Angiogenesis and anti-leukaemia activity of novel indole derivatives as potent colchicine binding site inhibitors

References

• Fang C, Rao S, Crispino JD, Ntziachristos P. Determinants and role of chromatin organization in acute leukemia. Leukemia 2020;34:2561–75.
   PubMed Web of Science ®Google Scholar
• Brown P, Pieters R, Biondi A. How I treat infant leukemia. Blood 2019;133:205–14.
   PubMed Web of Science ®Google Scholar
• Ruan Y, Kim HN, Ogana H, Kim YM. Wnt signaling in leukemia and its bone marrow microenvironment. Int J Mol Sci 2020;21:6247.
   PubMed Web of Science ®Google Scholar
• Pandey N, Yadav G, Kushwaha R, et al. Effect of imatinib on bone marrow morphology and angiogenesis in chronic myeloid leukemia. Adv Hematol 2019;2019:1835091.
   PubMedGoogle Scholar
• Shirzad R, Shahrabi S, Ahmadzadeh A, et al. Signaling and molecular basis of bone marrow niche angiogenesis in leukemia. Clin Transl Oncol 2016;18:957–71.
   PubMed Web of Science ®Google Scholar
• Jászai J, Schmidt MHH. Trends and challenges in tumor anti-angiogenic therapies. Cells 2019;8:1102.
   PubMed Web of Science ®Google Scholar
• Jingtian S, Hai-liang Z, Yongfang Y, Yongtao D. Antiangiogenic therapy: challenges and future directions. Curr Top Med Chem 2021;21:87–9.
   Web of Science ®Google Scholar
• Wang DP, Liu KL, Li XY, et al. Design, synthesis, and in vitro and in vivo anti-angiogenesis study of a novel vascular endothelial growth factor receptor-2 (VEGFR-2) inhibitor based on 1,2,3-triazole scaffold. Eur J Med Chem 2021;211:113083.
   PubMed Web of Science ®Google Scholar
• Zhang L, Shan Y, Li C, et al. Discovery of novel anti-angiogenesis agents. Part 6: Multi-targeted RTK inhibitors. Eur J Med Chem 2017;127:275–85.
   PubMed Web of Science ®Google Scholar
• Pan X, Liang L, Si R, et al. Discovery of novel anti-angiogenesis agents. Part 10: Multi-target inhibitors of VEGFR-2, Tie-2 and EphB4 incorporated with 1,2,3-triazol. Eur J Med Chem 2019;163:1–9.
   PubMed Web of Science ®Google Scholar
• Duan Y, Liu W, Tian L, et al. Targeting tubulin-colchicine site for cancer therapy: inhibitors, antibody- drug conjugates and degradation agents. Curr Top Med Chem 2019;19:1289–304.
   PubMed Web of Science ®Google Scholar
• Wang Y, Yao Y, Zhu HL, Duan Y. Butterfly structure: a privileged scaffold targeting tubulin-colchicine binding site. Curr Top Med Chem 2020;20:1505–8.
   PubMed Web of Science ®Google Scholar
• Ki SM, Kim JH, Won SY, et al. CEP41-mediated ciliary tubulin glutamylation drives angiogenesis through AURKA-dependent deciliation. EMBO Rep 2020;21:e48290.
   PubMed Web of Science ®Google Scholar
• Petit I, Karajannis MA, Vincent L, et al. The microtubule-targeting agent CA4P regresses leukemic xenografts by disrupting interaction with vascular cells and mitochondrial-dependent cell death. Blood 2008;111:1951–61.
   PubMed Web of Science ®Google Scholar
• Uckun FM, Cogle CR, Lin TL, et al. A Phase 1B Clinical Study of Combretastatin A1 Diphosphate (OXi4503) and Cytarabine (ARA-C) in Combination (OXA) for Patients with Relapsed or Refractory Acute Myeloid Leukemia. Cancers. 2019;12:74.,
   PubMed Web of Science ®Google Scholar
• Gaynon PS, Harned TM, Therapeutic Advances in Childhood Leukemia/Lymphoma Consortium. ABT-751 in relapsed childhood acute lymphoblastic leukemia. J Pediatr Hematol Oncol 2012;34:583–4.
   PubMed Web of Science ®Google Scholar
• Chen X, Yang C, Xu Y, et al. The microtubule depolymerizing agent CYT997 effectively kills acute myeloid leukemia cells via activation of caspases and inhibition of PI3K/Akt/mTOR pathway proteins. Exp Ther Med 2013;6:299–304.
   PubMed Web of Science ®Google Scholar
• Zhang YL, Yang R, Xia LY, et al. Synthesis, anticancer activity and molecular docking studies on 1,2-diarylbenzimidazole analogues as anti-tubulin agents. Bioorg Chem 2019;92:103219.
   PubMed Web of Science ®Google Scholar
• Xia LY, Yang R, Zhang YL, et al. Design, synthesis, and biological evaluation of 2,3-diphenyl-cycloalkyl pyrazole derivatives as potential tubulin polymerization inhibitors. Chem Biol Drug Des 2019;94:1894–904.
   PubMed Web of Science ®Google Scholar
• Chen K, Zhang YL, Fan J, et al. Novel nicotinoyl pyrazoline derivates bearing N-methyl indole moiety as antitumor agents: design, synthesis and evaluation. Eur J Med Chem 2018;156:722–37.
