Synthesis, characterization, and anticancer activity of Schiff bases

References

• Alaghaz, A., & Bayoumi, H. A. (2013). Synthesis, spectral properties and potentiometric studies on some metal Schiff base complexes derived from 4-chlorophenyl-2-aminothiazole. International Journal of Electrochemical Science, 8, 11860–11876.
   Web of Science ®Google Scholar
• Alyar, S., Şen, T., Şen, C., Alyar, H., Adem, Ş., & Özdemir, Ü. Ö. (2019). Synthesis, spectroscopic characterizations, enzyme inhibition, molecular docking study and DFT calculations of new Schiff bases of sulfa drugs. Journal of Molecular Structure, 1185, 416. doi: 10.1016/j.molstruc.2019.03.002
   Web of Science ®Google Scholar
• Amiri, M., Ajloo, D., Fazli, M., Mokhtarieh, A., Grivani, G., & Saboury, A. A. (2018). Spectroscopic, electrochemical, docking and molecular dynamics studies on the interaction of three oxovanadium (IV) Schiff base complexes with bovine serum albumin and their cytotoxicity against cancer. Journal of Biomolecular Structure and Dynamics, 36(14), 3753–3772. doi: 10.1080/07391102.2017.1400467
   PubMed Web of Science ®Google Scholar
• Armarego, W. L. (2017). Purification of laboratory chemicals. USA: Elsevier, Butterworth-Heinemann.
   Google Scholar
• Arshad, N., & Farooqi, S. I. (2018). Cyclic voltammetric DNA Binding investigations on some anticancer potential metal complexes: A review. Applied Biochemistry and Biotechnology, 186(4), 1090–1110. doi: 10.1007/s12010-018-2818-z
   PubMed Web of Science ®Google Scholar
• Aslanoglu, M., & Ayne, G. (2004). Voltammetric studies of the interaction of quinacrine with DNA. Analytical and Bioanalytical Chemistry, 380(4), 658–663. doi: 10.1007/s00216-004-2797-5
   PubMed Web of Science ®Google Scholar
• Cree, I. A., & Charlton, P. (2017). Molecular chess? Hallmarks of anti-cancer drug resistance. BMC Cancer, 17(1), 10doi: 10.1186/s12885-016-2999-1
   PubMed Web of Science ®Google Scholar
• Crissman, H. A., & Tobey, R. A. (1974). Cell-cycle analysis in 20 minutes. Science (New York, N.Y.), 184(4143), 1297–1298. doi: 10.1126/science.184.4143.1297
   PubMed Web of Science ®Google Scholar
• Crowley, L. C., Scott, A. P., Marfell, B. J., Boughaba, J. A., Chojnowski, G., & Waterhouse, N. J. (2016). Measuring cell death by propidium iodide uptake and flow cytometry. Cold Spring Harbor Protocols, 2016(7), pdb-prot087163. doi: 10.1101/pdb.prot087163
   Google Scholar
• Darzynkiewicz, Z., Halicka, H. D., & Zhao, H. (2010). Analysis of cellular DNA content by flow and laser scanning cytometry. In R. Y. C. Poon (Ed.), Polyploidization and cancer (pp. 137–147). New York, NY: Springer.
   Google Scholar
• Dehkhodaei, M., Sahihi, M., & Amiri Rudbari, H. (2018). Spectroscopic and molecular docking studies on the interaction of Pd (II) & Co (II) Schiff base complexes with β-lactoglobulin as a carrier protein. Journal of Biomolecular Structure and Dynamics, 36(12), 3130–3136. doi: 10.1080/07391102.2017.1380537
   PubMed Web of Science ®Google Scholar
• Dengler, W. A., Schulte, J., Berger, D. P., Mertelsmann, R., & Fiebig, H. H. (1995). Development of a propidium iodide fluorescence assay for proliferation and cytotoxicity assays. Anti-Cancer Drugs, 6(4), 522–532. doi: 10.1097/00001813-199508000-00005
   PubMed Web of Science ®Google Scholar
• Deshmukh, P., Soni, P. K., Kankoriya, A., Halve, A. K., & Dixit, R. (2015). 4-Aminoantipyrine: A significant tool for the synthesis of biologically active Schiff bases and metal complexes. International Journal of Pharmaceutical Sciences and Research, 34(1), 162–170.
