Piperlongumine | Piplartine | CAS#20069-09-4 | Antimetastatic/antiangiogenic agent

MedKoo Cat#: 406245 | Name: Piperlongumine

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Description:

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

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.

Chemical Structure

Piperlongumine

CAS#20069-09-4

Theoretical Analysis

MedKoo Cat#: 406245

Name: Piperlongumine

CAS#: 20069-09-4

Chemical Formula: C17H19NO5

Exact Mass: 317.1263

Molecular Weight: 317.34

Elemental Analysis: C, 64.34; H, 6.03; N, 4.41; O, 25.21

Price and Availability

Size	Price	Availability	Quantity
100mg	USD 650.00
200mg	USD 950.00
500mg	USD 1,650.00
1g	USD 2,250.00
2g	USD 3,950.00
5g	USD 5,950.00

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Synonym

Piperlongumine; Piplartine.

IUPAC/Chemical Name

(E)-1-(3-(3,4,5-trimethoxyphenyl)acryloyl)-5,6-dihydropyridin-2(1H)-one

InChi Key

VABYUUZNAVQNPG-BQYQJAHWSA-N

InChi Code

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+

SMILES Code

O=C1C=CCCN1C(/C=C/C2=CC(OC)=C(OC)C(OC)=C2)=O

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

>5 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

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Product Data

Product Data

Instruction

View handling instruction

Biological target:

Piperlongumine is a alkaloid, possesses anti-inflammatory, antibacterial, antiangiogenic, antioxidant, antitumor, and antidiabetic activities. Piperlongumine induces ROS, and induces apoptosis in cancer cell lines.

In vitro activity:

Treatment of Panc1 and L3.6pL pancreatic, A549 lung, 786-O kidney, and SKBR3 breast cancer cell lines with 5 to 15 μmol/L piperlongumine inhibited cell proliferation and induced apoptosis and ROS, and these responses were attenuated after cotreatment with the antioxidant glutathione. Piperlongumine also downregulated expression of Sp1, Sp3, Sp4, and several pro-oncogenic Sp-regulated genes, including cyclin D1, survivin, cMyc, EGFR and hepatocyte growth factor receptor (cMet), and these responses were also attenuated after cotreatment with glutathione. Mechanistic studies in Panc1 cells showed that piperlongumine-induced ROS decreased expression of cMyc via an epigenetic pathway, and this resulted in downregulation of cMyc-regulated miRNAs miR-27a, miR-20a, and miR-17 and induction of the transcriptional repressors ZBTB10 and ZBTB4. These repressors target GC-rich Sp-binding sites to decrease transactivation. Reference: Cancer Prev Res (Phila). 2017 Aug;10(8):467-477. https://pubmed.ncbi.nlm.nih.gov/28673967/

In vivo activity:

PANC-1 human pancreatic cancer cells were injected subcutaneously into athymic nude mice. Tumor growth was significantly suppressed in mice treated with 2.4 mg PPLGM (piperlongumine)/kg (daily for 30 days) as compared to those treated with DMSO (1%) vehicle (Fig. 4). PPLGM-treated animals had, on average, tumors that were 50% the mass of tumors from control-treated animals (Table 1). The PPLGM treatment was well-tolerated and no significant changes were detected in overall animal mass or organ mass, as shown in Table 1. Reference: Toxicol Rep. 2014;1:309-318. https://pubmed.ncbi.nlm.nih.gov/25530945/

	Solvent	mg/mL	mM
Solubility
	DMF	20.0	63.02
	DMSO	60.0	189.07
	DMSO:PBS (pH 7.2) (1:10)	0.1	0.32
	Ethanol	0.2	0.47

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 317.34 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.

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:

1. Wu X, Liu Y, An J, Li J, Lv W, Geng S, Zhang Y. Piperlongumine inhibits angiotensin II-induced extracellular matrix expression in cardiac fibroblasts. J Cell Biochem. 2018 Dec;119(12):10358-10364. doi: 10.1002/jcb.27379. Epub 2018 Aug 26. PMID: 30145839. 2. 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. PMID: 28673967; PMCID: PMC6357769. 3. Zou P, Xia Y, Ji J, Chen W, Zhang J, Chen X, Rajamanickam V, Chen G, Wang Z, Chen L, Wang Y, Yang S, Liang G. Piperlongumine as a direct TrxR1 inhibitor with suppressive activity against gastric cancer. Cancer Lett. 2016 May 28;375(1):114-126. doi: 10.1016/j.canlet.2016.02.058. Epub 2016 Mar 7. PMID: 26963494. 4. Dhillon H, Chikara S, Reindl KM. Piperlongumine induces pancreatic cancer cell death by enhancing reactive oxygen species and DNA damage. Toxicol Rep. 2014;1:309-318. doi: 10.1016/j.toxrep.2014.05.011. PMID: 25530945; PMCID: PMC4268771.

