L2037
β-Lapachone
synthetic (organic), ≥98% (TLC), DNA topoisomerase typeI inhibitor, powder
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
Product Name
β-Lapachone, ≥98% (TLC)
biological source
synthetic (organic)
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
Related Categories
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 Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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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 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
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
Dong-Oh Moon et al.
International immunopharmacology, 7(4), 506-514 (2007-02-27)
beta-Lapachone (LAPA) is a chemotherapeutic agent that can inhibit the expression of nitric oxide (NO) and inducible NO synthase (iNOS) in alveolar macrophages. No other information on the agent's anti-inflammatory activity has been reported. In the present study, we investigated
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