Spectroscopic analyses on the binding interaction of thiosemicarbazone-derivated Cu(II) complex with DNA/BSA
Year 2021,
Volume: 17 Issue: 4, 387 - 395, 29.12.2021
Mükerrem Fındık
,
Asuman Uçar
,
Emine Akgemci
Abstract
Cu(II) complex of 2-hydroxy-5-methoxyacetophenone-N(4)-ethyl thiosemicarbazone (Cu(HMAET)Cl) was synthesized and characterized by spectroscopic methods such as FT-IR, 1H-NMR and UV-Vis. The DNA-binding capacity of the complex was studied with the UV-Vis absorption titrations and ethidium bromide (EB) displacement experiments using E. coli DNA. The results demonstrated that the complex could intercalate in the DNA's base pairs. The binding constant was found as 3.6×108 M−1. Also, the interaction study of the complex with bovine serum albumin (BSA) was investigated using the UV-Vis absorption and fluorescence spectroscopy techniques and it was concluded that the complex interacts strongly with BSA.
Thanks
The author is grateful to Dr. Suray Pehlivanoğlu, Department of Molecular Biology and Genetics, Faculty of Science, Necmettin Erbakan University, Konya, for providing E. coli DNA.
References
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- Referans27 Mathews, NA, Jacob, JM, Begum, PMS, Kurup, MRP. 2020. Cu(II) and Zn(II) complexes from a thiosemicarbazone derivative: Investigating the intermolecular interactions, crystal structures and cytotoxicity. Journal of Molecular Structure; 1202: 127319.
- Referans28 Nyawade, EA, Sibuyi, NRS, Meyer, M, Lalancette, R, Onani, MO. 2021. Synthesis, characterization and anticancer activity of new 2-acetyl-5-methyl thiophene and cinnamaldehyde thiosemicarbazones and their palladium(II) complexes. Inorganica Chimica Acta; 515: 120036.
- Referans29 Jacob, JM, Kurup, MRP, Nisha, K, Serdaroğlu, G, Kaya, S. 2020. Mixed ligand copper(II) chelates derived from an O, N, S- donor tridentate thiosemicarbazone: Synthesis, spectral aspects, FMO, and NBO analysis. Polyhedron; 189: 114736.
- Referans30 Omondi, RO, Ojwach, SO, Jagany, D. 2020. Review of comparative studies of cytotoxic activities of Pt(II), Pd(II), Ru(II)/(III) and Au(III) complexes, their kinetics of ligand substitution reactions and DNA/BSA interactions. Inorganica Chimica Acta; 512: 119883.
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- Referans33 Bashiri, M, Jarrahpour, A, Nabavizadeh, SM, Karimian, S, Rastegari, B, Haddadi, E, Turos, E. 2021. Potent antiproliferative active agents: novel bis Schiff bases and bis spiroβ-lactams bearing isatin tethered with butylene and phenylene as spacer and DNA/BSA binding behavior as well as studying molecular docking. Medicinal Chemistry Research; 30: 258–284.
- Referans34 Kalantari, R, Asadi, Z. 2020. DNA/BSA binding of a new oxovanadium (IV) complex of glycylglycine derivative Schiff base ligand. Journal of Molecular Structure; 1219: 128664.
- Referans35 Tyagi, N, Singh, O, Mishra, RK, Ghosh, K. 2020. Bio-macromolecular interaction studies: Synthesis, crystal structure of water-soluble manganese(II) complexes. Inorganica Chimica Acta; 512: 119882.
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Year 2021,
Volume: 17 Issue: 4, 387 - 395, 29.12.2021
Mükerrem Fındık
,
Asuman Uçar
,
Emine Akgemci
References
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- Referans2 Kaya, B, Yılmaz ZK, Şahin, O, Aslim, B, Ülküseven, B. 2020. Structural characterization of new zinc(II) complexes with N2O2 chelating thiosemicarbazidato ligand; Investigation of the relationship between their DNA interaction and in vitro antiproliferative activity on human cancer cells. New Journal of Chemistry; 44: 9313-9320.
- Referans3 Karami, K, Rahimi, M, Zakariazadeh, M, Buyukgungor, O, Amirghofran, Z. 2018. New phosphorus ylide palladacyclic: Synthesis, characterization, X-Ray crystal structure, biomolecular interaction studies, molecular docking and in vitro cytotoxicity evaluations. Journal of Organometallic Chemistry; 878: 60-76.