In vitro protocol:

In vivo protocol:

1. Zou P, Xia Y, Ji J, Chen W, Zhang J, Chen X, Rajamanickam V, Chen G, Wang Z, Chen L, Wang Y, Yang S, Liang G. Piperlongumine as a direct TrxR1 inhibitor with suppressive activity against gastric cancer. Cancer Lett. 2016 May 28;375(1):114-126. doi: 10.1016/j.canlet.2016.02.058. Epub 2016 Mar 7. PMID: 26963494. 2. Dhillon H, Chikara S, Reindl KM. Piperlongumine induces pancreatic cancer cell death by enhancing reactive oxygen species and DNA damage. Toxicol Rep. 2014;1:309-318. doi: 10.1016/j.toxrep.2014.05.011. PMID: 25530945; PMCID: PMC4268771.

1: Tran TTP, Dang NH, Nguyen XN, Pham HT, Phan UTT, Le TH. Alkaloids from Piper longum L and Their Anti-inflammatory Properties. Chem Biodivers. 2024 Aug 16:e202401224. doi: 10.1002/cbdv.202401224. Epub ahead of print. PMID: 39149874. 2: Schlichter Kadosh Y, Muthuraman S, Nisaa K, Ben-Zvi A, Karsagi Byron DL, Shagan M, Brandis A, Mehlman T, Gopas J, Saravana Kumar R, Kushmaro A. Pseudomonas aeruginosa quorum sensing and biofilm attenuation by a di- hydroxy derivative of piperlongumine (PL-18). Biofilm. 2024 Jul 18;8:100215. doi: 10.1016/j.bioflm.2024.100215. PMID: 39148892; PMCID: PMC11326495. 3: Shu L, Luo P, Chen Q, Liu J, Huang Y, Wu C, Pan X, Huang Z. Fibroin nanodisruptor with Ferroptosis-Autophagy synergism is potent for lung cancer treatment. Int J Pharm. 2024 Aug 12;664:124582. doi: 10.1016/j.ijpharm.2024.124582. Epub ahead of print. PMID: 39142466. 4: Loying R, Sharmah B, Barman H, Borah A, Bora HK, Kalita J, Manna P. Anti- inflammatory potential of Piper betleoides C. DC., a promising Piper species of Northeast India: in vitro and in vivo evidence and mechanistic insight. Inflammopharmacology. 2024 Aug 10. doi: 10.1007/s10787-024-01539-3. Epub ahead of print. PMID: 39126574. 5: Zallocchi M, Vijayakumar S, Fleegel J, Batalkina L, Brunette KE, Shukal D, Chen Z, Devuyst O, Liu H, He DZZ, Imami AS, Hamoud AA, McCullumsmith R, Conda- Sheridan M, De Campos LJ, Zuo J. Piplartine attenuates aminoglycoside-induced TRPV1 activity and protects from hearing loss in mice. Sci Transl Med. 2024 Aug 7;16(759):eadn2140. doi: 10.1126/scitranslmed.adn2140. Epub 2024 Aug 7. PMID: 39110778. 6: Piao M, Jin Y, Jin S, Min J, Lee SH, Cho YC, Lee KY. Piperlongumine inhibits the early stage of adipogenesis in 3T3-L1 cells. Biochem Biophys Res Commun. 2024 Jul 30;735:150458. doi: 10.1016/j.bbrc.2024.150458. Epub ahead of print. PMID: 39098274. 7: Zou Y, He Y, Tan L, Xu X, Qi C, Zhang Y. Discovery of Cytotoxic Nitric Oxide- Releasing Piperlongumine Derivatives Targeting Wnt/β-Catenin in Colon Cancer Cells. J Nat Prod. 2024 Aug 23;87(8):1893-1902. doi: 10.1021/acs.jnatprod.4c00084. Epub 2024 Jul 24. PMID: 39045852. 8: Jangid AK, Kim S, Kim K. Delivery of piperlongumine via hyaluronic acid/phenylboronic acid-mediated dual targetable polymersome for enhanced anticancer functionality against pancreatic tumor. Int J Biol Macromol. 2024 Aug;275(Pt 2):133738. doi: 10.1016/j.ijbiomac.2024.133738. Epub 2024 Jul 9. PMID: 38992536. 9: Tchelougou D, Malaquin N, Cardin GB, Desmul J, Turcotte S, Rodier F. Defining melanoma combination therapies that provide senolytic sensitivity in human melanoma cells. Front Cell Dev Biol. 2024 Jun 14;12:1368711. doi: 10.3389/fcell.2024.1368711. PMID: 38946802; PMCID: PMC11211604. 