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Piperlongumine

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https://www.readbyqxmd.com/read/28802122/piperlongumine-b-and-analogs-are-promising-and-selective-inhibitors-for-acetylcholinesterase
#1
Jana Wiemann, Julia Karasch, Anne Loesche, Lucie Heller, Wolfgang Brandt, René Csuk
Piperlongumine B (19), an alkaloid previously isolated from long pepper (Piper longum) has been synthesized for the first time in a short sequence and in good yield together with 19 analogs. Screening of these compounds in Ellman's assays showed several of them to be good inhibitors of acetylcholinesterase while being less active for butyrylcholinesterase. Activity of the compounds increased with the ring size of the heterocycle, and a maximum of activity was observed for an analog holding 12 methylene groups in the aliphatic side chain...
August 2, 2017: European Journal of Medicinal Chemistry
https://www.readbyqxmd.com/read/28734931/piperlongumine-inhibits-tgf-%C3%AE-induced-epithelial-to-mesenchymal-transition-by-modulating-the-expression-of-e-cadherin-snail1-and-twist1
#2
Min-Ju Park, Da-Eun Lee, Man Kyu Shim, Eun Hyang Jang, Jong Kil Lee, Seo Young Jeong, Jong-Ho Kim
Cancer is a life-threatening disease, and the occurrence of metastasis, which increases the lethality of primary tumors, is increasing. The epithelial-to-mesenchymal transition (EMT) is a biological process by which epithelial cells lose cell-cell adhesion properties and acquire mesenchymal properties, including motility and invasiveness. EMT is considered an early stage of metastasis; therefore, inhibiting EMT may be an effective anticancer therapy. In the present study, the antimetastatic effect of piperlongumine (PL) was assessed in human cancer cells...
July 19, 2017: European Journal of Pharmacology
https://www.readbyqxmd.com/read/28686911/synthesis-and-evaluation-of-n-heteroaromatic-ring-based-analogs-of-piperlongumine-as-potent-anticancer-agents
#3
Yu Zou, Chang Yan, Huibin Zhang, Jinyi Xu, Dayong Zhang, Zhangjian Huang, Yihua Zhang
Piperlongumine (PL) selectively targets a wide spectrum of cancer cells and induces their death by triggering various pathways, including apoptosis, necrosis and autophagy. However, the poor solubility is a serious concern for intensive study and clinical application. We synthesized its analogs 1-9 by replacement of the trimethoxyphenyl of PL with an N-heteroaromatic ring and/or not introduction of 2-Cl. These compounds improved aqueous solubility and displayed potent anticancer activity. The most active compound 9 selectively enhanced ROS levels in colon cancer cells and inhibited the cell proliferation but sparing non-tumor colon cells...
June 27, 2017: European Journal of Medicinal Chemistry
https://www.readbyqxmd.com/read/28673967/piperlongumine-induces-reactive-oxygen-species-ros-dependent-downregulation-of-specificity-protein-transcription-factors
#4
Keshav Karki, Erik Hedrick, Ravi Kasiappan, Un-Ho Jin, Stephen Safe
Piperlongumine is a natural product found in the plant species Piper longum, and this compound exhibits potent anticancer activity in multiple tumor types and has been characterized as an inducer of reactive oxygen species (ROS). 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...
August 2017: Cancer Prevention Research
https://www.readbyqxmd.com/read/28552690/co-loaded-nanoparticles-of-paclitaxel-and-piperlongumine-for-enhancing-synergistic-anti-tumor-activities-and-reducing-toxicity
#5
Qi Liu, Di Zhao, Xiaojie Zhu, Huili Chen, Yue Yang, Jiaqiu Xu, Qing Zhang, Ali Fan, Ning Li, Chaorui Guo, Ying Kong, Yang Lu, Xijing Chen
The purpose of this study was to develop a nano-carrier system for co-delivery of paclitaxel (PTX) and piperlongumine (PL) and investigate the therapeutic potential of improving efficacy and reducing toxicity. PTX and PL were formulated into poly lactic-co-glycolic acid (PLGA) and D-α-tocopheryl polyethylene glycol succinate (TPGS) via organic solvent evaporation method. The average diameter was 117.1 ± 1.9 nm and the zeta potential was -43.25 ± 2.76 mV. PL facilitated the cellular uptake of PTX and the increased cytotoxicity was similarly displayed...
