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MedKoo Cat#: 562780 | Name: Piperlonguminine
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Description:

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

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

Chemical Structure

Piperlonguminine
Piperlonguminine
CAS#5950-12-9

Theoretical Analysis

MedKoo Cat#: 562780

Name: Piperlonguminine

CAS#: 5950-12-9

Chemical Formula: C16H19NO3

Exact Mass: 273.1365

Molecular Weight: 273.33

Elemental Analysis: C, 70.31; H, 7.01; N, 5.12; O, 17.56

Price and Availability

Size Price Availability Quantity
10mg USD 600.00
25mg USD 900.00
50mg USD 1,325.00
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Related CAS #
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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
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Piperlonguminine is an inhibitor of Akt/mTOR signalling.
In vitro activity:
The present study evaluated the effect of piperlongumine on cell proliferation, cell cycle, apoptosis, and autophagy in FTC cells with flowcytometry and Western blot. This study observed that piperlongumine caused growth inhibition, cell cycle arrest, apoptosis induction, and autophagy elevation in FTC cells. Activities of reactive oxygen species and the downstream PI3K/Akt pathway were the underlying mechanisms involved in piperlongumine mediated anti-FTC effects. Reference: Int J Mol Sci. 2023 Apr 28;24(9):8048. https://pubmed.ncbi.nlm.nih.gov/37175755/
In vivo activity:
The aim of this study was to explore the therapeutic potential of piperlonguminine on SAP-induced lung injury in rat models. This study found that piperlonguminine significantly ameliorated pulmonary architectural distortion, hemorrhage, interstitial edema, and alveolar thickening in rats with SAP. In addition, NOX2, NOX4, ROS, and inflammatory cytokine levels in pulmonary tissues were notably decreased in piperlonguminine-treated rats. Piperlonguminine also attenuated the expression levels of toll-like receptor 4 (TLR4) and nuclear factor-kappa B (NF-κB). Reference: Eur J Histochem. 2023 Mar 20;67(2):3639. https://pubmed.ncbi.nlm.nih.gov/36951266/
Solvent mg/mL mM comments
Solubility
DMF 20.0 73.17
DMSO 20.0 73.17
DMSO:PBS (pH 7.2) (1:2) 5.0 18.29
Ethanol 3.0 10.98
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 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:
1. Lin TH, Kuo CH, Zhang YS, Chen PT, Chen SH, Li YZ, Lee YR. Piperlongumine Induces Cellular Apoptosis and Autophagy via the ROS/Akt Signaling Pathway in Human Follicular Thyroid Cancer Cells. Int J Mol Sci. 2023 Apr 28;24(9):8048. doi: 10.3390/ijms24098048. PMID: 37175755; PMCID: PMC10179299. 2. Zhou L, Wu K, Gao Y, Qiao R, Tang N, Dong D, Li XQ, Nong Q, Luo DQ, Xiao Q, Fan X, Duan Q, Cao W. Piperlonguminine attenuates renal fibrosis by inhibiting TRPC6. J Ethnopharmacol. 2023 Apr 29;313:116561. doi: 10.1016/j.jep.2023.116561. Epub ahead of print. PMID: 37121453. 3. Hu Q, Tao R, Hu X, Wu H, Xu J. Effects of piperlonguminine on lung injury in severe acute pancreatitis via the TLR4/NF-κB pathway. Eur J Histochem. 2023 Mar 20;67(2):3639. doi: 10.4081/ejh.2023.3639. PMID: 36951266; PMCID: PMC10080291. 4. Yang T, Sun S, Wang T, Tong X, Bi J, Wang Y, Sun Z. Piperlonguminine is neuroprotective in experimental rat stroke. Int Immunopharmacol. 2014 Dec;23(2):447-51. doi: 10.1016/j.intimp.2014.09.016. Epub 2014 Sep 22. PMID: 25257731.
