CAS Number4707-32-8
Synonyms3,4-Dihydro-2,2-dimethyl-2H-naphtho(1,2-b)pyran-5,6-dione; Beta-Lapachone; 3,4-Dihydro-2,2-dimethyl-2H-naphtho[2,3-b]pyran-5,10-dione; β-lapachone; 3,4-dihydro-2,2-dimethyl-2H-naphthol[1,2-b]-pyran-5,6-dione; 2,2-Dimethyl-3,4-dihydro-2H-benzo[h]chromene-5,6-dione; 2,2-dimethyl-3,4-dihydrobenzo[h]chromene-5,6-dione; ARQ-501; CO-501
Molecular FormulaC15H14O3
Molecular Weight242.27
Density1.3±0.1 g/cm3
Boiling Point381.4±42.0 °C at 760 mmHg
Melting Point>110ºC (dec.)
Appearancepowder
Symbol
Signal WordWarning
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 4707-32-8 |
| Catalog No. | 2A-1192583 |
| Chinese Name | β-拉帕醌 |
| Synonyms | 3,4-Dihydro-2,2-dimethyl-2H-naphtho(1,2-b)pyran-5,6-dione; Beta-Lapachone; 3,4-Dihydro-2,2-dimethyl-2H-naphtho[2,3-b]pyran-5,10-dione; β-lapachone; 3,4-dihydro-2,2-dimethyl-2H-naphthol[1,2-b]-pyran-5,6-dione; 2,2-Dimethyl-3,4-dihydro-2H-benzo[h]chromene-5,6-dione; 2,2-dimethyl-3,4-dihydrobenzo[h]chromene-5,6-dione; ARQ-501; CO-501 |
| Molecular Formula | C15H14O3 |
| Molecular Weight | 242.27 |
| Density | 1.3±0.1 g/cm3 |
| Boiling Point | 381.4±42.0 °C at 760 mmHg |
| Melting Point | >110ºC (dec.) |
| Appearance | powder |
| Storage Condition | -20?C Freezer |
| Application | β-Lapachone is a natural naphthoquinone compound and a topoisomerase I inhibitor that induces apoptosis by inhibiting cell cycle progression. |
| HTC | 2914399090 |
| PubChem ID | 24278512 |
| MDL Number | MFCD01712233 |
| NACRES Code | NA.77 |
| UNSPSC | 12352200 |
| Hazard Symbols | transportation |
| Bioactivity | β-Lapachone is a naturally occurring O-naphthoquinone, acts as a topoisomerase I inhibitor, and induces apoptosis by inhibiting cell cycle progression. Related Catalog Signaling Pathways >> Autophagy >> Autophagy Signaling Pathways >> Cell Cycle/DNA Damage >> Topoisomerase Research Areas >> Cancer Natural Products >> Quinones Target Topoisomerase I In Vitro β-Lapachone is a topoisomerase I inhibitor. β-Lapachone (25 μM) inhibits camptothecin-induced DNA cleavage[1]. β-Lapachone (10-40 μM) significantly reduces the colony-forming ability of CHO cells, and is cytotoxic in S phase. β-Lapachone at above 10 μM, causes a heavy DNA-strand breaks in CHO cells[2]. β-Lapachone (10 μM) suppresses JCPyV replication in IMR-32 cells. β-Lapachone (1.0 µM) potently affects JCPyV propagation in JCI cells. β-Lapachone (0.01-0.1 μM) inhibits VP1 production in JCI cells[4]. In Vivo β-Lapachone (0.066%) ameliorates cisplatin-induced renal injury and when in combination with cisplatin, the affect is more significant in mice. β-Lapachone increases Mre11-Rad50-Nbs1 (MRN) complex expression in mice[3]. Kinase Assay DNA topoisomerase I is incubated in the presence or absence of drugs (including β-Lapachone), in 20 μL of relaxation buffer (50 mM Tris (pH 7.5). 50 mM KCl, 10 mM MgCl2, 0.5 mM dithiothreitol, 0.5 mM EDTA, 30 μg/mL bovine serum albumin) for 30 min at 37°C. Reactions are stopped by adding 1% SDS and proteinase K (50 μg/mL). After an additional 1-h incubation at 37°C, the products are separated by electrophoresis in 1% agarose gel in TAE buffer (0.04 M tris acetate, 0.001 M EDTA). The gel is stained with ethidium bromide after electrophoresis. The photographic negative is scanned with an NIH image analysis system[1]. Cell Assay Cytotoxicity is measured by an MTT assay. IMR-32 and JCI cells are plated in 96-well microtiter plates at a concentration of 5.0 × 104 (topotecan) or 2.5 × 104 (β-lapachone) cells/well/100 µL medium 24 hr prior to addition of various concentrations of topotecan or β-lapachone. The cells are then incubated for 72 hr at 37°C in a CO2 incubator. Cell proliferation is assessed using a Cell Proliferation Kit I. Experiments are performed using four independent cultures[4]. Animal Admin Male Balb/c mice are provided