Bisantrene dihydrochloride

• CAT Number: I042685
• CAS Number: 71439-68-4
• Molecular Formula: C22H24Cl2N8
• Molecular Weight: 471.39
• Purity: ≥95%
• Synonyms: N-[(E)-[10-[(E)-(4,5-dihydro-1H-imidazol-2-ylhydrazinylidene)methyl]anthracen-9-yl]methylideneamino]-4,5-dihydro-1H-imidazol-2-amine;dihydrochloride
• InChI: InChI=1S/C22H22N8.2ClH/c1-2-6-16-15(5-1)19(13-27-29-21-23-9-10-24-21)17-7-3-4-8-18(17)20(16)14-28-30-22-25-11-12-26-22;;/h1-8,13-14H,9-12H2,(H2,23,24,29)(H2,25,26,30);2*1H/b27-13+,28-14+
• InChIKey: KINULKKPVJYRON-PVNXHVEDSA-N
• SMILES: C1CN=C(N1)NN=CC2=C3C=CC=CC3=C(C4=CC=CC=C42)C=NNC5=NCCN5.Cl.Cl

Bisantrene dihydrochloride is a highly effective antitumor agent, it exerts its cytotoxicity by affecting DNA intercalation. Bisantrene dihydrochloride targets eukaryotic type II topoisomerases. Bisantrene dihydrochloride is a substrate of MDR1[1][2][3][4].
Bisantrene dihydrochloride promots DNase I cleavage at oligopurine-oligopyrimidine tracts and slightly reduces the cleavage activity at alternating purine-pyrimidine sequences[1].
Bisantrene dihydrochloride is an inhibitor of [3H]uridine incorporation into RNA and [3H]thymidine incorporation into DNA[2].
Bisantrene dihydrochloride is an antitumor agent active against a number of experimental tumors, including P388 leukemia, L1210 leukemia, Lieberman plasma cell tumor, B16 melanoma, colon tumor 26, and Ridgway osteogenic sarcoma[3].
Bisantrene dihydrochloride is effective over a dose range of 1.56 to 150 mg/kg depending upon the frequency, route, and schedule of the treatment and the tumor model used[3].
Bisantrene dihydrochloride (25, 50 and 100 mg/kg; i.p.; once) pretreats with macrophages shows antitumor effect to mice with P815 tumor cells injection[3].
Bisantrene dihydrochloride (10-150 mg/kg; i.v.; once) dose-dependently induces leukopenia in Neo mice. B cells and macrophages are targets for bisantrene dihydrochloride toxicity[4].

Reference

[1]. Sissi C, et al. DNA-binding preferences of Bisantrene analogues: relevance to the sequence specificity of drug-mediated topoisomerase II poisoning. Mol Pharmacol. 1998 Dec;54(6):1036-45.
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[2]. Yap HY, et al. Bisantrene, an active new drug in the treatment of metastatic breast cancer. Cancer Res. 1983 Mar;43(3):1402-4.
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[3]. Wang BS, et al. Activation of tumor-cytostatic macrophages with the antitumor agent 9,10-anthracenedicarboxaldehyde bis[(4,5-dihydro-1H-imidazole-2-yl)hydrazone] dihydrochloride (bisantrene). Cancer Res. 1984 Jun;44(6):2363-7.
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[4]. Aksentijevich I, et al. Retroviral transfer of the human MDR1 gene confers resistance to bisantrene-specific hematotoxicity. Clin Cancer Res. 1996 Jun;2(6):973-80.
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