In vitro protocol:
1. Lin TH, Kuo CH, Zhang YS, Chen PT, Chen SH, Li YZ, Lee YR. Piperlongumine Induces Cellular Apoptosis and Autophagy via the ROS/Akt Signaling Pathway in Human Follicular Thyroid Cancer Cells. Int J Mol Sci. 2023 Apr 28;24(9):8048. doi: 10.3390/ijms24098048. PMID: 37175755; PMCID: PMC10179299. 2. Zhou L, Wu K, Gao Y, Qiao R, Tang N, Dong D, Li XQ, Nong Q, Luo DQ, Xiao Q, Fan X, Duan Q, Cao W. Piperlonguminine attenuates renal fibrosis by inhibiting TRPC6. J Ethnopharmacol. 2023 Apr 29;313:116561. doi: 10.1016/j.jep.2023.116561. Epub ahead of print. PMID: 37121453.
In vivo protocol:
1. Hu Q, Tao R, Hu X, Wu H, Xu J. Effects of piperlonguminine on lung injury in severe acute pancreatitis via the TLR4/NF-κB pathway. Eur J Histochem. 2023 Mar 20;67(2):3639. doi: 10.4081/ejh.2023.3639. PMID: 36951266; PMCID: PMC10080291. 2. Yang T, Sun S, Wang T, Tong X, Bi J, Wang Y, Sun Z. Piperlonguminine is neuroprotective in experimental rat stroke. Int Immunopharmacol. 2014 Dec;23(2):447-51. doi: 10.1016/j.intimp.2014.09.016. Epub 2014 Sep 22. PMID: 25257731.
1: Sruthi D, John Zachariah T. Volatile and non-volatile metabolite profiling of under-explored crop Piper colubrinum Link. with chromatography mass spectrometry approach and its biochemical diversity from medicinally valued Piper species. J Chromatogr B Analyt Technol Biomed Life Sci. 2024 Aug 3;1245:124260. doi: 10.1016/j.jchromb.2024.124260. Epub ahead of print. PMID: 39178608. 2: 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. 3: 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. 4: Liao CP, Dong SQ, Liu YL, Enirile, Gao Y, Fan HR, Cai QJ, Dai JG, Tu Y. [Intestinal absorption components and absorption characteristics of Wuwei Qingzhuo San by everted intestinal sac models]. Zhongguo Zhong Yao Za Zhi. 2024 Jan;49(2):509-517. Chinese. doi: 10.19540/j.cnki.cjcmm.20230728.201. PMID: 38403326. 5: Jo HG, Baek CY, Kim D, Kim S, Han Y, Park C, Song HS, Lee D. Network analysis, in vivo, and in vitro experiments identified the mechanisms by which Piper longum L. [Piperaceae] alleviates cartilage destruction, joint inflammation, and arthritic pain. Front Pharmacol. 2024 Jan 24;14:1282943. doi: 10.3389/fphar.2023.1282943. PMID: 38328576; PMCID: PMC10847597. 6: Luo N, Zhang L, Xiu C, Luo X, Hu S, Ji K, Liu Q, Chen J. Piperlongumine, a Piper longum-derived amide alkaloid, protects mice from ovariectomy- induced osteoporosis by inhibiting osteoclastogenesis via suppression of p38 and JNK signaling. Food Funct. 2024 Feb 19;15(4):2154-2169. doi: 10.1039/d3fo03830k. PMID: 38311970. 7: Baranoski A, Semprebon SC, Biazi BI, Zanetti TA, Corveloni AC, Areal Marques L, Lepri SR, Coatti GC, Mantovani MS. Piperlongumine inhibits antioxidant enzymes, increases ROS levels, induces DNA damage and G2/M cell cycle arrest in breast cell lines. J Toxicol Environ Health A. 2024 Apr 2;87(7):294-309. doi: 10.1080/15287394.2024.2308801. Epub 2024 Feb 5. PMID: 38279841. 8: Ibrahim FAR, Hussein NA, Soliman AYM, Shalaby TI, Rashad MM, Matar NA, El- Sewedy TS. Chitosan-loaded piperlongumine nanoparticles and kaempferol enhance the anti-cancer action of doxorubicin in targeting of Ehrlich solid adenocarcinoma: in vivo and in silico modeling study. Med Oncol. 2024 Jan 23;41(2):61. doi: 10.1007/s12032-023-02282-5. PMID: 38253759; PMCID: PMC10803394. 