New ruthenium(II)-arene complexes bearing hydrazides and the corresponding (thio)semicarbazones of 3-and 4-acetylpyridine: Synthesis, characterization, crystal structure determination and antiproliferative activity
Samo za registrovane korisnike
2013
Autori
Ivanović, IvankaGligorijević, Nevenka
Aranđelović, Sandra
Radulović, Siniša
Roller, Alexander
Keppler, Bernhard K.
Tešić, Živoslav Lj.
Grgurić-Šipka, Sanja
Članak u časopisu (Objavljena verzija)
Metapodaci
Prikaz svih podataka o dokumentuApstrakt
Metal semicarbazone and thiosemicarbazone complexes have attracted much attention due to their diverse biological activities. Because of the ability of ruthenium(II)-arene species to coordinate to different classes of ligands, they are suitable for fine-tuning chemical and pharmaceutical properties. Ruthenium(II) arene-complexes containing different types of ligands: namely caprylic hydrazide (a hydrazide with a long hydrocarbon chain), isonicotinic acid hydrazide (a hydrazide with an aromatic pyridine ring), thiosemicarbazones and semicarbazones (derived from the reaction of 3- and 4-acetylpyridine with either thiosemicarbazide or caprylic hydrazide), were obtained in the reaction of [(eta(6)-p-cymene)RuCl2](2) with the corresponding ligands in a 1:2 or 1:2.2 molar ratio in methanol, ethanol or isopropanol with mild heating. The complexes were characterized by elemental analysis, mass spectrometry, IR and NMR spectroscopies. The structure of complex 1 was determined by X-ray crystallo...graphy. Antiproliferative activity of the investigated complexes, determined for three human cancer cell lines (HeLa, A549 and LS-174) revealed moderate activity without significant influence on the matrix metalloproteinases (MMP-2 and MMP-9) activity.
Ključne reči:
Ruthenium(II)-arene / Hydrazides / Thiosemicarbazones / Semicarbazones / CytotoxicityIzvor:
Polyhedron, 2013, 61, 112-118Izdavač:
- Pergamon-Elsevier Science Ltd, Oxford
Finansiranje / projekti:
- Farmakodinamska i farmakogenomska ispitivanja novijih lekova u lečenju solidnih tumora (RS-41026)
- Korelacija strukture i osobina prirodnih i sintetičkih molekula i njihovih kompleksa sa metalima (RS-172017)
- COST Action [CM1105]
DOI: 10.1016/j.poly.2013.05.050
ISSN: 0277-5387
WoS: 000322938100016
Scopus: 2-s2.0-84879210266
Kolekcije
Institucija/grupa
Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Ivanović, Ivanka AU - Gligorijević, Nevenka AU - Aranđelović, Sandra AU - Radulović, Siniša AU - Roller, Alexander AU - Keppler, Bernhard K. AU - Tešić, Živoslav Lj. AU - Grgurić-Šipka, Sanja PY - 2013 UR - https://cherry.chem.bg.ac.rs/handle/123456789/1386 AB - Metal semicarbazone and thiosemicarbazone complexes have attracted much attention due to their diverse biological activities. Because of the ability of ruthenium(II)-arene species to coordinate to different classes of ligands, they are suitable for fine-tuning chemical and pharmaceutical properties. Ruthenium(II) arene-complexes containing different types of ligands: namely caprylic hydrazide (a hydrazide with a long hydrocarbon chain), isonicotinic acid hydrazide (a hydrazide with an aromatic pyridine ring), thiosemicarbazones and semicarbazones (derived from the reaction of 3- and 4-acetylpyridine with either thiosemicarbazide or caprylic hydrazide), were obtained in the reaction of [(eta(6)-p-cymene)RuCl2](2) with the corresponding ligands in a 1:2 or 1:2.2 molar ratio in methanol, ethanol or isopropanol with mild heating. The complexes were characterized by elemental analysis, mass spectrometry, IR and NMR spectroscopies. The structure of complex 1 was determined by X-ray crystallography. Antiproliferative activity of the investigated complexes, determined for three human cancer cell lines (HeLa, A549 and LS-174) revealed moderate activity without significant influence on the matrix metalloproteinases (MMP-2 and MMP-9) activity. PB - Pergamon-Elsevier Science Ltd, Oxford T2 - Polyhedron T1 - New ruthenium(II)-arene complexes bearing hydrazides and the corresponding (thio)semicarbazones of 3-and 4-acetylpyridine: Synthesis, characterization, crystal structure determination and antiproliferative activity VL - 61 SP - 112 EP - 118 DO - 10.1016/j.poly.2013.05.050 ER -
