Theoretical and Spectroscopic Studies of SN Donor Thiosemicarbazone Ligand and Its Pt(II) Complex
Article Sidebar
-
Bidentate, Binding Energy, Docking Results, Thiosemicarbazone, Pt (II) Complex
Abstract
Sulphur-nitrogen (SN) donor thiosemicarbazone ligand [(Z)-N-ethyl-2-(5-methyl-2-oxoindolin-3-ylidene)hydrazinecarbothioamide] and its Pt(II) complex were synthesized by the condensation method. The compounds were structurally characterized by elemental analysis (CHNS), FT-IR, and NMR analysis. The elemental analysis data for the compounds were in good agreement with the theoretical values. The melting point of the complex was higher than the ligand, as expected. The FT-IR spectral data reflect a bidentate bonding of the thiosemicarbazone ligand to the Pt(II) ion through thioketo sulfur and azomethine nitrogen. The docking results (theoretical results) of these compounds show that the binding energy between DNA and the Pt(II) complex was found to be less than that of the Schiff base ligand (L) in the sense that it has higher stability at various stages and angles. The strength of docking between DNA and the Pt(II) complex was also found to be stronger than that of the Schiff base ligand (L).
Full text article
References
[1]- Pahontu E, Julea F, Rosu T, Purcarea V, Chumakov Y, Petrenco P, Gulea A. Antibacterial, antifungal and in vitro antileukaemia activity of metal complexes with thiosemicarbazones. Journal of cellular and molecular medicine. 2015 Apr;19(4):865-878. https://doi.org/10.1111/jcmm.12508
[2]- More M.S, Joshi P.G, Mishra Y.K, Khanna P.K. Metal complexes driven from Schiff bases and semicarbazones for biomedical and allied applications: a review. Materials Today Chemistry. 2019 Dec 1;14:100195. https://doi.org/10.1016/j.mtchem.2019.100195
[3]- Hassan M, Ghaffari R, Sardari S, Farahani Y.F, Mohebbi S. Discovery of novel isatin-based thiosemicarbazones: synthesis, antibacterial, antifungal, and antimycobacterial screening. Research in Pharmaceutical Sciences. 2020 Jun;15(3):281. https://dx.doi.org/10.4103%2F1735-5362.288435
[4]- Singh G.S, Desta Z.Y. Isatins as privileged molecules in design and synthesis of spiro-fused cyclic frameworks. Chemical Reviews. 2012 Nov 14;112(11):6104-6155. DOI: 10.1021/cr300135y
[5]- Tardito S, Marchio L. Copper compounds in anticancer strategies. Current medicinal chemistry. 2009 Apr 1;16(11):1325-1348. https://doi.org/10.2174/092986709787846532
[6]- Şen, B., Kalhan, H. K., Demir, V., Güler, E. E., Kayalı, H. A., & Subaşı, E. (2019). Crystal structures, spectroscopic properties of new cobalt (II), nickel (II), zinc (II) and palladium (II) complexes derived from 2-acetyl-5-chloro thiophene thiosemicarbazone: anticancer evaluation. Materials Science and Engineering: C,98,550-559. https://doi.org/10.1016/j.msec.2018.12.080
[7]- Kandemirli F, Arslan T, Karadayı N, Ebenso EE, Köksoy B. Synthesis and theoretical study of 5-methoxyisatin-3-(N-cyclohexyl)thiosemica- rbazone and its Ni (II) and Zn (II) complexes. Journal of Molecular Structure. 2009 Dec 16;938(1-3):89-96. https://doi.org/10.1016/j.molstruc.2009.09.009
[8]- Kandemirli, F.; Arslan, T.; Koksoy, B. & Yılmaz, M. Synthesis, Characterization and Theoretical Calculations of 5-Methoxyisatin-3-thiosemicarbazone Derivatives. J. Chem. Soc. Pakistan, 2009, Vol. 31, No. , pp. 498-504.
[9]- Bal T.R, Anand B, Yogeeswari P, Sriram D. Synthesis and evaluation of anti-HIV activity of isatin β-thiosemicarbazone derivatives. Bioorganic & medicinal chemistry letters. 2005 Oct,15;15(20):4451-4455. https://doi.org/10.1016/j.bmcl.2005.07.046
[10]- Sagdinc S, Köksoy B, Kandemirli F, Bayari SH. Theoretical and spectroscopic studies of 5-fluoro-isatin-3-(N-benzylthiosemicarbazone) and its zinc (II) complex. Journal of Molecular Structure. 2009 Jan 15;917(2-3):63-70. https://doi.org/10.1016/j.molstruc.2008.06.033
[11]- Hager, S., Ackermann, C. J., Joerger, M., Gillessen, S., & Omlin, A. Anti-tumour activity of platinum compounds in advanced prostate cancer—a systematic literature review. Annals of Oncology; 2016, 27(6), 975-984. https://doi.org/10.1093/annonc/mdw156
[12]- Pasetto, L. M., D’Andrea, M. R., Brandes, A. A., Rossi, E., & Monfardini, S. The development of platinum compounds and their possible combination. Critical Reviews in Oncology/Hematology, 2006, 60(1), 59-75. https://doi.org/10.1016/j.critrevonc.2006.02.003
[13]- Muggia, F. Platinum compounds 30 years after the introduction of cisplatin: implications for the treatment of ovarian cancer. Gynecologic oncology, 2009,112(1), 275-281. https://doi.org/10.1016/j.ygyno.2008.09.034
[14]- Morris, G.M., Goodsell, D.S., Huey, R. et al. Distributed automated docking of flexible ligands to proteins: Parallel applications of AutoDock 2.4. J Computer-Aided Mol Des 10, 293–304,(1996). https://doi.org/10.1007/BF00124499
[15]- Fouzia. P., Rumana. Q., Farzana. L. A., S. Kalsoom, and Saima. K. S. A. Investigations of drug–DNA interactions using molecular docking, cyclic voltammetry and UV–Vis spectroscopy. Journal of Molecular Structure 2011,1004,67-73. https://doi.org/10.1016/j.molstruc.2011.07.027
[16]- Amna. Q. A., Siang. G. T., Abdussalam. S., Naser. E. .E., Mohamed B., K. and Amin M. S. A. Synthesis of isatin thiosemicarbazones derivatives: In vitro anti-cancer, DNA binding and cleavage activities. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2014, 125 440-448. https://doi.org/10.1016/j.saa.2014.01.086
[17]- Ali A.Q, Teoh S.G, Salhin A, Eltayeb N.E, Ahamed M.B, Majid A.A. Synthesis of platinum (II) complexes of isatin thiosemicarbazones derivatives: In vitro anti-cancer and deoxyribose nucleic acid binding activities. Inorganica Chimica Acta. 2014 May 24;416:235-244 https://doi.org/10.1016/j.ica.2014.03.029.
