Antioxidant and cytotoxic activities of selected salicylidene imines: experimental and computational study

Hodnett E, Dunn W (1970) Structure-antitumor activity correlation of some Schiff bases. J Med Chem 13:768–770. https://doi.org/10.1021/jm00298a054 Da Silva C et al (2011) Schiff bases: a short review of their antimicrobial activities. J Adv Res 2:1–8. https://doi.org/10.1016/j.jare.2010.05.004 Sztanke K et al (2013) An insight into synthetic Schiff bases revealing antiproliferative activities in vitro. Bioorg Med Chem 21:3648–3666. https://doi.org/10.1016/j.bmc.2013.04.037 Ariyaeifar M et al (2018) Chiral halogenated Schiff base compounds: green synthesis, anticancer activity and DNA-binding study. J Mol Struct 1161:497–511. https://doi.org/10.1016/j.molstruc.2018.02.042 Bharathi Dileepan A et al (2018) Isatin based macrocyclic Schiff base ligands as novel candidates for antimicrobial and antioxidant drug design: In vitro DNA binding and biological studies. J Photochem Photobiol B Biol 183:191–200. https://doi.org/10.1016/j.jphotobiol.2018.04.029 García-Valle F et al (2018) Aluminates with fluorinated Schiff bases: influence of the alkali metal-fluorine interactions in structure stabilization. Molecules 23:3108. https://doi.org/10.3390/molecules23123108 Tan X et al (2019) Synthesis, structure and antiproliferative and optical activities of two new biphenyl-derived Schiff bases. Acta Cryst C 75:97–106. https://doi.org/10.1107/S2053229618017989 Shao J et al (2005) Determination of the potency and subunit-selectivity of ribonucleotide reductase inhibitors with a recombinant-holoenzyme-based in vitro assay. Biochem Pharmacol 69:627–634. https://doi.org/10.1016/j.bcp.2004.11.016 Gama S et al (2011) Copper(II) complexes with tridentate pyrazole-based ligands: synthesis, characterization, DNA cleavage activity and cytotoxicity. J Inorg Biochem 105:637–644. https://doi.org/10.1016/j.jinorgbio.2011.01.013 Kraicheva I et al (2012) Synthesis, antiproliferative activity and genotoxicity of novel anthracene-containing aminophosphonates and a new anthracene-derived Schiff base. Bioorg Med Chem 20:117–124. https://doi.org/10.1016/j.bmc.2011.11.024 Kamel M et al (2010) Synthesis, antitumor activity and molecular docking study of novel Sulfonamide-Schiff’s bases, thiazolidinones, benzothiazinones and their C-nucleoside derivatives. Eur J Med Chem 45:572–580. https://doi.org/10.1016/j.ejmech.2009.10.044 Vicini P et al (2003) Synthesis and biological evaluation of benzo[d]isothiazole, benzothiazole and thiazole Schiff bases. Bioorg Med Chem 11:4785–4789. https://doi.org/10.1016/S0968-0896(03)00493-0 Tang Y, Liu Z (2007) Insight into the free-radical-scavenging mechanism of hydroxyl-substituent Schiff bases in the free-radical-induced hemolysis of erythrocytes. Cell Biochem Funct 25:701–710. https://doi.org/10.1002/cbf.1378 Zhang Y et al (2013) Synthesis and antioxidant activities of 2-oxo-quinoline-3-carbaldehyde Schiff-base derivatives. Bioorg Med Chem Lett 23:107–111. https://doi.org/10.1016/j.bmcl.2012.11.006 Kotora P et al (2016) The scavenging of DPPH, galvinoxyl and ABTS radicals by imine analogs of resveratrol. Molecules 21:127. https://doi.org/10.3390/molecules21010127 Lushchak V (2014) Free radicals, reactive oxygen species, oxidative stress and its classification. Chem Biol Interact 224:164–175. https://doi.org/10.1016/j.cbi.2014.10.016 Waris G, Ahsan H (2006) Reactive oxygen species: role in the development of cancer and various chronic conditions. J Carcinog 5:1–8. https://doi.org/10.1186/1477-3163-5-14 Labunskyy V, Gladyshev V (2013) Role of reactive oxygen species-mediated signaling in aging. Antioxid Redox Signal 19:1362–1372. https://doi.org/10.1089/ars.2012.4891 Zhao F, Liu Z (2009) The protective effect of hydroxyl-substituted Schiff bases on the radical-induced oxidation of DNA. J Phys Org Chem 22:791–798. https://doi.org/10.1002/poc.1517 Yusuff O et al (2019) Kinetics and mechanism of the antioxidant activities of C. olitorius and V. amygdalina by Spectrophotometric and DFT methods. ACS Omega 4:13671–13680. https://doi.org/10.1021/acsomega.9b00851 Craft B et al (2012) Phenol-based antioxidants and the In Vitro methods used for their assessment. Compr Rev Food Sci Food Saf 