Novel sulfonamide benzoquinazolinones as dual EGFR/HER2 inhibitors, apoptosis inducers and radiosensitizers

References

• Kerr JF, Wyllie AH, Currie AR. Apoptosis: a basic biological phenomenon with wide-ranging implications in tissue kinetics. Br J Cancer 1972;26:239–57.
   PubMed Web of Science ®Google Scholar
• Fischer U, Janssen K, Schulze-Osthoff K. Cutting-edge apoptosis-based therapeutics. Biodrugs 2007;21:273–97.
   PubMed Web of Science ®Google Scholar
• Chen Z, Liang X, Zhang H, et al. A new class of naphthalimide-based antitumor agents that inhibit topoisomerase II and induce lysosomal membrane permeabilization and apoptosis. J Med Chem 2010;53:2589–600.
   PubMed Web of Science ®Google Scholar
• Tian Z, Xie S, Du Y, et al. Synthesis, cytotoxicity and apoptosis of naphthalimide polyamine conjugates as antitumor agents. Eur J Med Chem 2009;44:393–9.
   PubMed Web of Science ®Google Scholar
• Bredesen DE. Apoptosis: overview and signal transduction pathways. J Neurotrauma 2000;17:801–10.
   PubMed Web of Science ®Google Scholar
• DeSantis C, Ma J, Bryan L, Jemal A. Breast cancer statistics, 2013. CA Cancer J Clin 2014;64:52–62.
   PubMed Web of Science ®Google Scholar
• Slamon DJ, Clark GM, Wong SG, et al. Human breast cancer: correlation of relapse and survival with amplification of the HER-2/neu oncogene. Science 1987;235:177–82.
   PubMed Web of Science ®Google Scholar
• Clauditz TS, Gontarewicz A, Lebok P, et al. Epidermal growth factor receptor (EGFR) in salivary gland carcinomas: potentials as therapeutic target. Oral Oncol 2012;48:991–6.
   PubMed Web of Science ®Google Scholar
• Arteaga CL, Engelman JA. ERBB receptors: from oncogene discovery to basic science to mechanism-based cancer therapeutics. Cancer Cell 2014;25:282–303.
   PubMed Web of Science ®Google Scholar
• Ohashi K, Sequist LV, Arcila ME, et al. Characteristics of lung cancers harboring NRAS mutations. Clin Cancer Res 2013;19:1–8.
   Web of Science ®Google Scholar
• Narayan M, Wilken JA, Harris LN, et al. Trastuzumab-induced HER reprogramming in “resistant” breast carcinoma cells. Cancer Res 2009;69:2191–4.
   PubMed Web of Science ®Google Scholar
• Olayioye MA, Neve RM, Lane HA, Hynes NE. The ErbB signaling network: receptor heterodimerization in development and cancer. Embo J 2000;19:3159–67.
   PubMed Web of Science ®Google Scholar
• Nagarsenkar A, Prajapti SK, Guggilapu SD, et al. Investigation of triazole-linked indole and oxindole glycoconjugates as potential anticancer agents: novel Akt/PKB signaling pathway inhibitors. Med Chem Comm 2016;7:646–53.
   Web of Science ®Google Scholar
• Alsaid MS, Al-Mishari AA, Soliman AM, et al. Discovery of benzo [g] quinazolin benzenesulfonamide derivatives as dual EGFR/HER2 inhibitors. Eur J Med Chem 2017;141:84–91.
   PubMed Web of Science ®Google Scholar
• Ghorab MM, Alsaid MS, Soliman AM, Al-Mishari AA. Benzo[g]quinazolin-based scaffold derivatives as dual EGFR/HER2 inhibitors . J Enzyme Inhib Med Chem 2018;33:67–73.
   PubMed Web of Science ®Google Scholar
• Elkamhawy A, Farag AK, Viswanath ANI, et al. Targeting EGFR/HER2 tyrosine kinases with a new potent series of 6-substituted 4-anilinoquinazoline hybrids: design, synthesis, kinase assay, cell-based assay, and molecular docking. Bioorg Med Chem Lett 2015;25:5147–54.
