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| | BETA-LAPACHONE Basic information |
| Product Name: | BETA-LAPACHONE | | Synonyms: | BETA-LAPACHONE;2-b)pyran-5,6-dione,3,4-dihydro-2,2-dimethyl-2h-naphtho(;b-Lapachone;B-LAPACHONE,2,2-DIMETHYL-3,4-DIHYDRO-2H-BENZO[H]CHROMENE-5,6-DIONE;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;2,2-Dimethyl-3,4,5,6-tetrahydro-2H-naphtho[1,2-b]pyran-5,6-dione;2,2-dimethyl-3,4-dihydrobenzo[h]chromene-5,6-dione | | CAS: | 4707-32-8 | | MF: | C15H14O3 | | MW: | 242.27 | | EINECS: | | | Product Categories: | Inhibitors;Aromatics;DNA Repair RegulatorsCancer Research;Gene RegulationEnzyme Inhibitors by Enzyme;Heterocycles;Isotope Labelled Compounds;Topoisomerase I;Apoptosis and Cell Cycle;Chemopreventive Agents;DNA metabolism;R to | | Mol File: | 4707-32-8.mol |  |
| | BETA-LAPACHONE Chemical Properties |
| 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) |
| WGK Germany | 3 | | RTECS | QL6127400 | | HS Code | 2932990090 |
| | BETA-LAPACHONE Usage And Synthesis |
| 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 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
| | 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. | | 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 |
| | BETA-LAPACHONE Preparation Products And Raw materials |
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