3,222
Views
63
CrossRef citations to date
0
Altmetric
Research Article

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

, , , , , , & show all
Pages 600-613 | Received 10 Aug 2016, Accepted 01 Jan 2017, Published online: 08 Feb 2017

References

  • Gottesman MM. Mechanisms of cancer drug resistance. Annu Rev Med 2002;53:615–27.
  • Rahmani-Nezhad S, Safavi M, Pordeli M, et al. Synthesis, in vitro cytotoxicity and apoptosis inducing study of 2-aryl-3-nitro-2H-chromene derivatives as potent anti-breast cancer agents. Eur J Med Chem 2014;86:562–9.
  • Sørlie T. Molecular portraits of breast cancer: tumour subtypes as distinct disease entities. Eur J Cancer 2004;40:2667–75.
  • Early Breast Cancer Trialists’ Collaborative Group. Effects of chemotherapy and hormonal therapy for early breast cancer on recurrence and 15-year survival: an overview of the randomised trials. Lancet 2005;365:1687–717.
  • Santos K, Laranjo M, Abrantes AM, et al. Targeting triple-negative breast cancer cells with 6,7-bis(hydroxymethyl)-1H,3H-pyrrolo[1,2-c]thiazoles. Eur J Med Chem 2014;79:273–81.
  • Rahman M, Davis SR, Pumphrey JG, et al. TRAIL induces apoptosis in triple-negative breast cancer cells with a mesenchymal phenotype. Breast Cancer Res Treat 2009;113:217–30.
  • Mbatia HW, Ramalingam S, Ramamurthy VP, et al. Novel C-4 Heteroaryl 13-cis-retinamide Mnk/AR degrading agents inhibit cell proliferation and migration and induce apoptosis in human breast and prostate cancer cells and suppress growth of MDA-MB-231 human breast and CWR22Rv1 human prostate tumor xenografts in mice. J Med Chem 2015;58:1900–14.
  • Senwar KR, Reddy TS, Thummuri D, et al. Design, synthesis and apoptosis inducing effect of novel (Z)-3-(3’-methoxy-4’-(2-amino-2-oxoethoxy)-benzylidene)indolin-2-ones as potential antitumour agents. Eur J Med Chem 2016;118:34–46.
  • Maire V, Baldeyron C, Richardson M, et al. TTK/hMPS1 is an attractive therapeutic target for triple-negative breast cancer. PLoS One 2013;20:e63712.
  • Jo EH, Lee SJ, Ahn NS, et al. Induction of apoptosis in MCF-7 and MDA-MB-231 breast cancer cells by oligonol is mediated by Bcl-2 family regulation and MEK/ERK signaling. Eur J Cancer Prev 2007;16:342–7.
  • Zhu Y, Tchkonia T, Fuhrmann-Stroissnigg H, et al. Identification of a novel senolytic agent, navitoclax, targeting the Bcl-2 family of anti-apoptotic factors. Aging Cell 2016;15:428–35.
  • Deeks ED. Venetoclax: first global approval. Drugs 2016;76:979–87.
  • Viegas-Junior C, Danuello A, Bolzani VDS, et al. Molecular hybridization: a useful tool in the design of new drug prototypes. Curr Med Chem 2007;14:1829–52.
  • Meunier B. Hybrid molecules with a dual mode of action: dream or reality? Acc Chem Res 2008;41:69–77.
  • Fortin S, Berube G. Advances in the development of hybrid anticancer drugs. Expert Opin Drug Discov 2013;8:1029–47.
  • Bansal Y, Silakari O. Multifunctional compounds: smart molecules for multifactorial diseases. Eur J Med Chem 2014;76:31–42.
  • Rana A, Alex JM, Chauhan M, et al. A review on pharmacophoric designs of antiproliferative agents. Med Chem Res 2015;24:903–20.
