Synthesis and in vitro Anticancer Activity of Ruthenium-Cymene Complexes with Cyclohexyl-Functionalized Ethylenediamine-N,N '-diacetate-Type Ligands
Samo za registrovane korisnike
2011
Autori
Savić, AleksandarDulović, Marija
Poljarević, Jelena
Misirlić-Denčić, Sonja
Jovanović, Maja
Bogdanović, Andrija
Trajković, Vladimir S.
Sabo, Tibor
Grgurić-Šipka, Sanja
Marković, Ivanka
Članak u časopisu (Objavljena verzija)
Metapodaci
Prikaz svih podataka o dokumentuApstrakt
Herein we describe the synthesis, characterization, and anticancer activity of novel p-cymeneruthenium(II) complexes containing methyl, ethyl, n-propyl, and n-butyl esters of (S, S)-ethylenediamine-N,N'-di-2-(3-cyclohexyl)propanoic acid. The results of IR, UV/Vis, ESIMS, (1)H, and (13)C NMR characterization reveal that ligand coordination occurs through nitrogen donor atoms of the ester ligands, with the organoruthenium moiety being kept in complex. These ruthenium(II) complexes are cytotoxic toward various cancer cell lines including leukemic HL-60, K562, and REH cells (IC(50) : 1.0-20.2 mu m), with the n-butyl ester complex being the most effective. It causes apoptotic cell death associated with mitochondrial depolarization, caspase activation, phosphatidylserine exposure, and DNA fragmentation. Importantly, the n-butyl ester complex is more effective against leukemic patients' blood mononuclear cells relative to those from healthy control subjects, thus indicating a fairly selective... antileukemic action of Ru(II)-based compounds.
Ključne reči:
apoptosis / cancer / leukemia / mitochondrial depolarization / rutheniumIzvor:
ChemMedChem, 2011, 6, 10, 1884-1891Izdavač:
- Wiley-Blackwell, Malden
Finansiranje / projekti:
- Modulacija signalnih puteva koji kontrolišu intracelularni energetski balans u terapiji tumora i neuro-imuno-endokrinih poremećaja (RS-MESTD-Integrated and Interdisciplinary Research (IIR or III)-41025)
- Racionalni dizajn i sinteza biološki aktivnih i koordinacionih jedinjenja i funkcionalnih materijala, relevantnih u (bio)nanotehnologiji (RS-MESTD-Basic Research (BR or ON)-172035)
DOI: 10.1002/cmdc.201100232
ISSN: 1860-7179
PubMed: 21805645
WoS: 000296417000015
Scopus: 2-s2.0-80053430580
Kolekcije
Institucija/grupa
Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Savić, Aleksandar AU - Dulović, Marija AU - Poljarević, Jelena AU - Misirlić-Denčić, Sonja AU - Jovanović, Maja AU - Bogdanović, Andrija AU - Trajković, Vladimir S. AU - Sabo, Tibor AU - Grgurić-Šipka, Sanja AU - Marković, Ivanka PY - 2011 UR - https://cherry.chem.bg.ac.rs/handle/123456789/1215 AB - Herein we describe the synthesis, characterization, and anticancer activity of novel p-cymeneruthenium(II) complexes containing methyl, ethyl, n-propyl, and n-butyl esters of (S, S)-ethylenediamine-N,N'-di-2-(3-cyclohexyl)propanoic acid. The results of IR, UV/Vis, ESIMS, (1)H, and (13)C NMR characterization reveal that ligand coordination occurs through nitrogen donor atoms of the ester ligands, with the organoruthenium moiety being kept in complex. These ruthenium(II) complexes are cytotoxic toward various cancer cell lines including leukemic HL-60, K562, and REH cells (IC(50) : 1.0-20.2 mu m), with the n-butyl ester complex being the most effective. It causes apoptotic cell death associated with mitochondrial depolarization, caspase activation, phosphatidylserine