Synthesis of New Pt(II) Complex Bearing Organoselenium Ligands and Evaluation of Cytotoxic Activity of Some Structurally Related Pd(II) Complexes

Authors

  • Ninko Radenković University of Kragujevac, Faculty of Science, Department of Chemistry
  • Marina Kostić University of Kragujevac, Institute for Information Technologies, Department of Science
  • Nataša Đorđević State University of Novi Pazar, Department of Biomedical Science, Vuka Karadzica bb, 36300 Novi Pazar
  • Zana Doličanin State University of Novi Pazar, Department of Biomedical Science, Vuka Karadzica bb, 36300 Novi Pazar
  • Tanja Soldatović State University of Novi Pazar, Department of Biomedical Science, Vuka Karadzica bb, 36300 Novi Pazar
  • Marko Živanović University of Kragujevac, Institute for Information Technologies, Department of Science
  • Vera M Divac University of Kragujevac, Faculty of Science, Department of Chemistry

DOI:

https://doi.org/10.20450/mjcce.2020.1905

Keywords:

Organoselenium chemistry, Palladium, Platinum, Cytotoxic activity, Colon carcinoma

Abstract

Herein we report the synthesis of new trans-bis(2-phenylselenylmethyl)oxolane)dichloroplatinum(II) complex Pt1. Newly synthetized complex, together with two, structurally related trans-Pd(II) complexes (trans-bis(2-(phenylselenylmethyl)oxolane)dichloropalladium(II) Pd1 and trans-bis(2-(phenylselenylmethyl)oxane)dichloropalladium(II)) Pd2, were screened for cytotoxic activity through in vitro study on the HCT-116 colorectal carcinoma cell line and on the MRC-5 healthy lung pleura cell line. Activity of complexes was assessed by comparing it to the cisplatin. The cells viability and proliferation were determined using MTT assay.

References

G. Mugesh, W. du Mont, H. Sies, The Chemistry of Biologically Important Synthetic Organoselenium Compunds, Chem. Rev. 101, 2125-2179 (2001).

C. Sanmartín, D. Plano, A. K. Sharma, J. A. Palop, Selenium compounds, apoptosis and other types of cell death: an overview for cancer therapy, Int. J. Mol. Sci.; 13, 9649-9672 (2012).

A. Kumar, G. K. Rao, F. Saleem, A. K. Singh, Organoselenium ligands in catalysis, J. Chem. Soc. Dalton. Trans.; 41, 11949-11977 (2012).

E. Meggers, Exploring biologically relevant chemical space with metal complexes, Curr. Opin. Chem. Biol. 11, 287-292 (2007).

E. G. Hope, W. Levason, Recent developments in the coordination chemistry of selenoether and telluroether ligands, Coord. Chem. Rev. 122, 109-170 (1993).

M. K. Davies, M. C. Durrant, W. Levason, G. Reid, R. L. Richards, Synthesis, spectroscopic and structural studies on transition metal carbonyl complexes of cyclic di- and tetra-selenoether ligands, J. Chem. Soc. Dalton. Trans. 0, 1077-1084 (1999).

J. Arnold, The Chemistry of Metal Complexes with Selenolate and Tellurolate Ligands in: Progress in Inorganic Chemistry, K. D. Karlin (Ed), Hoboken: John Wiley & Sons Inc, 1995, Vol. 43, pp. 353-417.

S. Fujimoto, H. Yasui, Y. Yasukawa, Development of a novel antidiabetic zinc complex with an organoselenium ligand at the lowest dosage in KK-Ay mice, J. Inorg. Biochem. 121, 10-15 (2013).

T. R. Todorovic, A. Bacchi, D. M. Sladic, N. M. Todorovic, T. T. Bozic, D. D. Radanovic, N. R. Filipovic, G. Pelizzi, K. K. Andjelkovic, Synthesis, characterization and biological activity evaluation of Pt(II), Pd(II), Co(III) and Ni(II) complexes with N-heteroaromatic selenosemicarbazones, Inorg. Chim. Acta. 362, 3813- 3820 (2009).

G. Zhao, H. Lin, S Zhu, H. Sun, Y. Chen, Dinuclear palladium(II) complexes containing two monofunctional [Pd(en)(pyridine)Cl]+ units bridged by Se or S. Synthesis, characterization, cytotoxicity and kinetic studies of DNA-binding, J. Inorg. Biochem. 70, 219-226 (1998).

