Ruthenium(II)-arene complexes with functionalized pyridines: Synthesis, characterization and cytotoxic activity
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2010
Authors
Grgurić-Šipka, Sanja
Ivanovic, Ivanka
Rakic, Gordana
Todorović, Nina

Gligorijević, Nevenka

Radulovic, Sinisa
Arion, Vladimir B.

Keppler, Bernhard K.

Tešić, Živoslav

Article (Published version)

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Ruthenium(II)-arene complexes of general formulae [(eta(6)-p-cymene)Ru(L1-3)Cl-2], where L1-3 is 3-acetylpyridine (1), 4-acetylpyridine (2) and 2-amino-5-chloropyridine (3), Correspondingly, [(eta(6)-p-cymene)Ru(HL4,5)Cl-2], where HL4 and HL5 are respectively isonicotinic acid (4) and nicotinic acid (5) and [(eta(6)-p-cymene)Ru(HL6-9)Cl], where H2L6-9 represent 2,3-pyridinedicarboxylic acid (6), 2,4-pyidinedicarboxylic acid (7), 2,5-pyridinedicarboxylic acid (8) and 2,6-pyridinedicarboxylic acid (9), were prepared by the reaction of (eta(6)-p-cymene)(2)RuCl2](2) (10) with the corresponding ligand in 1:2 molar ratio in isopropanol. The complexes were characterized by elemental analysis, mass spectrometry, IR and NMR spectroscopies. According to these data the molecules adopt the usual "three-leg piano-stool" geometry which is common for this type of complexes. The structures of I and 7 were determined by X-ray crystallography. The complexes revealed low antiproliferative activity in six... investigated tumor cell lines (HeLa, B16, FemX, MDA-MB-361, MDA-MB-453 and LS-174). The reaction of 6 with 9-methyladenine was studied by H-1 NMR, H-1, H-1 COSY and H-1, H-1 NOESY spectroscopy.
Keywords:
Ruthenium(II)-arene / Pyridine derivatives / CytotoxicitySource:
European Journal of Medicinal Chemistry, 2010, 45, 3, 1051-1058Publisher:
- Elsevier France-Editions Scientifiques Medicales Elsevier, Issy-Les-Moulineaux
Funding / projects:
- Synthesis, characterization and activity of organic and coordination composition and their application in (bio) nanotechnology (RS-142010)
- Sinteza, analiza i aktivnost novih organskih polidentatnih liganada i njihovih kompleksa sa d-metalima (RS-142062)
- Farmakodinamska i farmakogenetska istraživanja novih lekova i prediktivna/prognostička vrednost farmakoterapije u onkologiji (RS-145035)
DOI: 10.1016/j.ejmech.2009.11.055
ISSN: 0223-5234
PubMed: 20053483
WoS: 000275404900024
Scopus: 2-s2.0-75949128866
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Institution/Community
IHTMTY - JOUR AU - Grgurić-Šipka, Sanja AU - Ivanovic, Ivanka AU - Rakic, Gordana AU - Todorović, Nina AU - Gligorijević, Nevenka AU - Radulovic, Sinisa AU - Arion, Vladimir B. AU - Keppler, Bernhard K. AU - Tešić, Živoslav PY - 2010 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/646 AB - Ruthenium(II)-arene complexes of general formulae [(eta(6)-p-cymene)Ru(L1-3)Cl-2], where L1-3 is 3-acetylpyridine (1), 4-acetylpyridine (2) and 2-amino-5-chloropyridine (3), Correspondingly, [(eta(6)-p-cymene)Ru(HL4,5)Cl-2], where HL4 and HL5 are respectively isonicotinic acid (4) and nicotinic acid (5) and [(eta(6)-p-cymene)Ru(HL6-9)Cl], where H2L6-9 represent 2,3-pyridinedicarboxylic acid (6), 2,4-pyidinedicarboxylic acid (7), 2,5-pyridinedicarboxylic acid (8) and 2,6-pyridinedicarboxylic acid (9), were prepared by the reaction of (eta(6)-p-cymene)(2)RuCl2](2) (10) with the corresponding ligand in 1:2 molar ratio in isopropanol. The complexes were characterized by elemental analysis, mass spectrometry, IR and NMR spectroscopies. According to these data the molecules adopt the usual "three-leg piano-stool" geometry which is common for this type of