3,281
Views
9
CrossRef citations to date
0
Altmetric
Brief Report

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

, , , , &
Pages 39-50 | Received 18 Aug 2021, Accepted 28 Sep 2021, Published online: 11 Dec 2021

References

  • Wild C, Weiderpass E, Stewart BW World cancer report: cancer research for cancer prevention. Lyon: IARC Press 2020.
  • da Silva JL, Cardoso Nunes NC, Izetti P, et al. Triple negative breast cancer: a thorough review of biomarkers. Crit Rev Oncol Hematol 2020;145:102855.
  • Won KA, Spruck C. Triple‑negative breast cancer therapy: current and future perspectives (Review). Int J Oncol 2020;57:1245–61.
  • Wahba HA, El-Hadaad HA. Current approaches in treatment of triple-negative breast cancer. Cancer Biol Med 2015;12:106–16.
  • Li JW-H, Vederas JC. Drug discovery and natural products: end of an era or an endless frontier? Science 2009;325:161–5.
  • Stojanović-Radić Z, Pejčić M, Dimitrijević M, et al. Piperine-a major principle of black pepper: a review of its bioactivity and studies. Appl Sci 2019;9:4270.
  • Haq I-U, Imran M, Nadeem M, et al. Piperine: a review of its biological effects. Phytother Res 2021;35:680–700.
  • Chen D, Ma Y, Guo Z, et al. Two natural alkaloids synergistically induce apoptosis in breast cancer cells by inhibiting STAT3 activation. Molecules 2020;25:216.
  • Do MT, Kim HG, Choi JH, et al. Antitumor efficacy of piperine in the treatment of human HER2-overexpressing breast cancer cells. Food Chem 2013;141:2591–9.
  • Greenshields AL, Doucette CD, Sutton KM, et al. Piperine inhibits the growth and motility of triple-negative breast cancer cells. Cancer Lett 2015;357:129–40.
  • Umadevi P, Deepti K, Venugopal DVR. Synthesis, anticancer and antibacterial activities of piperine analogs. Med Chem Res 2013;22:5466–71.
  • Chavarria D, Silva T, Magalhães e Silva D, et al. Lessons from black pepper: piperine and derivatives thereof. Expert Opin Ther Pat 2016;26:245–64.
  • Inder Pal S, Alka C. Piperine and derivatives: trends in structure-activity relationships. Curr Top Med Chem 2015;15:1722–34.
  • Ghosh AK, Brindisi M, Sarkar A. The curtius rearrangement: applications in modern drug discovery and medicinal chemistry. ChemMedChem 2018;13:2351–73.
  • Skehan P, Storeng R, Scudiero D, et al. New colorimetric cytotoxicity assay for anticancer-drug screening. J Natl Cancer Inst 1990;82:1107–12.
  • Elgazar AA, Knany HR, Ali MS. Insights on the molecular mechanism of anti-inflammatory effect of formula from Islamic traditional medicine: An in-silico study. J Tradit Complement Med 2019;9:353–63.
  • Elsbaey M, Ibrahim MAA, Bar FA, Elgazar AA. Chemical constituents from coconut waste and their in silico evaluation as potential antiviral agents against SARS-CoV-2. S Afr J Bot 2021;141:278–89.
  • Xu X, Huang M, Zou X. Docking-based inverse virtual screening: methods, applications, and challenges. Biophys Rep 2018;4:1–16.
  • Badria FA, Elgazar AA Chapter 37 – Revealing the molecular mechanism of Olea europaea L. in treatment of cataract. In: Preedy VR, Watson RR, eds. Olives and olive oil in health and disease prevention. 2nd ed. San Diego: Academic Press; 2021:445–456.
  • SwissTargetPrediction. Available from http://www.swisstargetprediction.ch/ [accessed 8 May 2021].
  • Babyshkina N, Zavyalova M, Tarabanovskaya N, et al. Predictive value of vascular endothelial growth factor receptor type 2 in triple-negative breast cancer patients treated with neoadjuvant chemotherapy. Mol Cell Biochem 2018;444:197–206.
  • Linderholm BK, Hellborg H, Johansson U, et al. Significantly higher levels of vascular endothelial growth factor (VEGF) and shorter survival times for patients with primary operable triple-negative breast cancer. Ann Oncol 2009;20:1639–46.
