Beta-Lapachone

• Background:

  β-Lapachone is a naturally occurring quinone obtained from the bark of the lapacho tree (Tabebuia avellanedae) with cancer chemopreventive properties. A novel DNA topoisomerase I inhibitor which unlike camptothecin does not stabilize the cleavable complex indicating a novel mode of action (1). Induces apoptosis in a number of cancer cell lines (2). In cancer cells overexpressing NAD(P)H:quinone oxidoreductase, reduction of β-lapachone leads to futile cycling between quinone and hydroquinone forms (3) resulting in the production of reactive oxygen species (4). Suppresses radiation-induced activation of NFĸB (5). Attenuates cognitive impairment and inflammation in amyloid-induced mouse model.

• Description:

  DNA topoisomerase I inhibitor

• Product Name Alternative:

  3,4-Dihydro-2,2-dimethyl-2H-naphtho[1,2-b]pyran-5,6-dione; NSC-26326

• UNSPSC:

  41116105

• Type:

  Inhibitor

• Source:

  Synthetic

• Field of Research:

  Cell Signaling | Epigenetics and Nuclear Signaling | DNA/RNA | DNA Synthesis | Topoisomerases | Neuroscience | Neurodegeneration | Alzheimer's Disease

• Purity:

  >98% (HPLC) ; NMR (Conforms)

• Weight:

  0.005

• Format:

  Orange powder

• Solubility:

  May be dissolved in DMSO (35 mg/ml); or Ethanol (15 mg/ml)

• Molecular Formula:

  C15H14O3

• Molecular Weight:

  242.3

• Precautions:

  Not for use in humans. Not for use in diagnostics or therapeutics. For in vitro research use only.

• References & Citations:

  1. CJ Li et al. J. Biol. Chem. 1993 268:22463 2. SM Wuerzberger et al. Cancer Res. 1998 58:1876 3. JJ Pink et al. J. Biol. Chem. 2000 275:5416 4. D Siegel et al. Biochem. Pharmacol. 2012 83:1033 5. GZ Dong et al. Exp. Mol. Med. 2010 42:327

• CAS Number:

  4707-32-8