Comparative solution equilibrium and structural studies of half-sandwich ruthenium(II)(eta(6)-toluene) complexes of picolinate derivatives
Само за регистроване кориснике
2018
Аутори
Poljarević, JelenaGal, Tamas G.
May, Nora V.
Spengler, Gabriella
Domotor, Orsolya
Savić, Aleksandar
Grgurić-Šipka, Sanja
Enyedy, Eva A.
Чланак у часопису (Објављена верзија)
Метаподаци
Приказ свих података о документуАпстракт
Five Ru(II)(eta(6)-toluene) complexes formed with 2-picolinic acid and its various derivatives have been synthesized and characterized. X-ray structures of four complexes are also reported. Complex formation processes of [Ru(II) (eta(6)-toluene)(H2O)(3)](2+) organometallic cation with the metal-free ligands were studied in aqueous solution in the presence of chloride ions by the combined use of H-1 NMR spectroscopy, UV-visible spectrophotometry and pH-potentiometry. Solution stability, chloride ion affinity and lipophilicity of the complexes were characterized together with in vitro cytotoxic and antiproliferative activity in cancer cell lines being sensitive and resistant to classic chemotherapy and in normal cells as well. Formation of mono complexes such as [Ru(eta(6)-toluene)(L) (Z)](+/0) (L: completely deprotonated ligand; Z = H2O/Cl-) with high stability and [Ru(eta(6)-toluene)(L)(OH)] was found in solution. The plc values (8.3-8.7) reflect the formation of low amount of mixed hy...droxido species at pH 7.4 at 0.2 M KCl ionic strength. The complexes are fairly hydrophilic and show moderate chloride ion affinity and fast chloride-water exchange processes. The studied complexes exhibit no cytotoxic activity in human cancer cells (IC50 gt 100 mu M), only complexes formed with 2-picolinic acid (1) and its 3-methyl derivative (2) represented a moderate antiproliferative effect (IC50 = 84.8 (1), 79.2 mu M (2)) on a multidrug resistant colon adenocarcinoma cell line revealing considerable multidrug resistant selectivity. Complexes 1 and 2 bind to human serum albumin covalently and relatively slowly with moderate strength at multiple binding sites without ligand cleavage.
Кључне речи:
Stability constants / X-ray crystal structures / Half-sandwich complexes / Speciation / Antiproliferative activityИзвор:
Journal of Inorganic Biochemistry, 2018, 181, 74-85Издавач:
- Elsevier Science Inc, New York
Финансирање / пројекти:
- Рационални дизајн и синтеза биолошки активних и координационих једињења и функционалних материјала, релевантних у (био)нанотехнологији (RS-MESTD-Basic Research (BR or ON)-172035)
- Hungarian Academy of Sciences
- Ministry of Human Capacities [UNKP-17-4]
- National Research, Development and Innovation Office-NKFIA [GINOP-2.3.2-15-2016-00038, FK 124240, K 115762]
Напомена:
- Supplementary material: http://cherry.chem.bg.ac.rs/handle/123456789/3123
DOI: 10.1016/j.jinorgbio.2017.12.017
ISSN: 0162-0134
PubMed: 29407910
WoS: 000428599900008
Scopus: 2-s2.0-85041419138
Колекције
Институција/група
Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Poljarević, Jelena AU - Gal, Tamas G. AU - May, Nora V. AU - Spengler, Gabriella AU - Domotor, Orsolya AU - Savić, Aleksandar AU - Grgurić-Šipka, Sanja AU - Enyedy, Eva A. PY - 2018 UR - https://cherry.chem.bg.ac.rs/handle/123456789/2119 AB - Five Ru(II)(eta(6)-toluene) complexes formed with 2-picolinic acid and its various derivatives have been synthesized and characterized. X-ray structures of four complexes are also reported. Complex formation processes of [Ru(II) (eta(6)-toluene)(H2O)(3)](2+) organometallic cation with the metal-free ligands were studied in aqueous solution in the presence of chloride ions by the combined use of H-1 NMR spectroscopy, UV-visible spectrophotometry and pH-potentiometry. Solution stability, chloride ion affinity and lipophilicity of the complexes were characterized together with in vitro cytotoxic and antiproliferative activity in cancer cell lines being sensitive and resistant to classic chemotherapy and in normal cells as well. Formation of mono complexes such as [Ru(eta(6)-toluene)(L) (Z)](+/0) (L: completely deprotonated ligand; Z = H2O/Cl-) with high stability and [Ru(eta(6)-toluene)(L)(OH)] was found in solution. The plc values (8.3-8.7) reflect the formation of low amount of mixed hydroxido species at pH 7.4 at 0.2 