   Google Scholar
• Doonan, F., & Cotter, T. G. (2008). Morphological assessment of apoptosis. Methods (San Diego, Calif.), 44(3), 200–204. doi: 10.1016/j.ymeth.2007.11.006
   PubMed Web of Science ®Google Scholar
• Elmore, S. (2007). Apoptosis: A review of programmed cell death. Toxicologic Pathology, 35(4), 495–516. doi: 10.1080/01926230701320337
   PubMed Web of Science ®Google Scholar
• Frisch, M., Trucks, G., Schlegel, H., Scuseria, G. W., Robb, M., Cheeseman, J., … Fox, D. J. (2009). Gaussian 09, Revision E.01 Gaussian, Inc., Wallingford, CT.
   Google Scholar
• Goel, P., Kumar, D., & Chandra, S. (2014). Schiff’s base ligands and their transition metal complexes as antimicrobial agents. Journal of Chemical, Biological and Physical Sciences, 4, 1946–1964.
   Google Scholar
• Gomes, F., Ramos, I., Wendt, C., Girard-Dias, W., De Souza, W., Machado, E., & Miranda, E. (2013). New insights into the in situ microscopic visualization and quantification of inorganic polyphosphate stores by 4’, 6-diamidino-2-phenylindole (DAPI)-staining. European Journal of Histochemistry, 57(4), 34. doi: 10.4081/ejh.2013.e34
   Web of Science ®Google Scholar
• Gottlieb, H. E., Kotlyar, V., & Nudelman, A. (1997). NMR chemical shifts of common laboratory solvents as trace impurities. The Journal of Organic Chemistry, 62(21), 7512–7515. doi: 10.1021/jo971176v
   PubMed Web of Science ®Google Scholar
• Gurova, K. (2009). New hopes from old drugs: Revisiting DNA-binding small molecules as anticancer agents. Future Oncology, 5(10), 1685–1704. doi: 10.2217/fon.09.127
   PubMed Web of Science ®Google Scholar
• Hassanpour, S. H., & Dehghani, M. (2017). Review of cancer from perspective of molecular. Journal of Cancer Research and Practice, 4(4), 127–129. doi: 10.1016/j.jcrpr.2017.07.001
   Google Scholar
• Hyndman, I. J. (2016). Review: the Contribution of both nature and nurture to carcinogenesis and progression in solid tumours. Cancer Microenvironment: Official Journal of the International Cancer Microenvironment Society, 9(1), 63–69. doi: 10.1007/s12307-016-0183-4
   PubMed Web of Science ®Google Scholar
• Hyndman, I. J. (2016). The contribution of both nature and nurture to carcinogenesis and progression in solid tumours. Cancer Microenvironment, 9(1), 63–69. doi: 10.1007/s12307-016-0183-4
   PubMed Web of Science ®Google Scholar
• Iqbal, J., Ejaz, S. A., Saeed, A., & Al-Rashida, M. (2018). Detailed investigation of anticancer activity of sulfamoyl benz (sulfon) amides and 1H-pyrazol-4-yl benzamides: An experimental and computational study. European Journal of Pharmacology, 832, 11–24.
