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
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
MDL number:
Product Name
β-Lapachone, ≥98% (TLC)
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
biological source
synthetic (organic)
assay
≥98% (TLC)
form
powder
Quality Level
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
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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Byung Tae Choi et al.
Anti-cancer drugs, 14(10), 845-850 (2003-11-05)
beta-Lapachone is a naturally occurring quinone obtained from the bark of the lapacho tree (Tabebuia avellanedae) with cancer chemopreventive properties. The objective of the present study was to investigate the effect of beta-lapachone on the cell growth and apoptosis in
Cleverson Neves-Pinto et al.
Journal of medicinal chemistry, 45(10), 2112-2115 (2002-05-03)
An intensive effort has been directed toward finding alternative drugs for treatment of Chagas' disease, caused by Trypanosoma cruzi, and prophylaxis of blood in endemic areas. Our research comprises the synthesis and trypanocidal screening of derivatives from naphthoquinones. Herein a
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
Carla Ríos-Luci et al.
European journal of medicinal chemistry, 53, 264-274 (2012-05-09)
In this study, we describe the synthesis of a series of α- and β-lapachone containing hydroxyl or methoxyl groups on the benzene ring, by means of the selective acid promoted cyclization of the appropriate lapachol analog. The evaluation of the
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