A novel piperine analogue exerts in vivo antitumor effect by inducing oxidative, antiangiogenic and immunomodulatory actions

Ferreira, Rafael Carlos; Batista, Tatianne Mota; Duarte, Sâmia Sousa; Silva, Daiana Karla Frade; Lisboa, Thaís; Cavalcanti, Raquel Fragoso Pereira; Leite, Fagner Carvalho; Mangueira, Vivianne Mendes; Sousa, Tatyanna Kélvia Gomes de; Abrantes, Renata Albuquerque de; Trindade, Emmely O.; Athayde-Filho, Petrônio Filgueiras de; Brandão, Maria Cláudia Rodrigues; Medeiros, Karina Carla de Paula; Farias, Davi Felipe; Sobral, Marianna Vieira

doi:10.1016/j.biopha.2020.110247

Cited by 20 publications

(9 citation statements)

References 64 publications

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“…Among the top five predicted targets, as shown in Table S2 , VEGFR-2 was suggested. It is worth highlighting that suggestion of VEGFR-2 as a possible target is perfectly matched with its known overexpression in TNBC cells 21 , 22 , as well as, with the reported anti-angiogenic activity of piperine and its analogous 23 , 24 . Consequently, a molecular docking analysis was further conducted to examine the possible binding modes and interactions of target piperine-based ureas within the vicinity of VEGFR-2 active site.…”

Section: Resultssupporting

confidence: 57%

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Natural inspired piperine-based ureas and amides as novel antitumor agents towards breast cancer

Elimam

Elgazar

El-Senduny

et al. 2021

Journal of Enzyme Inhibition and Medicinal Chemistry

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In this work, the natural piperine moiety was utilised to develop two sets of piperine-based amides ( 5a–i ) and ureas ( 8a–y ) as potential anticancer agents. The anticancer action was assessed against triple negative breast cancer (TNBC) MDA-MB-231, ovarian A2780CP and hepatocellular HepG2 cancer cell lines. In particular, 8q stood out as the most potent anti-proliferative analogue against TNBC MDA-MB-231 cells with IC 50 equals 18.7 µM, which is better than that of piperine (IC 50 = 47.8 µM) and 5-FU (IC 50 = 38.5 µM). Furthermore, 8q was investigated for its possible mechanism of action in MDA-MB-231 cells via Annexin V-FITC apoptosis assay and cell cycle analysis. Moreover, an in-silico analysis has proposed VEGFR-2 as a probable enzymatic target for piperine-based derivatives, and then has explored the binding interactions within VEGFR-2 active site (PDB:4ASD). Finally, an in vitro VEGFR-2 inhibition assay was performed to validate the in silico findings, where 8q showed good VEGFR-2 inhibitory activity with IC 50 = 231 nM.

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Section: Resultssupporting

confidence: 57%

“…This inhibition impact could be attributed to the presence of several common structural features required for VEGFR-2 inhibition in compound 8q 26 . Also, as mentioned above piperine and its analogous were reported to possess anti-angiogenic activity in breast cancer 24 .…”

Section: Resultsmentioning

confidence: 72%

Natural inspired piperine-based ureas and amides as novel antitumor agents towards breast cancer

Elimam

Elgazar

El-Senduny

et al. 2021

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…The results showed that Pip-PLGA NPs could inhibit the migration and proliferative activity of HeLa cells compared to control, which is evident from the graph (Figure B) showing the quantitatively analysis using ImageJ software. Notably, the cytotoxic nature of Pip interferes with HeLa cell proliferation, as a result boosting its chemotherapeutic efficiency against cancer. ,,, …”

Section: Results and Discussionmentioning

confidence: 99%

“…Pip is also reported to have antiparasitic, antimicrobial, anti-inflammatory (due to inhibition of the NF-κB pathway), − antidepressant, , and anti-angiogenic properties . As a chemotherapeutic molecule, it can modulate oxidative stress and thus shows cytotoxic and antimetastatic properties towards cancer cells. ,, A toxicity evaluation of Pip showed that a 1.12 mg/kg dose concentration has no adverse effects in Swiss male mice, but a dose concentration more than that was able to create a depression in the central nervous system and reproductive toxicity. , …”

Section: Introductionmentioning

confidence: 99%

Piperine-Loaded PLGA Nanoparticles as Cancer Drug Carriers

Kaur

Singh

Khan

et al. 2021

ACS Appl. Nano Mater.