   PubMed Web of Science ®Google Scholar
• Iqbal, M., Ahmad, I., Ali, S., Muhammad, N., Ahmed, S., & Sohail, M. (2013). Dimeric “paddle-wheel” carboxylates of copper (II): Synthesis, crystal structure and electrochemical studies. Polyhedron, 50(1), 524–531. doi: 10.1016/j.poly.2012.11.037
   Web of Science ®Google Scholar
• Jeyaraman, P., Alagarraj, A., & Natarajan, R. (2019). In silico and in vitro studies of transition metal complexes derived from curcumin–isoniazid Schiff base. Journal of Biomolecular Structure and Dynamics, 37, 1–12. doi: 10.1080/07391102.2019.1581090
   PubMedGoogle Scholar
• Kajal, A., Bala, S., Kamboj, S., Sharma, N., & Saini, V. (2013). Schiff bases: A versatile pharmacophore. Journal of Catalysts, 2013, 1. doi: 10.1155/2013/893512
   Google Scholar
• Kapuscinski, J. (1995). DAPI: A DNA-specific fluorescent probe. Biotechnic & Histochemistry, 70(5), 220–233. doi: 10.3109/10520299509108199
   PubMed Web of Science ®Google Scholar
• Kim, S. (2015). New and emerging factors in tumorigenesis: An overview. Cancer Management and Research, 7, 225doi: 10.2147/CMAR.S47797
   PubMed Web of Science ®Google Scholar
• Kumaran, J. S., Priya, S., Gowsika, J., Jayachandramani, N., & Mahalakshmi, S. (2013). Synthesis, spectroscopic characterization, in silica DNA studies and antibacterial activities of copper (II) and zinc (II) complexes derived from thiazole based pyrazolone derivatives. Research Journal of Pharmaceutical, Biological and Chemical Science, 4(279), e287.
   Google Scholar
• Kutzelnigg, W., Fleischer, U., & Schindler, M. (1990). In Diehl, P., Fluck, and Kosfeld, R. (Eds.), NMR basic principles and progress. Springer, Berlin, 23, 165.
   Google Scholar
• Lin, G.-J., Jiang, G.-B., Xie, Y.-Y., Huang, H.-L., Liang, Z.-H., & Liu, Y.-J. (2013). Cytotoxicity, apoptosis, cell cycle arrest, reactive oxygen species, mitochondrial membrane potential, and Western blotting analysis of ruthenium (II) complexes. JBIC Journal of Biological Inorganic Chemistry, 18(8), 873–882. doi: 10.1007/s00775-013-1032-2
   PubMed Web of Science ®Google Scholar
• Lin, S.-F., Lin, J.-D., Hsueh, C., Chou, T.-C., & Wong, R. J. (2018). Activity of roniciclib in medullary thyroid cancer. Oncotarget, 9(46), 28030doi: 10.18632/oncotarget.25555
   PubMedGoogle Scholar
• Mosmann, T. (1983). Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxicity assays. Journal of Immunological Methods, 65(1–2), 55–63. doi: 10.1016/0022-1759(83)90303-4
   PubMed Web of Science ®Google Scholar
• Niks, M. (1990). Towards an optimized MTT assay. Journal of Immunological Methods, 130(1), 149–151. doi: 10.1016/0022-1759(90)90309-j
   PubMed Web of Science ®Google Scholar
• Nunez, R. (2001). DNA measurement and cell cycle analysis by flow cytometry. Current Issues in Molecular Biology, 3(3), 67–70.
   PubMedGoogle Scholar
• Olsson, M., & Zhivotovsky, B. (2011). Caspases and cancer. Cell Death & Differentiation, 18(9), 1441. doi: 10.1038/cdd.2011.30
   PubMed Web of Science ®Google Scholar
• Pan, J., Xu, G., & Yeung, S.-C. J. (2001). Cytochrome c release is upstream to activation of caspase-9, caspase-8, and caspase-3 in the enhanced apoptosis of anaplastic thyroid cancer cells induced by manumycin and paclitaxel. Journal of Clinical Endocrinology & Metabolism, 86(10), 4731–4740. doi: 10.1210/jc.86.10.4731
   PubMed Web of Science ®Google Scholar
• Popovic, Z., Roje, Z., & Pavlovic, G. (2001). Matkovic-Calogovic D and Giester G. Journal of Molecular Structure, 2001, 597.