   PubMed Web of Science ®Google Scholar
• Zhang C, Li W. Regioselective synthesis of 6-aryl-benzo [h][1, 2, 4]-triazolo [5, 1-b] quinazoline-7, 8-diones as potent antitumoral agents. Bioorg Med Chem Lett 2013;23:5002–5.
   PubMed Web of Science ®Google Scholar
• Schuler M, Yang JH, Park K, et al. Afatinib beyond progression in patients with non-small-cell lung cancer following chemotherapy, erlotinib/gefitinib and afatinib: phase III randomized LUX-Lung 5 trial. Ann Oncol 2016;27:417–23.
   PubMed Web of Science ®Google Scholar
• Lee CK, Brown C, Gralla RJ, et al. Impact of EGFR inhibitor in non-small cell lung cancer on progression-free and overall survival: a meta-analysis. J Natl Cancer Inst 2013;105:595–605.
   PubMed Web of Science ®Google Scholar
• Pao W, Miller V, Zakowski M, et al. EGF receptor gene mutations are common in lung cancers from “never smokers” and are associated with sensitivity of tumors to gefitinib and erlotinib. Proc Natl Acad Sci USA 2004;101:13306–11.
   PubMed Web of Science ®Google Scholar
• Yin S, Tang C, Wang B, et al. Design, synthesis and biological evaluation of novel EGFR/HER2 dual inhibitors bearing a oxazolo [4, 5-g] quinazolin-2 (1H)-one scaffold. Eur J Med Chem 2016;120:26–36.
   PubMed Web of Science ®Google Scholar
• Ghorab MM, El Ella DAA, Heiba HI, Soliman AM. Synthesis of certain new thiazole derivatives bearing a sulfonamide moiety with expected anticancer and radiosensitizing activities. J Mater Sci Eng A 2011;1:684–91.
   Google Scholar
• El Ella DAA, Ghorab MM, Heiba HI, Soliman AM. Synthesis of some new thiazolopyrane and thiazolopyranopyrimidine derivatives bearing a sulfonamide moiety for evaluation as anticancer and radiosensitizing agents. Med Chem Res 2012;21:2395–407.
   Web of Science ®Google Scholar
• Supuran CT, Scozzafava A. Carbonic anhydrase inhibitors. Curr Med Chem Immunol Endocr Metab Agents 2001;1:61–97.
   Google Scholar
• Casini A, Scozzafava A, Supuran CT. Sulfonamide derivatives with protease inhibitory action as anticancer, anti-inflammatory and antiviral agents. Expert Opin Ther Pat 2002;12:1307–27.
   Web of Science ®Google Scholar
• Villar R, Encio I, Migliaccio M, et al. activity of lipophilic sulfonamide derivatives of the benzo [b] thiophene 1, 1-dioxide. Bioorg Med Chem 2004;12:963–8.
   PubMed Web of Science ®Google Scholar
• Payne JE, Bonnefous C, Hassig CA, et al. Identification of KD5170: a novel mercaptoketone-based histone deacetylase inhibitor. Bioorg Med Chem Lett 2008;18:6093–6.
   PubMed Web of Science ®Google Scholar
• Wurz RP, Liu L, Yang K, et al. Synthesis and structure–activity relationships of dual PI3K/mTOR inhibitors based on a 4-amino-6-methyl-1, 3, 5-triazine sulfonamide scaffold. Bioorg Med Chem Lett 2012;22:5714–20.
   PubMed Web of Science ®Google Scholar
• Ghorab MM, Alsaid MS, Soliman AM, Ragab FA. VEGFR-2 inhibitors and apoptosis inducers: synthesis and molecular design of new benzo [g] quinazolin bearing benzenesulfonamide moiety. J Enzyme Inhib Med Chem 2017;32:893–907.
   PubMed Web of Science ®Google Scholar
• Mosmann T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods 1983;65:55–63.
   PubMed Web of Science ®Google Scholar
• Emily HYC, Wei MC, Weiler S, et al. BCL-2, BCL-X L sequester BH3 domain-only molecules preventing BAX-and BAK-mediated mitochondrial apoptosis. Mol Cell 2001;8:705–11.