a commercial pellet diet and water ad libitum. After 1 week of acclimation, the mice are randomly allocated to one of the following groups (5 per group): control, β-lapachone, cisplatin (18 mg/kg, ip), and β-lapachone + cisplatin (18 mg/kg, ip). The β-lapachone groups are fed a diet containing the drug (0.066) for 2 weeks prior to cisplatin injection. All mice are sacrificed under carbon dioxide anesthesia 3 days after cisplatin injection. The blood samples are subjected to serum BUN and CRE analyses. Half of the kidney is quickly removed for histopathological and immunohistochemical (IHC) studies. The other half is stored at −70°C until western blot assay[3]. References [1]. Li CJ, et al. beta-Lapachone, a novel DNA topoisomerase I inhibitor with a mode of action different from camptothecin. J Biol Chem. 1993 Oct 25;268(30):22463-8. [2]. Vanni A, et al. DNA damage and cytotoxicity induced by beta-lapachone: relation to poly(ADP-ribose) polymerase inhibition. Mutat Res. 1998 Jun 5;401(1-2):55-63. [3]. Kim TW, et al. β-Lapachone enhances Mre11-Rad50-Nbs1 complex expression in cisplatin-induced nephrotoxicity. Pharmacol Rep. 2016 Feb;68(1):27-31. Chemical & Physical Properties Density 1.3±0.1 g/cm3 Boiling Point 381.4±42.0 °C at 760 mmHg Melting Point >110ºC (dec.) Molecular Formula C15H14O3 Molecular Weight 242.270 Flash Point 169.7±27.9 °C Exact Mass 242.094299 PSA 43.37000 LogP 2.82 Vapour Pressure 0.0±0.9 mmHg at 25°C Index of Refraction 1.595 Storage condition -20?C Freezer |
| Use of | β-Lapachone is a naturally occurring O-naphthoquinone, acts as a topoisomerase I inhibitor, and induces apoptosis by inhibiting cell cycle progression. Properties Articles34 Name β-lapachone Synonym More Synonyms Beta-Lapachone Biological Activity Description β-Lapachone is a naturally occurring O-naphthoquinone, acts as a topoisomerase I inhibitor, and induces apoptosis by inhibiting cell cycle progression. Related Catalog Signaling Pathways >> Autophagy >> Autophagy Signaling Pathways >> Cell Cycle/DNA Damage >> Topoisomerase Research Areas >> Cancer Natural Products >> Quinones Topoisomerase I In Vivo β-Lapachone (0.066%) ameliorates cisplatin-induced renal injury and when in combination with cisplatin, the affect is more significant in mice. β-Lapachone increases Mre11-Rad50-Nbs1 (MRN) complex expression in mice[3]. References [1]. Li CJ, et al. beta-Lapachone, a novel DNA topoisomerase I inhibitor with a mode of action different from camptothecin. J Biol Chem. 1993 Oct 25;268(30):22463-8. [2]. Vanni A, et al. DNA damage and cytotoxicity induced by beta-lapachone: relation to poly(ADP-ribose) polymerase inhibition. Mutat Res. 1998 Jun 5;401(1-2):55-63. Chemical & Physical Properties Molecular Formula C15H14O3 Exact Mass 242.094299 PSA 43.37000 Index of Refraction 1.595 Storage condition -20?C Freezer |
| Tax Rebate | 13.0% |
| Supervision | None. MFN tariff: 5.5%. Ordinary tariff: 30.0% |
| Transport Info | Product name: Purity: 99.0% |
| MSDS Transport Info | Module 14. Shipping information 14.1 UN dangerous goods number European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.2 Names specified by the United Nations (UN) European Land Transport Dangerous Regulations: Non-dangerous goods IMDG Code: Non-dangerous goods International air transport dangerous goods regulations: non-dangerous goods 14.3 Transport hazard categories European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.4 Package group European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.5 Environmental hazards European Land Transport Dangerous Regulations: No International Maritime Transport Dangerous Regulations Maritime Pollutants: No International Air Transport Risk Regulations: No 14.6 Special reminder to users No data available |
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