ARQ-501

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WARNING: This product is for research use only, not for human or veterinary use.

Description:ARQ-501, also known as beta-lapachone,is a naphthoquinone compound derived from bark of Tabebuia sp., with antitumor, antibacterial, antifungal and antitrypanosomal activities. Beta-lapachone exerts its anti-tumor effect by indirect actions of inducing p53-independent apoptosis and cell cycle arrest mediated through altered activities of cell cycle control regulatory proteins; including down-regulating retinoblastoma protein (pRB), a transcriptional repressor target at transcription factor E2F-1, as well as induces expression of cyclin dependent kinase inhibitor 1A (CDKN1A or p21). Both E2F-1 and p21 are required for G1/S-phase transition during cell cycle. This agent also inhibits DNA topoisomerase I by a mechanism distinct from that of camptothecin, and thereby blocks the formation of a cleavable complex leading to enzyme inhibition and prevent DNA repair. Furthermore, beta-lapachone could induce reactive oxygen species in vivo, and result in cytotoxicity.

Price and Availability

ARQ-501,purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.

Chemical Structure

Theoretical Analysis

MedKoo Cat#: 200284Name: ARQ-501CAS#: 4707-32-8Chemical Formula: C15H14O3Exact Mass: 242.09429Molecular Weight: 242.27Elemental Analysis:C, 74.36; H, 5.82; O, 19.81

Synonym:ARQ501; ARQ-501; ARQ 501; beta-lapachone

IUPAC/Chemical Name:2,2-dimethyl-3,4-dihydro-2H-benzo[h]chromene-5,6-dione

InChi Key:QZPQTZZNNJUOLS-UHFFFAOYSA-N

InChi Code:InChI=1S/C15H14O3/c1-15(2)8-7-11-13(17)12(16)9-5-3-4-6-10(9)14(11)18-15/h3-6H,7-8H2,1-2H3

SMILES Code:O=C1C(CCC(C)(C)O2)=C2C3=CC=CC=C3C1=O

Technical Data

Additional Information

References

1: Kim JH, Lee SM, Myung CH, Lee KR, Hyun SM, Lee JE,Park YS, Jeon SR, Park JI, Chang SE, Hwang JS. Melanogenesis inhibitionof β-lapachone, a natural product from Tabebuia avellanedae, witheffective in vivo lightening potency. Arch Dermatol Res. 2015 Feb 8.[Epub ahead of print] PubMed PMID: 25663088.

2: Moore Z, Chakrabarti G, Luo X, Ali A, Hu Z, Fattah FJ, Vemireddy R,DeBerardinis RJ, Brekken RA, Boothman DA. NAMPT inhibition sensitizespancreatic adenocarcinoma cells to tumor-selective, PAR-independentmetabolic catastrophe and cell death induced by β-lapachone. Cell DeathDis. 2015 Jan 15;6:e1599. doi: 10.1038/cddis.2014.564. PubMed PMID:25590809.

3: Menacho-Márquez M, Rodríguez-Hernández CJ, Villaronga MÃ