   Google Scholar
• Rambabu, A., Pradeep Kumar, M., Ganji, N., Daravath, S. &  Shivaraj, (2019). DNA binding and cleavage, cytotoxicity and antimicrobial studies of Co (II), Ni (II), Cu (II) and Zn (II) complexes of 1-((E)-(4-(trifluoromethoxy) phenylimino) methyl) naphthalen-2-ol Schiff base. Journal of Biomolecular Structure and Dynamics, 1–10.
   PubMed Web of Science ®Google Scholar
• Rastogi, R. P., , Singh, S. P., Hader, D.-P., & Sinha, R. P. (2010). Detection of reactive oxygen species (ROS) by the oxidant sensing probe 2',7'- dichlorodihydrofluorescein diacetate in the cyanobacterium Anabaena variabilis PCC 7937. Biochemical and Biophysical Research Communications, 397(3), 603–607. doi: 10.1016/j.bbrc.2010.06.006
   PubMed Web of Science ®Google Scholar
• Saito, Y., Uchida, N., Tanaka, S., Suzuki, N., Tomizawa-Murasawa, M., Sone, A., … Ishikawa, F. (2010). Induction of cell cycle entry eliminates human leukemia stem cells in a mouse model of AML. Nature Biotechnology, 28(3), 275. doi: 10.1038/nbt.1607
   PubMed Web of Science ®Google Scholar
• Shabbir, M., Akhter, Z., Ahmad, I., Ahmed, S., Bolte, M., & McKee, V. (2017). Synthesis and bioelectrochemical behavior of aromatic amines. Bioorganic Chemistry, 75, 224–234.
   PubMed Web of Science ®Google Scholar
• Shabbir, M., Akhter, Z., Ahmad, I., Ahmed, S., Ismail, H., Mirza, B., … Bolte, M. (2015). Synthesis, biological and electrochemical evaluation of novel nitroaromatics as potential anticancerous drugs. Bioelectrochemistry, 104, 85–92. doi: 10.1016/j.bioelechem.2015.03.007
   PubMed Web of Science ®Google Scholar
• Shahraki, S., & Heydari, A. (2018). Binding forces between a novel Schiff base palladium (II) complex and two carrier proteins: Human serum albumi and β-lactoglobulin. Journal of Biomolecular Structure and Dynamics, 36(11), 2807–2821. doi: 10.1080/07391102.2017.1367723
   PubMed Web of Science ®Google Scholar
• Shahraki, S., Shiri, F., & Saeidifar, M. (2018). Synthesis, characterization, in silico ADMET prediction, and protein binding analysis of a novel zinc (II) Schiff-base complex: Application of multi-spectroscopic and computational techniques. Journal of Biomolecular Structure and Dynamics, 36(7), 1666–1680. doi: 10.1080/07391102.2017.1334595
   PubMed Web of Science ®Google Scholar
• Shokohi-Pour, Z., Chiniforoshan, H., Sabzalian, M. R., Esmaeili, S.-A., & Momtazi-Borojeni, A. A. (2018). Cobalt (II) complex with novel unsymmetrical tetradentate Schiff base (ON) ligand: In vitro cytotoxicity studies of complex, interaction with DNA/protein, molecular docking studies, and antibacterial activity. Journal of Biomolecular Structure and Dynamics, 36(2), 532–549. doi: 10.1080/07391102.2017.1287006
   PubMed Web of Science ®Google Scholar
• Siddiqui, H., Iqbal, A., Ahmad, S., & Weaver, W. (2006). Synthesis and spectroscopic studies of new Schiff bases. Molecules (Basel, Switzerland), 11(2), 206–211. doi: 10.3390/11020206
   PubMed Web of Science ®Google Scholar
• Sirajuddin, M., Ali, S., & Badshah, A. (2013). Drug–DNA interactions and their study by UV–Visible, fluorescence spectroscopies and cyclic voltametry. Journal of Photochemistry and Photobiology B: Biology, 124, 1–19. doi: 10.1016/j.jphotobiol.2013.03.013