9: Cui Y, Chen XB, Liu Y, Wang Q, Tang J, Chen MJ. Piperlongumine inhibits esophageal squamous cell carcinoma in vitro and in vivo by triggering NRF2/ROS/TXNIP/NLRP3-dependent pyroptosis. Chem Biol Interact. 2024 Feb 25;390:110875. doi: 10.1016/j.cbi.2024.110875. Epub 2024 Jan 18. PMID: 38242274. 10: Mandal SK, Rehman MM, Katyal A, Rajvanshi K, Kannan M, Garg M, Murugesan S, Deepa PR. In silico anti-viral assessment of phytoconstituents in a traditional (Siddha Medicine) polyherbal formulation - Targeting Mpro and pan- coronavirus post-fusion Spike protein. J Tradit Complement Med. 2023 Jul 13;14(1):55-69. doi: 10.1016/j.jtcme.2023.07.004. PMID: 38223813; PMCID: PMC10785248. 11: Ishaniya W, Sumithaa C, Subramani M, Karanath-Anilkumar A, Munuswamy- Ramanujam G, Madan Kumar A, Rajendran S, Ganeshpandian M. Polydiacetylene/lipid- coated red-emissive silica nanorods for the sustained release and ameliorated anticancer efficacy of a Ru(arene) complex bearing piperlongumine natural product. Dalton Trans. 2024 Jan 23;53(4):1616-1629. doi: 10.1039/d3dt02940a. PMID: 38165714. 12: Zhang X, He Y, Liu X, Zhang X, Shi P, Wang Y, Zhou D, Zheng G. Design and optimization of piperlongumine analogs as potent senolytics. Bioorg Med Chem Lett. 2024 Jan 15;98:129593. doi: 10.1016/j.bmcl.2023.129593. Epub 2023 Dec 15. PMID: 38104906. 13: Singh P, Sen K, Sa P, Khuntia A, Raghav SK, Swain RK, Sahoo SK. Piperlongumine based nanomedicine impairs glycolytic metabolism in triple negative breast cancer stem cells through modulation of GAPDH & FBP1. Phytomedicine. 2024 Jan;123:155181. doi: 10.1016/j.phymed.2023.155181. Epub 2023 Nov 2. PMID: 38091824. 14: Noguchi K, Teramura M, Kitagawa A, Ejima M, Ueda C, Kanae H. Relaxant Effects of Piperine and Piperlongumine from Piper longum Fruits on Porcine Coronary Artery. Biol Pharm Bull. 2024 Jan 1;47(1):130-137. doi: 10.1248/bpb.b23-00694. Epub 2023 Nov 21. PMID: 37989300. 15: Kumar M, Sahoo GC, Ansari WA, Mohammad AA, Mohammad AF, Lee J. Molecular docking analysis of Omt-A protein model from Aspergillus flavus with synthetic compounds. Bioinformation. 2023 Oct 31;19(10):990-994. doi: 10.6026/97320630019990. PMID: 37969662; PMCID: PMC10640793. 16: Singh I, Das R, Kumar A. Network pharmacology-based anti-colorectal cancer activity of piperlonguminine in the ethanolic root extract of Piper longum L. Med Oncol. 2023 Oct 5;40(11):320. doi: 10.1007/s12032-023-02185-5. PMID: 37796360. 17: Zhou L, Wu K, Gao Y, Qiao R, Tang N, Dong D, Li XQ, Nong Q, Luo DQ, Xiao Q, Fan X, Duan Q, Cao W. Piperlonguminine attenuates renal fibrosis by inhibiting TRPC6. J Ethnopharmacol. 2023 Sep 15;313:116561. doi: 10.1016/j.jep.2023.116561. Epub 2023 Apr 29. PMID: 37121453. 18: Hu Q, Tao R, Hu X, Wu H, Xu J. Effects of piperlonguminine on lung injury in severe acute pancreatitis via the TLR4/NF-κB pathway. Eur J Histochem. 2023 Mar 20;67(2):3639. doi: 10.4081/ejh.2023.3639. PMID: 36951266; PMCID: PMC10080291. 19: Meng H, Li S, Li Q, Wang Y, Wang G, Qu Y. Chemokine-like factor-like MARVEL transmembrane domain containing 6: Bioinformatics and experiments in vitro analyze in glioblastoma multiforme. Front Mol Neurosci. 2023 Jan 9;15:1026927. doi: 10.3389/fnmol.2022.1026927. PMID: 36698778; PMCID: PMC9869805. 20: Goswami MJ, Dutta U, Seema T, Bharali SJ, Yanka H, Tag H, Bharali P, Kakati D. Antioxidant and Antidiabetic Properties of Extracts from Three Underutilized Food Plants of North East India. Chem Biodivers. 2023 Feb;20(2):e202200718. doi: 10.1002/cbdv.202200718. Epub 2023 Jan 10. PMID: 36562215.