- Referans4 Beebe, SJ, Celestine, MJ, Bullock, JL, Sandhaus, S, Arca, JF, Cropek, DM, Ludvig, TA, Foster, SR, Clark, JS, Beckford, FA, Tano, CM, Tonsel-White, EA, Gurung, RK, Stankavich, CE, Tse-Dinh, YC, Jarrett, WL, Holder, AA. 2020. Synthesis, characterization, DNA binding, topoisomerase inhibition, and apoptosis induction studies of a novel cobalt(III) complex with a thiosemicarbazone ligand. Journal of Inorganic Biochemistry; 203: 110907.
- Referans5 Milani, NC, Maghsoud, Y, Hosseini, M, Babaei, A, Rahmani, H, Roe, SM, Gholivand, K. 2020. A new class of copper(I) complexes with imine-containing chelators which show potent anticancer activity. Applied Organometallic Chemistry; 34(8): 5526.
- Referans6 Gupta, RK, Sharma, G, Pandey, R, Kumar, A, Koch, B, Li, PZ, Xu, Q, Pandey, DS. 2013. DNA/Protein Binding, Molecular Docking, and in Vitro Anticancer Activity of Some Thioether-Dipyrrinato Complexes. Inorganic Chemistry; 52(24): 13984–13996.
- Referans7 Asadi, Z, Zarei, L, Golchin, M, Skorepova, E, Eigner, V, Amirghofran, Z. 2020. A novel Cu(II) distorted cubane complex containing Cu4O4 core as the first tetranuclear catalyst for temperature dependent oxidation of 3,5-di-tert-butyl catechol and in interaction with DNA&protein (BSA). Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy; 227: 117593.
- Referans8 Bhunia, A, Vojtísek, P, Bertolasi, V, Manna, SC. 2019. Tridentate Schiff base coordinated trigonal bipyramidal/square pyramidal copper(II) complexes: Synthesis, crystal structure, DFT/TD-DFT calculation, catecholase activity and DNA binding. Journal of Molecular Structure; 1189: 94-101.
- Referans9 Kiraz, S, İnci, D, Aydın, R, Vatan, Ö, Zorlu, Y, Cavaş, T. 2019. Antiproliferative activity of copper(II) glutamine complexes with N,N donor ligands: Synthesis, characterization, potentiometric studies and DNA/BSA interactions. Journal of Molecular Structure; 1194: 245-255.
- Referans10 Balakrishnan, N, Haribabu, J, Dhanabalan, AK, Swaminathan, S, Sun, S, Dibwe, DF, Bhuvanesh, N, Awale, S, Karvembu, R. 2020. Thiosemicarbazone(s)-anchored water soluble mono- and bimetallic Cu(II) complexes: Enzymes-like activities, biomolecular interactions, anticancer property and real-time live cytotoxicity. Dalton Transactions; 49(22): 9411-9424.
- Referans11 Amitha, GS, Vasudevan, S. 2020. DNA binding and cleavage studies of novel Betti base substituted quaternary Cu(II) and Zn(II) phthalocyanines. Polyhedron; 190: 114773.
- Referans12 Liu, MC, Lin, TC, Sartorelli, AC. 1992. Synthesis and antitumor activity of amino derivatives of pyridine-2-carboxaldehyde thiose micarbazone. Journal of Medicinal Chemistry; 35(20): 3672–3677.
- Referans13 Zarei, L, Asadi, Z, Samolova, E, Dusek, M, Amirghofran, Z. 2020. Pyrazolate as bridging ligand in stabilization of self-assemble Cu(II) Schiff base complexes: Synthesis, structural investigations, DNA/protein (BSA) binding and growth inhibitory effects on the MCF7, CT-26, MDA-MB-231 cell lines. Inorganica Chimica Acta; 509: 119674.
- Referans14 Bhunia, A, Mistri, S, Manne, RK, Santra, MK, Manna, SC. 2019. Synthesis, crystal structure, cytotoxicity study, DNA/protein binding and molecular docking of dinuclear copper(II) complexes. Inorganica Chimica Acta; 491: 25–33.
- Referans15 Kumar, P, Gorai, S, Santra, MK, Mondal, B, Manna, D. 2012. DNA binding, nuclease activity and cytotoxicity studies of Cu(II) complexes of tridentate ligands. Dalton Transactions; 41(25): 7573-7581.