May 25, 2017: Journal of Pharmaceutical Sciences
https://www.readbyqxmd.com/read/28538206/spectroscopic-far-or-terahertz-mid-infrared-and-raman-investigation-thermal-analysis-and-biological-activity-of-piplartine
#6
Anubha Srivastava, T Karthick, B D Joshi, Rashmi Mishra, Poonam Tandon, A P Ayala, Javier Ellena
Research in the field of medicinal plants including Piper species like long pepper (Piper longum L.- Piperaceae) is increasing all over the world due to its use in traditional and Ayurvedic medicine. Piplartine (piperlongumine, 5,6-dihydro-1-[(2E)-1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propenyl]-2(1H)-pyridinone), a biologically active alkaloid/amide was isolated from the phytochemical investigations of Piper species, as long pepper. This alkaloid has cytotoxic, anti-fungal, anti-diabetic, anti-platelet aggregation, anti-tumoral, anxiolytic, anti-depressant, anti-leishmanial, and genotoxic activities, but, its anticancer property is the most promising and has been widely explored...
May 5, 2017: Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy
https://www.readbyqxmd.com/read/28439094/selective-targeting-of-cancer-cells-by-oxidative-vulnerabilities-with-novel-curcumin-analogs
#7
Christopher Pignanelli, Dennis Ma, Megan Noel, Jesse Ropat, Fadi Mansour, Colin Curran, Simon Pupulin, Kristen Larocque, Jianzhang Wu, Guang Liang, Yi Wang, Siyaram Pandey
Recently, research has focused on targeting the oxidative and metabolic vulnerabilities in cancer cells. Natural compounds like curcumin that target such susceptibilities have failed further clinical advancements due to the poor stability and bioavailability as well as the need of high effective doses. We have synthesized and evaluated the anti-cancer activity of several monocarbonyl analogs of curcumin. Interestingly, two novel analogs (Compound A and I) in comparison to curcumin, have increased chemical stability and have greater anti-cancer activity in a variety of human cancer cells, including triple-negative, inflammatory breast cancer cells...
April 24, 2017: Scientific Reports
https://www.readbyqxmd.com/read/28434764/novel-non-trimethoxylphenyl-piperlongumine-derivatives-selectively-kill-cancer-cells
#8
Youjun Zhang, Hao Ma, Yuelin Wu, Zhongli Wu, Zhengguang Yao, Wannian Zhang, Chunlin Zhuang, Zhenyuan Miao
Piperlongumine (PL) is a natural alkaloid with broad biological activities. Twelve analogues have been designed and synthesized with non-substituted benzyl rings or heterocycles in this work. Most of the compounds showed better anticancer activities than the parent PL without apparent toxicity in normal cells. Elevation of cellular ROS levels was one of the main anticancer mechanisms of these compounds. Cell apoptosis and cell cycle arrest for the best compound ZM90 were evaluated and similar mechanism of action with PL was demonstrated...
April 13, 2017: Bioorganic & Medicinal Chemistry Letters
https://www.readbyqxmd.com/read/28377224/piperlongumine-downregulates-the-expression-of-her-family-in-breast-cancer-cells
#9
Hyeon-Ok Jin, Jin-Ah Park, Hyun-Ah Kim, Yoon Hwan Chang, Young Jun Hong, In-Chul Park, Jin Kyung Lee
HER family receptors are frequently deregulated in breast cancer and the deregulation of these receptors is associated with poor prognosis. Thus, these receptors are considered therapeutic targets. In the present study, we found that piperlongumine (PL) downregulates the expression of HER family receptors HER1, HER2, and HER3 in breast cancer cells. Downregulation of these receptors by PL is mediated through the generation of reactive oxygen species (ROS), as N-acetyl-cysteine blocks it. Interestingly, the HER2-overexpressing cell lines BT474 and SkBr3 are somewhat more sensitive to PL than the low HER2-expressing cell line MCF7...
May 13, 2017: Biochemical and Biophysical Research Communications
https://www.readbyqxmd.com/read/28273655/new-agents-that-target-senescent-cells-the-flavone-fisetin-and-the-bcl-xl-inhibitors-a1331852-and-a1155463
#10
Yi Zhu, Ewald J Doornebal, Tamar Pirtskhalava, Nino Giorgadze, Mark Wentworth, Heike Fuhrmann-Stroissnigg, Laura J Niedernhofer, Paul D Robbins, Tamara Tchkonia, James L Kirkland
Senescent cells accumulate with aging and at sites of pathology in multiple chronic diseases. Senolytics are drugs that selectively promote apoptosis of senescent cells by temporarily disabling the pro-survival pathways that enable senescent cells to resist the pro-apoptotic, pro-inflammatory factors that they themselves secrete. Reducing senescent cell burden by genetic approaches or by administering senolytics delays or alleviates multiple age- and disease-related adverse phenotypes in preclinical models...
