Amonafide dihydrochloride

    WARNING: This product is for research use only, not for human or veterinary use.

Description: Amonafide dihydrochloride is the dihydrochloride salt of amonafide, an imide derivative of naphthalic acid. Amonafide intercalates into DNA and inhibits topoisomerase II, resulting in protein-associated strand breaks and impaired DNA and RNA synthesis.

Price and Availability

Amonafide dihydrochloride, purity > 98%, is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.

Related CAS #: 69408-81-7 (free base)   150091-68-2 (2HCl)   618863-54-0 (malate)   618863-60-8    

Synonym: amonafide; amonafide hydrochloride; benzisoquinolinedione; nafidimide. US brand name: Quinamed. Abbreviations: AMON. BIDA. Code name: MFA142.

IUPAC/Chemical Name: 5-amino-2-(2-(dimethylamino)ethyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione dihydrochloride

InChi Key: AEMLYYQEBPJIEO-UHFFFAOYSA-N

InChi Code: InChI=1S/C16H17N3O2.2ClH/c1-18(2)6-7-19-15(20)12-5-3-4-10-8-11(17)9-13(14(10)12)16(19)21;;/h3-5,8-9H,6-7,17H2,1-2H3;2*1H

SMILES Code: O=C1N(CCN(C)C)C(C2=CC(N)=CC3=CC=CC1=C23)=O.[H]Cl.[H]Cl

Technical Data

Additional Information

References

1: Chen Z, Liang X, Zhang H, Xie H, Liu J, Xu Y, Zhu W, Wang Y, Wang X, Tan S, Kuang D, Qian X. A new class of naphthalimide-based antitumor agents that inhibit topoisomerase II and induce lysosomal membrane permeabilization and apoptosis. J Med Chem. 2010 Mar 25;53(6):2589-600. PubMed PMID: 20170164.

2: Lv M, Xu H. Overview of naphthalimide analogs as anticancer agents. Curr Med Chem. 2009;16(36):4797-813. Review. PubMed PMID: 19929786.

3: Zhu H, Miao ZH, Huang M, Feng JM, Zhang ZX, Lu JJ, Cai YJ, Tong LJ, Xu YF, Qian XH, Ding J. Naphthalimides induce G(2) arrest through the ATM-activated Chk2-executed pathway in HCT116 cells. Neoplasia. 2009 Nov;11(11):1226-34. PubMed PMID: 19881958; PubMed Central PMCID: PMC2767224.

4: Mei ZH, Tian ZY, Ma HX, Xie SQ, Zhao J, Wang CJ. [Synthesis and in vitro cytotoxicity of naphthalimide polyamine conjugates as antitumor agents]. Yao Xue Xue Bao. 2009 Jul;44(7):754-7. Chinese. PubMed PMID: 19806915.

5: Allen SL, Kolitz JE, Lundberg AS, Bennett JM, Capizzi RL, Budman DR. Phase I trials of amonafide as monotherapy and in combination with cytarabine in patients with poor-risk acute myeloid leukemia. Leuk Res. 2010 Apr;34(4):487-91. Epub 2009 Sep 12. PubMed PMID: 19748672.

6: Wu A, Xu Y, Qian X, Wang J, Liu J. Novel naphthalimide derivatives as potential apoptosis-inducing agents: design, synthesis and biological evaluation. Eur J Med Chem. 2009 Nov;44(11):4674-80. Epub 2009 Jul 16. PubMed PMID: 19643513.

7: Wang J, Wu A, Xu Y, Liu J, Qian X. M(2)-A induces apoptosis and G(2)-M arrest via inhibiting PI3K/Akt pathway in HL60 cells. Cancer Lett. 2009 Oct 8;283(2):193-202. Epub 2009 May 10. PubMed PMID: 19435648.

8: Ingrassia L, Lefranc F, Kiss R, Mijatovic T. Naphthalimides and azonafides as promising anti-cancer agents. Curr Med Chem. 2009;16(10):1192-213. Review. PubMed PMID: 19355879.

9: Tallman M. Existing and emerging therapeutic options for the treatment of acute myeloid leukemia. Clin Adv Hematol Oncol. 2008 Nov;6(11):3-5. PubMed PMID: 19205108.

10: Xie L, Xu Y, Wang F, Liu J, Qian X, Cui J. Synthesis of new amonafide analogues via coupling reaction and their cytotoxic evaluation and DNA-binding studies. Bioorg Med Chem. 2009 Jan 15;17(2):804-10. Epub 2008 Nov 27. PubMed PMID: 19070496.