- Referans16 Lu, JJ, Bao, JL, Wu, GS, Xu, WS, Huang, MQ, Chen, XP, Wang, YT. 2013. Quinones Derived from Plant Secondary Metabolites as Anti-cancer Agents. Anti-Cancer Agents in Medicinal Chemistry; 13(3): 456-463.
- Referans17 Rahman, AJ, Sharma, D, Kumar, D, Pathak, M, Singh, A, Kumar, V, Chawla, R, Ojha, H. 2021. Spectroscopic and molecular modelling study of binding mechanism of bovine serum albumin with phosmet. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy; 244: 118803.
- Referans18 Türkkan, E, Sayin, U, Erbilen, N, Pehlivanoglu, S, Erdogan, G, Tasdemir, HU, Saf, AO, Guler, L, Akgemci, EG. 2017. Anticancer, antimicrobial, spectral, voltammetric and DFT studies with Cu(II) complexes of 2-hydroxy-5-methoxyacetophenone thiosemicarbazone and its N(4)- substituted derivatives. Journal of Organometallic Chemistry; 831: 23-35.
- Referans19 Beckford, FA, Thessing, J, Shaloski, Jr M, Mbarushimana, PC, Brock, A, Didion, J, Woods, J, Gonzalez-Sarrías, A, Seeram, NP. 2011. Synthesis and characterization of mixed-ligand diimine-piperonal thiosemicarbazone complexes of ruthenium(II): Biophysical investigations and biological evaluation as anticancer and antibacterial agents. Journal of Molecular Structure; 992: 39–47.
- Referans20 Ishaq, M, Taslimi, P, Shafiq, Z, Khan, S, Salmas, RE, Zangeneh, MM, Saeed, A, Zangeneh, A, Sadeghian, N, Asari, A, Mohamad, H. 2020. Synthesis, bioactivity and binding energy calculations of novel 3-ethoxysalicylaldehyde based thiosemicarbazone derivatives. Bioorganic Chemistry; 100: 103924.
- Referans21 Zhang, X, Li, S, Yang, L, Fan, C. 2007. Synthesis, characterization of Ag(I), Pd(II) and Pt(II) complexes of a triazine-3-thione and their interactions with bovine serum albumin. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy; 68(3): 763-770.
- Referans22 Huseynovaa, M, Farzaliyev, V, Medjidov, A, Aliyeva, M, Taslimi, P, Sahin, O, Yalçın, B. 2020. Novel zinc compound with thiosemicarbazone of glyoxylic acid: Synthesis, crystal structure, and bioactivity properties. Journal of Molecular Structure; 1200: 127082.
- Referans23 Balakrishnan, N, Haribabu, J, Krishnan, DA, Swaminathan, S, Mahendiran, D, Bhuvanesh, NSP, Karvembu, R. 2019. Zinc(II) complexes of indole thiosemicarbazones: DNA/protein binding, molecular docking andin vitro cytotoxicity studies. Polyhedron; 170: 188–201.
- Referans24 Kalaiarasi, G, Umadevi, C, Shanmugapriya, A, Kalaivani, P, Dallemer, F, Prabhakaran, R. 2016. DNA(CT), protein(BSA) binding studies, anti-oxidant and cytotoxicity studies of new binuclear Ni(II) complexes containing 4(N)-substituted thiosemicarbazones. Inorganica Chimica Acta; 453: 547–558.
- Referans25 Kılıç-Cıkla, I, Güveli, S, Yavuz, M, Bal-Demirci, T, Ülküseven, B. 2016. 5-Methyl-2-hydroxy-acetophenone-thiosemicarbazone and its nickel(II) complex: Crystallographic, spectroscopic (IR, NMR and UV) and DFT studies. Polyhedron; 105: 104–114.
- Referans26 Arafath, MA, Adam, F, Razali, MR, Ahmed Hassan, LE, Ahamed, MBK, Majid, AMSA. 2017. Synthesis, characterization and anticancer studies of Ni(II), Pd(II) and Pt(II) complexes with Schiff base derived from N-methylhydrazinecarbothioamide and 2-hydroxy-5-methoxy-3-nitrobenzaldehyde. Journal of Molecular Structure; 1130: 791-798.
- Referans27 Mathews, NA, Jacob, JM, Begum, PMS, Kurup, MRP. 2020. Cu(II) and Zn(II) complexes from a thiosemicarbazone derivative: Investigating the intermolecular interactions, crystal structures and cytotoxicity. Journal of Molecular Structure; 1202: 127319.