[18]- Pahontu E, Julea F, Rosu T, Purcarea V, Chumakov Y, Petrenco P, Gulea A. Antibacterial, antifungal and in vitro antileukaemia activity of metal complexes with thiosemicarbazones. Journal of cellular and molecular medicine. 2015 Apr;19(4):865-878. https://doi.org/10.1111/jcmm.12508
[19]- Balan G, Burduniuc O, Usataia I, Graur V, Chumakov Y, Petrenko P, Gudumac V, Gulea A, Pahontu E. Novel 2‐formylpyridine 4‐allyl‐S‐methylisothiosemicarbazone and Zn (II), Cu (II), Ni (II) and Co (III) complexes: Synthesis, characterization, crystal structure, antioxidant, antimicrobial and antiproliferative activity. Applied Organometallic Chemistry. 2020,Mar;34(3):e5423. https://doi.org/10.1002/aoc.5423
[20]- Pahonțu E, Paraschivescu C, Ilieș D.C, Poirier D, Oprean C, Păunescu V, Gulea A, Roșu T, Bratu O. Synthesis and Characterization of Novel Cu (II), Pd (II) and Pt (II) Complexes with 8-Ethyl-2-hydroxytricyclo (7.3.1.02,7)tridecan-13-onethiosemicarbazone: Antimicrobial and in Vitro Antiproliferative Activity. Molecules. 2016 May;21(5):674. https://doi.org/10.3390/molecules21050674
[21]- Wiles, D.M., Gingras, B.A., Suprunchuk, T. The C=S stretching vibration in the infrared spectra of some thiosemicarbazones. Canadian Journal of Chemistry. 1967 45, 469-473. doi:10.1139/v67-081. https://doi.org/10.1139/v67-081
[22]- Sharma D, Jasinski JP, Smolinski VA, Kaur M, Paul K, Sharma R. Synthesis and structure of complexes (NiII, AgI) of substituted benzaldehyde thiosemicarbazones and antitubercular activity of NiII complex. Inorganica Chimica Acta. 2020 Jan 1;499:119187. https://doi.org/10.1016/j.ica.2019.119187
[23]- Ilic SB, Konstantinovic SS, Todorovic ZB, Lazic ML, Veljkovic VB, Jokovic N, Radovanovic BC. Characterization and antimicrobial activity of the bioactive metabolites in streptomycete isolates. Microbiology. 2007 Aug 1;76(4):421-428. https://doi.org/10.1134/S0026261707040066
[24]- Matesanz AI, Pérez JM, Navarro P, Moreno JM, Colacio E, Souza P. Synthesis and characterization of novel palladium (II) complexes of bis (thiosemicarbazone). Structure, cytotoxic activity and DNA binding of Pd (II)-benzyl bis (thiosemicarbazonate). Journal of inorganic biochemistry. 1999 Jul 30;76(1):29-37. https://doi.org/10.1016/S0162-0134(99)00105-1
[25]- Mbugua, S. N., Sibuyi, N., Njenga, L. W., Odhiambo, R. A., Wandiga, S. O., Meyer, M., Lalancette, R. A., & Onani, M. O. (2020). New Palladium(II) and Platinum(II) Complexes Based on Pyrrole Schiff Bases: Synthesis, Characterization, X-ray Structure, and Anticancer Activity. ACS omega, 5(25), 14942–14954. https://doi.org/10.1021/acsomega.0c00360.
Authors
This work is licensed under a Creative Commons Attribution 4.0 International License.
In a brief statement, the rights relate to the publication and distribution of research published in the journal of the University of Sebha where authors who have published their articles in the journal of the university of Sebha should how they can use or distribute their articles. They reserve all their rights to the published works, such as (but not limited to) the following rights:
- Copyright and other property rights related to the article, such as patent rights.
- Research published in the journal of the University of Sebha and used in its future works, including lectures and books, the right to reproduce articles for their own purposes, and the right to self-archive their articles.
- The right to enter a separate article, or for a non-exclusive distribution of their article with an acknowledgment of its initial publication in the journal of Sebha University.
Privacy Statement The names and e-mail addresses entered on the Sabha University Journal site will be used for the aforementioned purposes only and for which they were used.