L2037
β-Lapachone
≥98% (TLC)
Sinónimos:
ARQ 501, NSC 26326, NSC 629749, SL 11001
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About This Item
Fórmula empírica (notación de Hill):
C15H14O3
Número de CAS:
Peso molecular:
242.27
Número MDL:
Código UNSPSC:
12352200
ID de la sustancia en PubChem:
NACRES:
NA.77
Productos recomendados
origen biológico
synthetic (organic)
Ensayo
≥98% (TLC)
Formulario
powder
cadena SMILES
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
Clave InChI
QZPQTZZNNJUOLS-UHFFFAOYSA-N
Aplicación
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[1]
- as a naphthoquinone to study its effects on the growth and differentiation of mice granulocyte and macrophage progenitor cells[2]
- as a substrate to study the enzyme activity of human recombinant NAD(P)H dehydrogenase 1 (NQO1) protein[3]
Acciones bioquímicas o fisiológicas
β-Lapachone acts as a DNA topoisomerase type I inhibitor.[4] It exhibits anti-fungal, anti-bacterial,[4] trypanocidal, and antiviral properties.[5] β-Lapachone also inhibits nitric oxide (NO) and inducible NO synthase (iNOS) in alveolar macrophages.[6]
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.[7]
Código de clase de almacenamiento
11 - Combustible Solids
Clase de riesgo para el agua (WGK)
WGK 3
Punto de inflamabilidad (°F)
Not applicable
Punto de inflamabilidad (°C)
Not applicable
Equipo de protección personal
Eyeshields, Gloves, type N95 (US)
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Los clientes también vieron
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
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
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
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
Mary L S Queiroz et al.
Journal of ethnopharmacology, 117(2), 228-235 (2008-03-18)
The effects of Tabebuia avellanedae (TACE), traditionally prescribed in the treatment of cancer, and the naphtoquinone beta-lapachone (beta-lap) on the growth and differentiation of granulocyte and macrophage progenitor cells (CFU-GM) were studied in Ehrlich ascites tumour-bearing mice. Myelosuppression concomitant with
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