Structural and functional insight into thiazolidinone derivatives as novel candidates for anticancer drug design: in vitro biological and in-silico strategies

References

• Anand, P., Kunnumakkara, A. B., Newman, R. A., & Aggarwal, B. B. (2007). Bioavailability of curcumin: problems and promises. Molecular Pharmaceutics, 4(6), 807–818. https://doi.org/10.1021/mp700113r
   PubMed Web of Science ®Google Scholar
• Chabner, B. A., & Roberts, T. G. (2005). Timeline: Chemotherapy and the war on cancer. Nature Reviews. Cancer, 5(1), 65–72. https://doi.org/10.1038/nrc1529
   PubMed Web of Science ®Google Scholar
• Channar, P. A., Saeed, A., Larik, F. A., Rafiq, M., Ashraf, Z., Jabeen, F., & Fattah, T. A. (2017). Synthesis, computational studies and enzyme inhibitory kinetics of substituted methyl[2-(4-dimethylamino-benzylidene)-hydrazono)-4-oxo-thiazolidin-5-ylidene]acetates as mushroom tyrosinase inhibitors. Bioorganic & Medicinal Chemistry, 25(21), 5929–5938. https://doi.org/10.1016/j.bmc.2017.09.009
   PubMed Web of Science ®Google Scholar
• Childers, M. C., & Daggett, V. (2018). Validating molecular dynamics simulations against experimental observables in light of underlying conformational ensembles. The Journal of Physical Chemistry. B, 122(26), 6673–6689. https://doi.org/10.1021/acs.jpcb.8b02144
   PubMed Web of Science ®Google Scholar
• DeVita, V. T., & Chu, E. (2008). A history of cancer chemotherapy. Cancer Research, 68(21), 8643–8653. https://doi.org/10.1158/0008-5472.CAN-07-6611
   PubMed Web of Science ®Google Scholar
• Elford, H. L., Freese, M., Passamani, E., & Morris, H. P. (1970). Ribonucleotide Reductase and Cell Proliferation: I. Variations of ribonucleotide reductase activity with tumor growth rate in a series of rat hepatomas. Journal of Biological Chemistry, 245(20), 5228–5233. https://doi.org/10.1016/S0021-9258(18)62745-0
   PubMed Web of Science ®Google Scholar
• Fadok, V. A., Voelker, D. R., Campbell, P. A., Cohen, J. J., Bratton, D. L., & Henson, P. M. (1992). Exposure of phosphatidylserine on the surface of apoptotic lymphocytes triggers specific recognition and removal by macrophages. Journal of Immunology (Baltimore, MD: 1950), 148(7), 2207–2216.
   PubMed Web of Science ®Google Scholar
• Fuchs, Y., & Steller, H. (2011). Programmed cell death in animal development and disease. Cell, 147(4), 742–758. https://doi.org/10.1016/j.cell.2011.10.033
   PubMed Web of Science ®Google Scholar
• GaussView version 5. (2009). K. R Dennington, T. Keith, J. Millam - Semichem Inc, Shawnee Mission, GaussView, version 5.
   Google Scholar
• Gul-e-Saba, C., Ismail, M., Ismail, N., Habsah, M., & Muhammad, T. S. (2018). Induction of apoptosis by Aaptos sp., fractions in human breast cancer. Int J Res Pharm Sci, 9, 237–328.
   Google Scholar
• Hiss, D. C., & Gabriels, G. A. (2009). Implications of endoplasmic reticulum stress, the unfolded protein response and apoptosis for molecular cancer therapy. Part I: targeting p53, Mdm2, GADD153/CHOP, GRP78/BiP and heat shock proteins. Expert Opinion on Drug Discovery, 4(8), 799–821. https://doi.org/10.1517/17460440903052559
   PubMed Web of Science ®Google Scholar
• Huang, J., & MacKerell, J. A. (2013). CHARMM36 all-atom additive protein force field: validation based on comparison to NMR data . Journal of Computational Chemistry, 34(25), 2135–2145. https://doi.org/10.1002/jcc.23354
   PubMed Web of Science ®Google Scholar
• Hussein, R. K., & Elkhair, H. M. (2021). Molecular docking identification for the efficacy of some zinc complexes with chloroquine and hydroxychloroquine against main protease of COVID-19. Journal of Molecular Structure, 1231, 129979. https://doi.org/10.1016/j.molstruc.2021.129979
   PubMed Web of Science ®Google Scholar
• Iqbal, J., Ejaz, S. A., Khan, I., Ausekle, E., Miliutina, M., & Langer, P. (2019). Exploration of quinolone and quinoline derivatives as potential anticancer agents. Daru : journal of Faculty of Pharmacy, Tehran University of Medical Sciences, 27(2), 613–626. https://doi.org/10.1007/s40199-019-00290-3
   PubMed Web of Science ®Google Scholar
• Johnstone, R. W., Ruefli, A. A., & Lowe, S. W. (2002). Apoptosis: a link between cancer genetics and chemotherapy. Cell, 108(2), 153–164. https://doi.org/10.1016/S0092-8674(02)00625-6
   PubMed Web of Science ®Google Scholar
• Jordheim, L. P., Thomas, X. G., & Dumontet, C. M. (2006). Exposure of MCF-7 cells to gemcitabine induces a modification of the large subunit of ribonucleotide reductase, RNR R1, 26, 492–493.