  • Zahra Z, Tina Nayerpour D, Armaghan L, et al. The effect of piperine on MMP-9, VEGF, and E-cadherin expression in breast cancer MCF-7 cell line. Basic Clin Cancer Res 2021;12:5767.
  • Ferreira RC, Batista TM, Duarte SS, et al. A novel piperine analogue exerts in vivo antitumor effect by inducing oxidative, antiangiogenic and immunomodulatory actions. Biomed Pharmacother 2020;128:110247.
  • Kilpatrick LE, Friedman-Ohana R, Alcobia DC, et al. Real-time analysis of the binding of fluorescent VEGF165a to VEGFR2 in living cells: effect of receptor tyrosine kinase inhibitors and fate of internalized agonist-receptor complexes. Biochem Pharmacol 2017;136:62–75.
  • Xie Q-Q, Xie H-Z, Ren J-X, et al. Pharmacophore modeling studies of type I and type II kinase inhibitors of Tie2. J Mol Graph Model 2009;27:751–8.
  • Aziz MA, Serya RAT, Lasheen DS, et al. Discovery of potent VEGFR-2 inhibitors based on furopyrimidine and thienopyrimidne scaffolds as cancer targeting agents. Sci Rep 2016;6:24460.
  • Wahab A, Sultana A, Sherwani SK, et al. Antioxidant and nematicidal activity of (2E,4E)-5-(benzo(d) (1,3)dioxol-5yl)penta-2,4-dienamides. J Chem Soc Pak 2015;37:1008–1014.
  • Joardar N, Shit P, Halder S, et al. Disruption of redox homeostasis with synchronized activation of apoptosis highlights the antifilarial efficacy of novel piperine derivatives: an in vitro mechanistic approach. Free Rad Biol Med 2021;169:343–360.
  • Eldehna WM, Fares M, Ibrahim HS, et al. Synthesis and cytotoxic activity of biphenylurea derivatives containing indolin-2-one moieties. Molecules 2016;21:762.
  • Abdel-Aziz HA, Ghabbour HA, Eldehna WM, et al. Synthesis, crystal structure, and biological activity of cis/trans amide rotomers of (Z)-N’-(2-oxoindolin-3-ylidene)formohydrazide. J Chem 2014;2014:1–7.
  • Sabt A, Eldehna WM, Al-Warhi T, et al. Discovery of 3,6-disubstituted pyridazines as a novel class of anticancer agents targeting cyclin-dependent kinase 2: synthesis, biological evaluation and in silico insights. J Enzyme Inhib Med Chem 2020;35:1616–1630.
  • Al-Rashood ST, Hamed AR, Hassan GS, et al. Antitumor properties of certain spirooxindoles towards hepatocellular carcinoma endowed with antioxidant activity. J Enzyme Inhib Med Chem 2020;35:831–839.
  • Eldehna WM, Al-Rashood ST, Al-Warhi T, et al. Novel oxindole/benzofuran hybrids as potential dual CDK2/GSK-3β inhibitors targeting breast cancer: design, synthesis, biological evaluation, and in silico studies. J Enzyme Inhib Med Chem 2021;36:270–285.
  • Eldehna WM, El Kerdawy AM, Al-Ansary GH, et al. Type IIA - Type IIB protein tyrosine kinase inhibitors hybridization as an efficient approach for potent multikinase inhibitor development: design, synthesis, anti-proliferative activity, multikinase inhibitory activity and molecular modeling of novel indolinone-based ureides and amides. Eur J Med Chem 2019;163:37–53.
  • Daina A, Michielin O, Zoete V. SwissTargetPrediction: updated data and new features for efficient prediction of protein targets of small molecules. Nucleic Acids Res 2019;47:W357–W364.
  • C.J.C. ChemOffice. Cambridge, MA: Cambridge Scientific Computing Inc.
  • C.C.G.C. Inc., Molecular Operating Environment (MOE), Montreal, QC; 2016.
  • Böhm H-J. Prediction of binding constants of protein ligands: a fast method for the prioritization of hits obtained from de novo design or 3D database search programs. J Comp Aided Mol Des 1998;12:309–309.
  • Kramer B, Rarey M, Lengauer T. Evaluation of the FLEXX incremental construction algorithm for protein–ligand docking. Proteins 1999;37:228–241.
  • Schneider N, Lange G, Hindle S, et al. A consistent description of HYdrogen bond and DEhydration energies in protein-ligand complexes: methods behind the HYDE scoring function. J Comp Aided Mol Des 2013;27:15–29.
  • D.J.A.I.S.D. Studio, CA, USA, version 2.5; 2009.