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

Hodoodo CAT#: H562780

CAS#: 5950-12-9

Description: Piperlonguminine is an inhibitor of Akt/mTOR signalling. It acts by promoting autophagy and mediating cancer cell death.

Chemical Structure

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Piperlonguminine
CAS# 5950-12-9
Instruction

Theoretical Analysis

Hodoodo Cat#: H562780
Name: Piperlonguminine
CAS#: 5950-12-9
Chemical Formula: C16H19NO3
Exact Mass: 273.14
Molecular Weight: 273.332
Elemental Analysis: C, 70.31; H, 7.01; N, 5.12; O, 17.56

Price and Availability

Size Price Availability Quantity
10mg USD 230 2 Weeks
25mg USD 380 2 Weeks
50mg USD 610 2 Weeks
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Synonym: Piperlonguminine; NSC-125178; NSC 125178; NSC125178;

IUPAC/Chemical Name: (2E,4E)-5-(1,3-Benzodioxol-5-yl)-N-(2-methylpropyl)penta-2,4-dienamide

InChi Key: WHAAPCGHVWVUEX-GGWOSOGESA-N

InChi Code: InChI=1S/C16H19NO3/c1-12(2)10-17-16(18)6-4-3-5-13-7-8-14-15(9-13)20-11-19-14/h3-9,12H,10-11H2,1-2H3,(H,17,18)/b5-3+,6-4+

SMILES Code: O=C(NCC(C)C)/C=C/C=C/C1=CC=C(OCO2)C2=C1

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 273.33 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Bosc E, Nastri J, Lefort V, Valli M, Contiguiba F, Pioli R, Furlan M, Bolzani VDS, El Amri C, Reboud-Ravaux M. Piperlongumine and some of its analogs inhibit selectively the human immunoproteasome over the constitutive proteasome. Biochem Biophys Res Commun. 2018 Feb 12;496(3):961-966. doi: 10.1016/j.bbrc.2018.01.100. Epub 2018 Feb 2. PubMed PMID: 29355526.

2: Seok JS, Jeong CH, Petriello MC, Seo HG, Yoo H, Hong K, Han SG. Piperlongumine decreases cell proliferation and the expression of cell cycle-associated proteins by inhibiting Akt pathway in human lung cancer cells. Food Chem Toxicol. 2018 Jan;111:9-18. doi: 10.1016/j.fct.2017.10.058. Epub 2017 Nov 7. PubMed PMID: 29109039.

3: Liu D, Qiu XY, Wu X, Hu DX, Li CY, Yu SB, Pan F, Chen XQ. Piperlongumine suppresses bladder cancer invasion via inhibiting epithelial mesenchymal transition and F-actin reorganization. Biochem Biophys Res Commun. 2017 Dec 9;494(1-2):165-172. doi: 10.1016/j.bbrc.2017.10.061. Epub 2017 Oct 14. PubMed PMID: 29037814.

4: He H, Guo WW, Chen XQ, Zhao HY, Wu X. [Comparative metabolism of three amide alkaloids from Piper longum in five different species of liver microsomes]. Zhongguo Zhong Yao Za Zhi. 2016 Aug;41(16):3084-3089. doi: 10.4268/cjcmm20161624. Chinese. PubMed PMID: 28920353.

5: Wiemann J, Karasch J, Loesche A, Heller L, Brandt W, Csuk R. Piperlongumine B and analogs are promising and selective inhibitors for acetylcholinesterase. Eur J Med Chem. 2017 Oct 20;139:222-231. doi: 10.1016/j.ejmech.2017.07.081. Epub 2017 Aug 2. PubMed PMID: 28802122.

6: Park MJ, Lee DE, Shim MK, Jang EH, Lee JK, Jeong SY, Kim JH. Piperlongumine inhibits TGF-β-induced epithelial-to-mesenchymal transition by modulating the expression of E-cadherin, Snail1, and Twist1. Eur J Pharmacol. 2017 Oct 5;812:243-249. doi: 10.1016/j.ejphar.2017.07.036. Epub 2017 Jul 19. PubMed PMID: 28734931.

7: Zou Y, Yan C, Zhang H, Xu J, Zhang D, Huang Z, Zhang Y. Synthesis and evaluation of N-heteroaromatic ring-based analogs of piperlongumine as potent anticancer agents. Eur J Med Chem. 2017 Sep 29;138:313-319. doi: 10.1016/j.ejmech.2017.06.046. Epub 2017 Jun 27. PubMed PMID: 28686911.

8: Karki K, Hedrick E, Kasiappan R, Jin UH, Safe S. Piperlongumine Induces Reactive Oxygen Species (ROS)-Dependent Downregulation of Specificity Protein Transcription Factors. Cancer Prev Res (Phila). 2017 Aug;10(8):467-477. doi: 10.1158/1940-6207.CAPR-17-0053. Epub 2017 Jul 3. PubMed PMID: 28673967.