11:148–173. https://doi.org/10.1111/j.1541-4337.2011.00173.x Di Meo F et al (2013) Free radical scavenging by natural polyphenols: atom versus electron transfer. J Phys Chem 117:2082–2092. https://doi.org/10.1021/jp3116319 Farrokhnia M (2020) Density functional theory studies on the antioxidant mechanism and electronic properties of some bioactive marine meroterpenoids: Sargahydroquionic acid and sargachromanol. ACS Omega 5:20382–20390. https://doi.org/10.1021/acsomega.0c02354 Alov P, Tsakovska I, Pajeva I (2014) Computational studies of free radical-scavenging properties of phenolic compounds. Curr Top Med Chem 15:85–104. https://doi.org/10.2174/1568026615666141209143702 Kirschenbaum A et al (2001) The role of cyclooxygenase-2 in prostate cancer. Urology 58:127–131. https://doi.org/10.1016/S0090-4295(01)01255-9 Half E et al (2002) Cyclooxygenase-2 expression in human breast cancers and adjacent ductal carcinoma in situ. Cancer Res 62:1676–1681 Singh-Ranger G, Mokbel K (2002) The role of cyclooxygenase-2 (COX-2) in breast cancer, and implications of COX-2 inhibition. Eur J Surg Oncol 28:729–737. https://doi.org/10.1053/ejso.2002.1329 Sooriakumaran P, Kaba R (2005) The risks and benefits of cyclo-oxygenase-2 inhibitors in prostate cancer: a review. Int J Surg 3:278–285. https://doi.org/10.1016/j.ijsu.2005.10.002 Mazhar D, Ang R, Waxman J (2006) COX inhibitors and breast cancer. Br J Cancer 94:346–350. https://doi.org/10.1038/sj.bjc.6602942 Khor L et al (2007) COX-2 expression predicts prostate-cancer outcome: analysis of data from the RTOG 92–02 trial. Lancet Oncol 8:912–920. https://doi.org/10.1016/S1470-2045(07)70280-2 Singh B et al (2007) COX-2 involvement in breast cancer metastasis to bone. Oncogene 26:3789–3796. https://doi.org/10.1038/sj.onc.1210154 Csepregi K et al (2016) Comparative evaluation of total antioxidant capacities of plant polyphenols. Molecules 21:1–17. https://doi.org/10.3390/molecules21020208 Velena A et al (2016) 1,4-dihydropyridine derivatives: dihydronicotinamide analogues-model compounds targeting oxidative stress. Oxid Med Cell Longev 2016:1892412. https://doi.org/10.1155/2016/1892412 Nikokavoura A et al (2011) Evaluation of antioxidant activity of hydrophilic and lipophilic compounds in edible oils by a novel fluorimetric method. Talanta 84:874–880. https://doi.org/10.1016/j.talanta.2011.02.007 Li S, Wang X, Kong L (2014) Design, synthesis and biological evaluation of imine resveratrol derivatives as multi-targeted agents against Alzheimer’s disease. Eur J Med Chem 71:36–45. https://doi.org/10.1016/j.ejmech.2013.10.068 Slassi S et al (2019) Imidazole and Azo-based Schiff bases ligands as highly active antifungal and antioxidant components. Heteroat Chem 2019:1–8. https://doi.org/10.1155/2019/6862170 Yang H et al (2017) Design, synthesis and evaluation of coumarin-pargyline hybrids as novel dual inhibitors of monoamine oxidases and amyloid-β aggregation for the treatment of Alzheimer’s disease. Eur J Med Chem 138:715–728. https://doi.org/10.1016/j.ejmech.2017.07.008 Krokidis M et al (2019) Assessment of dna topoisomerase i unwinding activity, radical scavenging capacity, and inhibition of breast cancer cell viability of N-alkylacridones and N, Nʹ-dialkyl-9,9ʹ-biacridylidenes. Biomolecules 9:1–15. https://doi.org/10.3390/biom9050177 da Silva C et al (2017) Studies on free radical scavenging, cancer cell antiproliferation, and calf thymus DNA interaction of Schiff bases. J Photochem Photobiol B 172:129–138. https://doi.org/10.1016/j.jphotobiol.2017.05.020 Adsule S et al (2006) Novel Schiff base copper complexes of quinoline-2 carboxaldehyde as proteasome inhibitors in human prostate cancer cells. J Med Chem 49:7242–7246. https://doi.org/10.1021/jm060712l Antonczak S (2008) Electronic description of four flavonoids revisited by DFT method. J Mol Struct-Theochem 856:38–45. https://doi.org/10.1016/j.theochem.2008.01.014 Petrović Z et al (2015) Experimental and theoretical study of antioxidative properties of some salicylaldehyde and vanillic Schiff bases. RSC Adv 5:24094–24100. https://doi.org/10.1039/c5ra02134k Xie J, Schaich K (2014) Re-evaluation of the 2,2-diphenyl-1-picrylhydrazyl free radical (DPPH) assay for antioxidant activity. J Agric Food Chem 62:4251–4260. https://doi.org/10.1021/jf500180u