M KCl ionic strength. The complexes are fairly hydrophilic and show moderate chloride ion affinity and fast chloride-water exchange processes. The studied complexes exhibit no cytotoxic activity in human cancer cells (IC50 gt 100 mu M), only complexes formed with 2-picolinic acid (1) and its 3-methyl derivative (2) represented a moderate antiproliferative effect (IC50 = 84.8 (1), 79.2 mu M (2)) on a multidrug resistant colon adenocarcinoma cell line revealing considerable multidrug resistant selectivity. Complexes 1 and 2 bind to human serum albumin covalently and relatively slowly with moderate strength at multiple binding sites without ligand cleavage. PB - Elsevier Science Inc, New York T2 - Journal of Inorganic Biochemistry T1 - Comparative solution equilibrium and structural studies of half-sandwich ruthenium(II)(eta(6)-toluene) complexes of picolinate derivatives VL - 181 SP - 74 EP - 85 DO - 10.1016/j.jinorgbio.2017.12.017 ER -
@article{ author = "Poljarević, Jelena and Gal, Tamas G. and May, Nora V. and Spengler, Gabriella and Domotor, Orsolya and Savić, Aleksandar and Grgurić-Šipka, Sanja and Enyedy, Eva A.", year = "2018", abstract = "Five Ru(II)(eta(6)-toluene) complexes formed with 2-picolinic acid and its various derivatives have been synthesized and characterized. X-ray structures of four complexes are also reported. Complex formation processes of [Ru(II) (eta(6)-toluene)(H2O)(3)](2+) organometallic cation with the metal-free ligands were studied in aqueous solution in the presence of chloride ions by the combined use of H-1 NMR spectroscopy, UV-visible spectrophotometry and pH-potentiometry. Solution stability, chloride ion affinity and lipophilicity of the complexes were characterized together with in vitro cytotoxic and antiproliferative activity in cancer cell lines being sensitive and resistant to classic chemotherapy and in normal cells as well. Formation of mono complexes such as [Ru(eta(6)-toluene)(L) (Z)](+/0) (L: completely deprotonated ligand; Z = H2O/Cl-) with high stability and [Ru(eta(6)-toluene)(L)(OH)] was found in solution. The plc values (8.3-8.7) reflect the formation of low amount of mixed hydroxido species at pH 7.4 at 0.2 M KCl ionic strength. The complexes are fairly hydrophilic and show moderate chloride ion affinity and fast chloride-water exchange processes. The studied complexes exhibit no cytotoxic activity in human cancer cells (IC50 gt 100 mu M), only complexes formed with 2-picolinic acid (1) and its 3-methyl derivative (2) represented a moderate antiproliferative effect (IC50 = 84.8 (1), 79.2 mu M (2)) on a multidrug resistant colon adenocarcinoma cell line revealing considerable multidrug resistant selectivity. Complexes 1 and 2 bind to human serum albumin covalently and relatively slowly with moderate strength at multiple binding sites without ligand cleavage.", publisher = "Elsevier Science Inc, New York", journal = "Journal of Inorganic Biochemistry", title = "Comparative solution equilibrium and structural studies of half-sandwich ruthenium(II)(eta(6)-toluene) complexes of picolinate derivatives", volume = "181", pages = "74-85", doi = "10.1016/j.jinorgbio.2017.12.017" }
Poljarević, J., Gal, T. G., May, N. V., Spengler, G., Domotor, O., Savić, A., Grgurić-Šipka, S.,& Enyedy, E. A.. (2018). Comparative solution equilibrium and structural studies of half-sandwich ruthenium(II)(eta(6)-toluene) complexes of picolinate derivatives. in Journal of Inorganic Biochemistry Elsevier Science Inc, New York., 181, 74-85. https://doi.org/10.1016/j.jinorgbio.2017.12.017
Poljarević J, Gal TG, May NV, Spengler G, Domotor O, Savić A, Grgurić-Šipka S, Enyedy EA. Comparative solution equilibrium and structural studies of half-sandwich ruthenium(II)(eta(6)-toluene) complexes of picolinate derivatives. in Journal of Inorganic Biochemistry. 2018;181:74-85. doi:10.1016/j.jinorgbio.2017.12.017 .
Poljarević, Jelena, Gal, Tamas G., May, Nora V., Spengler, Gabriella, Domotor, Orsolya, Savić, Aleksandar, Grgurić-Šipka, Sanja, Enyedy, Eva A., "Comparative solution equilibrium and structural studies of half-sandwich ruthenium(II)(eta(6)-toluene) complexes of picolinate derivatives" in Journal of Inorganic Biochemistry, 181 (2018):74-85, https://doi.org/10.1016/j.jinorgbio.2017.12.017 . .