  • Ibrahim HS, Abou-Seri SAM, Abdel-Aziz HA. 3-Hydrazinoindolin-2-one derivatives: chemical classification and investigation of their targets as anticancer agents. Eur J Med Chem 2016;122:366–81.
  • Goodman VL, Rock EP, Dagher R, et al. Approval summary: sunitinib for the treatment of imatinib refractory or intolerant gastrointestinal stromal tumors and advanced renal cell carcinoma. Clin Cancer Res 2007;13:1367–73.
  • McCormack PL. Nintedanib: first global approval. Drugs 2015;75:129–39.
  • Selvam TP, Kumar PV. Quinazoline marketed drugs – a review. Res Pharm 2011;1:1–21.
  • Eldehna WM, Ibrahim HS, Abdel-Aziz HA, et al. Design, synthesis and in vitro antitumor activity of novel N-substituted-4-phenyl/benzylphthalazin-1-ones. Eur J Med Chem 2015;89:549–60.
  • 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.
  • 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.
  • Deeks ED. Olaparib: first global approval. Drugs 2015;75:231–40.
  • Havrylyuk D, Zimenkovsky B, Vasylenko O, et al. Synthesis of new 4-thiazolidinone-, pyrazoline-, and isatin-based conjugates with promising antitumor activity. J Med Chem 2012;55:8630–41.
  • Wang S, Zhao Y, Zhang G, et al. Design, synthesis and biological evaluation of novel 4-thiazolidinones containing indolin-2-one moiety as potential antitumor agent. Eur J Med Chem 2011;46:3509–18.
  • Ramshid PK, Jagadeeshan S, Krishnan A, et al. Synthesis and in vitro evaluation of some isatin-thiazolidinone hybrid analogues as anti-proliferative agents. Med Chem 2010;6:306–12.
  • Solomon VR, Hu C, Lee H. Hybrid pharmacophore design and synthesis of isatin–benzothiazole analogs for their anti-breast cancer activity. Bioorg Med Chem 2009;17:7585–92.
  • Karthikeyan C, Solomon VR, Lee H, Trivedi P. Design, synthesis and biological evaluation of some isatin-linked chalcones as novel anti-breast cancer agents: a molecular hybridization approach. Biomed Prev Nutr 2013;3:325–30.
  • Xu L, Russu WA. Molecular docking and synthesis of novel quinazoline analogues as inhibitors of transcription factors NF-jB activation and their anti-cancer activities. Bioorg Med Chem 2013;21:540–6.
  • Alafeefy AM, Ashour AE, Prasad O, et al. Development of certain novel N-(2-(2-(2-oxoindolin-3-ylidene)hydrazinecarbonyl)phenyl)-benzamides and 3-(2-oxoindolin-3-ylideneamino)-2-substituted quinazolin-4(3H)-ones as CFM-1 analogs: design, synthesis, QSAR analysis and anticancer activity. Eur J Med Chem 2015;92:191–201.
  • Alanazi AM, Abdel-Aziz AAM, Al-Suwaidan IA, et al. Design, synthesis and biological evaluation of some novel substituted quinazolines as antitumor agents. Eur J Med Chem 2014;79:446–54.
  • Mahdavi M, Pedrood K, Safavi M, et al. Synthesis and anticancer activity of N-substituted 2-arylquinazolinones bearing trans-stilbene scaffold. Eur J Med Chem 2015;95:492–9.
  • Rhee HK, Yoo JH, Lee E, et al. Synthesis and cytotoxicity of 2-phenylquinazolin-4(3H)-one derivatives. Eur J Med Chem 2011;95:3900–8.
  • Zhang SL, Liu YJ, Zhao YF, et al. Synthesis and antitumor activities of novel 1,4-substituted phthalazine derivatives. Chin Chem Lett 2010;21:1071–4.
  • Zhang S, Zhao Y, Liu Y, et al. Synthesis and antitumor activities of novel 1,4-disubstituted phthalazine derivatives. Eur J Med Chem 2010;45:3504–10.
