beta-Lapachone CAS: 4707-32-8
MF: C15H14O3
MW: 242.27
A selective DNA topoisomerase I inhibitor.

β-Lapachone (CAS 4707-32-8)

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Synonyme: 3,4-Dihydro-2,2-dimethyl-2H-naphtho[1,2-b]pyran-5,6-dione
Application: A selective DNA topoisomerase I inhibitor
Numéro CAS: 4707-32-8
Pureté: ≥98%
Masse Moléculaire: 242.27
Formule Moléculaire: C15H14O3
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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.


Références

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

Utilisation :
Store, as supplied, at room temperature for up to 1 year. Store solutions at - 20°C for up to 3 months.
État Physique :
Solid
Solubilité :
Soluble in DMSO (>25 mg/ml), ethanol (20 mg/ml), chloroform, and DMF.
STOCKAGE :
Store at -20° C
Point de fusion :
~151-153° C (dec.)
Point d'Ébullition :
~381.4° C at 760 mmHg (Predicted)
Densité :
1.25 g/cm3 (Predicted)
Indice de Réfraction :
n20D 1.60
Activité Optique :
α20/D -43.9°, 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)
Pour la Recherche Uniquement. Non conforme pour le Diagnostic ou pour une Utilisation Thérapeutique.
WGK Allemagne :
3
RTECS :
QL6127400
PubChem CID :
3885
Numéro MDL :
MFCD01712233
Registre Beilstein :
0181499
SMILES :
CC1(CCC2=C(O1)C3=CC=CC=C3C(=O)C2=O)C

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beta-Lapachone  Références bibliographiques

Consultez les publications faisant référence à l' utilisation de beta-Lapachone. Cliquez sur le lien pour afficher lentrée PubMed .

Citations 1 à 6 sur un total de 6

PMID: # 17609380  Bey, EA. et al. 2007. Proc. Natl. Acad. Sci. USA. 104: 11832-11837.

PMID: # 15044484  Lin, MT et al. 2004. J Biol Chem. 279: 24015-23.

PMID: # 12598645  Li, Y. et al. 2003. Proc. Natl. Acad. Sci. U.S.A. 100: 2674-2678.

PMID: # 9927052  Shiah, SG. et al. 1999. Cancer Res. 59: 391-398.

PMID: # 9927052  Shiah, SG. et al. 1999. Cancer Res. 59: 391-398.

PMID: # 2740334  Boothman, DA. et al. 1989. Proc. Natl. Acad. Sci. U.S.A. 86: 4963-4967.

Citations 1 à 6 sur un total de 6
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