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Research Paper

In vitro anticancer potentiality and molecular modelling study of novel amino acid derivatives based on N1,N3-bis-(1-hydrazinyl-1-oxopropan-2-yl) isophthalamide

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Pages 1247-1258 | Received 14 Feb 2019, Accepted 23 Apr 2019, Published online: 09 Jul 2019

References

  • Eckhardt S. Recent progress in the development of anticancer agents. Curr Med Chem Anticancer Agents 2002;2:419–39.
  • World Health Organization. 2. Results; A. Annex, 2.1. Global patterns of health risk. In: Global health risks: mortality and burden of disease attributable to selected major risks. Geneva: World Health Organization; 2009.
  • Khanna I. Drug discovery in pharmaceutical industry: productivity challenges and trends. Drug Discov Today 2012;17:1088–102.
  • Moghaddam G, Ebrahimi SA, Rahbar-Roshandel N, Foroumadi A. Antiproliferative activity of flavonoids: influence of the sequential methoxylation state of the flavonoid structure. Phytother Res 2012;26:1023–8.
  • 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.
  • Liechty WB, Kryscio DR, Slaughter BV, Peppas NA. Polymers for drug delivery systems. Annu Rev Chem Biomol Eng 2010;1:149–73.
  • Efentakis M, Politis S. Comparative evaluation of various structures in polymer controlled drug delivery systems and the effect of their morphology and characteristics on drug release. Eur Polym J 2006;42:1183–95.
  • Leite NB, Aufderhorst-Roberts A, Palma MS, et al. PE and PS lipids synergistically enhance membrane poration by a peptide with anticancer properties. Biophys J 2015;109:936–47.
  • Meng L, Zhang X, Lu Q, et al. Single walled carbon nanotubes as drug delivery vehicles: targeting doxorubicin to tumors. Biomaterials 2012;33:1689–98.
  • Ziemba B, Matuszko G, Appelhans D, et al. Genotoxicity of poly (propylene imine) dendrimers. Biopolymers 2012;97:642–8.
  • Duncan R. The dawning era of polymer therapeutics. Nat Rev Drug Discov 2003;2:347–60.
  • Mercado SA, Orellana-Tavra C, Chen A, Slater NKH. The intracellular fate of an amphipathic pH-responsive polymer: key characteristics towards drug delivery. Mater Sci Eng C 2016;69:1051–7.
  • Ho VHB, Slater NKH, Chen R. pH-responsive endosomolytic pseudo-peptides for drug delivery to multicellular spheroids tumour models. Biomaterials 2011;32:2953–8.
  • Felício MR, Silva ON, Gonçalves S, et al. Peptides with dual antimicrobial and anticancer activities. Front Chem 2017;5:5.
  • Dennison S, Whittaker M, Harris F, Phoenix D. Anticancer alpha-helical peptides and structure/function relationships underpinning their interactions with tumour cell membranes. Curr Protein Pept Sci 2006;7:487–99.
  • Mader JS, Hoskin DW. Cationic antimicrobial peptides as novel cytotoxic agents for cancer treatment. Expert Opin Investig Drugs 2006;15:933–46.
  • Sourav DE, Babu NM, Babu ST, et al. A review article on importance of heterocyclic compounds. Mintage J Pharma Med Sci 2016;5:18–27.
  • Ammar YA, Sh El-Sharief AM, Belal A, et al. Design, synthesis, antiproliferative activity, molecular docking and cell cycle analysis of some novel (morpholinosulfonyl) isatins with potential EGFR inhibitory activity. Eur J Med Chem 2018;156:918–32.
  • Dweedar HE, Mahrous H, Ibrahim HS, Abdel-Aziz HA. Analogue-based design, synthesis and biological evaluation of 3-substituted-(methylenehydrazono) indolin-2-ones as anticancer agents. Eur J Med Chem 2014;78:275–80.
  • 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.
  • Chen G, Weng Q, Fu L, et al. Synthesis and biological evaluation of novel oxindole-based RTK inhibitors as anti-cancer agents. Bioorg Med Chem 2014;22:6953–60.
  • Bajaj S, Roy PP, Singh J. Synthesis, thymidine phosphorylase inhibitory and computational study of novel 1, 3, 4-oxadiazole-2-thione derivatives as potential anticancer agents. Comput Biol Chem 2018;76:151–60.
  • Ahsan MJ, Rathod VPS, Singh M, et al. Synthesis, anticancer and molecular docking studies of 2-(4-chlorophenyl)-5-aryl-1,3,4-oxadiazole analogues. Med Chem 2013;3:294–7.
  • Abdelazeem AH, El-Saadi MT, Said EG, et al. Novel diphenylthiazole derivatives with multi-target mechanism: synthesis, docking study, anticancer and anti-inflammatory activities. Bioorg Chem 2017;75:127–38.
  • Suthar SK, Jaiswal V, Lohan S, et al. Novel quinolone substituted thiazolidin-4-ones as anti-inflammatory, anticancer agents: design, synthesis and biological screening. Eur J Med Chem 2013;63:589–602.
  • Abo-Ghalia MH, Moustafa GO, Alwasidi AS, Naglah AM. Cytotoxic investigation of isophthaloyl cyclopentapeptides. Latin Am J Pharm 2017;36:1957–62. ISSN 2362–3853.
  • Moustafa GO, El-Sawy AA, Abo-Ghalia MH. Synthesis of novel cyclopeptide candidates: I-cyclo-[Nα-isophthaloyl-bis-(glycine-amino acid)-L-lysine] derivatives with expected anticancer activity. Egypt J Chem 2013;5:473–94.
