L2037
β-Lapachone
≥98% (TLC)
Synonym(s):
ARQ 501, NSC 26326, NSC 629749, SL 11001
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About This Item
Empirical Formula (Hill Notation):
C15H14O3
CAS Number:
Molecular Weight:
242.27
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
Recommended Products
biological source
synthetic (organic)
Quality Level
assay
≥98% (TLC)
form
powder
SMILES string
CC1(C)CCC2=C(O1)c3ccccc3C(=O)C2=O
InChI
1S/C15H14O3/c1-15(2)8-7-11-13(17)12(16)9-5-3-4-6-10(9)14(11)18-15/h3-6H,7-8H2,1-2H3
InChI key
QZPQTZZNNJUOLS-UHFFFAOYSA-N
Application
β-Lapachone has been used:
- as an anticancer compound in catalase-inhibitable luminol/hydrogen peroxide (HRP)-dependent chemiluminometric assay in Lewis lung carcinoma (LLC) cells and isolated mitochondria
- as a naphthoquinone to study its effects on the growth and differentiation of mice granulocyte and macrophage progenitor cells
- as a substrate to study the enzyme activity of human recombinant NAD(P)H dehydrogenase 1 (NQO1) protein
Biochem/physiol Actions
β-Lapachone acts as a DNA topoisomerase type I inhibitor. It exhibits anti-fungal, anti-bacterial, trypanocidal, and antiviral properties. β-Lapachone also inhibits nitric oxide (NO) and inducible NO synthase (iNOS) in alveolar macrophages.
β-Lapachone is a naturally occurring quinone obtained from the bark of the lapacho tree (Tabebuia avellanedae) with cancer chemopreventive properties. Induces apoptosis in HL-60 and human prostate cancer cells.
Storage Class
11 - Combustible Solids
wgk_germany
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
Certificates of Analysis (COA)
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Customers Also Viewed
S M Wuerzberger et al.
Cancer research, 58(9), 1876-1885 (1998-05-15)
Beta-lapachone (beta-lap) affects a number of enzymes in vitro, including type I topoisomerase (Topo I); however, its exact intracellular target(s) and mechanism of cell killing remain unknown. We compared the cytotoxic responses of MCF-7:WS8 (MCF-7) human breast cancer cells after
C J Li et al.
The Journal of biological chemistry, 268(30), 22463-22468 (1993-10-25)
beta-Lapachone is a plant product that has been found to have many pharmacological effects. To date, very little is known about its biochemical target. In this study, we found that beta-lapachone inhibits the catalytic activity of topoisomerase I from calf
David Siegel et al.
Biochemical pharmacology, 83(8), 1033-1040 (2012-01-03)
Quinones represent a large and diverse class of antitumor drugs and many quinones are approved for clinical use or are currently undergoing evaluation in clinical trials. For many quinones reduction to the hydroquinone has been shown to play a key
S M Planchon et al.
Cancer research, 55(17), 3706-3711 (1995-09-01)
beta-Lapachone and certain of its derivatives directly bind and inhibit topoisomerase I (Topo I) DNA unwinding activity and form DNA-Topo I complexes, which are not resolvable by SDS-K+ assays. We show that beta-lapachone can induce apoptosis in certain cells, such
Gang Huang et al.
Theranostics, 3(2), 116-126 (2013-02-21)
Superparamagnetic iron oxide nanoparticles (SPION) are an important and versatile nano- platform with broad biological applications. Despite extensive studies, the biological and pharmacological activities of SPION have not been exploited in therapeutic applications. Recently, β-lapachone (β-lap), a novel anticancer drug
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