March 8, 2017: Aging
https://www.readbyqxmd.com/read/28159415/identification-of-novel-ros-inducer-by-merging-the-fragments-of-piperlongumine-and-dicoumarol
#11
Xiaojuan Xu, Xia Fang, Jun Wang, Hong Zhu
A series of novel ROS inducers were designed by merging the fragments of piperlongumine and dicoumarol. Most of these derivatives showed potent in vitro activity against three cancer cell lines and good selectivity towards normal lung cells. The most potent and selective compound 3e was proven to exhibit obvious ROS elevation and excellent in vivo antitumor activity with suppressed tumor growth by 48.46% at the dose of 5mg/kg. Supported by these investigation, these findings encourage further investigation around this interesting antitumor chemotype...
August 6, 2016: Bioorganic & Medicinal Chemistry Letters
https://www.readbyqxmd.com/read/28011150/piperlongumine-attenuates-experimental-autoimmune-encephalomyelitis-through-inhibition-of-nf-kappab-activity
#12
Sun Mi Gu, Jaesuk Yun, Dong Ju Son, Hoi Yeong Kim, Kyung Tak Nam, Hae Deun Kim, Min Gi Choi, Jeong Soon Choi, Young Min Kim, Sang-Bae Han, Jin Tae Hong
Multiple sclerosis (MS) is a chronic, autoimmune and neurodegenerative disease in which demyelination sporadically and repeatedly occurs in the central nervous system (CNS). The activity of nuclear factor kappa B (NF-κB), a family of transcription factors, was increased in the cerebrospinal fluid (CSF) and/or the serum and brain and/or spinal cord of MS patients than in a healthy donors. In our study, we investigated whether piperlongumine (PL), which is known to have inhibitory effect on activity of NF-κB, can alleviate an experimental autoimmune encephalomyelitis (EAE)...
December 21, 2016: Free Radical Biology & Medicine
https://www.readbyqxmd.com/read/27987486/piperlongumine-derived-cyclic-sulfonamides-sultams-synthesis-and-in%C3%A2-vitro-exploration-for-therapeutic-potential-against-hela-cancer-cell-lines
#13
Nitin P Lad, Sarang Kulkarni, Rajiv Sharma, Malcolm Mascarenhas, Mahesh R Kulkarni, Shivaji S Pandit
A novel modification of piperlongumine is designed, bearing a cyclic sulphonamide (sultam) and its synthesis is described. For the first time herein we report the synthesis and biological evaluation of the natural product derived cyclic sulfonamides using Grubbs second generation catalyst (Grubbs II) via ring closing metathesis approach. Synthesis of a series of piperlongumine derived sultams is done in a moderate to good yield using Wittig reaction, Ring-Closing Metathesis (RCM) and, amide synthesis by using mixed anhydride, approach...
January 27, 2017: European Journal of Medicinal Chemistry
https://www.readbyqxmd.com/read/27914365/developing-piperlongumine-directed-glutathione-s-transferase-inhibitors-by-an-electrophilicity-based-strategy
#14
Hai-Bo Wang, Xiao-Ling Jin, Jia-Fang Zheng, Fu Wang, Fang Dai, Bo Zhou
We report a case of successful design of glutathione S-transferase (GST) inhibitors via a natural product-inspired and electrophilicity-based strategy. Based on this strategy, a novel piperlongumine analog (PL-13) bearing a para-trifluoromethyl group and an α-chlorine on its aromatic and lactam rings, respectively, surfaced as a promising GST inhibitor, thereby overcoming cisplatin resistance in lung cancer A549 cells.
January 27, 2017: European Journal of Medicinal Chemistry
https://www.readbyqxmd.com/read/27913811/discovery-of-piperlongumine-as-a-potential-novel-lead-for-the-development-of-senolytic-agents
#15
Yingying Wang, Jianhui Chang, Xingui Liu, Xuan Zhang, Suping Zhang, Xin Zhang, Daohong Zhou, Guangrong Zheng
Accumulating evidence indicates that senescent cells play an important role in many age-associated diseases. The pharmacological depletion of senescent cells (SCs) with a "senolytic agent", a small molecule that selectively kills SCs, is a potential novel therapeutic approach for these diseases. Recently, we discovered ABT-263, a potent and highly selective senolytic agent, by screening a library of rationally-selected compounds. With this screening approach, we also identified a second senolytic agent called piperlongumine (PL)...