- Referans28 Nyawade, EA, Sibuyi, NRS, Meyer, M, Lalancette, R, Onani, MO. 2021. Synthesis, characterization and anticancer activity of new 2-acetyl-5-methyl thiophene and cinnamaldehyde thiosemicarbazones and their palladium(II) complexes. Inorganica Chimica Acta; 515: 120036.
- Referans29 Jacob, JM, Kurup, MRP, Nisha, K, Serdaroğlu, G, Kaya, S. 2020. Mixed ligand copper(II) chelates derived from an O, N, S- donor tridentate thiosemicarbazone: Synthesis, spectral aspects, FMO, and NBO analysis. Polyhedron; 189: 114736.
- Referans30 Omondi, RO, Ojwach, SO, Jagany, D. 2020. Review of comparative studies of cytotoxic activities of Pt(II), Pd(II), Ru(II)/(III) and Au(III) complexes, their kinetics of ligand substitution reactions and DNA/BSA interactions. Inorganica Chimica Acta; 512: 119883.
- Referans31 Ayyannan, G, Mohanraj, M, Gopiraman, M, Uthayamalar, R, Raja, G, Bhuvanesh, N, Nandhakumar, R, Jayabalakrishnan, C. 2020. New Palladium(II) complexes with ONO chelated hydrazone ligand:Synthesis, characterization, DNA/BSA interaction, antioxidant and cytotoxicity. Inorganica Chimica Acta; 512: 119868.
- Referans32 Bağda, E, Yabas, E, Bağda, E. 2017. Analytical approaches for clarification of DNAdouble decker phthalocyanine binding mechanism: as an alternative anticancer chemotherapeutic. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy; 172: 199-204.
- Referans33 Bashiri, M, Jarrahpour, A, Nabavizadeh, SM, Karimian, S, Rastegari, B, Haddadi, E, Turos, E. 2021. Potent antiproliferative active agents: novel bis Schiff bases and bis spiroβ-lactams bearing isatin tethered with butylene and phenylene as spacer and DNA/BSA binding behavior as well as studying molecular docking. Medicinal Chemistry Research; 30: 258–284.
- Referans34 Kalantari, R, Asadi, Z. 2020. DNA/BSA binding of a new oxovanadium (IV) complex of glycylglycine derivative Schiff base ligand. Journal of Molecular Structure; 1219: 128664.
- Referans35 Tyagi, N, Singh, O, Mishra, RK, Ghosh, K. 2020. Bio-macromolecular interaction studies: Synthesis, crystal structure of water-soluble manganese(II) complexes. Inorganica Chimica Acta; 512: 119882.
- Referans36 Lakowicz, JR. Principles of fluorescence spectroscopy. New York: Springer Science & Business Media, 2013.
- Referans37 Mo, D, Shi, J, Zhao, D, Zhang, Y, Guan, Y, Shen, Y, Bian, H, Huang, F, Wu, S. 2021. Synthesis and characterization of FeIII/CoIII/CuII complexes with Schiff base ligand and their hybrid proteins, SOD activity and asymmetric catalytic oxidation of sulfides. Journal of Molecular Structure; 1223: 129229.
- Referans38 Shanmugapriya, A, Dallemer, F, Prabhakaran, R. 2018. Synthesis, characterisation, crystal structures and biological studies of palladium(II) complexes containing 5-(2-hydroxy-3-methoxy-phenyl)-2,4-dihydro[1,2,4]triazole-3-thione derivatives. New Journal of Chemistry; 42(23): 18850-18864.
- Referans39 Haribabu, J, Sabapathi, G, Tamizh, MM, Balachandran, C, Bhuvanesh, NSP, Venuvanalingam, P, Karvembu, R. 2018. Water-Soluble Mono- and Binuclear Ru(η6‑p‑cymene) Complexes Containing Indole Thiosemicarbazones: Synthesis, DFT Modeling, Biomolecular Interactions, and In Vitro Anticancer Activity through Apoptosis. Organometallics; 37(8): 1242–1257.
- Referans40 Feng, XZ, Lin, Z, Yang, LJ, Wang, C, Bai, CL. 1998. Investigation of the interaction between acridine orange and bovine serum albümin. Talanta; 47(5): 1223–1229.