Banoxantrone dihydrochloride

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Cat.No. 4219 - Banoxantrone dihydrochloride | C22H28N4O6.2HCl | CAS No. 252979-56-9
Description: Prodrug topoisomerase II inhibitor
Alternative Names: AQ4N
Chemical Name: 1,4-Bis[[2-(dimethyloxidoamino)ethyl]amino]-5,8-dihydroxy-9,10-anthracenedione dihydrochloride
Purity: ≥98% (HPLC)
Datasheet
Citations
Literature

Biological Activity

Bioreductive prodrug; activated by hypoxia to yield the topoisomerase II inhibitor AQ4. Displays little to no cytotoxic activity against 60 tumor cell lines tested under oxic conditions (IC50 >100 μM). Exhibits anti-tumor efficacy in vivo when combined with oxic cell cytotoxins; enhances the anti-tumor effect of cyclophosphamide (Cat. No. 4091) in a mouse tumor model.

Technical Data

M. Wt 517.4
Formula C22H28N4O6.2HCl
Storage Store at +4°C
Purity ≥98% (HPLC)
CAS Number 252979-56-9
PubChem ID 72941779
InChI Key SBWCPHUXRZRTDP-UHFFFAOYSA-N
Smiles OC1=CC=C(O)C2=C1C(C(C(NCC[N+]([O-])(C)C)=CC=C3NCC[N+]([O-])(C)C)=C3C2=O)=O.Cl.Cl

The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.

All Tocris products are intended for laboratory research use only.

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 12.94 25
water 25.87 50

Preparing Stock Solutions

The following data is based on the product molecular weight 517.4. Batch specific molecular weights may vary from batch to batch due to solvent of hydration, which will affect the solvent volumes required to prepare stock solutions.

Select a batch to recalculate based on the batch molecular weight:
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.93 mL 9.66 mL 19.33 mL
5 mM 0.39 mL 1.93 mL 3.87 mL
10 mM 0.19 mL 0.97 mL 1.93 mL
50 mM 0.04 mL 0.19 mL 0.39 mL

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Product Datasheets

Safety Datasheet

References

References are publications that support the products' biological activity.

Friery et al (2000) Enhancement of the anti-tumour effect of cyclophosphamide by the bioreductive drugs AQ4N and tirapazamine. Br.J.Cancer 82 1469 PMID: 10780528

Patterson and McKeown (2000) AQ4N: a new approach to hypoxia-activated cancer chemotherapy. Br.J.Cancer 83 1589 PMID: 11104551

Mehibel et al (2009) Effects of cytokine-induced macrophages on the response of tumor cells to banoxantrone (AQ4N). Mol.Cancer Ther. 8 1261 PMID: 19435866


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Keywords: AQ4N prodrug hypoxia hypoxic cytotoxic topoisomerase II inhibitors inhibits antitumor antitumour chemotherapeutics AQ4N DNA Topoisomerase

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Cancer

Cancer Research Product Guide

A collection of over 750 products for cancer research, the guide includes research tools for the study of:

  • Cancer Metabolism
  • Epigenetics in Cancer
  • Receptor Signaling
  • Cell Cycle and DNA Damage Repair
  • Angiogenesis
  • Invasion and Metastasis
Cell Cycle & DNA Damage Repair

Cell Cycle & DNA Damage Repair Poster

In normal cells, each stage of the cell cycle is tightly regulated, however in cancer cells many genes and proteins that are involved in the regulation of the cell cycle are mutated or over expressed. Adapted from the 2015 Cancer Product Guide, Edition 3, this poster summarizes the stages of the cell cycle and DNA repair. It also highlights strategies for enhancing replicative stress in cancer cells to force mitotic catastrophe and cell death.

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