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Factors like oxidative stress, environmental risk factors, genetics, chemical treatments, and resistance to treatment strategies all have serious impediments in scientific progress for treating diseases. Naturally occurring bioactive compounds when associated with nanocarriers could provide a solution for tackling problems as therapeutic agents against cancer. This report investigates a facile method of using ultrasonic atomization for synthesizing piperine-loaded poly(D,L-lactide-co-glycolic acid) (PLGA) nanocomposites specialized for targeted drug delivery for their potential use against cancer. The nanoformulation was characterized using dynamic light scattering (DLS), microscopic techniques like scanning electron microscopy (SEM), transmission electron microscopy (TEM), and confocal laser scanning microscopy (CLSM), spectroscopic methods for determination of encapsulation efficiency, sustained-release kinetics, and cellular studies like cellular uptake study and in vitro antitumor activity against different cancer cell lines. The ultrasonic atomization led to the formation of NPs with a mean size of 95 ± 10 nm and a zeta (ζ) potential of −19.29 mV. In vitro release was sustained up to 312 h with about 28% cumulative release at pH 7.2 and 91% at pH 5.5. The tailored delivery of nanocarriers suppressed cancer cell growth and migration in a variety of cancer cell lines, indicating anticancer properties. This nanocarrier formulation showed low cytotoxicity towards HEK-293 in comparison to HeLa, A549, HT1080, PC-3, and MCF-7 cancer cell lines when analyzed for cell viability through 3-(4,5-dimethylthiazol-2-yl)-2,5 diphenyltetrazolium bromide dye (MTT) assay. The results suggest that nanocarrier-mediated delivery of piperine (Pip) could prove to be efficient against cancer and aid in reaching inaccessible sites, overcome physiological barriers, and maintain the concentration of drugs, and has higher targeting capability and reduced cellular toxicity.

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“…Piperine has displayed a vast biological profile which includes anti-cancer (Ferreira et al, 2020), antialzheimer (Yang et al, 2021), anti-parkinsonian (Wang et al, 2020), anti-filarial (Joardar et al, 2021), anti-leishmanial (Ferreira et al, 2011), trypnocidal (Da Silva et al, 2008, larvicidal (Tantawy et al, 2020), anti-inflammatory (Shahbazi et al, 2020), anti-convulsant (Khom et al, 2013), MAO inhibition (Chavarria et al, 2020), carbonic anhydrase inhibition (Elimam et al, 2021), anti-bacterial (Shivahsanmugam andVelmathi, 2022) and blood brain barrier permeation enhancer (Eigenmann et al, 2016) (Figure 3).…”

Section: Introductionmentioning

confidence: 99%

Piperine: A Mini Review on its Pharmacological Profile and Synthetic Derivatives

2022

EAJSE

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Piperine, known for its vast biological profile, is obtained from black pepper (Piper nigrum, Family: Piperaceae) which is one of the most commonly used spice in major parts of the world and is known for its pungent taste. Piperine is also found to act as an important bioenhancer by increasing the bioavailability of drug molecules and reducing their dosing frequency and dosage. This review article aims at providing various biological activities exhibited by piperine and its numerous synthetic derivatives in order to get some potential lead molecule for future drug discovery.

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A novel piperine analogue exerts in vivo antitumor effect by inducing oxidative, antiangiogenic and immunomodulatory actions

Cited by 20 publications

References 64 publications

Natural inspired piperine-based ureas and amides as novel antitumor agents towards breast cancer

Natural inspired piperine-based ureas and amides as novel antitumor agents towards breast cancer

Piperine-Loaded PLGA Nanoparticles as Cancer Drug Carriers

Piperine: A Mini Review on its Pharmacological Profile and Synthetic Derivatives

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