Antitumour Efficacy of Piper tuberculatum and Piplartine Based on the Hollow Fiber Assay

Bezerra, Daniel P.; Ferreira, Paulo Michel Pinheiro; Machado, Camila Maria Longo; Aquino, Nayara Coriolano de; Silveira, Edilberto R.; Chammas, Roger; Pessoa, Cláudia

doi:10.1055/s-0034-1383363

Cited by 19 publications

(20 citation statements)

References 23 publications

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“…Therefore, it can be concluded that analogue 10 induced oxidative stress that was restored by overexpressed PRDX4 in cultured U87MG cells. Due to this, 1 was found to be less effective in SF-295 human glioblastoma cells as compared to HCT-8 human colon carcinoma cells [ 29 ].…”

Section: Discussionmentioning

confidence: 99%

Piplartine Analogues and Cytotoxic Evaluation against Glioblastoma

et al. 2018

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Piplartine (1) is an alkamide extracted from plants of the genus Piper which shows several pharmacological properties, including antitumor activity. To improve this activity, a series of analogues based on 1 have been synthesized by esterification and amidation using the 3,4,5-trimethoxycinnamic acid-like starting material. During the study, the moieties 3-(3,4,5-trimethoxyphenyl)acrylate and 3-(3,4,5-trimethoxyphenyl)acrylamide were maintained on esters and amides respectively. Meanwhile, functional changes were exploited, and it was revealed that the presence of two aromatic rings in the side-chain was important to improve the cytotoxic activity against the U87MG cell line, such as the compound (E)-benzhydryl 3-(3,4,5-trimethoxyphenyl)acrylate (10), an ester that exhibited strong cytotoxicity and a similar level of potency to that of paclitaxel, a positive control. Compound 10 had a marked concentration-dependent inhibitory effect on the viability of the U87MG cell line with apoptotic and oxidative processes, showing good potential for altering main molecular pathways to prevent tumor development. Moreover, it has strong bioavailability with non-genotoxic and non-cytotoxic properties on human blood cells. In conclusion, the findings of the present study demonstrated that compound 10 is a promising agent that may find applications combatting diseases associated with oxidative stress and as a prototype for the development of novel drugs used in the treatment of glioblastoma.

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Section: Discussionmentioning

confidence: 99%

Piplartine Analogues and Cytotoxic Evaluation against Glioblastoma

et al. 2018

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“…Piplartine is an amide alkaloid found in several Piper species (Piperaceae). It has been shown that piplartine has potential anticancer properties [9,10]. Piplartine also shows benefits in the treatment of the parasitic infection schistosomiasis, caused by helminth flatworms of the genus Schistosoma [11].…”

Section: Introductionmentioning

confidence: 99%

Piper Species: A Comprehensive Review on Their Phytochemistry, Biological Activities and Applications

et al. 2019

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Piper species are aromatic plants used as spices in the kitchen, but their secondary metabolites have also shown biological effects on human health. These plants are rich in essential oils, which can be found in their fruits, seeds, leaves, branches, roots and stems. Some Piper species have simple chemical profiles, while others, such as Piper nigrum, Piper betle, and Piper auritum, contain very diverse suites of secondary metabolites. In traditional medicine, Piper species have been used worldwide to treat several diseases such as urological problems, skin, liver and stomach ailments, for wound healing, and as antipyretic and anti-inflammatory agents. In addition, Piper species could be used as natural antioxidants and antimicrobial agents in food preservation. The phytochemicals and essential oils of Piper species have shown strong antioxidant activity, in comparison with synthetic antioxidants, and demonstrated antibacterial and antifungal activities against human pathogens. Moreover, Piper species possess therapeutic and preventive potential against several chronic disorders. Among the functional properties of Piper plants/extracts/active components the antiproliferative, anti-inflammatory, and neuropharmacological activities of the extracts and extract-derived bioactive constituents are thought to be key effects for the protection against chronic conditions, based on preclinical in vitro and in vivo studies, besides clinical studies. Habitats and cultivation of Piper species are also covered in this review. In this current work, available literature of chemical constituents of the essential oils Piper plants, their use in traditional medicine, their applications as a food preservative, their antiparasitic activities and other important biological activities are reviewed.

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“…Piplartine (piperlongumine) is a plant-derived compound found in some Piper species that became a novel potential antineoplastic agent. Potent cytotoxicity, genotoxicity, antitumor, antiangiogenic and antimetastatic properties, in addition to presenting adequate bioavailability and safety profile have been attributed for this molecule and its derivatives [3] , [4] , [5] , [6] , [7] , [8] , [9] , [10] , [11] , [12] , [13] , [14] , [15] , [16] , [17] , [18] , [19] . Although its cytotoxic properties have been known for over three decades, the great interest in this molecule has arisen after its cytotoxicity and ability to induce the production of reactive oxygen species (ROS) selectively in cancer cells were described [11] , [12] .…”

Section: Introductionmentioning

confidence: 99%

A novel platinum complex containing a piplartine derivative exhibits enhanced cytotoxicity, causes oxidative stress and triggers apoptotic cell death by ERK/p38 pathway in human acute promyelocytic leukemia HL-60 cells

et al. 2019

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Piplartine (piperlongumine) is a plant-derived compound found in some Piper species that became a novel potential antineoplastic agent. In the present study, we synthesized a novel platinum complex containing a piplartine derivative cis-[PtCl(PIP-OH)(PPh3)2]PF6 (where, PIP-OH = piplartine demethylated derivative; and PPh3 = triphenylphosphine) with enhanced cytotoxicity in different cancer cells, and investigated its apoptotic action in human promyelocytic leukemia HL-60 cells. The structure of PIP-OH ligand was characterized by X-ray crystallographic analysis and the resulting platinum complex was characterized by infrared, molar conductance measurements, elemental analysis and NMR experiments. We found that the complex is more potent than piplartine in a panel of cancer cell lines. Apoptotic cell morphology, increased internucleosomal DNA fragmentation, without cell membrane permeability, loss of the mitochondrial transmembrane potential, increased phosphatidylserine externalization and caspase-3 activation were observed in complex-treated HL-60 cells. Treatment with the complex also caused a marked increase in the production of reactive oxygen species (ROS), and the pretreatment with N-acetyl-L-cysteine, an antioxidant, reduced the complex-induced apoptosis, indicating activation of ROS-mediated apoptosis pathway. Important, pretreatment with a p38 MAPK inhibitor (PD 169316) and MEK inhibitor (U-0126), known to inhibit ERK1/2 activation, also prevented the complex-induced apoptosis. The complex did not induce DNA intercalation in cell-free DNA assays. In conclusion, the complex exhibits more potent cytotoxicity than piplartine in a panel of different cancer cells and triggers ROS/ERK/p38-mediated apoptosis in HL-60 cells.

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Antitumour Efficacy of Piper tuberculatum and Piplartine Based on the Hollow Fiber Assay

Cited by 19 publications

References 23 publications

Piplartine Analogues and Cytotoxic Evaluation against Glioblastoma

Piplartine Analogues and Cytotoxic Evaluation against Glioblastoma

Piper Species: A Comprehensive Review on Their Phytochemistry, Biological Activities and Applications

A novel platinum complex containing a piplartine derivative exhibits enhanced cytotoxicity, causes oxidative stress and triggers apoptotic cell death by ERK/p38 pathway in human acute promyelocytic leukemia HL-60 cells

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