N. Gligorijevic, T. Todorovic, S. Radulovic, D. Sladic, N. Filipovic, D. Glođevac, D. Jeremic, K. Andjelkovic, Synthesis and characterization of new Pt(II) and Pd(II) complexes with 2-quinolinecarboxaldehyde selenosemicarbazone: cytotoxic activity evaluation of Cd(II), Zn(II), Ni(II), Pt(II) and Pd(II) complexes with heteroaromatic selenosemicarbazones, Eur. J. Med. Chem. 44, 1623-1629 (2009).

P. Scovill, D. L. Klayman, C. F. Franchino, 2-Acetylpyridine thiosemicarbazones. Complexes with transition metals as antimalarial and antileukemic agents, J. Med. Chem. 25, 1261-1264 (1982).

M. Carland, B. F. Abrahams, T. Rede, J. Stephenson, V. Murray, W. A. Denny, W. D. McFadyen, Syntheses and structural studies of platinum(II) complexes of O-methylselenomethionine and related ligands, Inorg. Chim. Acta. 359, 3252-3256 (2006).

A. Molter, C. W. Lehmann, G. Deepa, P. Chiba, F. Mohr, Synthesis, structures and anti-malaria activity of some gold(I) phosphine complexes containing seleno- and thiosemicarbazonato ligands, Dalton Trans. 40, 9810-9820 (2011).

E. Z. Jahromi, A. Divsalar, A. A. Saboury, S. Khaleghizadeh, H. Mansouri-Torshizi, I. Kostova, Palladium complexes: new candidates for anti-cancer drugs, J. Iran. Chem. Soc. 13, 967-989 (2016).

A. R. Kapdi, I. J. Fairlamb, Anti-cancer palladium complexes: a focus on PdX2L2, palladacycles and related complexes, Chem. Soc. Rev. 43, 4751-4777 (2014).

L. Tusek-Bozic, A. Furlani, V. Scarcia, E. De Clercq, J. Balzarini, Spectroscopic and biological properties of palladium(II) complexes of ethyl 2-quinolylmethylphosphonate, J. Inorg. Biochem. 72, 201-210 (1998).

E. Gao, C. Liu, M. Zhu, H. Lin, Q. Wu, L. Liu, Current Development of Pd(II) Complexes as Potential Antitumor Agents, Anticanc. Agents Med. Chem. 9, 356-368 (2009).

A. Divsalar, A. A. Saboury, H. Mansoori-Torshizi, F. Ahmad, Design, synthesis, and biological evaluation of a new palladium(II) complex: beta-lactoglobulin and K562 as targets, J. Phys. Chem. B, 114, 3639-3647 (2010).

Z. M. Bugarcic, B. M. Mojsilovic, V. M. Divac, Facile pyridine-catalyzed phenylselenoetherification of alkenols , J. Mol. Catal. A Chem. 272, 288-292 (2007).

Z. M. Bugarcic, V. M. Divac, M. D. Kostic, N. Jankovic, F. Heinemann, N. Radulovic, Z. Stojanovic-Radic, Synthesis, crystal and solution structures and antimicrobial screening of palladium(II) complexes with 2-(phenyselanylmethyl)oxolane and 2-(phenylselanylmethyl)oxane as ligands, J. Inorg. Biochem. 143, 9-19 (2015).

T. Mosmann, Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays, J. Immuno Methods, 65, 55-63 (1983).

J. V. Kosaric, D. M. Cvetkovic, M. N. Zivanovic, M.G. Curcic, D. S. Seklic, Z. M. Bugarcic, S. D. Markovic, Antioxidative and antiproliferative evaluation of 2-(phenylselenomethyl)tetrahydrofuran and 2-(phenylselenomethyl)tetrahydropyran, JBUON, 19, 283-290 (2014).

V. M. Divac, A. Mijatovic, M. D. Kostic, J. Bogojeski, The interaction of organoselenium trans-palladium(II) complexes toward small-biomolecules and CT-DNA, Inorg. Chim. Acta. 466, 464-469 (2017).

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Published

2020-05-28

How to Cite

Radenković, N., Kostić, M., Đorđević, N., Doličanin, Z., Soldatović, T., Živanović, M., & Divac, V. M. (2020). Synthesis of New Pt(II) Complex Bearing Organoselenium Ligands and Evaluation of Cytotoxic Activity of Some Structurally Related Pd(II) Complexes. Macedonian Journal of Chemistry and Chemical Engineering, 39(1), 59–64. https://doi.org/10.20450/mjcce.2020.1905

Issue

Vol. 39 No. 1 (2020)

Section

Inorganic Chemistry

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