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Bisantrene (CL 216942; NSC 337766) is potent inhibitor of topoisomerase II and DNA intercalators. It could be employed as model compounds to investigate multiple drug resistance (MDR1) mediated by P-glycoprotein. You could use bisantrene as a Rac1 inhibitor. DNA single-strand breaks, DNA-protein crosslinking, and the inhibition of DNA replication are all caused by bisantrene intercalating with DNA and altering its configuration. In terms of activity, this agent is comparable to doxorubicin; however, it does not show cardiotoxicity.
| Targets |
Topoisomerase II
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|---|---|
| ln Vitro |
At oligonucleotide-oligonucleotide junctions, bisantrene stimulates DNase I cleavage, whereas at alternating purine-nucleotide junctions, it marginally diminishes cleavage activity [1]. Two nucleotides, [3H] uracil and [3H] thoracic, which can be imported into RNA and DNA, respectively, make up bisantrene [2].
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| ln Vivo |
Bisantrene is an antineoplastic agent with activity against a variety of experimental tumors, including P388 white, L1210 white, Lieberman plasmacytoma, B16 melanoma, tumor 26, and Ridgway sarcoblastoma [3]. Bisantrene ranges from 1.56 to 150. Effective within a dose range of mg/kg, depending on the frequency, method and timing of treatment and the tumor model utilized [3]. Bisantrene (25, 50, and 100 mg/kg; i.p.; once) ablate macrophages. Bisantrene (10-150 mg/kg; i.v.; once) induces a profound leukopenia in Neo mice. Anti-tumor effects were shown in mice injected with P815 tumor cells [3]. It is the target of Bisantrene toxicity [4].
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| Enzyme Assay |
In ETN buffer (1 mM EDTA, 10 mM Tris, pH 7.0, with NaCl to obtain the desired ionic strength), measurements are performed at 25°C. Spectrophotometric or fluorometric methods are used to observe binding in the ligand absorption or emission region, respectively, following the addition of scalar quantities of DNA to a newly made drug solution. The range of bound drug fractions is 0.15-0.85 in order to prevent significant systematic errors that could arise from experimental errors in extinction coefficients or fluorescence quantum yield. Data are assessed. A Perkin-Elmer Lambda 5 apparatus and an MPF66 fluorometer, both of which have a Haake F3-C thermostat, are used for spectroscopic measurements[1].
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| References |
[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.
[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. [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. [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 |
| Molecular Formula |
C₂₂H₂₂N₈
|
|---|---|
| Molecular Weight |
398.46
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| Exact Mass |
398.2
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| CAS # |
78186-34-2
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| Related CAS # |
78186-34-2 71439-68-4 (2HCl) 97910-18-4 (4HCl) 97910-19-5 (nitrate) 97910-20-8 (sulfate) 101218-44-4 (acetate)
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| Appearance |
Powder
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| SMILES |
C1NC(=NC1)N/N=C/C2=C3C(=C(C4=CC=CC=C24)/C=N/NC5=NCCN5)C=CC=C3
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| InChi Key |
NJSMWLQOCQIOPE-OCHFTUDZSA-N
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| InChi Code |
InChI=1S/C22H22N8/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)/b27-13+,28-14+
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| Chemical Name |
N-[(E)-[10-[(E)-(4,5-dihydro-1H-imidazol-2-ylhydrazinylidene)methyl]anthracen-9-yl]methylideneamino]-4,5-dihydro-1H-imidazol-2-amine
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| Synonyms |
Bisantrene; CL216942
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO: ~1 mg/mL (~2.5 mM)
H2O: 0.1 mg/mL (~0.3 mM) |
|---|---|
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.5097 mL | 12.5483 mL | 25.0966 mL | |
| 5 mM | 0.5019 mL | 2.5097 mL | 5.0193 mL | |
| 10 mM | 0.2510 mL | 1.2548 mL | 2.5097 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
| NCT Number | Recruitment | interventions | Conditions | Sponsor/Collaborators | Start Date | Phases |
| NCT04989335 | Recruiting | Drug: Bisantrene Drug: Fludarabine |
MMyelogenous Leukemia, Acute | Sheba Medical Center | August 2, 2021 | Phase 2 |
| NCT03820908 | Completed | Drug: Bisantrene | Allogeneic Stem Cell Transplantation Acute Myelogenous Leukemia |
Sheba Medical Center | July 18, 2019 | Phase 2 |
| NCT05456269 | Withdrawn | Drug: Cytarabine Hydrochloride Drug: Bisantrene Dihydrochloride (low dose) |
Acute Myeloid Leukemia | Race Oncology Ltd | July 29, 2022 | Phase 1 |
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