beta-Lapachone β-Lapachone, a novel topoisomerase I (Topo I) inhibitor, does not stabilize the cleavable complex indicating a novel mode of action, unlike Camptothecin (sc-200871).

β-Lapachone  (CAS 4707-32-8)

beta-Lapachone is rated 5.0 out of 5 by 1.
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| See 5 Citations
Synonym: 3,4-Dihydro-2,2-dimethyl-2H-naphtho[1,2-b]pyran-5,6-dione
Application: A selective DNA topoisomerase I inhibitor
CAS Number: 4707-32-8
Purity: ≥98%
Molecular Weight: 242.27
Molecular Formula: C15H14O3
* Refer to Certificate of Analysis for lot specific data (including water content).
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Ordering Information

PRODUCT NAME CATALOG # UNIT PRICE QTY FAVORITES
β-Lapachone sc-200875 5 mg $70.00
β-Lapachone sc-200875A 25 mg $295.00

β-Lapachone, a novel Topo I (topoisomerase I) inhibitor, does not stabilize the cleavable complex indicating a novel mode of action, unlike camptothecin (sc-200871). Apoptosis has been demonstrated in HL-60 and human prostate cancer cells treated with β-Lapachone via a p53-independent mechanism and cell cycle arrest at G0/G1,2. β-Lapachone has been observed to accelerate wound healing by increasing cell proliferation in cells such as: keratinocytes, fibroblasts and endothelial while also increasing the migration of fibroblasts and endothelial cells. β-Lapachone has exhibited anti-inflammatory properties by suppressing the NF-κB activation by blocking IκBα degradation and downregulating the ERK, p38 mitogen-activated protein kinase and Akt pathway.


References

1. Planchon, S M., et al., 1995. Beta-lapachone-mediated apoptosis in human promyelocytic leukemia (HL-60) and human prostate cancer cells: a p53-independent response. Cancer research. 55(17): 3706-11. PMID: 7641180
2. Li, C J., et al., 1993. beta-Lapachone, a novel DNA topoisomerase I inhibitor with a mode of action different from camptothecin. The Journal of biological chemistry. 268(30): 22463-8. PMID: 8226754
3. Choi, Byung Tae., et al., 2003. beta-Lapachone-induced apoptosis is associated with activation of caspase-3 and inactivation of NF-kappaB in human colon cancer HCT-116 cells. Anti-cancer drugs. 14(10): 845-50. PMID: 14597880
4. Moon, Dong-Oh., et al., 2007. Anti-inflammatory effects of beta-lapachone in lipopolysaccharide-stimulated BV2 microglia. International immunopharmacology. 7(4): 506-14. PMID: 17321474
5. Kung, Hsiu-Ni., et al., 2008. In vitro and in vivo wound healing-promoting activities of beta-lapachone. American journal of physiology. Cell physiology. 295(4): C931-43. PMID: 18650264
6. Dong, Guang Zhi., et al., 2010. Beta-lapachone suppresses radiation-induced activation of nuclear factor-kappaB. Experimental & molecular medicine. 42(5): 327-34. PMID: 20200474

Usage :
Store, as supplied, at room temperature for up to 1 year. Store solutions at - 20°C for up to 3 months.
Physical State :
Solid
Derived From :
Synthetic
Solubility :
Soluble in DMSO (>25 mg/ml) at 5° C, ethanol (20 mg/ml), chloroform, and DMF.
Storage :
Store at -20° C
Melting Point :
~151-153° C (dec.)
Boiling Point :
~381.4 °C at 760 mmHg (Predicted)
Density :
1.25 g/cm3 (Predicted)
Refractive Index :
n20D 1.60
Optical Activity :
α20/D -43.9º, c = 2 in water
IC50 :
HIV-1 LTR: IC50 = 0.3 µM (human); HOS: IC50 = 1400 nM (human); MDA-MB-435 : IC50 = 0.06 ug.mL-1 (human); HL-60: IC50 = 1650 nM (human)
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
RTECS :
QL6127400
PubChem CID :
3885
MDL Number :
MFCD01712233
Beilstein Registry :
0181499
SMILES :
CC1(CCC2=C(O1)C3=CC=CC=C3C(=O)C2=O)C

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Certificate of Analysis

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beta-Lapachone Product Citations

See how others have used beta-Lapachone. Click on the entry to view the PubMed entry .

Citations 1 to 5 of 5 total

PMID: # 17609380
Bey, EA. et al. 2007. An NQO1- and PARP-1-mediated cell death pathway induced in non-small-cell lung cancer cells by beta-lapachone Proc. Natl. Acad. Sci. USA. 104: 11832-11837.

PMID: # 15044484
Lin, MT et al. 2004. Cyr61 expression confers resistance to apoptosis in breast cancer MCF-7 cells by a mechanism of NF-kB-dependent XIAP up-regulation. J Biol Chem.. 279: 24015-23.

PMID: # 12598645
Li, Y. et al. 2003. Selective killing of cancer cells by beta -lapachone: direct checkpoint activation as a strategy against cancer. Proc. Natl. Acad. Sci. U.S.A.. 100: 2674-2678.

PMID: # 9927052
Shiah, SG. et al. 1999. Activation of c-Jun NH2-terminal kinase and subsequent CPP32/Yama during topoisomerase inhibitor beta-lapachone-induced apoptosis through an oxidation-dependent pathway. Cancer Res.. 59: 391-398.

PMID: # 2740334
Boothman, DA. et al. 1989. Inhibition of radiation-induced neoplastic transformation by beta-lapachone. Proc. Natl. Acad. Sci. U.S.A.. 86: 4963-4967.

Citations 1 to 5 of 5 total
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Rated 5 out of 5 by from Bey et al Bey et al. (PubMed ID 17609380) used -Lapachone, a proven chemotherapeutic and radiosensitizing agent, to selectively destroy non-small-cell lung cancer (NSCLCs) cells with abnormally high expression of NQO1. -SCBT Publication Review
Date published: 2015-04-20
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