exposure, and DNA fragmentation. Importantly, the n-butyl ester complex is more effective against leukemic patients' blood mononuclear cells relative to those from healthy control subjects, thus indicating a fairly selective antileukemic action of Ru(II)-based compounds. PB - Wiley-Blackwell, Malden T2 - ChemMedChem T1 - Synthesis and in vitro Anticancer Activity of Ruthenium-Cymene Complexes with Cyclohexyl-Functionalized Ethylenediamine-N,N '-diacetate-Type Ligands VL - 6 IS - 10 SP - 1884 EP - 1891 DO - 10.1002/cmdc.201100232 ER -
@article{ author = "Savić, Aleksandar and Dulović, Marija and Poljarević, Jelena and Misirlić-Denčić, Sonja and Jovanović, Maja and Bogdanović, Andrija and Trajković, Vladimir S. and Sabo, Tibor and Grgurić-Šipka, Sanja and Marković, Ivanka", year = "2011", abstract = "Herein we describe the synthesis, characterization, and anticancer activity of novel p-cymeneruthenium(II) complexes containing methyl, ethyl, n-propyl, and n-butyl esters of (S, S)-ethylenediamine-N,N'-di-2-(3-cyclohexyl)propanoic acid. The results of IR, UV/Vis, ESIMS, (1)H, and (13)C NMR characterization reveal that ligand coordination occurs through nitrogen donor atoms of the ester ligands, with the organoruthenium moiety being kept in complex. These ruthenium(II) complexes are cytotoxic toward various cancer cell lines including leukemic HL-60, K562, and REH cells (IC(50) : 1.0-20.2 mu m), with the n-butyl ester complex being the most effective. It causes apoptotic cell death associated with mitochondrial depolarization, caspase activation, phosphatidylserine exposure, and DNA fragmentation. Importantly, the n-butyl ester complex is more effective against leukemic patients' blood mononuclear cells relative to those from healthy control subjects, thus indicating a fairly selective antileukemic action of Ru(II)-based compounds.", publisher = "Wiley-Blackwell, Malden", journal = "ChemMedChem", title = "Synthesis and in vitro Anticancer Activity of Ruthenium-Cymene Complexes with Cyclohexyl-Functionalized Ethylenediamine-N,N '-diacetate-Type Ligands", volume = "6", number = "10", pages = "1884-1891", doi = "10.1002/cmdc.201100232" }
Savić, A., Dulović, M., Poljarević, J., Misirlić-Denčić, S., Jovanović, M., Bogdanović, A., Trajković, V. S., Sabo, T., Grgurić-Šipka, S.,& Marković, I.. (2011). Synthesis and in vitro Anticancer Activity of Ruthenium-Cymene Complexes with Cyclohexyl-Functionalized Ethylenediamine-N,N '-diacetate-Type Ligands. in ChemMedChem Wiley-Blackwell, Malden., 6(10), 1884-1891. https://doi.org/10.1002/cmdc.201100232
Savić A, Dulović M, Poljarević J, Misirlić-Denčić S, Jovanović M, Bogdanović A, Trajković VS, Sabo T, Grgurić-Šipka S, Marković I. Synthesis and in vitro Anticancer Activity of Ruthenium-Cymene Complexes with Cyclohexyl-Functionalized Ethylenediamine-N,N '-diacetate-Type Ligands. in ChemMedChem. 2011;6(10):1884-1891. doi:10.1002/cmdc.201100232 .
Savić, Aleksandar, Dulović, Marija, Poljarević, Jelena, Misirlić-Denčić, Sonja, Jovanović, Maja, Bogdanović, Andrija, Trajković, Vladimir S., Sabo, Tibor, Grgurić-Šipka, Sanja, Marković, Ivanka, "Synthesis and in vitro Anticancer Activity of Ruthenium-Cymene Complexes with Cyclohexyl-Functionalized Ethylenediamine-N,N '-diacetate-Type Ligands" in ChemMedChem, 6, no. 10 (2011):1884-1891, https://doi.org/10.1002/cmdc.201100232 . .