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Merck
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Principaux documents

L2037

Sigma-Aldrich

β-Lapachone

≥98% (TLC)

Synonyme(s) :

ARQ 501, NSC 26326, NSC 629749, SL 11001

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About This Item

Formule empirique (notation de Hill):
C15H14O3
Numéro CAS:
Poids moléculaire :
242.27
Numéro MDL:
Code UNSPSC :
12352200
ID de substance PubChem :
Nomenclature NACRES :
NA.77

Source biologique

synthetic (organic)

Niveau de qualité

Essai

≥98% (TLC)

Forme

powder

Chaîne 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

Clé InChI

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

Actions biochimiques/physiologiques

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.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)


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Consulter la Bibliothèque de documents

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
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
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
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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