  • Amr AE, Abo-Ghalia MH, Moustafa GO, et al. Design, synthesis and docking studies of novel macrocyclic pentapeptides as anticancer multi-targeted kinase inhibitors. Molecules 2018;23:2416.
  • White BD, Mallen J, Arnold KA, et al. Peptide side-arm derivatives of lariat ethers and bibracchial lariat ethers: syntheses, cation binding properties, and solid state structural data. J Org Chem 1989;54:937–47.
  • Rao MV, Rojivadia AJ, Parsania PH, Parekh HH. Synthesis and characterization of the poly 1, 1’-bis (3-methyl-4-hydroxyphenyl) cyclohexane iso-terephthalate (PMeBCIT). J Macromol Sci Chem Ed 1990;A27:53–61.
  • Joshi NB, Parsania PH. Synthesis and physico-chemical characterization of halogenated partly aromatic cardo copolyesters. Polym-Plas Technol Eng 2007;46:1151–9.
  • Thabrew M, Hughes RD, Mcfarlane IG. Screening of hepatoprotective plant components using a HepG2 cell cytotoxicity assay. J Pharm Pharmacol 1997;49:1132–5.
  • Selim MS, Amer SK, Mohamed SS, et al. Production and characterization of exopolysaccharide from Streptomyces carpaticus isolated from marine sediments in Egypt and its effect on breast and colon cell lines. J Genetic Eng Biotechnol 2018;16:23–8.
  • Mosmann T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Meth 1983;65:55–63.
  • Onur R, Semerciöz A, Orhan I, Yekeler H. The effects of melatonin and the antioxidant defense system on apoptosis regulator proteins (Bax and Bcl-2) in experimentally induced varicocele. Urol Res 2004;32:204–8.
  • Barbareschi M, Caffo O, Veronese S, et al. Bcl-2 and p53 expression in node-negative breast carcinoma: a study with long-term follow-up. Human Pathol 1996;27:1149–55.
  • Thomas MD, McIntosh GG, Anderson JJ, et al. Novel quantitative immunoassay system for p53 using antibodies selected for optimum designation of p53 status. J Clin Pathol 1997;50:143–7.
  • Denault JB, Salvesen GS. Human caspase-7 activity and regulation by its N-terminal peptide. J Biol Chem 2003;278:34042–50.
  • Liliom K, Lehotzky A, Molnar A, Ovadi J. Characterization of tubulin-alkaloid interactions by enzyme-linked immunosorbent assay. Anal Biochem 1995;228:18–26.
  • Cohen JJ, Duke RC. Glucocorticoid activation of a calcium-dependent endonuclease in thymocyte nuclei leads to cell death. J Immunol 1984;132:38–42.
  • Burton KA. Study of the conditions and mechanism of the diphenylamine reaction for the colorimetric estimation of deoxyribonucleic acid. Biochem J 1956;62:315–23.
  • Molecular Operating Environment (MOE). Chemical Computing Group ULC, 1010 Sherbrooke St. West, Suite #910, Montreal, QC, Canada, H3A 2R7. 2008. Available online: https://www.chemcomp.com/MOEMolecular_Operating_Environment.htm.
  • Nossier ES, Abd El-Karim SS, Khalifa NM, et al. Kinase inhibitory activities and molecular docking of a novel series of anticancer pyrazole derivatives. Molecules 2018;23:3074.
  • Moustafa G, Khalaf H, Naglah A, et al. Synthesis, molecular docking studies, in vitro antimicrobialand antifungal activities of novel dipeptide derivatives based on N-(2-(2-hydrazinyl-2-oxoethylamino)-2-oxoethyl)-nicotinamide. Molecules 2018;23:761.
  • Naglah AM, Moustafa GO, Al-Omar MA, et al. Synthesis, characterization and in vitro antimicrobial investigation of novel amino acids and dipeptides based on dibenzofuran-2-sulfonyl-chloride. J Comput Theor Nanosci 2017;14:3183–90.
  • Al-Salem HSA, Naglah AM, Moustafa GO, et al. Synthesis of novel tripeptides based on dibenzofuran-2-sulfonyl-[aromatic and hydroxy aromatic residues]: towards antimicrobial and antifungal agents. J Comput Theor Nanosci 2017;14:3958–66.
  • Elhenawy AA, AL-Harbi LM, Moustafa GO, et al. Synthesis, comparative docking and pharmacological activity of naproxenyl amino acid derivatives as possible anti-inflammatory and analgesic agents. Drug Des Dev Therapy 2019;13:1773–90.
  • Hassan AS, Moustafa GO, Askar AA, et al. Synthesis and antibacterial evaluation of fused pyrazoles and Schiff bases. Synthetic Commun 2018;48:2761–72.
  • Moustafa GO, Younis A, Al-Yousef SA, Mahmoud SY. Design, synthesis of novel cyclic pentapeptide derivatives based on 1, 2-benzenedicarbonyl chloride with expected anticancer activity. J Comput Theoret Nanosci (CTN) 2019;16:1–7.
  • Hassan AS, Moustafa GO, Awad HM. Synthesis and in vitro anticancer activity of pyrazolo[1,5-a]pyrimidines and pyrazolo [3,4-d] [1, 2, 3] triazines. Synthetic Commun 2017;47:1963–72.
  • Miyashita T, Krajewski S, Krajewska M, et al. Tumor suppressor p53 is a regulator of bcl-2 and bax gene expression in vitro and in vivo. Oncogene 1994;9:1799–805.
  • Zimmermann KC, Green DR. How cells die: apoptosis pathways. J Allergy Clin Immunol 2001;108:99–103.
  • Elmore S. Apoptosis: a review of programmed cell death. Toxicol Pathol 2007;35:495–516.