In this study, the antimicrobial activity, DNA cleavage, DNA binding and antioxidant properties of a sulfonic acid-based imine compound were investigated. The antimicrobial activity of the compound was investigated for minimum inhibitory concentration (MIC) against some bacteria and yeast cultures. The DNA cleavage activity of the compound was investigated as hydrolytic and oxidative with the gel electrophoresis method. H2O2 was used as an oxidizing agent for detection of the cleavage activity mechanism. The Ultraviolet-Visible (UV-Vis) field absorption spectroscopy method was used to determine the binding effect to DNA. The sulfonic acid-based imine compound reacted with Calf Thymus DNA (CT-DNA) which was examined by UV-Vis absorption spectroscopy. The free radical scavenging activity was determined using the 2,2-Diphenyl-1-picrylhydrazyl (DPPH) method.
The studied compound was found to be effective on yeast and bacteria at different concentrations. The compound was found to be more effective on Staphylococcus aureus ATCC 25923 and Enterococcus faecalis ATCC 29212 bacteria. DNA cleavage study showed that the compound cleaved DNA without any external agents in hydrolytic and oxidative manner. UV-Vis spectroscopy studies of the interactions between the compound and CT-DNA showed that the compound interacts with CT-DNA via electrostatic binding. The compound to be tested was compared with the butylated hydroxytoluene (BHT) solution used as standard. It was found that the compound exhibits good antioxidant activity.
AKOCAK, S., LOLAK, N., NOCENTINI, A., KARAKOC, G., TUFAN, A., SUPURAN, C.T., 2017, Synthesis and biological evaluation of novel aromatic and heterocyclicbis-sulfonamide Schiff bases as carbonic anhydrase I, II, VII and IXinhibitors, Bioorganic & Medical Chemistry, 25, 3093-3067.
ALIZADEH, R., AFZAL, M., ARJMAND, F., 2014, In vitro DNA binding, pBR322 plasmid cleavage and molecular modeling study of chiral benzothiazole Schiff-base-valine Cu(II) and Zn(II) complexes to evaluate their enantiomeric biological disposition for molecular target DNA, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 131, 625–635.
ALIZADEH, R., YOUSUF, I., AFZAL, M., SRIVASTAV, S., SRIKISHNA, S., ARJMAND, F., 2015, Enantiomeric Fluoro-Substituted Benzothiazole Schiff Base-Valine Cu(II)/Zn(II) complexes as Chemotherapeutic Agents: DNA Binding Profile, Cleavage Activity, MTT Assay and Cell Imaging Studies, Journal of Photochemistry and Photobiology B: Biology, 143, 63-73.
BLOIS M.S., 1958, Antioxidant determinations by the use of a free free radical, Nature, 181,1199- 1200.
BRANCHAUD, B.P., 1983, Studies on the Preparation and Reactions of Tritylsulfenimines, Journal of Organic Chemistry, 48 (20), 1331-1338.
CHOUAI, A., WICKE, S.E., TURRO, C., BASCA, J., DUNBAR, K.R., WANG, R.P., 2005, Ruthenium(II) Complexes of 1,12-diazaperylene and Their Intercalations with DNA, Inorg. Chem., 44(17), 5996-603.
DOMBROWSKI, K.E., BALDWIN, W., SHEATS, J.E.J., 1986, Metallocenes in Biochemistry: Microbiology and Medicine. Journal of Organometallic Chemistry, 302, 281-306.
ERKKİLA, K.E., ODOM, D.T., BARTON, J.K., 1999, Recognition and Reaction of Metallointercalators with DNA, Chem. Rew., 99(9), 2777-2796.
GLOBAL BURDEN OF DISEASE CANCER COLLABORATION, 2015, The Global Burden of Cancer 2013. JAMA Oncology, 1(4), 505-527.
GÖÇMEN, E., 2014, Synthesis, Characterization, Structure, DNA Binding and Biological Activity of New Silver (I) Saccharin Complexes Containing Some Single and Double Threaded Tertiary Phosphine Ligands, Master Thesis, Uludag University, Bursa.
GUPTA, S.D., REVATHI, B., MAZAIRA, G.I., GALIGNIANA, M.D., SUBRAHMANYAM, C.V.S., GOWRISHANKAR, N.L., RAGHAVENDRA, N.M., 2015, 2,4-dihydroxy benzaldehyde derived Schiff bases as small moleculeHsp90 inhibitors: Rational identification of a new anticancer lead, Bioorganic Chemistry, 59, 97-105.
ISENBERG, H.D., 1998, Essential Procedures for Clinical Microbiology, Washingtoon DC, American Society for Clinical Microbiology, 126-223.
KIRAN, T., PRASANTH, V.G., BALAMURALI, M.M., VASAVI, C.S., MUNUSAMI, P., SATHIYANARAYANAN, K.L., & PATHAK, M., 2015. Synthesis, Spectroscopic Characterisation and in vitroStudies of New Heteroleptic Copper(II) Complexes Derived From 2-hydroxy Napthaldehyde Schiff’s Bases and N, N Donor Ligands: Antimicrobial, DNA Binding and Cytotoxic Investigations, Inorganica Chimica Acta, 433, 26-34.
