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Statements

Subject Item
n2:RIV%2F00216208%3A11310%2F12%3A10126170%21RIV13-MSM-11310___
rdf:type
n8:Vysledek skos:Concept
rdfs:seeAlso
http://dx.doi.org/10.1007/s00775-012-0911-2
dcterms:description
A series of cationic dinuclear p-cymene ruthenium trithiophenolato complexes of the type [(eta(6)-p-MeC6H4Pr(i))2Ru2(SC6H4-p-X)3](+) have been synthesized from the reaction of [(eta(6)-p-MeC6H4Pr(i) )RuCl2]2 with the corresponding thiol, isolated as the chloride salts, and further studied for their electrochemical properties, cytotoxicity towards human ovarian cancer cells, and catalytic activity for glutathione (GSH) oxidation. Complex 1 was also compared with the benzene and hexamethylbenzene analogues [(eta(6)-C6H6)2Ru2(SC6H5)3](+) (12) and [(eta(6)-C6Me6)2Ru2(SC6H5)3](+) (13). The most active compound [11]Cl was structurally studied by single-crystal X-ray diffraction analysis. The concentrations corresponding to 50 % inhibition of cancer cell growth (IC50 values) in the A2780 and A2780cisR cell lines of these complexes except for 6 were in the submicromolar range, complex 11 showing an IC50 value of 0.03 A mu M in both cell lines. The high in vitro anticancer activity of these complexes may be at least partially due to their catalytic potential for the oxidation of GSH, although there is no clear correlation between the IC50 values and the turnover frequencies at about 50 % conversion. However, the cytotoxicity is tentatively correlated to the physicochemical properties of the compounds determined by the electronic influence of the substituents X (Hammett constants sigma (p)) and the lipophilicity of the thiols p-XC6H4SH (calculated log P parameters). A series of cationic dinuclear p-cymene ruthenium trithiophenolato complexes of the type [(eta(6)-p-MeC6H4Pr(i))2Ru2(SC6H4-p-X)3](+) have been synthesized from the reaction of [(eta(6)-p-MeC6H4Pr(i) )RuCl2]2 with the corresponding thiol, isolated as the chloride salts, and further studied for their electrochemical properties, cytotoxicity towards human ovarian cancer cells, and catalytic activity for glutathione (GSH) oxidation. Complex 1 was also compared with the benzene and hexamethylbenzene analogues [(eta(6)-C6H6)2Ru2(SC6H5)3](+) (12) and [(eta(6)-C6Me6)2Ru2(SC6H5)3](+) (13). The most active compound [11]Cl was structurally studied by single-crystal X-ray diffraction analysis. The concentrations corresponding to 50 % inhibition of cancer cell growth (IC50 values) in the A2780 and A2780cisR cell lines of these complexes except for 6 were in the submicromolar range, complex 11 showing an IC50 value of 0.03 A mu M in both cell lines. The high in vitro anticancer activity of these complexes may be at least partially due to their catalytic potential for the oxidation of GSH, although there is no clear correlation between the IC50 values and the turnover frequencies at about 50 % conversion. However, the cytotoxicity is tentatively correlated to the physicochemical properties of the compounds determined by the electronic influence of the substituents X (Hammett constants sigma (p)) and the lipophilicity of the thiols p-XC6H4SH (calculated log P parameters).
dcterms:title
Highly cytotoxic trithiophenolatodiruthenium complexes of the type [(eta(6)-p-MeC6H4Pr(i))2Ru2(SC6H4-p-X)3](+): synthesis, molecular structure, electrochemistry, cytotoxicity, and glutathione oxidation potential Highly cytotoxic trithiophenolatodiruthenium complexes of the type [(eta(6)-p-MeC6H4Pr(i))2Ru2(SC6H4-p-X)3](+): synthesis, molecular structure, electrochemistry, cytotoxicity, and glutathione oxidation potential
skos:prefLabel
Highly cytotoxic trithiophenolatodiruthenium complexes of the type [(eta(6)-p-MeC6H4Pr(i))2Ru2(SC6H4-p-X)3](+): synthesis, molecular structure, electrochemistry, cytotoxicity, and glutathione oxidation potential Highly cytotoxic trithiophenolatodiruthenium complexes of the type [(eta(6)-p-MeC6H4Pr(i))2Ru2(SC6H4-p-X)3](+): synthesis, molecular structure, electrochemistry, cytotoxicity, and glutathione oxidation potential
skos:notation
RIV/00216208:11310/12:10126170!RIV13-MSM-11310___
n8:predkladatel
n18:orjk%3A11310
n3:aktivita
n14:Z n14:I
n3:aktivity
I, Z(MSM0021620857)
n3:cisloPeriodika
6
n3:dodaniDat
n4:2013
n3:domaciTvurceVysledku
n20:8116997
n3:druhVysledku
n17:J
n3:duvernostUdaju
n11:S
n3:entitaPredkladatele
n13:predkladatel
n3:idSjednocenehoVysledku
139004
n3:idVysledku
RIV/00216208:11310/12:10126170
n3:jazykVysledku
n19:eng
n3:klicovaSlova
glutathione oxidation; lipophilicity; cytotoxicity; cancer; ruthenium
n3:klicoveSlovo
n6:lipophilicity n6:glutathione%20oxidation n6:cytotoxicity n6:cancer n6:ruthenium
n3:kodStatuVydavatele
DE - Spolková republika Německo
n3:kontrolniKodProRIV
[1BE4E7701D58]
n3:nazevZdroje
Journal of Biological Inorganic Chemistry
n3:obor
n16:CA
n3:pocetDomacichTvurcuVysledku
1
n3:pocetTvurcuVysledku
9
n3:rokUplatneniVysledku
n4:2012
n3:svazekPeriodika
17
n3:tvurceVysledku
Štěpnička, Petr Baquie, Mathurin Furrer, Julien Suess-Fink, Georg Ibao, Anne-Flore Dyson, Paul J. Zava, Olivier Therrien, Bruno Giannini, Federico
n3:wos
000306731100010
n3:zamer
n12:MSM0021620857
s:issn
0949-8257
s:numberOfPages
10
n7:doi
10.1007/s00775-012-0911-2
n21:organizacniJednotka
11310