   PubMed Web of Science ®Google Scholar
• Yao YF, Wang ZC, Wu SY, et al. Identification of novel 1-indolyl acetate-5-nitroimidazole derivatives of combretastatin A-4 as potential tubulin polymerization inhibitors. Biochem Pharmacol 2017;137:10–28.
   PubMed Web of Science ®Google Scholar
• Duan YT, Man RJ, Tang DJ, et al. Design, Synthesis and Antitumor Activity of Novel link-bridge and B-Ring Modified Combretastatin A-4 (CA-4) Analogues as Potent Antitubulin Agents. Sci Rep 2016;6:25387.
   PubMed Web of Science ®Google Scholar
• Wang YT, Qin YJ, Yang N, et al. Synthesis, biological evaluation, and molecular docking studies of novel 1-benzene acyl-2-(1-methylindol-3-yl)-benzimidazole derivatives as potential tubulin polymerization inhibitors. Eur J Med Chem 2015;99:125–37.
   PubMed Web of Science ®Google Scholar
• Qin YJ, Li YJ, Jiang AQ, et al. Design, synthesis and biological evaluation of novel pyrazoline-containing derivatives as potential tubulin assembling inhibitors. Eur J Med Chem 2015;94:447–57.
   PubMed Web of Science ®Google Scholar
• Duan YT, Sang YL, Makawana JA, et al. Discovery and molecular modeling of novel 1-indolyl acetate-5-nitroimidazole targeting tubulin polymerization as antiproliferative agents. Eur J Med Chem 2014;85:341–51.
   PubMed Web of Science ®Google Scholar
• Zhang YL, Qin YJ, Tang DJ, et al. Synthesis and biological evaluation of 1-methyl-1H-indole-pyrazoline hybrids as potential tubulin polymerization inhibitors. Chem Med Chem 2016;11:1446–58.
   Web of Science ®Google Scholar
• Kuday H, Sonmez F, Bilen C, et al. Synthesis and in vitro inhibition effect of new pyrido[2,3-d]pyrimidine derivatives on erythrocyte carbonic anhydrase I and II. Biomed Res Int 2014;2014:594879.
   PubMed Web of Science ®Google Scholar
• Aranda E, Owen GI. A semi-quantitative assay to screen for angiogenic compounds and compounds with angiogenic potential using the EA.hy926 endothelial cell line. Biol Res 2009;42:377–89.
   PubMed Web of Science ®Google Scholar
• Sana S, Reddy VG, Bhandari S, et al. Exploration of carbamide derived pyrimidine-thioindole conjugates as potential VEGFR-2 inhibitors with anti-angiogenesis effect. Eur J Med Chem 2020;200:112457.
   PubMed Web of Science ®Google Scholar
• Reddy VG, Reddy TS, Jadala C, et al. Pyrazolo-benzothiazole hybrids: Synthesis, anticancer properties and evaluation of antiangiogenic activity using in vitro VEGFR-2 kinase and in vivo transgenic zebrafish model. Eur J Med Chem 2019;182:111609.
   PubMed Web of Science ®Google Scholar
• Sun M, Wang Y, Yuan M, et al. Angiogenesis, anti-tumor, and anti-metastatic activity of novel α-substituted hetero-aromatic chalcone hybrids as inhibitors of microtubule polymerization. Angiogenesis 2021;9:766201.
   Google Scholar
• Wang Y, Sun M, Wang Y, et al. Discovery of novel tubulin/HDAC dual-targeting inhibitors with strong antitumor and antiangiogenic potency. Eur J Med Chem 2021;225:113790.
   PubMed Web of Science ®Google Scholar
• Iftikhar S, Khan S, Bilal A, et al. Synthesis and evaluation of modified chalcone based p53 stabilizing agents. Bioorg Med Chem Lett 2017;27:4101–6.
   PubMed Web of Science ®Google Scholar
• Weldon DJ, Saulsbury MD, Goh J, et al. One-pot synthesis of cinnamylideneacetophenones and their in vitro cytotoxicity in breast cancer cells. Bioorg Med Chem Lett 2014;24:3381–4.
   PubMed Web of Science ®Google Scholar
• Tantak M, Mukherjee D, Kumar A, et al. A facile and microwave-assisted rapid synthesis of 2-arylamino-4-(3′-indolyl)- thiazoles as Apoptosis Inducing Cytotoxic Agents. Anti-Cancer Agents Med Chem 2017;17:442–55.
   PubMed Web of Science ®Google Scholar
• Sun M, Yuan M, Kang Y, et al. Identification of novel non-toxic and anti-angiogenic α-fluorinated chalcones as potent colchicine binding site inhibitors. J Enzyme Inhib Med Chem 2022;37:339–54.
   PubMed Web of Science ®Google Scholar
• Tsai WC, Hsu CC, Chen HC, et al. Ciprofloxacin-mediated inhibition of tenocyte migration and down-regulation of focal adhesion kinase phosphorylation. Eur J Pharmacol 2009;607:23–6.
   PubMed Web of Science ®Google Scholar
• Chen YH, Chang CY, Chang CF, et al. Pro-angiogenic effects of chalcone derivatives in zebrafish embryos in vivo. Molecules 2015;20:12512–24.
   PubMed Web of Science ®Google Scholar