10: Lee KH, Kang DG, Kim DW, Do HK, Kim DY, Kim W. Piperlongumine regulates genes involved in the skin barrier in epidermal keratinocyte HaCaT cells. Anim Cells Syst (Seoul). 2024 Jun 25;28(1):326-339. doi: 10.1080/19768354.2024.2361144. PMID: 38933927; PMCID: PMC11207940. 11: Zou Y, Wan X, Ding Z, Tang C, Wang C, Chen X. Design, synthesis, and biological studies of nitric oxide-donating piperlongumine derivatives triggered by lysyl oxidase as anti-triple negative breast cancer agents. Fitoterapia. 2024 Sep;177:106091. doi: 10.1016/j.fitote.2024.106091. Epub 2024 Jun 20. PMID: 38908760. 12: Golubnitschaja O, Kapinova A, Sargheini N, Bojkova B, Kapalla M, Heinrich L, Gkika E, Kubatka P. Mini-encyclopedia of mitochondria-relevant nutraceuticals protecting health in primary and secondary care-clinically relevant 3PM innovation. EPMA J. 2024 Apr 18;15(2):163-205. doi: 10.1007/s13167-024-00358-4. PMID: 38841620; PMCID: PMC11148002. 13: Zhang HX, Lin LF, Liu YL, Li H. [Research progress in anti-tumor activity and nano-drug delivery system of piperlongumine]. Zhongguo Zhong Yao Za Zhi. 2024 Apr;49(8):2117-2127. Chinese. doi: 10.19540/j.cnki.cjcmm.20231206.301. PMID: 38812227. 14: Chi Y, Zhu X, Chen Y, Li X, Jiang Z, Jian X, Lian M, Wu X, Wang L, Sun M, Shi X. Metabolic activation and cytochrome P450 inhibition of piperlonguminine mediated by CYP3A4. Int J Biol Macromol. 2024 May;268(Pt 2):131502. doi: 10.1016/j.ijbiomac.2024.131502. Epub 2024 Apr 16. PMID: 38626834. 15: Swain SS, Sahoo SK. Piperlongumine and its derivatives against cancer: A recent update and future prospective. Arch Pharm (Weinheim). 2024 Jul;357(7):e2300768. doi: 10.1002/ardp.202300768. Epub 2024 Apr 9. PMID: 38593312. 16: Zhong Y, Zheng C, Zhang W, Wu H, Zhang Q, Li D, Ju H, Feng H, Chen Y, Fan Y, Chen W, Wang M, Wang G. Pan-cancer analysis of Sushi domain-containing protein 4 (SUSD4) and validated in colorectal cancer. Aging (Albany NY). 2024 Apr 4;16(7):6417-6444. doi: 10.18632/aging.205712. Epub 2024 Apr 4. PMID: 38579174; PMCID: PMC11042942. 17: Kang HJ, Truong Hoang Q, Min J, Son MS, Tram LTH, Kim BC, Song Y, Shim MS. Efficient Combination Chemo-Sonodynamic Cancer Therapy Using Mitochondria- Targeting Sonosensitizer-Loaded Polysorbate-Based Micelles. Int J Mol Sci. 2024 Mar 20;25(6):3474. doi: 10.3390/ijms25063474. PMID: 38542447; PMCID: PMC10971048. 18: Zhang Q, Hui M, Chen G, Huang H, Wang S, Ye Y, Wang Y, Wang M, Zhang S, Huang L, Zhang F, Liu Z. Curcumin-Piperlongumine Hybrid Molecule Increases Cell Cycle Arrest and Apoptosis in Lung Cancer through JNK/c-Jun Signaling Pathway. J Agric Food Chem. 2024 Apr 3;72(13):7244-7255. doi: 10.1021/acs.jafc.4c00882. Epub 2024 Mar 22. PMID: 38517372. 19: Rodrigues ACBDC, Silva SLR, Dias IRSB, Costa RGA, Oliveira MS, Soares MBP, Dias RB, Valverde LF, Rocha CAG, Johnson EM, Pina C, Bezerra DP. Piplartine eliminates CD34 + AML stem/progenitor cells by inducing oxidative stress and suppressing NF-κB signalling. Cell Death Discov. 2024 Mar 19;10(1):147. doi: 10.1038/s41420-024-01909-4. PMID: 38503729; PMCID: PMC10951277. 20: Sa P, Singh P, Panda S, Swain RK, Dash R, Sahoo SK. Reversal of cisplatin resistance in oral squamous cell carcinoma by piperlongumine loaded smart nanoparticles through inhibition of Hippo-YAP signaling pathway. Transl Res. 2024 Jun;268:63-78. doi: 10.1016/j.trsl.2024.03.004. Epub 2024 Mar 16. PMID: 38499286.