LI X., LIN, Y., WANG, Q., YUAN, Y., ZHANG, H., QIAN, X., 2011,The Novel Anti-tumor Agents of 4-triazol-1,8-napthalimides: Synthesis, Cytotoxicity, DNA Interaction and Photocleavage. European Journal of Medicinal Chemistry, 46,1274-1279.
LIU, Z.C., WANG, B.D., LI, B., Wang Q., YANG, Z.Y., LI, T.R., LI, Y., 2010, Crystal Structures, DNA-binding and Cytotoxic Activities Studies of Cu(II) Complexes with 2-oxo-quinoline-3-carbaldehyde Schiff-bases, European Journal of Medicinal Chemistry, 45:5353-5361.
MERMER, A., DEMIRBAS, N., USLU, H., DEMIRBAS, A., CEYLAN, Ş., ŞIRIN, Y., 2019, Synthesis of novel Schiff bases using green chemistry techniques; antimikrobial, antioksidant, antiurease activity screening and molecular docking studies, Journal of Molecular Structure. 1181, 412-422.
QIAO, X., MA, Z.Y., XIE, C.Z., XUE, F., ZHANG, Y.W., XU, J.Y., QIANG, Z.Y., LOU, J.S., CHEN, G.J., YANG, S.P., 2011, Study on Potential Antitumor Mechanism of a Novel Schiff Base Copper (II) Complex: Synthesis, Crystal Structure, DNA Binding, Cytotoxicity and Apoptosis Induction Activity. Journal of Inorganic Biochemistry, 105, 728-737.
PANNERSELVAM, P., NAIR, R.R., VIJAYALAKSHMI, G., SUBRAMANIAN, E.H., SRIDHAR, S.K., 2005, Synthesis of Schiff bases of 4-(4-aminophenyl)-morpholineas potential antimicrobial agents, European Journal of Medicinal Chemistry, 40, 225–229.
RAMBABU, A., KUMAR, M.P., GANJI, N., DARAVATH & SHIVARAJ, S., 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, 24,1-10
SARIKAYA, B., CERUSO, M., CARTA, F., SUPURAN, C.T., 2014, Inhibition of carbonic anhydrase isoforms I, II, IX and XII with novelSchiff bases: Identification of selective inhibitors for the tumor-associated isoforms over the cytosolic ones, Bioorganic & Medical Chemistry, 22, 5883-5890.
SCHIFF, H., 1869, Über die Aldehyd und Amin Reaktionen, Liebigs Annalen der Chemie, 150-197.
SHAHABADI, N., KASHANIAN & DARABI, F., 2010, DNA binding and DNA cleavage studies of a water soluble cobalt(II) complex containing dinitrogen Schiff base ligand: The effect of metal on the mode of binding, European Journal of Medicinal Chemistry, 45,4239-4245.
SILVA C.M., SILVA D.L., MODOLO L.V. ALVES R.B., RESENDE M.A., MARTINS C.V.B. FATIMA A., 2011, Schiff Base: A Short Review of Their Antimicrobial Activities, Journal of Advanced Research, 2, 1-8.
SOBHA, S., MAHALAKSHMI, R., RAMAN, N., 2012, Studies on DNA Binding Behaviour of Biologically Active Transition Metal Complexes of New Tetradentate N2O2 Donor Schiff bases: Inhibitory Activity Against Bacteria, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 92, 75–183.
SRIDHAR, S.K., SARAVANAN, M., RAMESH, A., 2001, Synthesis and Antibacterial Screening of Hydrazones, Schiff and Mannich Bases of Isatin Derivatives, European Journal of Medicinal Chemistry, 36, 615-625.
STREKOWSKI, L., WILSON, B., 2007, Noncovalent Interaction with DNA: An Overview, Mutation Research, 623, 3-13.
TABASSUM, S., AMIR, S., ARJMAND, F., PETTINARI, C., MARCHETTI, F., MASCIOCCHI, N., LUPIDI, G., PETTINARI, R., 2013, Mixed-Ligand Cu(II)-Vanilin Schiff Base Complexes; Effect of Coligands on Their DNA Binding, DNA Cleavage, SOD Mimetic and Anticancer Activity, European Journal of Medicinal Chemistry, 60, 216-232.
TADAVI, S.K. , YADAV, A.A, BENDRE, R.S., 2018, Synthesis and characterization of a novel schiff base of 1,2-diaminopropane with substituted salicyaldehyde and its transition metal complexes: Single crystal structures and biological activities, Journal of Molecular Structure, 1152, 223-231.
TAŞKIN, I., 2012, N-Aminopyrimidine-2-thion 2-Furfural Derived From A New Schiff Base And Some Metal Complexes Synthesis and Investigation of Some Biological Activities, Master Thesis, Gaziantep University, Gaziantep, Turkey.
WANG, B., YANG, Z.Y., WANG, Q., CAI, T., CREWDSON, P., 2006, Synthesis, Characterisation, Cytotoxic Activityes, and DNA-binding Properties of the La(III) Complex with Narigenin Schiff-base, Bioorganic & Medicinal Chemistry, 14,1880-1888.
YILDIRIM, N., 2016. Investigation of DNA Binding Properties and Biological Activities of Some Schiff Bases and Complexes, Thesis (PhD). Çanakkale Onsekiz Mart University, Canakkale, Turkey.
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