complexes. The structures of I and 7 were determined by X-ray crystallography. The complexes revealed low antiproliferative activity in six investigated tumor cell lines (HeLa, B16, FemX, MDA-MB-361, MDA-MB-453 and LS-174). The reaction of 6 with 9-methyladenine was studied by H-1 NMR, H-1, H-1 COSY and H-1, H-1 NOESY spectroscopy. PB - Elsevier France-Editions Scientifiques Medicales Elsevier, Issy-Les-Moulineaux T2 - European Journal of Medicinal Chemistry T1 - Ruthenium(II)-arene complexes with functionalized pyridines: Synthesis, characterization and cytotoxic activity VL - 45 IS - 3 SP - 1051 EP - 1058 DO - 10.1016/j.ejmech.2009.11.055 ER -
@article{ author = "Grgurić-Šipka, Sanja and Ivanovic, Ivanka and Rakic, Gordana and Todorović, Nina and Gligorijević, Nevenka and Radulovic, Sinisa and Arion, Vladimir B. and Keppler, Bernhard K. and Tešić, Živoslav", year = "2010", abstract = "Ruthenium(II)-arene complexes of general formulae [(eta(6)-p-cymene)Ru(L1-3)Cl-2], where L1-3 is 3-acetylpyridine (1), 4-acetylpyridine (2) and 2-amino-5-chloropyridine (3), Correspondingly, [(eta(6)-p-cymene)Ru(HL4,5)Cl-2], where HL4 and HL5 are respectively isonicotinic acid (4) and nicotinic acid (5) and [(eta(6)-p-cymene)Ru(HL6-9)Cl], where H2L6-9 represent 2,3-pyridinedicarboxylic acid (6), 2,4-pyidinedicarboxylic acid (7), 2,5-pyridinedicarboxylic acid (8) and 2,6-pyridinedicarboxylic acid (9), were prepared by the reaction of (eta(6)-p-cymene)(2)RuCl2](2) (10) with the corresponding ligand in 1:2 molar ratio in isopropanol. The complexes were characterized by elemental analysis, mass spectrometry, IR and NMR spectroscopies. According to these data the molecules adopt the usual "three-leg piano-stool" geometry which is common for this type of complexes. The structures of I and 7 were determined by X-ray crystallography. The complexes revealed low antiproliferative activity in six investigated tumor cell lines (HeLa, B16, FemX, MDA-MB-361, MDA-MB-453 and LS-174). The reaction of 6 with 9-methyladenine was studied by H-1 NMR, H-1, H-1 COSY and H-1, H-1 NOESY spectroscopy.", publisher = "Elsevier France-Editions Scientifiques Medicales Elsevier, Issy-Les-Moulineaux", journal = "European Journal of Medicinal Chemistry", title = "Ruthenium(II)-arene complexes with functionalized pyridines: Synthesis, characterization and cytotoxic activity", volume = "45", number = "3", pages = "1051-1058", doi = "10.1016/j.ejmech.2009.11.055" }
Grgurić-Šipka, S., Ivanovic, I., Rakic, G., Todorović, N., Gligorijević, N., Radulovic, S., Arion, V. B., Keppler, B. K.,& Tešić, Ž.. (2010). Ruthenium(II)-arene complexes with functionalized pyridines: Synthesis, characterization and cytotoxic activity. in European Journal of Medicinal Chemistry Elsevier France-Editions Scientifiques Medicales Elsevier, Issy-Les-Moulineaux., 45(3), 1051-1058. https://doi.org/10.1016/j.ejmech.2009.11.055
Grgurić-Šipka S, Ivanovic I, Rakic G, Todorović N, Gligorijević N, Radulovic S, Arion VB, Keppler BK, Tešić Ž. Ruthenium(II)-arene complexes with functionalized pyridines: Synthesis, characterization and cytotoxic activity. in European Journal of Medicinal Chemistry. 2010;45(3):1051-1058. doi:10.1016/j.ejmech.2009.11.055 .
Grgurić-Šipka, Sanja, Ivanovic, Ivanka, Rakic, Gordana, Todorović, Nina, Gligorijević, Nevenka, Radulovic, Sinisa, Arion, Vladimir B., Keppler, Bernhard K., Tešić, Živoslav, "Ruthenium(II)-arene complexes with functionalized pyridines: Synthesis, characterization and cytotoxic activity" in European Journal of Medicinal Chemistry, 45, no. 3 (2010):1051-1058, https://doi.org/10.1016/j.ejmech.2009.11.055 . .