Half-sandwich ruthenium(II)-arene complexes: synthesis, spectroscopic studies, biological properties, and molecular modeling
Authors
Nikolić, Stefan
Grgurić-Šipka, Sanja

Đorđević, Ivana

Dahmani, Rahma

Dekanski, Dragana

Vidičević, Sašenka
Tošić, Jelena
Mitić, Dragana

Grubišić, Sonja

Article (Accepted Version)
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In search for antitumor metal-based drugs that would mitigate the severe side-effects of cisplatin, Ru(II) complexes are gaining increasing recent interest. In this work, we report on the synthesis, characterization (1H- and 13C-NMR, FT-IR), and cytotoxicity studies of two new half-sandwich organometallic Ru(II) complexes of the general formula [Ru(η6-arene)(XY)Cl](PF6) where arene = benzene or toluene and XY = bidentates: dipyrido[3,2-a:2′,3′-c]phenazine (dppz) or 2-(9-anthryl)-1H-imidazo[4,5-f][1,10]phenanthroline (aip), which are bound to Ru(II) via two phenanthroline-N atoms in a characteristic “piano-stool” configuration of Ru(II)-arene complexes—as confirmed by vibrational and NMR spectra. In addition, cytotoxic studies were performed for similar half-sandwich organometallic [Ru(η6-p-cymene)(Me2dppz)Cl]PF6 complex (Me2dppz = 11,12-dimethyl-dipyrido[3,2-a:2′,3′-c]phenazine). This study is complemented with elaborate modeling with density functional theory (DFT) calculations, which... provided insight into reactive sites of Ru(II) structures, further detailed by molecular docking on the B-DNA dodecamer, which identified binding sites and affinities: most pronounced for the [Ru(η6-benzene)(aip)Cl](PF6) in both A-T and G-C regions of the DNA minor groove. Cytotoxic activity was probed versus tumor cell lines B16, C6, and U251 (B16 mouse melanoma, C6 rat glioma, U251 human glioblastoma) and non-tumor cell line HACAT (HACAT normal human keratinocytes).
Keywords:
cytotoxicity studies / DFT calculations / DNA docking / intercalation / Ruthenium complexesSource:
Journal of Coordination Chemistry, 2019, 72, 1, 148-163Publisher:
- Taylor & Francis
Funding / projects:
- Rational design and synthesis of biologically active and coordination compounds and functional materials, relevant for (bio)nanotechnology (RS-172035)
- COST CMST-Action CM1405 Molecules in Motion (MOLIM)
Note:
- This is the peer-reviewed version of the following article: Nikolić, S.; Grgurić-Šipka, S.; Djordjević, I. S.; Dahmani, R.; Dekanski, D.; Vidičević, S.; Tošić, J.; Mitić, D.; Grubišić, S. Half-Sandwich Ruthenium(II)-Arene Complexes: Synthesis, Spectroscopic Studies, Biological Properties, and Molecular Modeling. Journal of Coordination Chemistry 2019, 72 (1), 148–163. https://doi.org/10.1080/00958972.2018.1553298.
- The published version: http://cer.ihtm.bg.ac.rs/handle/123456789/3259
DOI: 10.1080/00958972.2018.1553298
ISSN: 0095-8972
WoS: 000465181600009
Scopus: 2-s2.0-85064599205
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IHTMTY - JOUR AU - Nikolić, Stefan AU - Grgurić-Šipka, Sanja AU - Đorđević, Ivana AU - Dahmani, Rahma AU - Dekanski, Dragana AU - Vidičević, Sašenka AU - Tošić, Jelena AU - Mitić, Dragana AU - Grubišić, Sonja PY - 2019 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/3260 AB - In search for antitumor metal-based drugs that would mitigate the severe side-effects of cisplatin, Ru(II) complexes are gaining increasing recent interest. In this work, we report on the synthesis, characterization (1H- and 13C-NMR, FT-IR), and cytotoxicity studies of two new half-sandwich organometallic Ru(II) complexes of the general formula [Ru(η6-arene)(XY)Cl](PF6) where arene = benzene or toluene and XY = bidentates: dipyrido[3,2-a:2′,3′-c]phenazine (dppz) or 2-(9-anthryl)-1H-imidazo[4,5-f][1,10]phenanthroline (aip), which are bound to Ru(II) via two phenanthroline-N atoms in a characteristic “piano-stool” configuration of Ru(II)-arene complexes—as confirmed by vibrational and NMR spectra. In addition, cytotoxic studies were performed for similar half-sandwich organometallic [Ru(η6-p-cymene)(Me2dppz)Cl]PF6 