9: Sriwiriyajan S, Sukpondma Y, Srisawat T, Madla S, Graidist P. (-)-Kusunokinin and piperloguminine from Piper nigrum: An alternative option to treat breast cancer. Biomed Pharmacother. 2017 Aug;92:732-743. doi: 10.1016/j.biopha.2017.05.130. Epub 2017 Jun 4. PubMed PMID: 28586745.

10: Liu Q, Zhao D, Zhu X, Chen H, Yang Y, Xu J, Zhang Q, Fan A, Li N, Guo C, Kong Y, Lu Y, Chen X. Coloaded Nanoparticles of Paclitaxel and Piperlongumine for Enhancing Synergistic Antitumor Activities and Reducing Toxicity. J Pharm Sci. 2017 Oct;106(10):3066-3075. doi: 10.1016/j.xphs.2017.05.027. Epub 2017 May 26. PubMed PMID: 28552690.

11: Fan L, Cao X, Yan H, Wang Q, Tian X, Zhang L, He X, Borjihan G, Morigen. The synthetic antihyperlipidemic drug potassium piperate selectively kills breast cancer cells through inhibiting G1-S-phase transition and inducing apoptosis. Oncotarget. 2017 Jul 18;8(29):47250-47268. doi: 10.18632/oncotarget.16872. PubMed PMID: 28467790; PubMed Central PMCID: PMC5564562.

12: Zhang Y, Ma H, Wu Y, Wu Z, Yao Z, Zhang W, Zhuang C, Miao Z. Novel non-trimethoxylphenyl piperlongumine derivatives selectively kill cancer cells. Bioorg Med Chem Lett. 2017 Jun 1;27(11):2308-2312. doi: 10.1016/j.bmcl.2017.04.035. Epub 2017 Apr 13. PubMed PMID: 28434764.

13: Jin HO, Park JA, Kim HA, Chang YH, Hong YJ, Park IC, Lee JK. Piperlongumine downregulates the expression of HER family in breast cancer cells. Biochem Biophys Res Commun. 2017 May 13;486(4):1083-1089. doi: 10.1016/j.bbrc.2017.03.166. Epub 2017 Apr 1. PubMed PMID: 28377224.

14: 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. Elevated PRC1 in gastric carcinoma exerts oncogenic function and is targeted by piperlongumine in a p53-dependent manner. J Cell Mol Med. 2017 Jul;21(7):1329-1341. doi: 10.1111/jcmm.13063. Epub 2017 Feb 12. PubMed PMID: 28190297; PubMed Central PMCID: PMC5487922.

15: Xu X, Fang X, Wang J, Zhu H. Identification of novel ROS inducer by merging the fragments of piperlongumine and dicoumarol. Bioorg Med Chem Lett. 2017 Mar 1;27(5):1325-1328. doi: 10.1016/j.bmcl.2016.08.016. Epub 2016 Aug 6. PubMed PMID: 28159415.

16: Gu SM, Yun J, Son DJ, Kim HY, Nam KT, Kim HD, Choi MG, Choi JS, Kim YM, Han SB, Hong JT. Piperlongumine attenuates experimental autoimmune encephalomyelitis through inhibition of NF-kappaB activity. Free Radic Biol Med. 2017 Feb;103:133-145. doi: 10.1016/j.freeradbiomed.2016.12.027. Epub 2016 Dec 21. PubMed PMID: 28011150.

17: Lad NP, Kulkarni S, Sharma R, Mascarenhas M, Kulkarni MR, Pandit SS. Piperlongumine derived cyclic sulfonamides (sultams): Synthesis and in vitro exploration for therapeutic potential against HeLa cancer cell lines. Eur J Med Chem. 2017 Jan 27;126:870-878. doi: 10.1016/j.ejmech.2016.12.022. Epub 2016 Dec 10. PubMed PMID: 27987486.

18: Wang HB, Jin XL, Zheng JF, Wang F, Dai F, Zhou B. Developing piperlongumine-directed glutathione S-transferase inhibitors by an electrophilicity-based strategy. Eur J Med Chem. 2017 Jan 27;126:517-525. doi: 10.1016/j.ejmech.2016.11.034. Epub 2016 Nov 15. PubMed PMID: 27914365.

19: Wang Y, Chang J, Liu X, Zhang X, Zhang S, Zhang X, Zhou D, Zheng G. Discovery of piperlongumine as a potential novel lead for the development of senolytic agents. Aging (Albany NY). 2016 Nov 19;8(11):2915-2926. doi: 10.18632/aging.101100. PubMed PMID: 27913811; PubMed Central PMCID: PMC5191878.

20: Harshbarger W, Gondi S, Ficarro SB, Hunter J, Udayakumar D, Gurbani D, Singer WD, Liu Y, Li L, Marto JA, Westover KD. Structural and Biochemical Analyses Reveal the Mechanism of Glutathione S-Transferase Pi 1 Inhibition by the Anti-cancer Compound Piperlongumine. J Biol Chem. 2017 Jan 6;292(1):112-120. doi: 10.1074/jbc.M116.750299. Epub 2016 Nov 21. PubMed PMID: 27872191; PubMed Central PMCID: PMC5217671.