 Nov 7;4(21):4005-14. Epub 2006 Oct 2. PubMed PMID: 17047882.

5: Shchekotikhin AE, Glazunova VA, Luzikov YN, Buyanov VN, Susova OY, Shtil AA, Preobrazhenskaya MN. Synthesis and structure-activity relationship studies of 4,11-diaminonaphtho[2,3-f]indole-5,10-diones. Bioorg Med Chem. 2006 Aug 1;14(15):5241-51. Epub 2006 May 2. PubMed PMID: 16631372.

6: Reszka KJ, Wagner BA, Burns CP, Britigan BE. Effects of peroxidase substrates on the Amplex red/peroxidase assay: antioxidant properties of anthracyclines. Anal Biochem. 2005 Jul 15;342(2):327-37. PubMed PMID: 15913534.

7: Tarasiuk J, Mazerski J, Tkaczyk-Gobis K, Borowski E. Molecular basis of the low activity of antitumor anthracenediones, mitoxantrone and ametantrone, in oxygen radical generation catalyzed by NADH dehydrogenase. Enzymatic and molecular modelling studies. Eur J Med Chem. 2005 Apr;40(4):321-8. Epub 2004 Dec 15. PubMed PMID: 15804531.

8: Huang HS, Chou CL, Guo CL, Yuan CL, Lu YC, Shieh FY, Lin JJ. Human telomerase inhibition and cytotoxicity of regioisomeric disubstituted amidoanthraquinones and aminoanthraquinones. Bioorg Med Chem. 2005 Mar 1;13(5):1435-44. PubMed PMID: 15698759.

9: Sadeghi-Aliabadi H, Tabarzadi M, Zarghi A. Synthesis and cytotoxic evaluation of two novel anthraquinone derivatives. Farmaco. 2004 Aug;59(8):645-9. PubMed PMID: 15262534.

10: O'Malley YQ, Reszka KJ, Britigan BE. Direct oxidation of 2',7'-dichlorodihydrofluorescein by pyocyanin and other redox-active compounds independent of reactive oxygen species production. Free Radic Biol Med. 2004 Jan 1;36(1):90-100. PubMed PMID: 14732293.



Additional Information

Ametantrone is anticancer drug candidate targeting DNA. Ametantrone induces interstrand DNA cross-links in HeLa S3 cells. These cross-links were observed only in cellular system suggesting that metabolism of the drugs is a necessary step leading to DNA cross-linking. Biologically inactive analogue of mitoxantrone, compound NSC 321458, did not induce cross-links in DNA of tumour cells which suggests that DNA cross-linking is associated with the cytotoxic and anti-tumour activity of these compounds. Source: Br J Cancer. 2000 Apr;82(7):1300-4. or  http://www.ncbi.nlm.nih.gov/pubmed/10755405.
 
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