WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 201320
Description: Ethonafide is an anthracene-containing derivative of amonafide that belongs to the azonafide series of anticancer agents. The lack of cross-resistance in multidrug-resistant cancer cell lines and the absence of a quinone and hydroquinone moiety make ethonafide a potentially less cardiotoxic replacement for existing anthracene-containing anticancer agents. Ethonafide was cytotoxic against three human prostate cancer cell lines at nanomolar concentrations. Ethonafide was found to be better tolerated and more effective at inhibiting tumor growth compared with mitoxantrone in a human xenograft tumor regression mouse model. Mechanistically, we found that ethonafide inhibited topoisomerase II activity by stabilizing the enzyme-DNA complex, involving both topoisomerase IIalpha and -beta. In addition, ethonafide induced a potent G(2) cell cycle arrest in the DU 145 human prostate cancer cell line. By creating stable cell lines with decreased expression of topoisomerase IIalpha or -beta, we found that a decrease in topoisomerase IIalpha protein expression renders the cell line resistant to ethonafide. The decrease in sensitivity to ethonafide was associated with a decrease in DNA damage and an increase in DNA repair as measured by the neutral comet assay. These data demonstrate that ethonafide is a topoisomerase II poison and that it is topoisomerase IIalpha-specific in the DU 145 human prostate cancer cell line. (See http://www.ncbi.nlm.nih.gov/pubmed/17351106.)
MedKoo Cat#: 201320
Chemical Formula: C22H22N2O3
Exact Mass: 362.16304
Molecular Weight: 362.42
Elemental Analysis: C, 72.91; H, 6.12; N, 7.73; O, 13.24
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IUPAC/Chemical Name: 2-(2'-(dimethylamino)ethyl)-1,2-dihydro-7-ethoxydibenz(de, h)isoquinoline-1,3-dione
InChi Key: CQZISUJEDPJJNF-UHFFFAOYSA-N
InChi Code: InChI=1S/C22H22N2O3/c1-4-27-20-15-9-6-5-8-14(15)19-18-16(20)10-7-11-17(18)21(25)24(22(19)26)13-12-23(2)3/h5-11H,4,12-13H2,1-3H3
SMILES Code: O=C1N(CCN(C)C)C(C2=CC=CC3=C(OCC)C4=CC=CC=C4C1=C23)=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
The following data is based on the product molecular weight 362.42 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.
|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|
1: Congdon LM, Pourpak A, Escalante AM, Dorr RT, Landowski TH. Proteasomal inhibition stabilizes topoisomerase IIalpha protein and reverses resistance to the topoisomerase II poison ethonafide (AMP-53, 6-ethoxyazonafide). Biochem Pharmacol. 2008 Feb 15;75(4):883-90. Epub 2007 Nov 4. PubMed PMID: 18062937; PubMed Central PMCID: PMC2271051.
2: Piao WH, Wong R, Bai XF, Huang J, Campagnolo DI, Dorr RT, Vollmer TL, Shi FD. Therapeutic effect of anthracene-based anticancer agent ethonafide in an animal model of multiple sclerosis. J Immunol. 2007 Dec 1;179(11):7415-23. PubMed PMID: 18025185.
3: Pourpak A, Landowski TH, Dorr RT. Ethonafide-induced cytotoxicity is mediated by topoisomerase II inhibition in prostate cancer cells. J Pharmacol Exp Ther. 2007 Jun;321(3):1109-17. Epub 2007 Mar 9. PubMed PMID: 17351106.
4: Dorr RT, Liddil JD, Sami SM, Remers W, Hersh EM, Alberts DS. Preclinical antitumor activity of the azonafide series of anthracene-based DNA intercalators. Anticancer Drugs. 2001 Mar;12(3):213-20. PubMed PMID: 11290869.