   PubMed Web of Science ®Google Scholar
• Alnemri ES, Livingston DJ, Nicholson DW, et al. Human ICE/CED-3 protease nomenclature. Cell 1996;87:171.
   PubMed Web of Science ®Google Scholar
• Harrington HA, Ho KL, Ghosh S, Tung K. Construction and analysis of a modular model of caspase activation in apoptosis. Theor Biol Med Model 2008;5:26–41.
   PubMed Web of Science ®Google Scholar
• Ghavami S, Hashemi M, Ande SR, et al. Apoptosis and cancer: mutations within caspase genes. J Med Genet 2009;46:497–510.
   PubMed Web of Science ®Google Scholar
• Rudel T. Caspase inhibitors in prevention of apoptosis. Herz 1999;24:236–41.
   PubMed Web of Science ®Google Scholar
• Tsujimoto Y. Cell death regulation by the Bcl-2 protein family in the mitochondria. J Cell Physiol 2003;195:158–67.
   PubMed Web of Science ®Google Scholar
• Hasnan J, Yusoff M, Damitri T, et al. Relationship between apoptotic markers (Bax and Bcl-2) and biochemical markers in type 2 diabetes mellitus. Singapore Med J 2010;51:50–6.
   PubMed Web of Science ®Google Scholar
• Callagy GM, Webber MJ, Pharoah PD, Caldas C. Meta-analysis confirms BCL2 is an independent prognostic marker in breast cancer. BMC Cancer 2008;8:153–8.
   PubMed Web of Science ®Google Scholar
• McDonnell TJ, Korsmeyer SJ. Progression from lymphoid hyperplasia to high-grade malignant lymphoma in mice transgenic for the t(14; 18)). Nature 1991;349:254–6.
   PubMed Web of Science ®Google Scholar
• Zhu H, Zhang J, Xue N, et al. Novel combretastatin A-4 derivative XN0502 induces cell cycle arrest and apoptosis in A549 cells. Invest New Drugs 2010;28:493–501.
   PubMed Web of Science ®Google Scholar
• MacLachlan TK, Sang N, Giordano A. Cyclins, cyclin-dependent kinases and cdk inhibitors: implications in cell cycle control and cancer. Crit Rev Eukaryot Gene Expr 1995;5:127–56.
   PubMed Web of Science ®Google Scholar
• DeVita VT, Lawrence TS, Rosenberg SA. Cancer: principles & practice of oncology: primer of the molecular biology of cancer. Philadelphia, PA: Lippincott Williams & Wilkins; 2012.
   Google Scholar
• Stamos J, Sliwkowski MX, Eigenbrot C. Structure of the epidermal growth factor receptor kinase domain alone and in complex with a 4-anilinoquinazoline inhibitor. J Biol Chem 2002;277:46265–72.
   PubMed Web of Science ®Google Scholar
• Ishikawa T, Seto M, Banno H, et al. Design and synthesis of novel human epidermal growth factor receptor 2 (HER2)/epidermal growth factor receptor (EGFR) dual inhibitors bearing a pyrrolo [3, 2-d] pyrimidine scaffold. J Med Chem 2011;54:8030–50.
   PubMed Web of Science ®Google Scholar
• Lin J, Shen W, Xue J, et al. Novel oxazolo[4,5-g]quinazolin-2(1H)-ones: dual inhibitors of EGFR and Src protein tyrosine kinases. Eur J Med Chem 2012;55:39–48.
   PubMed Web of Science ®Google Scholar
• Halmos B, Pennell NA, Fu P, et al. Randomized phase II trial of erlotinib beyond progression in advanced erlotinib-responsive non-small cell lung cancer. Oncologist 2015;20:1298–303.
   PubMed Web of Science ®Google Scholar
• Yousuf Z, Iman K, Iftikhar N, Mirza MU. Structure-based virtual screening and molecular docking for the identification of potential multi-targeted inhibitors against breast cancer. Breast Cancer (Dove Med Press) 2017;9:447–59.
   PubMed Web of Science ®Google Scholar