   Google Scholar
• Kaddouri, Y., Abrigach, F., Yousfi, E. B., Kodadi, M. El., & Touzani, R. (2020). New thiazole, pyridine and pyrazole derivatives as antioxidant candidates: synthesis, DFT calculations and molecular docking study. Heliyon, 6(1), e03185. https://doi.org/10.1016/j.heliyon.2020.e03185
   PubMed Web of Science ®Google Scholar
• Lin, C. M., Jiang, Y. Q., Chaudhary, A. G., Rimoldi, J. M., Kingston, D. G., & Hamel, E. (1996). A convenient tubulin-based quantitative assay for paclitaxel (Taxol) derivatives more effective in inducing assembly than the parent compound. Cancer Chemotherapy and Pharmacology, 38(2), 136–140. https://doi.org/10.1007/s002800050461
   PubMed Web of Science ®Google Scholar
• Lowndes, C. M. (2006). Vaccines for cervical cancer. Epidemiology and Infection, 134(1), 1–2. https://doi.org/10.1017/S0950268805005728
   PubMed Web of Science ®Google Scholar
• M. J., Frisch, G. W., Trucks, H. B., Schlegel, G. E., Scuseria, M. A., Robb, J. R., Cheeseman, G., Scalmani, V., Barone, B., Mennucci, G. A., Petersson, H., Nakatsuji, M., Caricato, X., Li, H. P., Hratchian, A. F., Izmaylov, J., Bloino, G., Zheng, J. L., Sonnenberg, M. Hada, … Fox, (2010). Gaussian 09 (D01), Inc.,
   Google Scholar
• Mossman, T. (1983). Rapid colorimetric assay for cellular growth and survivals: Application to proliferation and cytotoxicity assays. J Immunol Meth, 65, 55–63.
   PubMed Web of Science ®Google Scholar
• Oyebamiji, A. K., Mutiu, O. A., Amao, F. A., Oyawoye, O. M., Oyedepo, T. A., Adeleke, B. B., & Semire, B. (2021). Dataset on in-silico investigation on triazole derivatives via molecular modelling approach: A potential glioblastoma inhibitors. Data in Brief, 34, 106703. https://doi.org/10.1016/j.dib.2020.106703
   PubMed Web of Science ®Google Scholar
• Patel, H. D., Divatia, S. M., & Clercq, E. D. (2013). Synthesis of some novel thiosemicarbazone derivatives having anti-cancer, anti-HIV as well as anti-bacterial activity. ChemInform, 44(32), no–no. https://doi.org/10.1002/chin.201332140
   Google Scholar
• Raff, M. C. (1992). Social controls on cell survival and cell death. Nature, 356(6368), 397–400. https://doi.org/10.1038/356397a0
   PubMed Web of Science ®Google Scholar
• Saeed, A., Ejaz, S. A., Ul-Hamid, A., El-Seedi, H. R., & Iqbal, J. (2021). Synthesis of and Molecular Docking Studies of Azomethine-Tethered Sulfonamides as Carbonic Anhydrase II & 15-Lipoxygenase Inhibitors. Journal of Molecular Structure, 1243, 130821. https://doi.org/10.1016/j.molstruc.2021.130821
   Web of Science ®Google Scholar
• Sartorelli, A. C., Moore, E. C., Zedeck, M. S., & Agrawal, K. C. (1970). Inhibition of ribonucleoside diphosphate reductase by 1-formylisoquinoline thiosemicarbazone and related compounds . Biochemistry, 9(23), 4492–4498. https://doi.org/10.1021/bi00825a005
   PubMed Web of Science ®Google Scholar
• Schlegel, R. A., & Williamson, P. (2007). P.S. to PS (phosphatidylserine)--pertinent proteins in apoptotic cell clearance. Sci STKE, 2007(408), p. e57.