Hammamieh R, Jett M (2008) Potential roles for inhibitors of arachidonic acid metabolism in prevention and treatment of breast cancer. Future Lipidol 3:265–271. https://doi.org/10.2217/17460875.3.3.265 Yang P et al (2012) Arachidonic acid metabolism in human prostate cancer. Int J Oncol 41:1495–1503. https://doi.org/10.3892/ijo.2012.1588 Pang L, Hurst E, Argyle D (2016) Cyclooxygenase-2: a role in cancer stem cell survival and repopulation of cancer cells during therapy. Stem Cells Int 2016:2048731. https://doi.org/10.1155/2016/2048731 Hashemi Goradel N et al (2019) Cyclooxygenase-2 in cancer: a review. J Cell Physiol 234:5683–5699. https://doi.org/10.1002/jcp.27411 Brizzolara A et al (2017) The ErbB family and androgen receptor signaling are targets of Celecoxib in prostate cancer. Cancer Lett 400:9–17. https://doi.org/10.1016/j.canlet.2017.04.025 Shi L et al (2018) Celecoxib-induced self-assembly of smart albumin-doxorubicin conjugate for enhanced cancer therapy. ACS Appl Mater Interfaces 10:8555–8565. https://doi.org/10.1021/acsami.8b00875 Moustakali-Mavridis I, Hadjoudis E, Mavridis A (1978) Crystal and molecular structure of some thermochromic Schiff bases. Acta Crystallogr Sect B 34:3709–3715. https://doi.org/10.1107/S0567740878011930 Talati J, Desai M, Shah N (2005) Meta-substituted aniline-N-salicylidenes as corrosion inhibitors of zinc in sulphuric acid. Mater Chem Phys 93:54–64. https://doi.org/10.1016/j.matchemphys.2005.02.004 Chatziefthimiou S et al (2006) Keto forms of salicylaldehyde Schiff bases: Structural and theoretical aspects. J Phys Chem B 110:23701–23709. https://doi.org/10.1021/jp064110p Koar B et al (2009) (E)-2-[(4-chloro-phen-yl)imino-meth-yl]-5-methoxy-phenol and (E)-2-[(2-chloro-phen-yl)imino-meth-yl]-5-methoxy-phenol: X-ray and DFT-calculated structures. Acta Crystallogr Sect C Cryst Struct Commun 65:8–13. https://doi.org/10.1107/S0108270109034350 Al-Kahraman Y et al (2010) Antileishmanial, antimicrobial and antifungal activities of some new aryl azomethines. Molecules 15:660–671. https://doi.org/10.3390/molecules15020660 Christodouleas D, Papadopoulos K, Calokerinos A (2011) Determination of total antioxidant activity of edible oils as well as their aqueous and organic extracts by chemiluminescence. Food Anal Methods 4:475–484. https://doi.org/10.1007/s12161-010-9189-6 Dl Christodouleas et al (2015) Modified DPPH and ABTS assays to assess the antioxidant profile of untreated oils. Food Anal Methods 8:1294–1302. https://doi.org/10.1007/s12161-014-0005-6 Frisch M et al (2016) G16_C01. p. Gaussian 16, Revision C.01, Gaussian, Inc., Wallin Becke A (1993) Density-functional thermochemistry. III. The role of exact exchange. J Chem Phys 98:5648–5652. https://doi.org/10.1063/1.464913 Marenich A, Cramer C, Truhlar D (2009) Performance of SM6, SM8, and SMD on the SAMPL1 test set for the prediction of small-molecule solvation free energies. J Phys Chem B 113:4538–4543. https://doi.org/10.1021/jp809094y Marković Z et al (2016) Revisiting the solvation enthalpies and free energies of the proton and electron in various solvents. Comput Theor Chem 1077:11–17. https://doi.org/10.1016/j.comptc.2015.09.007 Orlando B, Malkowski M (2016) Substrate-selective inhibition of cyclooxygeanse-2 by fenamic acid derivatives is dependent on peroxide tone. J Biol Chem 291:15069–15081. https://doi.org/10.1074/jbc.M116.725713 Pettersen E et al (2004) UCSF chimera-a visualization system for exploratory research and analysis. J Comput Chem 25:1605–1612. https://doi.org/10.1002/jcc.20084 Simijonović D et al (2018) Dicoumarol derivatives: green synthesis and molecular modelling studies of their anti-LOX activity. Bioorg Chem 80:741–752. https://doi.org/10.1016/j.bioorg.2018.07.021 Fiser A, Šali A (2003) MODELLER: generation and refinement of homology-based protein structure models. Meth Enzymol 374:461–491. https://doi.org/10.1016/S0076-6879(03)74020-8 Kouzi O, Pontiki E, Hadjipavlou-Litina D (2019) 2-arylidene-1-indandiones as pleiotropic agents with antioxidant and inhibitory enzymes activities. Molecules 24:1–20. https://doi.org/10.3390/molecules24234411 Saeed A, Mumtaz A, Flörke U (2007) 1-(3,4-Dimethoxy-benz-oyl)-3,5-dimethyl-1H-pyrazole. Acta Crystallogr E 63(10):1098. https://doi.org/10.1107/S1600536807044960