The aim of this work was to synthesize chiral ionic liquids as chiral solvents for organic synthesis and to evaluate the phyto(eco)toxicity of the new products and starting N-alkylimidazoles and their potential environmental influence on soil and plants. Chiral ionic liquids containing anions such as Cl-, Br-, TsO-, PF6(-), NO3(-), CF3SO3(-), and (+)- and (-)-C6H5CH(OH)C(O)O- were synthesized using (-)-(1R)-6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-ethyl [(-)-(1R)-nopyl] halides (X = Cl, Br) and tosylate in 62-100% yields. The chloride 7 and the nitrate 13 ionic liquids possessed a toxicity dependent on the applied concentration. The lowest concentration causing a distinct reduction in plant germination/growth was 100 mg/kg. Spring barley better tolerated the ionic liquids (200 mg/kg) than common radish (100 mg/kg). The nitrate liquid did not exhibit an inhibiting effect on the germination ability of seeds. The starting N-methylimidazole used in lower concentrations (1 and 10 mg/kg of soil dry weight) was not phytotoxic, in contrast to higher doses (>1000 mg/kg).
Organic chemistryOrganic chemistry Z 0200 Resorcinarenes -[syntheses, reactivity as well as formation of complexes, host-guest systems and capsules; 134 refs. from 1998-2003]. -(SLIWA*, W.; ZUJEWSKA, T.; BACHOWSKA, B.; Pol.
Quaternary ammonium and phosphonium salts have been screened for their toxic effect on HeLa and K562 cancer cell lines, as well as on normal HUVEC cells. Tri-n-butyl-n-hexadecylphosphonium bromide, the first phosphonium salt with a halogen anion tested against HeLa cells, was 12 times more potent (IC50 <5 μm after 24 and 48 h) than the clinically used reference compound cisplatin and 17 times more potent than tri-n-hexyltetradecylphosphonium bis(trifluoromethylsulfonyl)imide, which, to the best of our knowledge, is the first phosphonium salt to be evaluated in HeLa cells. However, it was inactive against K562 cells (24 and 48 h). According to a caspase-3/7 assay, its toxicity has not been connected with the induction of apoptosis. In contrast, triphenylalkylphosphonium iodides with shorter C1–5 alkyl chains were inactive against HeLa cells but very active against K562 cells (IC50=6–10 μm after 48 h). Phosphonium cations with halide counterions proved to be more potent than those with (CF3SO2)2N− as the anion, as in the anticancer agent NSC 747251, or other anions in molecules with similar alkyl chain lengths. On the other hand, a series of ammonium salts containing a short methylthiomethyl or methoxymethyl side chain revealed low cytotoxicity (IC50 >500 μm after 24 and 48 h) against both HeLa and K562 cancer cell lines as well as normal HUVEC cells, showing that the nontoxic N+CH2YMe (Y=S, O) structural motif in ammonium salts could be suitable for further optimization and development, especially in transfection experiments.
Ionic liquids have attracted considerable interest in various areas as new, non-volatile and nonflammable organic solvents, catalysts, reaction additives, ligands, drugs and other dedicated materials etc. Their general use, sometimes in bulky quantities, requires determination of their potential ecotoxicity on selected organisms. In the present work, influence of triphenylmethylphosphonium iodide (1) and triphenylhexadecylphosphonium iodide (2), introduced to soil, on germination and early stages of growth and development of superior plants was investigated using the plant growth test based on the OECD/OCDE 208/2006. In this test, the seeds of selected species, i.e. land superior plants -spring barley (Hordeum vulgare) and common radish (Raphanus sativus L. subvar. radicula Pers.) were planted in pots containing soil to which a test chemical compound had been added and in pots with control soil. To evaluate the phytotoxicity of ionic liquids 1 and 2 germination and weight (dry and fresh) of control plant seedlings were determined and compared with the germination and weight (dry and fresh) of the seedlings of plants grown in the soil watered with appropriate amounts of the test chemicals. The visual assessment of any types of damage to the test species, such as growth inhibition, chlorosis and necrosis, was also carried out and documented by digital photographs. Based on the obtained results, magnitudes of the LOEC -the lowest concentration causing observable effects in the form of reduction in growth and germination compared with the control and the NOEC -the highest concentration not causing observable, toxic effects -were also determined.
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