   Google Scholar
• Shahid, W., Ejaz, S. A., Al-Rashida, M., Saleem, M., Ahmed, M., Rahman, J., Riaz, N., & Ashraf, M. (2021). Identification of NSAIDs as lipoxygenase inhibitors through highly sensitive chemiluminescence method, expression analysis in mononuclear cells and computational studies. Bioorganic Chemistry, 110, 104818. https://doi.org/10.1016/j.bioorg.2021.104818
   PubMed Web of Science ®Google Scholar
• Siegel, R. L., Miller, K. D., & Jemal, A. (2016). Cancer statistics, 2016. CA: a Cancer Journal for Clinicians, 66(1), 7–30. https://doi.org/10.3322/caac.21332
   PubMed Web of Science ®Google Scholar
• Sinha, S. K., & Saiz, L. (2014). Determinants of protein–ligand complex formation in the thyroid hormone receptor α: a Molecular Dynamics simulation study. Computational and Theoretical Chemistry, 1038, 57–66. https://doi.org/10.1016/j.comptc.2014.03.034
   Web of Science ®Google Scholar
• Sirion, U., Kasemsook, S., Suksen, K., Piyachaturawat, P., Suksamrarn, A., & Saeeng, R. (2012). New substituted C-19-andrographolide analogues with potent cytotoxic activities. Bioorganic & Medicinal Chemistry Letters, 22(1), 49–52. https://doi.org/10.1016/j.bmcl.2011.11.085
   PubMed Web of Science ®Google Scholar
• Thelander, L., & Reichard, P. (1979). Reduction of ribonucleotides. Annual Review of Biochemistry, 48, 133–158. https://doi.org/10.1146/annurev.bi.48.070179.001025
   PubMed Web of Science ®Google Scholar
• Van Genderen, H., Kenis, H., Lux, P., Ungeth, L., Maassen, C., Deckers, N., Narula, J., Hofstra, L., & Reutelingsperger, C. (2006). In vitro measurement of cell death with the annexin A5 affinity assay. Nature Protocols, 1(1), 363–367. https://doi.org/10.1038/nprot.2006.55
   PubMed Web of Science ®Google Scholar
• Vanommeslaeghe, K., Hatcher, E., Acharya, C., Kundu, S., Zhong, S., Shim, J., Darian, E., Guvench, O., Lopes, P., Vorobyov, I., & Mackerell, J. (2010). AD. CHARMM general force field: A force field for drug‐like molecules compatible with the CHARMM all‐atom additive biological force fields. J. comp. chem, 31, 671–690.
   PubMed Web of Science ®Google Scholar
• Wang, J., Wang, W., Kollman, P. A., & Case, D. A. (2006). Automatic atom type and bond type perception in molecular mechanical calculations. Journal of Molecular Graphics & Modelling, 25(2), 247–260. https://doi.org/10.1016/j.jmgm.2005.12.005
   PubMed Web of Science ®Google Scholar
• Xiong, G., Wu, Z., Yi, J., Fu, L., Yang, Z., Hsieh, C., Yin, M., Zeng, X., Wu, C., Lu, A., & Chen, X. (2021). ADMETlab 2.0: an integrated online platform for accurate and comprehensive predictions of ADMET properties. Nucleic Acids Research.
   Web of Science ®Google Scholar
• Zhang, Y., Zhang, T. J., Tu, S., Zhang, Z. H., & Meng, F. H. (2020). Identification of Novel Src Inhibitors: Pharmacophore-Based Virtual Screening, Molecular Docking and Molecular Dynamics Simulations. Molecules, 25(18), 4094. https://doi.org/10.3390/molecules25184094
   PubMed Web of Science ®Google Scholar
• Zhang, H. J., Qian, Y., Zhu, D. D., Yang, X. G., & Zhu, H. L. (2011). Synthesis, molecular modeling and biological evaluation of chalcone thiosemicarbazide derivatives as novel anticancer agents. European Journal of Medicinal Chemistry, 46(9), 4702–4708. https://doi.org/10.1016/j.ejmech.2011.07.016
   PubMed Web of Science ®Google Scholar
• Zheng, L. W., Wu, L. L., Zhao, B. X., Dong, W. L., & Miao, J. Y. (2009). Synthesis of novel substituted pyrazole-5-carbohydrazide hydrazone derivatives and discovery of a potent apoptosis inducer in A549 lung cancer cells. Bioorganic & Medicinal Chemistry, 17(5), 1957–1962. https://doi.org/10.1016/j.bmc.2009.01.037
   PubMed Web of Science ®Google Scholar