Ecotoxicity interspecies study of ionic liquids based on phosphonium and ammonium cations.

This work studies the effects of different bromide-based ionic liquids, with phosphonium and ammonium cations, towards several environmental biomodels: Daphnia magna, Allivibrio fischeri, Raphidocelis subcapitata. Results indicate that toxicity clearly depends on the biomodel, Allivibrio fischeri being the least sensitive one while Daphnia magna is more severely affected in the presence of the studied ionic liquids. In most of the cases, phosphonium moieties are less toxic than ammonium ionic liquids. Furthermore, a prediction about the oral toxicity and carcinogenicity of the studied ionic liquids has been also carried out, showing that these chemical structures may suggest significant toxicity but not present genotoxic or nongenotoxic carcinogenicity.

Glycine-betaine-derived ionic liquids: Synthesis, characterization and ecotoxicological evaluation.

Ionic Liquids (ILs) are generically regarded as environmentally "harmless" and thus, assumed as "non-toxic". However, due to the endless design possibilities, their ecotoxicological profile is still poorly known. An accurate knowledge on the toxicity of a substance is required, under the scope of environmental regulation worldwide, before their application and commercialization. Knowledge on the relationship between the chemical structure and toxic effects is essential for the future design of more biocompatible solvents. Focusing on the use of ILs as base lubricants, lubricant additives, or even as potential working fluids for absorption heat pumps, the knowledge on its environmental impact is of great importance, due to the possibility of spills. In this specific context, four analogues of glycine-betaine-based ILs (AGB-ILs) and four glycine-betaine based ILs (GB-ILs) were synthesized and characterized. Their ecotoxicity was assessed using representatives of two trophic levels in aquatic ecosystems, the bacteria Allivibrio fischeri (commonly used as a screening test organism) and the microalgae Raphidocelis subcapitata (as an alternative test organism that has been proven very sensitive to several IL families). The microalgae were more sensitive than the bacteria, hence, following a precautionary principle, we recommend considering the toxicity towards microalgae as an indicator in future studies regarding the focused ILs. Although four of the studied ILs were derived from a natural amino acid, all were considered hazardous for the aquatic environment, disproving the primary theory that all ILs derived from natural compounds are benign. Furthermore, the modification in the structure of anion and the cation can lead to the increase of toxicity.

Synthetic Rhamnolipid Bolaforms trigger an innate immune response in Arabidopsis thaliana.

Stimulation of plant innate immunity by natural and synthetic elicitors is a promising alternative to conventional pesticides for a more sustainable agriculture. Sugar-based bolaamphiphiles are known for their biocompatibility, biodegradability and low toxicity. In this work, we show that Synthetic Rhamnolipid Bolaforms (SRBs) that have been synthesized by green chemistry trigger Arabidopsis innate immunity. Using structure-function analysis, we demonstrate that SRBs, depending on the acyl chain length, differentially activate early and late immunity-related plant defense responses and provide local increase in resistance to plant pathogenic bacteria. Our biophysical data suggest that SRBs can interact with plant biomimetic plasma membrane and open the possibility of a lipid driven process for plant-triggered immunity by SRBs.

Synthesis and antimicrobial activity studies of ortho-chlorodiarylamines and heteroaromatic tetracyclic systems in the benzo[b]thiophene series.

ortho-Chlorodiarylamines in the 2,3,7-trimethylbenzo[b]thiophene series were prepared in high yields (70-85%) by C-N palladium-catalyzed cross-coupling using P(t-Bu)(3) as ligand and NaOt-Bu as base. A palladium-assisted C-C intramolecular cyclization of the coupling products gave thienocarbazoles and the dechlorinated diarylamines. Studies of antimicrobial activity of the compounds obtained, against representative species of bacteria (Escherichia coli, Pseudomonas aeruginosa, Bacillus cereus and Bacillus subtilis) and fungi (Candida albicans), were performed. We have also included in the biological assays some pyridine derivatives previously prepared by us, and it was possible to establish some structure-activity relationships (SARs).