Ruthenium(II) bipyridine complexes: from synthesis and crystal structures to electrochemical and cytotoxicity investigation
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2017
Authors
Baroud, Afya A.Mihajlović-Lalić, Ljiljana
Gligorijević, Nevenka
Aranđelović, Sandra
Stanković, Dalibor
Radulović, Siniša
Van Hecke, Kristof
Savić, Aleksandar
Grgurić-Šipka, Sanja
Article (Accepted Version)
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Complexes 1-4, [Ru(L)(bpy)(2)]PF6, where bpy=2,2-bipyridine; HL=3-methylpyridine-2-carboxylic acid (HL1), 6-methylpyridine-2-carboxylic acid (HL2), 5-bromopyridine-2-carboxylic acid (HL3) and 6-bromopyridine-2-carboxylic acid (HL4), were synthesized and characterized. The electrochemical character of the complexes was investigated by cyclic voltammetry revealing two reversible reduction waves in the negative range of potentials, most likely due to a reduction of the bipyridine moiety. Cytotoxicity studies by MTT assay for 72h of drug action revealed that 2-4 exhibited moderate activity in cervical human tumor cells (HeLa). Complex 2 exhibited low activity in colon cancer LS-174 cells (180 +/- 10), while all complexes were devoid of activity in lung cancer A549 and non-tumor MRC-5 cells, up to 200M. Combinational studies of the most active complex 2, with pharmacological modulators of cell redox status, L-buthionine-sulfoximine (L-BSO) or N-acetyl-L-cysteine (NAC), showed that when L-BS...O potentiated, 2 induced a sub-G1 peak of the cell cycle in the HeLa cell line. UV-vis and cyclic voltammetry were performed in order to investigate the binding mode of 2 to DNA and suggested intercalation for the complex-DNA interaction. [GRAPHICS]
Keywords:
Ruthenium(II) bipyridine complexes / crystal structure / redox properties / cytotoxicity / DNA intercalationSource:
Journal of Coordination Chemistry, 2017, 70, 5, 831-847Publisher:
- Taylor & Francis Ltd, Abingdon
Funding / projects:
- Rational design and synthesis of biologically active and coordination compounds and functional materials, relevant for (bio)nanotechnology (RS-MESTD-Basic Research (BR or ON)-172035)
- Pharmacodynamic and pharmacogenomic research of new drugs in the treatment of solid tumors (RS-MESTD-Integrated and Interdisciplinary Research (IIR or III)-41026)
- Reinforcement of the Faculty of Chemistry, University of Belgrade, towards becoming a Center of Excellence in the region of WB for Molecular Biotechnology and Food research (EU-FP7-256716)
- Strengthening of the MagBioVin Research and Innovation Team for Development of Novel Approaches for Tumour Therapy based on Nanostructured Materials (EU-FP7-621375)
- Research Fund-Flanders (FWO)
- Hercules Foundation (3D-SPACE: 3D Structural Platform Aiming for Chemical Excellence) [AUGE/11/029]
Note:
- This is the peer-reviewed version of the following article: Baroud, A. A.; Mihajlović-Lalić, L. E.; Gligorijević, N.; Aranđelović, S.; Stanković, D.; Radulović, S.; Van Hecke, K.; Savić, A.; Grgurić-Šipka, S. Ruthenium(II) Bipyridine Complexes: From Synthesis and Crystal Structures to Electrochemical and Cytotoxicity Investigation. Journal of Coordination Chemistry 2017, 70 (5), 831–847. https://doi.org/10.1080/00958972.2017.1282611
- Supplementary material: http://cherry.chem.bg.ac.rs/handle/123456789/3138
DOI: 10.1080/00958972.2017.1282611
ISSN: 0095-8972
WoS: 000395175800006
Scopus: 2-s2.0-85012257876
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Institution/Community
Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Baroud, Afya A. AU - Mihajlović-Lalić, Ljiljana AU - Gligorijević, Nevenka AU - Aranđelović, Sandra AU - Stanković, Dalibor AU - Radulović, Siniša AU - Van Hecke, Kristof AU - Savić, Aleksandar AU - Grgurić-Šipka, Sanja PY - 2017 UR - https://cherry.chem.bg.ac.rs/handle/123456789/2423 AB - Complexes 1-4, [Ru(L)(bpy)(2)]PF6, where bpy=2,2-bipyridine; HL=3-methylpyridine-2-carboxylic acid (HL1), 6-methylpyridine-2-carboxylic acid (HL2), 5-bromopyridine-2-carboxylic acid (HL3) and 6-bromopyridine-2-carboxylic acid (HL4), were synthesized and characterized. The electrochemical character of the complexes was investigated by cyclic voltammetry