   PubMed Web of Science ®Google Scholar
• Sirajuddin, M., Ali, S., McKee, V., Zaib, S., & Iqbal, J. (2014). Organotin (IV) carboxylate derivatives as a new addition to anticancer and antileishmanial agents: Design, physicochemical characterization and interaction with Salmon sperm DNA. RSC Adv., 4(101), 57505–57521. doi: 10.1039/C4RA10487K
   Web of Science ®Google Scholar
• Sirajuddin, M., Ali, S., Shah, N. A., Khan, M. R., & Tahir, M. N. (2012). Synthesis, characterization, biological screenings and interaction with calf thymus DNA of a novel azomethine 3-((3, 5-dimethylphenylimino) methyl) benzene-1, 2-diol. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 94, 134–142. doi: 10.1016/j.saa.2012.03.068
   PubMed Web of Science ®Google Scholar
• Sträuber, H., & Müller, S. (2010). Viability states of bacteria—Specific mechanisms of selected probes. Cytometry Part A, 77(7), 623–634. doi: 10.1002/cyto.a.20920
   PubMedGoogle Scholar
• Szczepaniak, J., Strojny, B., Chwalibog, E. S., Jaworski, S., Jagiello, J., Winkowska, M., … Grodzik, M. (2018). Effects of reduced graphene oxides on apoptosis and cell cycle of glioblastoma multiforme. International Journal of Molecular Sciences, 19(12), 3939. doi: 10.3390/ijms19123939
   Web of Science ®Google Scholar
• Tanious, F. A., Veal, J. M., Buczak, H., Ratmeyer, L. S., & Wilson, W. D. (1992). DAPI (4′, 6-diamidino-2-phenylindole) binds differently to DNA and RNA: Minor-groove binding at AT sites and intercalation at AU sites. Biochemistry, 31(12), 3103–3112. doi: 10.1021/bi00127a010
   PubMed Web of Science ®Google Scholar
• Trotta, E., Del Grosso, N., Erba, M., Melino, S., Cicero, D., & Paci, M. (2003). Interaction of DAPI with individual strands of trinucleotide repeats: Effects on replication in vitro of the AAT·ATT triplet. European Journal of Biochemistry, 270(23), 4755–4761. doi: 10.1046/j.1432-1033.2003.03877.x
   PubMedGoogle Scholar
• Uddin, M. N., Siddique, Z. A., Mase, N., Uzzaman, M., & Shumi, W. (2019). Oxotitanium (IV) complexes of some bis‐unsymmetric Schiff bases: Synthesis, structural elucidation and biomedical applications. Applied Organometallic Chemistry, 33(6), e4876. doi: 10.1002/aoc.4876
   Web of Science ®Google Scholar
• Virnig, B. A., Baxter, N. N., Habermann, E. B., Feldman, R. D., & Bradley, C. J. (2009). A matter of race: Early-versus late-stage cancer diagnosis. Health Affairs, 28(1), 160–168. doi: 10.1377/hlthaff.28.1.160
   Web of Science ®Google Scholar
• Zehra, S., Shavez Khan, M., Ahmad, I., & Arjmand, F. (2019). New tailored substituted benzothiazole Schiff base Cu (II)/Zn (II) antitumor drug entities: Effect of substituents on DNA binding profile, antimicrobial and cytotoxic activity. Journal of Biomolecular Structure and Dynamics, 37(7), 1863–1879. doi: 10.1080/07391102.2018.1467794
   PubMed Web of Science ®Google Scholar
• Zhang, Z., Bi, C., Fan, Y., Wang, H., & Bao, Y. (2015). Cefepime, a fourth-generation cephalosporin, in complex with manganese, inhibits proteasome activity and induces the apoptosis of human breast cancer cells. International Journal of Molecular Medicine, 36(4), 1143–1150. doi: 10.3892/ijmm.2015.2297
   PubMed Web of Science ®Google Scholar