  • Liu Y, Zhang S, Li Y, et al. Synthesis and cytotoxic evaluation of some new phthalazinylpiperazine derivatives. Arch Pharm (Weinheim) 2012;345:287–93.
  • Aboul-Fadl T, Kadi A, Abdel-Aziz HA. Novel N,N´-hydrazino-bis-isatin derivatives with selective activity against multidrug-resistant cancer cells, Patent US20120252860, USA, 2012.
  • 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.
  • Eldehna WM, Fares M, Abou-Seri SM, et al. Design, synthesis and in vitro antiproliferative activity of novel isatin‐quinazoline hybrids. Arch Pharm 2015;348:144–54.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • Ibrahim HS, Eldehna WM, Abdel-Aziz HA, et al. Improvement of antibacterial activity of some sulfa drugs through linkage to certain phthalazin-1(2H)-one scaffolds. Eur J Med Chem 2015;85:480–6.
  • Geuns-Meyer S, Cee VJ, Deak HL, et al. Discovery of N-(4-(3-(2-aminopyrimidin-4-yl) pyridin-2-yloxy) phenyl)-4-(4-methylthiophen-2-yl) phthalazin-1-amine (AMG 900), a highly selective, orally bioavailable inhibitor of aurora kinases with activity against multidrug-resistant cancer cell lines. J Med Chem 2015;58:5189–207.
  • Razvi M, Ramalingam T, Sattur PB. Synthesis and biological activity of 3,6-diaryl-1, 2,4-trizolo [3, 4-a]-phthalazines. Ind J Chem B 1989;28:987–9.
  • 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;73:211–15.
  • Longley D, Harkin D, Johnston P. 5-fluorouracil: mechanisms of action and clinical strategies. Nat Rev Cancer 2003;3:330–8.
  • Joensuu H, Gligorov J. Adjuvant treatments for triple-negative breast cancers. Ann Oncol 2012;23:40–5.
  • Cai SX, Nguyen B, Jia S, et al. Discovery of substituted N-phenyl nicotinamides as potent inducers of apoptosis using a cell- and caspase-based high throughput screening assay. J Med Chem 2003;46:2474–81.
  • Cordeu L, Cubedo E, Bandres E, et al. Biological profile of new apoptotic agents based on 2,4-pyrido[2,3-d]pyrimidine derivatives. Bioorg Med Chem 2007;15:1659–69.
  • Hu W, Kavanagh JJ. Anticancer therapy targeting the apoptotic pathway. Lancet Oncol 2003;4:721–9.
  • Fulda S. Tumor resistance to apoptosis. Int J Cancer 2009;124:511–15.
  • Reed JC. Apoptosis-based therapies. Nat Rev Drug Discov 2002;1:111–21.
  • Ding G, Liu F, Yang T, et al. A novel kind of nitrogen heterocycle compound induces apoptosis of human chronic myelogenous leukemia K562 cells. Bioorg Med Chem 2006;14:3766–74.
  • Breckenridge DG, Xue D. Regulation of mitochondrial membrane permeabilization by BCL-2 family proteins and caspases. Curr Opin Cell Biol 2004;16:647–52.
  • Chakravarti B, Ranjani M, Siddiqui JA, et al. In vitro anti-breast cancer activity of ethanolic extract of Wrightia tomentosa: role of pro-apoptotic effects of oleanolic acid and urosolic acid. J Ethnopharm 2012;142:72–9.
  • Szumilak M, Szulawska MA, Koprowska K, et al. Synthesis and in vitro biological evaluation of new polyamine conjugates as potential anticancer drugs. Eur J Med Chem 2010;45:5744–51.
  • Skehan P, Storeng R, Scudiero D, et al. New colorimetric cytotoxicity assay for anticancer-drug screening. J Natl Cancer Inst 1990;82:1107–12.