β-Lapachone

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Cat.No. 1293 - beta-Lapachone | C15H14O3 | CAS No. 4707-32-8
Description: DNA topoisomerase I inhibitor
Chemical Name: 3,4-Dihydro-2,2-dimethyl-2H-naphtho[1,2-b]pyran-5,6-dione
Purity: ≥98% (HPLC)
Datasheet
Citations
Literature

Biological Activity

DNA topoisomerase I inhibitor. Exhibits a different inhibitory mechanism to camptothecin (Cat. No. 1100). Induces apoptosis in a variety of cell lines, including prostate cancer and promyelocytic leukemia cells; blocks the cell cycle in G0/G1. Also has effects on DNA topoisomerase II, NF-κB, AP-1, and JNK.

Technical Data

M. Wt 242.27
Formula C15H14O3
Storage Store at +4°C
Purity ≥98% (HPLC)
CAS Number 4707-32-8
PubChem ID 3885
InChI Key QZPQTZZNNJUOLS-UHFFFAOYSA-N
Smiles O=C(C(C3=C2OC(C)(C)CC3)=O)C1=C2C=CC=C1

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 24.23 100
ethanol 12.11 50

Preparing Stock Solutions

The following data is based on the product molecular weight 242.27. 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 4.13 mL 20.64 mL 41.28 mL
5 mM 0.83 mL 4.13 mL 8.26 mL
10 mM 0.41 mL 2.06 mL 4.13 mL
50 mM 0.08 mL 0.41 mL 0.83 mL

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Product Datasheets

Certificate of Analysis / Product Datasheet
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Safety Datasheet

References

References are publications that support the products' biological activity.

Li et al (1993) Beta-Lapachone, a novel topoisomerase I inhibitor with a mode of action different from camptothecin. J.Biol.Chem. 268 22463 PMID: 8226754

Manna et al (1999) Suppression of tumor necrosis factor-activated nuclear transcription factor-κB, activator protein-1, c-Jun N-terminal kinase, and apoptosis by β lapachone. Biochem.Pharmacol. 57 763 PMID: 10075082

Shiah et al (1999) Activation of c-Jun NH2-terminal kinase and subsequent CPP32/Yama during topoisomerase inhibitor β-lapachone-induced apoptosis through an oxidation-dependent pathway Cancer Res. 59 391 PMID: 9927052

Wuerzberger et al (1998) Induction of apoptosis in MCF-7:WS8 breast cancer cells by β-Lapachone. Cancer Res. 58 1876 PMID: 9581828


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Citations for β-Lapachone

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Literature in this Area

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.

Pathways for β-Lapachone

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