beta-lapachone-topoisomerase-i-inhibitor

β-Lapachone (4707-32-8) is a naturally occurring quinone found in the bark of the Lapacho tree (Tabebuia avellanedae). 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 over-expressing NAD(P)H:quinone oxidoreductase, reduction of β-lapachone leads to futile cycling between quinone and hydroquinone forms3 resulting in the production of reactive oxygen species4. Suppresses radiation-induced activation of NFκB.5

References/Citations

1) Li et al. (1993), beta-Lapachone, a Novel DNA Topoisomerase I Inhibitor With a Mode of Action Different From Camptothecin; J. Biol. Chem., 268 22463
2) Wuerzberger et al. (1998), Induction of Apoptosis in MCF-7:WS8 Breast Cancer Cells by Beta-Lapachone; Cancer Res., 58 1876
3) Pink et al. (2000), NAD(P)H:Quinone Oxidoreductase Activity Is the Principal Determinant of Beta-Lapachone Cytotoxicity. J. Biol. Chem., 275 5416
4) Siegel et al. (2012), NAD(P)H:quinone Oxidoreductase 1 (NQO1) in the Sensitivity and Resistance to Antitumor Quinones; Biochem. Pharmacol., 83 1033
5) Dong et al. (2010), Beta-lapachone suppresses radiation-induced activation of nuclear factor-kappaB; Exp. Mol. Med., 42 327

Weight 0.01 mg
Dimensions 0.01 × 0.01 × 0.01 cm
Size:

5 mg, 25 mg

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CAS:
4707-32-8
Catalog Number:
10-2386
Activity:
Topoisomerase I inhibitor
Chemical Name:
3,4-Dihydro-2,2-dimethyl-2H-naphtho[1,2-b]pyran-5,6-dione
Alternate Name:
NSC-26326
Molecular Formula:
C15H14O3
Solubility:
Soluble in DMSO (up to 35 mg/ml) or in Ethanol (up to 15 mg/ml)
Physical Properties:
Orange solid
Purity:
98% by TLC
NMR (Conforms)
Storage Temperature:
-20°C (des.)
Stability:
Stable for 2 years as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months.
Shipping Code:
RT

beta-lapachone-topoisomerase-i-inhibitor

$52.00$200.00

CAS:
4707-32-8
Catalog Number:
10-2386
Activity:
Topoisomerase I inhibitor
Chemical Name:
3,4-Dihydro-2,2-dimethyl-2H-naphtho[1,2-b]pyran-5,6-dione
Alternate Name:
NSC-26326
Molecular Formula:
C15H14O3
Solubility:
Soluble in DMSO (up to 35 mg/ml) or in Ethanol (up to 15 mg/ml)
Physical Properties:
Orange solid
Purity:
98% by TLC
NMR (Conforms)
Storage Temperature:
-20°C (des.)
Stability:
Stable for 2 years as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months.
Shipping Code:
RT
  • 5 mg
  • 25 mg
Clear
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