1,611
Views
9
CrossRef citations to date
0
Altmetric
Brief Report

Novel piperidine derivatives as colchicine binding site inhibitors induce apoptosis and inhibit epithelial-mesenchymal transition against prostate cancer PC3 cells

, , & ORCID Icon
Pages 1403-1413 | Received 24 Feb 2020, Accepted 09 Jun 2020, Published online: 26 Jun 2020

References

  • Barrett I, Carr M, O'Boyle N, et al. Lead identification of conformationally restricted benzoxepin type combretastatin analogs: synthesis, antiproliferative activity, and tubulin effects. J Enzyme Inhib Med Chem 2010;25:180–94.
  • Tripathi A, Durrant D, Lee RM, et al. Hydropathic analysis and biological evaluation of stilbene derivatives as colchicine site microtubule inhibitors with anti-leukemic activity. J Enzyme Inhib Med Chem 2009;24:1237–44.
  • Jordan MA, Wilson L. Microtubules as a target for anticancer drugs. Nat Rev Cancer 2004;4:253–65.
  • Akhmanova A, Steinmetz MO. Control of microtubule organization and dynamics: two ends in the limelight. Nat Rev Mol Cell Biol 2015;16:711–26.
  • Lu Y, Chen J, Xiao M, et al. An overview of tubulin inhibitors that interact with the colchicine binding site. Pharm Res 2012;29:2943–71.
  • Tian C, Chen X, Zhang Z, et al. Design and synthesis of (2-(phenylamino)thieno[3,2-d]pyrimidin-4-yl)(3,4,5-trimethoxyphenyl)methanone analogues as potent anti-tubulin polymerization agents. Eur J Med Chem 2019;183:111679.
  • Banerjee S, Arnst KE, Wang Y, et al. Heterocyclic-fused pyrimidines as novel tubulin polymerization inhibitors targeting the colchicine binding site: structural basis and antitumor efficacy. J Med Chem 2018;61:1704–18.
  • Li W, Sun H, Xu S, et al. Tubulin inhibitors targeting the colchicine binding site: a perspective of privileged structures. Future Med Chem 2017;9:1765–94.
  • Bueno O, Tobajas G, Quesada E, et al. Conformational mimetics of the α-methyl chalcone TUB091 binding tubulin: design, synthesis and antiproliferative activity. Eur J Med Chem 2018;148:337–48.
  • Li W, Shuai W, Sun H, et al. Design, synthesis and biological evaluation of quinoline-indole derivatives as anti-tubulin agents targeting the colchicine binding site. Eur J Med Chem 2019;163:428–42.
  • Wang G, Liu W, Gong Z, et al. Synthesis, biological evaluation, and molecular modelling of new naphthalene-chalcone derivatives as potential anticancer agents on MCF-7 breast cancer cells by targeting tubulin colchicine binding site. J Enzyme Inhib Med Chem 2020;35:139–44.
  • Shao Y-Y, Yin Y, Lian B-P, et al. Synthesis and biological evaluation of novel shikonin-benzo[b]furan derivatives as tubulin polymerization inhibitors targeting the colchicine binding site. Eur J Med Chem 2020;190:112105.
  • Dumontet C, Jordan MA. Microtubule-binding agents: a dynamic field of cancer therapeutics. Nat Rev Drug Discov 2010;9:790–803.
  • Goel P, Alam O, Naim MJ, et al. Recent advancement of piperidine moiety in treatment of cancer - a review. Eur J Med Chem 2018;157:480–502.
  • Zeidner JF, Knaus HA, Zeidan AM, et al. Immunomodulation with pomalidomide at early lymphocyte recovery after induction chemotherapy in newly diagnosed AML and high-risk MDS. Leukemia 2020;34:1563–76.
  • Kumaraswamy G, Kumar RS, Sampath B, et al. A concise diastereoselective approach to enantioenriched substituted piperidines and their in vitro cytotoxicity evaluation. Bioorg Med Chem Lett 2014;24:4439–43.
  • Zeng Y, Cao R, Zhang T, et al. Design and synthesis of piperidine derivatives as novel human heat shock protein 70 inhibitors for the treatment of drug-resistant tumors. Eur J Med Chem 2015;97:19–31.
  • Liu X-H, Li J, Shi JB, et al. Design and synthesis of novel 5-phenyl-N-piperidine ethanone containing 4,5-dihydropyrazole derivatives as potential antitumor agents. Eur J Med Chem 2012;51:294–9.
  • Farooq M, Sharma A, Almarhoon Z, et al. Design and synthesis of mono-and di-pyrazolyl-s-triazine derivatives, their anticancer profile in human cancer cell lines, and in vivo toxicity in zebrafish embryos. Bioorg Chem 2019;87:457–64.
  • Jo J, Kim H, Oh JY, et al. SAR optimization studies on a novel series of 2-anilinopyrimidines as selective inhibitors against triple-negative breast cancer cell line MDA-MB-468. Bioorg Med Chem Lett 2019;29:126752.
  • Fu DJ, Fu L, Liu YC, et al. Structure-activity relationship studies of β-lactam-azide analogues as orally active antitumor agents targeting the tubulin colchicine site. Sci Rep 2017;7:12788.
  • Fu DJ, Liu JF, Zhao RH, et al. Design and antiproliferative evaluation of novel sulfanilamide derivatives as potential tubulin polymerization inhibitors. Molecules 2017;22:1470.
  • Fu D-J, Yang J-J, Li P, et al. Bioactive heterocycles containing a 3,4,5-trimethoxyphenyl fragment exerting potent antiproliferative activity through microtubule destabilization. Eur J Med Chem 2018;157:50–61.
  • Fu D-J, Li P, Wu B-W, et al. Molecular diversity of trimethoxyphenyl-1,2,3-triazole hybrids as novel colchicine site tubulin polymerization inhibitors. Eur J Med Chem 2019;165:309–22.
  • Fu DJ, Zhang SY, Liu YC, et al. Design, synthesis and antiproliferative activity studies of novel dithiocarbamate-chalcone derivates. Bioorg Med Chem Lett 2016;26:3918–22.
  • Fu DJ, Hou YH, Zhang SY, et al. Efficient click reaction towards novel sulfonamide hybrids by molecular hybridization strategy as antiproliferative agents. J Chem Sci 2018;130:6.
  • Mani SA, Guo W, Liao M-J, et al. The epithelial-mesenchymal transition generates cells with properties of stem cells. Cell 2008;133:704–15.