@article{ author = "Ivanović, Ivanka and Gligorijević, Nevenka and Aranđelović, Sandra and Radulović, Siniša and Roller, Alexander and Keppler, Bernhard K. and Tešić, Živoslav Lj. and Grgurić-Šipka, Sanja", year = "2013", abstract = "Metal semicarbazone and thiosemicarbazone complexes have attracted much attention due to their diverse biological activities. Because of the ability of ruthenium(II)-arene species to coordinate to different classes of ligands, they are suitable for fine-tuning chemical and pharmaceutical properties. Ruthenium(II) arene-complexes containing different types of ligands: namely caprylic hydrazide (a hydrazide with a long hydrocarbon chain), isonicotinic acid hydrazide (a hydrazide with an aromatic pyridine ring), thiosemicarbazones and semicarbazones (derived from the reaction of 3- and 4-acetylpyridine with either thiosemicarbazide or caprylic hydrazide), were obtained in the reaction of [(eta(6)-p-cymene)RuCl2](2) with the corresponding ligands in a 1:2 or 1:2.2 molar ratio in methanol, ethanol or isopropanol with mild heating. The complexes were characterized by elemental analysis, mass spectrometry, IR and NMR spectroscopies. The structure of complex 1 was determined by X-ray crystallography. Antiproliferative activity of the investigated complexes, determined for three human cancer cell lines (HeLa, A549 and LS-174) revealed moderate activity without significant influence on the matrix metalloproteinases (MMP-2 and MMP-9) activity.", publisher = "Pergamon-Elsevier Science Ltd, Oxford", journal = "Polyhedron", title = "New ruthenium(II)-arene complexes bearing hydrazides and the corresponding (thio)semicarbazones of 3-and 4-acetylpyridine: Synthesis, characterization, crystal structure determination and antiproliferative activity", volume = "61", pages = "112-118", doi = "10.1016/j.poly.2013.05.050" }
Ivanović, I., Gligorijević, N., Aranđelović, S., Radulović, S., Roller, A., Keppler, B. K., Tešić, Ž. Lj.,& Grgurić-Šipka, S.. (2013). New ruthenium(II)-arene complexes bearing hydrazides and the corresponding (thio)semicarbazones of 3-and 4-acetylpyridine: Synthesis, characterization, crystal structure determination and antiproliferative activity. in Polyhedron Pergamon-Elsevier Science Ltd, Oxford., 61, 112-118. https://doi.org/10.1016/j.poly.2013.05.050
Ivanović I, Gligorijević N, Aranđelović S, Radulović S, Roller A, Keppler BK, Tešić ŽL, Grgurić-Šipka S. New ruthenium(II)-arene complexes bearing hydrazides and the corresponding (thio)semicarbazones of 3-and 4-acetylpyridine: Synthesis, characterization, crystal structure determination and antiproliferative activity. in Polyhedron. 2013;61:112-118. doi:10.1016/j.poly.2013.05.050 .
Ivanović, Ivanka, Gligorijević, Nevenka, Aranđelović, Sandra, Radulović, Siniša, Roller, Alexander, Keppler, Bernhard K., Tešić, Živoslav Lj., Grgurić-Šipka, Sanja, "New ruthenium(II)-arene complexes bearing hydrazides and the corresponding (thio)semicarbazones of 3-and 4-acetylpyridine: Synthesis, characterization, crystal structure determination and antiproliferative activity" in Polyhedron, 61 (2013):112-118, https://doi.org/10.1016/j.poly.2013.05.050 . .