Cancer stem cells CD133 inhibition and cytotoxicity of certain 3-phenylthiazolo[3,2-a]benzimidazoles: design, direct synthesis, crystal study and in vitro biological evaluation

References

• Nguyen LV, Vanner R, Dirks P, Eaves CJ. Cancer stem cells: an evolving concept. Nat Rev Cancer 2012;12:133–43.
   PubMed Web of Science ®Google Scholar
• Abdel-Aziz HA, Ghabbour HA, Eldehna WM, et al. 2-((Benzimidazol-2-yl)thio)-1-arylethan-1-ones: synthesis, crystal study and cancer stem cells CD133 targeting potential. Eur J Med Chem 2015;104:1–10.
   PubMed Web of Science ®Google Scholar
• Denisenko TV, Sorokina IV, Gogvadze V, Zhivotovsky B. Mitotic catastrophe and cancer drug resistance: a link that must to be broken. Drug Resist Updat 2016;24:1–2.
   PubMed Web of Science ®Google Scholar
• Shackleton M, Quintana E, Fearon ER, Morrison SJ. Heterogeneity in cancer: cancer stem cells versus clonal evolution. Cell 2009;138:822–9.
   PubMed Web of Science ®Google Scholar
• Dick JE. Looking ahead in cancer stem cell research. Nat Biotechnol 2009;27:44–7.
   PubMed Web of Science ®Google Scholar
• Wahl GM, Spike BT. Cell state plasticity, stem cells, EMT, and the generation of intra-tumoral heterogeneity. NPJ Breast Cancer 2017;3:14.
   PubMed Web of Science ®Google Scholar
• Clevers H. The cancer stem cell: premises, promises and challenges. Nat Med 2011;17:313–9.
   PubMed Web of Science ®Google Scholar
• Soltysova A, Altanerova V, Altaner C. Cancer stem cells. Neoplasma 2005; 52:435.
   PubMed Web of Science ®Google Scholar
• Nguyen LV, Vanner R, Dirks P, Eaves C. Cancer stem cells: an evolving concept. J Nat Rev Cancer 2012;12:133–43.
   PubMed Web of Science ®Google Scholar
• Suresh R, Ali S, Ahmad A, et al. The role of cancer stem cells in recurrent and drug-resistant lung cancer. In: Ahmad A, Gadgeel SM, ed. Lung cancer and personalized medicine: novel therapies and clinical management. Switzerland: Springer International Publishing; 2016:57–74.
   Google Scholar
• Anthony H, Norbert F. Cancer stem cells: a promising concept and therapeutic challenge. Int J Cancer 2011;129:2309.
   PubMed Web of Science ®Google Scholar
• Horwitz EM, Le Blanc K, Dominici M, et al. Clarification of the nomenclature for MSC: The International Society for Cellular Therapy position statement. Cytotherapy 2005;7:393–5.
   PubMed Web of Science ®Google Scholar
• Grosse‐Gehling P, Fargeas CA, Dittfeld C, et al. CD133 as a biomarker for putative cancer stem cells in solid tumours: limitations, problems and challenges. J Pathol 2013;229:355–78.
   PubMed Web of Science ®Google Scholar
• Singh SK, Clarke ID, Terasaki M, et al. Identification of a cancer stem cell in human brain tumors. Cancer Res 2003;63:5821–8.
   PubMed Web of Science ®Google Scholar
• Ricci-Vitiani L, Lombardi DG, Pilozzi E, et al. Identification and expansion of human colon-cancer-initiating cells. Nature 2007; 445:111–5.
   PubMed Web of Science ®Google Scholar
• Han L, Gao X, Gu X, et al. Prognostic significance of cancer stem cell marker CD133 expression in breast cancer. Int J Clin Exp Med 2017;10:4829–37.
   Web of Science ®Google Scholar
• Ma S. Biology and clinical implications of CD133+ liver cancer stem cells. Exp Cell Res 2013;319:126.
   PubMed Web of Science ®Google Scholar
• Hermann PC, Huber SL, Herrler T, et al. Distinct populations of cancer stem cells determine tumor growth and metastatic activity in human pancreatic cancer. Cell Stem Cell 2007;1:313–23.
   PubMed Web of Science ®Google Scholar
• Yanagisawa S, Kadouchi I, Yokomori K, et al. Identification and metastatic potential of tumor-initiating cells in malignant rhabdoid tumor of the kidney. Clin Cancer Res 2009;15:3014–22.
   PubMed Web of Science ®Google Scholar
• Salnikov AV, Gladkich J, Moldenhauer G, et al. CD133 is indicative for a resistance phenotype but does not represent a prognostic marker for survival of non-small cell lung cancer patients . Int J Cancer 2010;126:950–8.
