Piperlongumine

• CAT Number: R052950
• CAS Number: 20069-09-4
• Molecular Formula: C17H19NO5
• Molecular Weight: 317.341
• Purity: ≥95%
• Target: Apoptosis Inducers
• Solubility: >10.45mg/mL in DMSO
• Storage: Store at -20°C
• IUPAC Name: 1-[(E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]-2,3-dihydropyridin-6-one
• InChI: InChI=1S/C17H19NO5/c1-21-13-10-12(11-14(22-2)17(13)23-3)7-8-16(20)18-9-5-4-6-15(18)19/h4,6-8,10-11H,5,9H2,1-3H3/b8-7+
• InChIKey: VABYUUZNAVQNPG-BQYQJAHWSA-N
• SMILES: COC1=CC(=CC(=C1OC)OC)C=CC(=O)N2CCC=CC2=O

Piperlongumine , also known as Piplartine , is a biologically active alkaloid/amide from peppers, as from long pepper (Piper longum L. – Piperaceae). Long pepper is one of the most widely used in Ayurvedic medicine, which is used to treat many diseases, including tumors. The reported pharmacological activities of piplartine include cytotoxic, genotoxic, antitumor, antiangiogenic, antimetastatic, antiplatelet aggregation, antinociceptive, anxiolytic, antidepressant, anti-atherosclerotic, antidiabetic, antibacterial, antifungal, leishmanicidal, trypanocidal, and schistosomicidal activities. Among the multiple pharmacological effects of piplartine, its anticancer property is the most promising.

Reference

1:Novel non-trimethoxylphenyl piperlongumine derivatives selectively kill cancer cells. Zhang Y, Ma H, Wu Y, Wu Z, Yao Z, Zhang W, Zhuang C, Miao Z.Bioorg Med Chem Lett. 2017 Jun 1;27(11):2308-2312. doi: 10.1016/j.bmcl.2017.04.035. Epub 2017 Apr 13. PMID: 28434764 2:Piperlongumine downregulates the expression of HER family in breast cancer cells. Jin HO, Park JA, Kim HA, Chang YH, Hong YJ, Park IC, Lee JK.Biochem Biophys Res Commun. 2017 May 13;486(4):1083-1089. doi: 10.1016/j.bbrc.2017.03.166. Epub 2017 Apr 1. PMID: 28377224 3:Elevated PRC1 in gastric carcinoma exerts oncogenic function and is targeted by piperlongumine in a p53-dependent manner. Zhang B, Shi X, Xu G, Kang W, Zhang W, Zhang S, Cao Y, Qian L, Zhan P, Yan H, To KF, Wang L, Zou X.J Cell Mol Med. 2017 Feb 12. doi: 10.1111/jcmm.13063. [Epub ahead of print] PMID: 28190297 Free Article4:Identification of novel ROS inducer by merging the fragments of piperlongumine and dicoumarol. Xu X, Fang X, Wang J, Zhu H.Bioorg Med Chem Lett. 2017 Mar 1;27(5):1325-1328. doi: 10.1016/j.bmcl.2016.08.016. Epub 2016 Aug 6. PMID: 28159415 5:Piperlongumine attenuates experimental autoimmune encephalomyelitis through inhibition of NF-kappaB activity. Gu SM, Yun J, Son DJ, Kim HY, Nam KT, Kim HD, Choi MG, Choi JS, Kim YM, Han SB, Hong JT.Free Radic Biol Med. 2017 Feb;103:133-145. doi: 10.1016/j.freeradbiomed.2016.12.027. Epub 2016 Dec 21. PMID: 28011150 6:Piperlongumine derived cyclic sulfonamides (sultams): Synthesis and in vitro exploration for therapeutic potential against HeLa cancer cell lines. Lad NP, Kulkarni S, Sharma R, Mascarenhas M, Kulkarni MR, Pandit SS.Eur J Med Chem. 2017 Jan 27;126:870-878. doi: 10.1016/j.ejmech.2016.12.022. Epub 2016 Dec 10. PMID: 27987486 7:Developing piperlongumine-directed glutathione S-transferase inhibitors by an electrophilicity-based strategy. Wang HB, Jin XL, Zheng JF, Wang F, Dai F, Zhou B.Eur J Med Chem. 2017 Jan 27;126:517-525. doi: 10.1016/j.ejmech.2016.11.034. Epub 2016 Nov 15. PMID: 27914365 8:Discovery of piperlongumine as a potential novel lead for the development of senolytic agents. Wang Y, Chang J, Liu X, Zhang X, Zhang S, Zhang X, Zhou D, Zheng G.Aging (Albany NY). 2016 Nov 19;8(11):2915-2926. doi: 10.18632/aging.101100. PMID: 27913811 Free PMC Article9:Structural and Biochemical Analyses Reveal the Mechanism of Glutathione S-Transferase Pi 1 Inhibition by the Anti-cancer Compound Piperlongumine. Harshbarger W, Gondi S, Ficarro SB, Hunter J, Udayakumar D, Gurbani D, Singer WD, Liu Y, Li L, Marto JA, Westover KD.J Biol Chem. 2017 Jan 6;292(1):112-120. doi: 10.1074/jbc.M116.750299. Epub 2016 Nov 21. PMID: 27872191 10:Two-stage nanoparticle delivery of piperlongumine and tumor necrosis factor-related apoptosis-inducing ligand (TRAIL) anti-cancer therapy. Sharkey CC, Li J, Roy S, Wu Q, King MR.Technology (Singap World Sci). 2016 Mar;4(1):60-69. Epub 2016 Feb 23. PMID: 27853735 Free PMC Article