Introduction of oxygenated side chain into imidazolium ionic liquids: evaluation of the effects at different biological organization levels.
The biological effects of a class of oxygenated imidazolium ionic liquids were studied in comparison with alkyl imidazolium salts (BMIM BF4 and BMIM N(CN)2).The cellular and subcellular effects were evaluated on rat pheochromocytoma PC12 cell lines, through MTT test, lactate dehydrogenase release and acetylcholinesterase inhibition; the eco-toxicological responses were assessed through the acute toxicity tests towards Daphnia magna and Vibrio fischeri. The introduction of ethoxy moieties in the lateral chain of imidazolium cations reduced the biological effects in all the tests. The acute toxicity towards D. magna was not affected by the number of ethoxy units, but the crustacean seemed to be sensitive to the type of anion; on the contrary, a further addition of ethoxy moieties increased the toxicity towards V. fischeri, M(OE)4MIM N(CN)2 being the most toxic oxygenated ionic liquid. In the cytotoxicity assays the salts with oxygenated cations resulted ineffective compared to BMIMs, independently from the anion and the number of ethoxy units in the lateral chain. In order to estimate the influence on membrane fluidity, an analysis of fluorescence anisotropy was done and it indicated that BMIM BF4, the most toxic ionic liquid among the tested ones, led to a destabilization of the model membranes at any molarity.
Samorì
Chiara
C
Centro Interdipartimentale di Ricerca in Scienze Ambientali (CIRSA), Università di Bologna, via S. Alberto 163, 48100 Ravenna, Italy.
Malferrari
Danilo
D
Valbonesi
Paola
P
Montecavalli
Adele
A
Moretti
Fabio
F
Galletti
Paola
P
Sartor
Giorgio
G
Tagliavini
Emilio
E
Fabbri
Elena
E
Pasteris
Andrea
A
D000110:Acetylcholinesterase / Q000378:metabolism; D048908:Aliivibrio fischeri / Q000187:drug effects*; D000818:Animals; D002470:Cell Survival / Q000187:drug effects; D003621:Daphnia / Q000187:drug effects*; D004785:Environmental Pollutants / Q000737:chemistry / Q000633:toxicity*; D007093:Imidazoles / Q000737:chemistry / Q000633:toxicity*; D052578:Ionic Liquids / Q000737:chemistry / Q000633:toxicity*; D007770:L-Lactate Dehydrogenase / Q000378:metabolism; D010084:Oxidation-Reduction; D016716:PC12 Cells; D051381:Rats; D013329:Structure-Activity Relationship; D023382:Toxicity Tests, Acute
D004785:Environmental Pollutants; D007093:Imidazoles; D052578:Ionic Liquids; D007770:L-Lactate Dehydrogenase; D000110:Acetylcholinesterase