   PubMed Web of Science ®Google Scholar
• Rutella S, Bonanno G, Procoli A, et al. Cells with characteristics of cancer stem/progenitor cells express the CD133 antigen in human endometrial tumors. Clin Cancer Res 2009;15:4299–311.
   PubMed Web of Science ®Google Scholar
• Long H, Xie R, Xiang T, et al. Autocrine CCL5 signaling promotes invasion and migration of CD133+ ovarian cancer stem‐like cells via NF‐κB‐mediated MMP‐9 upregulation. Stem Cells 2012;30:2309–19.
   PubMed Web of Science ®Google Scholar
• Tirino V, Desiderio V, d'Aquino R, et al. Detection and characterization of CD133+ cancer stem cells in human solid tumours. PloS One 2008;3:e3469.
   PubMed Web of Science ®Google Scholar
• O’Brien CA, Pollett A, Gallinger S, Dick JE. A human colon cancer cell capable of initiating tumour growth in immunodeficient mice. Nature 2007;445:106–10.
   PubMed Web of Science ®Google Scholar
• (a) Eldehna WM, Almahli H, Al-Ansary GH, et al. Synthesis and in vitro anti-proliferative activity of some novel isatins conjugated with quinazoline/phthalazine hydrazines against triple-negative breast cancer MDA-MB-231 cells as apoptosis-inducing agents. J Enzyme Inhib Med Chem 2017;32:600–13.
   PubMed Web of Science ®Google Scholar
  (b) Abdel-Aziz HA, Eldehna WM, Ghabbour HA, et al. Synthesis, crystal study, and anti-proliferative activity of some 2-benzimidazolylthioacetophenones towards triple-negative breast cancer MDA-MB-468 cells as apoptosis-inducing agents. Int J Mol Sci 2016;17:1221.
   Web of Science ®Google Scholar
  (c) Eldehna WM, Abou-Seri SM, El Kerdawy AM, et al. Increasing the binding affinity of VEGFR-2 inhibitors by extending their hydrophobic interaction with the active site: design, synthesis and biological evaluation of 1-substituted-4-(4-methoxybenzyl) phthalazine derivatives. Eur J Med Chem 2016;113:50–62.
   PubMed Web of Science ®Google Scholar
  (d) Eldehna WM, Fares M, Ibrahim HS, et al. Synthesis and cytotoxic activity of biphenylurea derivatives containing indolin-2-one moieties. Molecules 2016;21:762.
   PubMed Web of Science ®Google Scholar
  (e) Eldehna WM, Fares M, Ceruso M, et al. Amido/ureidosubstituted benzenesulfonamides-isatin conjugates as low nanomolar/subnanomolar inhibitors of the tumor-associated carbonic anhydrase isoform XII. Eur J Med Chem 2016;110:259–66.
   PubMed Web of Science ®Google Scholar
  (f) Alafeefy AM, Ahmad R, Abdulla M, et al. Development of certain new 2-substituted-quinazolin-4-yl-aminobenzenesulfonamide as potential antitumor agents. Eur J Med Chem 2016;109:247–53.
   PubMed Web of Science ®Google Scholar
  (g) Abou-Seri SM, Eldehna WM, Ali MM, El Ella DAA. 1-Piperazinylphthalazines as potential VEGFR-2 inhibitors and anticancer agents: synthesis and in vitro biological evaluation. Eur J Med Chem 2016;107:165–79.
   PubMed Web of Science ®Google Scholar
  (h) Eldehna WM, Fares M, Ibrahim HS, et al. Indoline ureas as potential anti-hepatocellular carcinoma agents targeting VEGFR-2: synthesis, in vitro biological evaluation and molecular docking. Eur J Med Chem 2015;100:89–97.
   PubMed Web of Science ®Google Scholar
  (i) Eldehna WM, Altoukhy A, Mahrous H, Abdel-Aziz HA. Design, synthesis and QSAR study of certain isatin-pyridine hybrids as potential anti-proliferative agents. Eur J Med Chem 2015;90:684–94.
   PubMed Web of Science ®Google Scholar
  (j) 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;2014:760434.
   Web of Science ®Google Scholar
• Ngamwongsatit P, Banada PP, Panbangred W, Bhunia AK. WST-1-based cell cytotoxicity assay as a substitute for MTT-based assay for rapid detection of toxigenic Bacillus species using CHO cell line. J Microbiol Methods 2008;73:211–5.
   PubMed Web of Science ®Google Scholar
• Sheldrick GM. A short history of SHELX. Acta Crystallogr A 2008;64:112–22.
   PubMed Web of Science ®Google Scholar