| Identification | Back Directory | [Name]
BETA-LAPACHONE | [CAS]
4707-32-8 | [Synonyms]
CO-501
ARQ 501
SL 11001
NSC 26326
NSC 629749
b-Lapachone
Β-LAPACHONE
BETA-LAPACHONE
β-Lapachone (90%)
β-Lapachone (ARQ-501)
ARQ-501 (beta lapachone)
BETA-LAPACHONE USP/EP/BP
beta-Lapachone (ARQ-501, CO-501)
2,2-dimethyl-3,4-dihydrobenzo[h]chromene-5,6-dione
2,2-dimethyl-3,4-dihydrobenzo[h]chromene-5,6-quinone
2,2-DiMethyl-3,4-dihydro-2H-benzo[h]chroMene-5,6-dione
2-b)pyran-5,6-dione,3,4-dihydro-2,2-dimethyl-2h-naphtho(
3,4-DIHYDRO-2,2-DIMETHYL-2H-NAPHTHO[1,2-B]PYRAN-5,6-DIONE
3,4-DIHYDRO-2,2-DIMETHYL-2H-NAPHTHOL[1,2-B]PYRAN-5,6-DIONE
2H-Naphtho[1,2-b]pyran-5,6-dione, 3,4-dihydro-2,2-dimethyl-
2,2-Dimethyl-3,4,5,6-tetrahydro-2H-naphtho[1,2-b]pyran-5,6-dione
B-LAPACHONE,2,2-DIMETHYL-3,4-DIHYDRO-2H-BENZO[H]CHROMENE-5,6-DIONE
ARQ-501; NSC-26326; NSC-629749; SL-11001; BETA-LAPACHONE; Β-LAPACHONE; ARQ-501 | [Molecular Formula]
C15H14O3 | [MDL Number]
MFCD01712233 | [MOL File]
4707-32-8.mol | [Molecular Weight]
242.27 |
| Chemical Properties | Back Directory | [Melting point ]
>110°C (dec.) | [Boiling point ]
381.4±42.0 °C(Predicted) | [density ]
1.25±0.1 g/cm3(Predicted) | [storage temp. ]
Inert atmosphere,Room Temperature | [solubility ]
Soluble in DMSO (up to 35 mg/ml) or in Ethanol (up to 15 mg/ml) | [form ]
Orange to brown solid. | [color ]
Orange | [Stability:]
Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months.Shipping Code | [InChIKey]
QZPQTZZNNJUOLS-UHFFFAOYSA-N | [LogP]
2.820 (est) |
| Hazard Information | Back Directory | [Description]
β-Lapachone (4707-32-8) is a naturally occurring quinone found in the bark of the Lapacho tree (Tabebuia avellanedae). A novel DNA topoisomerase I inhibitor which unlike camptothecin does not stabilize the cleavable complex indicating a novel mode of action.1?Induces apoptosis in a number of cancer cell lines.2?In cancer cells over-expressing NAD(P)H:quinone oxidoreductase, reduction of β-lapachone leads to futile cycling between quinone and hydroquinone forms3?resulting in the production of reactive oxygen species4. Suppresses radiation-induced activation of NFκB.5 | [Chemical Properties]
Orange Solid | [Uses]
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.
| [Definition]
ChEBI: A benzochromenone that is 3,4-dihydro-2H-benzo[h]chromene-5,6-dione substituted by geminal methyl groups at position 2. Isolated from Tabebuia avellanedae, it exhibits antineoplastic and anti-inflammatory activi
ies. | [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. | [storage]
Store at -20° C | [References]
1) Li?et al.?(1993),?beta-Lapachone, a Novel DNA Topoisomerase I Inhibitor With a Mode of Action Different From Camptothecin; J. Biol. Chem.,?268?22463
2) Wuerzberger?et al.?(1998),?Induction of Apoptosis in MCF-7:WS8 Breast Cancer Cells by Beta-Lapachone; Cancer Res.,?58?1876
3) Pink?et al.?(2000),?NAD(P)H:Quinone Oxidoreductase Activity Is the Principal Determinant of Beta-Lapachone Cytotoxicity. J. Biol. Chem.,?275?5416
4) Siegel?et al. (2012),?NAD(P)H:quinone Oxidoreductase 1 (NQO1) in the Sensitivity and Resistance to Antitumor Quinones; Biochem. Pharmacol.,?83?1033
5) Dong?et al.?(2010), Beta-lapachone suppresses radiation-induced activation of nuclear factor-kappaB; Exp. Mol. Med.,?42?327 |
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