revealing two reversible reduction waves in the negative range of potentials, most likely due to a reduction of the bipyridine moiety. Cytotoxicity studies by MTT assay for 72h of drug action revealed that 2-4 exhibited moderate activity in cervical human tumor cells (HeLa). Complex 2 exhibited low activity in colon cancer LS-174 cells (180 +/- 10), while all complexes were devoid of activity in lung cancer A549 and non-tumor MRC-5 cells, up to 200M. Combinational studies of the most active complex 2, with pharmacological modulators of cell redox status, L-buthionine-sulfoximine (L-BSO) or N-acetyl-L-cysteine (NAC), showed that when L-BSO potentiated, 2 induced a sub-G1 peak of the cell cycle in the HeLa cell line. UV-vis and cyclic voltammetry were performed in order to investigate the binding mode of 2 to DNA and suggested intercalation for the complex-DNA interaction. [GRAPHICS] PB - Taylor & Francis Ltd, Abingdon T2 - Journal of Coordination Chemistry T1 - Ruthenium(II) bipyridine complexes: from synthesis and crystal structures to electrochemical and cytotoxicity investigation VL - 70 IS - 5 SP - 831 EP - 847 DO - 10.1080/00958972.2017.1282611 ER -
@article{ author = "Baroud, Afya A. and Mihajlović-Lalić, Ljiljana and Gligorijević, Nevenka and Aranđelović, Sandra and Stanković, Dalibor and Radulović, Siniša and Van Hecke, Kristof and Savić, Aleksandar and Grgurić-Šipka, Sanja", year = "2017", abstract = "Complexes 1-4, [Ru(L)(bpy)(2)]PF6, where bpy=2,2-bipyridine; HL=3-methylpyridine-2-carboxylic acid (HL1), 6-methylpyridine-2-carboxylic acid (HL2), 5-bromopyridine-2-carboxylic acid (HL3) and 6-bromopyridine-2-carboxylic acid (HL4), were synthesized and characterized. The electrochemical character of the complexes was investigated by cyclic voltammetry revealing two reversible reduction waves in the negative range of potentials, most likely due to a reduction of the bipyridine moiety. Cytotoxicity studies by MTT assay for 72h of drug action revealed that 2-4 exhibited moderate activity in cervical human tumor cells (HeLa). Complex 2 exhibited low activity in colon cancer LS-174 cells (180 +/- 10), while all complexes were devoid of activity in lung cancer A549 and non-tumor MRC-5 cells, up to 200M. Combinational studies of the most active complex 2, with pharmacological modulators of cell redox status, L-buthionine-sulfoximine (L-BSO) or N-acetyl-L-cysteine (NAC), showed that when L-BSO potentiated, 2 induced a sub-G1 peak of the cell cycle in the HeLa cell line. UV-vis and cyclic voltammetry were performed in order to investigate the binding mode of 2 to DNA and suggested intercalation for the complex-DNA interaction. [GRAPHICS]", publisher = "Taylor & Francis Ltd, Abingdon", journal = "Journal of Coordination Chemistry", title = "Ruthenium(II) bipyridine complexes: from synthesis and crystal structures to electrochemical and cytotoxicity investigation", volume = "70", number = "5", pages = "831-847", doi = "10.1080/00958972.2017.1282611" }
Baroud, A. A., Mihajlović-Lalić, L., Gligorijević, N., Aranđelović, S., Stanković, D., Radulović, S., Van Hecke, K., Savić, A.,& Grgurić-Šipka, S.. (2017). Ruthenium(II) bipyridine complexes: from synthesis and crystal structures to electrochemical and cytotoxicity investigation. in Journal of Coordination Chemistry Taylor & Francis Ltd, Abingdon., 70(5), 831-847. https://doi.org/10.1080/00958972.2017.1282611
Baroud AA, Mihajlović-Lalić L, Gligorijević N, Aranđelović S, Stanković D, Radulović S, Van Hecke K, Savić A, Grgurić-Šipka S. Ruthenium(II) bipyridine complexes: from synthesis and crystal structures to electrochemical and cytotoxicity investigation. in Journal of Coordination Chemistry. 2017;70(5):831-847. doi:10.1080/00958972.2017.1282611 .
Baroud, Afya A., Mihajlović-Lalić, Ljiljana, Gligorijević, Nevenka, Aranđelović, Sandra, Stanković, Dalibor, Radulović, Siniša, Van Hecke, Kristof, Savić, Aleksandar, Grgurić-Šipka, Sanja, "Ruthenium(II) bipyridine complexes: from synthesis and crystal structures to electrochemical and cytotoxicity investigation" in Journal of Coordination Chemistry, 70, no. 5 (2017):831-847, https://doi.org/10.1080/00958972.2017.1282611 . .