November 19, 2016: Aging
https://www.readbyqxmd.com/read/27872191/structural-and-biochemical-analyses-reveal-the-mechanism-of-glutathione-s-transferase-pi-1-inhibition-by-the-anti-cancer-compound-piperlongumine
#16
Wayne Harshbarger, Sudershan Gondi, Scott B Ficarro, John Hunter, Durga Udayakumar, Deepak Gurbani, William D Singer, Yan Liu, Lianbo Li, Jarrod A Marto, Kenneth D Westover
Glutathione S-transferase pi 1 (GSTP1) is frequently overexpressed in cancerous tumors and is a putative target of the plant compound piperlongumine (PL), which contains two reactive olefins and inhibits proliferation in cancer cells but not normal cells. PL exposure of cancer cells results in increased reactive oxygen species and decreased GSH. These data in tandem with other information led to the conclusion that PL inhibits GSTP1, which forms covalent bonds between GSH and various electrophilic compounds, through covalent adduct formation at the C7-C8 olefin of PL, whereas the C2-C3 olefin of PL was postulated to react with GSH...
January 6, 2017: Journal of Biological Chemistry
https://www.readbyqxmd.com/read/27853735/two-stage-nanoparticle-delivery-of-piperlongumine-and-tumor-necrosis-factor-related-apoptosis-inducing-ligand-trail-anti-cancer-therapy
#17
Charles C Sharkey, Jiahe Li, Sweta Roy, Qianhui Wu, Michael R King
This study outlines a drug delivery mechanism that utilizes two independent vehicles, allowing for delivery of chemically and physically distinct agents. The mechanism was utilized to deliver a new anti-cancer combination therapy consisting of piperlongumine (PL) and TRAIL to treat PC3 prostate cancer and HCT116 colon cancer cells. PL, a small-molecule hydrophobic drug, was encapsulated in poly (lactic-co-glycolic acid) (PLGA) nanoparticles. TRAIL was chemically conjugated to the surface of liposomes. PL was first administered to sensitize cancer cells to the effects of TRAIL...
March 2016: Technology
https://www.readbyqxmd.com/read/27845365/computational-drug-target-screening-through-protein-interaction-profiles
#18
Santiago Vilar, Elías Quezada, Eugenio Uriarte, Stefano Costanzi, Fernanda Borges, Dolores Viña, George Hripcsak
The development of computational methods to discover novel drug-target interactions on a large scale is of great interest. We propose a new method for virtual screening based on protein interaction profile similarity to discover new targets for molecules, including existing drugs. We calculated Target Interaction Profile Fingerprints (TIPFs) based on ChEMBL database to evaluate drug similarity and generated new putative compound-target candidates from the non-intersecting targets in each pair of compounds. A set of drugs was further studied in monoamine oxidase B (MAO-B) and cyclooxygenase-1 (COX-1) enzyme through molecular docking and experimental assays...
November 15, 2016: Scientific Reports
https://www.readbyqxmd.com/read/27774429/preventive-potentials-of-piperlongumine-and-a-piper-longum-extract-against-stress-responses-and-pain
#19
Vaishali Yadav, Shyam Sunder Chatterjee, Muhammed Majeed, Vikas Kumar
AIM: To compare stress resistance increasing and analgesic activities of piperlongumine and a methanolic Piper longum fruit extract (PLE). METHODS: Efficacies of a single and repeated daily oral doses (1-256 mg/kg/day) of PLE, piperlongumine, and 50 mg/kg/day doxycycline against foot shock stress triggered alteration in body weights and core temperatures, and of their 11 daily doses on antidepressants like activity in tail suspension test and on pentobarbital induced sedation in male mice were compared...
October 2016: Journal of Traditional and Complementary Medicine
https://www.readbyqxmd.com/read/27689728/piperlongumine-piplartine-and-analogues-antiproliferative-microtubule-destabilising-agents
#20
Mary J Meegan, Seema Nathwani, Brendan Twamley, Daniela M Zisterer, Niamh M O'Boyle
Piperlongumine (piplartine, 1) is a small molecule alkaloid that is receiving intense interest due to its antiproliferative and anticancer activities. We investigated the effects of 1 on tubulin and microtubules. Using both an isolated tubulin assay, and a combination of sedimentation and western blotting, we demonstrated that 1 is a tubulin-destabilising agent. This result was confirmed by immunofluorescence and confocal microscopy, which showed that microtubules in MCF-7 breast cancer cells were depolymerized when treated with 1...
January 5, 2017: European Journal of Medicinal Chemistry
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