complex (Me2dppz = 11,12-dimethyl-dipyrido[3,2-a:2′,3′-c]phenazine). This study is complemented with elaborate modeling with density functional theory (DFT) calculations, which provided insight into reactive sites of Ru(II) structures, further detailed by molecular docking on the B-DNA dodecamer, which identified binding sites and affinities: most pronounced for the [Ru(η6-benzene)(aip)Cl](PF6) in both A-T and G-C regions of the DNA minor groove. Cytotoxic activity was probed versus tumor cell lines B16, C6, and U251 (B16 mouse melanoma, C6 rat glioma, U251 human glioblastoma) and non-tumor cell line HACAT (HACAT normal human keratinocytes). PB - Taylor & Francis T2 - Journal of Coordination Chemistry T1 - Half-sandwich ruthenium(II)-arene complexes: synthesis, spectroscopic studies, biological properties, and molecular modeling VL - 72 IS - 1 SP - 148 EP - 163 DO - 10.1080/00958972.2018.1553298 ER -
@article{ author = "Nikolić, Stefan and Grgurić-Šipka, Sanja and Đorđević, Ivana and Dahmani, Rahma and Dekanski, Dragana and Vidičević, Sašenka and Tošić, Jelena and Mitić, Dragana and Grubišić, Sonja", year = "2019", abstract = "In search for antitumor metal-based drugs that would mitigate the severe side-effects of cisplatin, Ru(II) complexes are gaining increasing recent interest. In this work, we report on the synthesis, characterization (1H- and 13C-NMR, FT-IR), and cytotoxicity studies of two new half-sandwich organometallic Ru(II) complexes of the general formula [Ru(η6-arene)(XY)Cl](PF6) where arene = benzene or toluene and XY = bidentates: dipyrido[3,2-a:2′,3′-c]phenazine (dppz) or 2-(9-anthryl)-1H-imidazo[4,5-f][1,10]phenanthroline (aip), which are bound to Ru(II) via two phenanthroline-N atoms in a characteristic “piano-stool” configuration of Ru(II)-arene complexes—as confirmed by vibrational and NMR spectra. In addition, cytotoxic studies were performed for similar half-sandwich organometallic [Ru(η6-p-cymene)(Me2dppz)Cl]PF6 complex (Me2dppz = 11,12-dimethyl-dipyrido[3,2-a:2′,3′-c]phenazine). This study is complemented with elaborate modeling with density functional theory (DFT) calculations, which provided insight into reactive sites of Ru(II) structures, further detailed by molecular docking on the B-DNA dodecamer, which identified binding sites and affinities: most pronounced for the [Ru(η6-benzene)(aip)Cl](PF6) in both A-T and G-C regions of the DNA minor groove. Cytotoxic activity was probed versus tumor cell lines B16, C6, and U251 (B16 mouse melanoma, C6 rat glioma, U251 human glioblastoma) and non-tumor cell line HACAT (HACAT normal human keratinocytes).", publisher = "Taylor & Francis", journal = "Journal of Coordination Chemistry", title = "Half-sandwich ruthenium(II)-arene complexes: synthesis, spectroscopic studies, biological properties, and molecular modeling", volume = "72", number = "1", pages = "148-163", doi = "10.1080/00958972.2018.1553298" }
Nikolić, S., Grgurić-Šipka, S., Đorđević, I., Dahmani, R., Dekanski, D., Vidičević, S., Tošić, J., Mitić, D.,& Grubišić, S.. (2019). Half-sandwich ruthenium(II)-arene complexes: synthesis, spectroscopic studies, biological properties, and molecular modeling. in Journal of Coordination Chemistry Taylor & Francis., 72(1), 148-163. https://doi.org/10.1080/00958972.2018.1553298
Nikolić S, Grgurić-Šipka S, Đorđević I, Dahmani R, Dekanski D, Vidičević S, Tošić J, Mitić D, Grubišić S. Half-sandwich ruthenium(II)-arene complexes: synthesis, spectroscopic studies, biological properties, and molecular modeling. in Journal of Coordination Chemistry. 2019;72(1):148-163. doi:10.1080/00958972.2018.1553298 .
Nikolić, Stefan, Grgurić-Šipka, Sanja, Đorđević, Ivana, Dahmani, Rahma, Dekanski, Dragana, Vidičević, Sašenka, Tošić, Jelena, Mitić, Dragana, Grubišić, Sonja, "Half-sandwich ruthenium(II)-arene complexes: synthesis, spectroscopic studies, biological properties, and molecular modeling" in Journal of Coordination Chemistry, 72, no. 1 (2019):148-163, https://doi.org/10.1080/00958972.2018.1553298 . .