Antimicrobial and Toxicity Evaluation of Imidazolium-Based Dicationic Ionic Liquids with Dicarboxylate Anions.

Imidazolium-based dicationic ILs (DILs) presenting antimicrobial activity and relatively low toxicity are highly desirable and are envisioned for use in live tissue to prevent bacterial or fungal infections. In this context, we present here DILs with dicarboxylate anions [Cn(MIM)2[Cn(MIM)2][CO2-(CH2)mCO2], in which n = 4, 6, 8, and 10, and m = 0, 1, 2, 3, 4, and 5. The results showed that DILs with an alkyl chain spacer of ten carbons were active against yeasts and the bacterial strains tested. However, most of the DILs were cytotoxic and toxic at 1 mM. By contrast, DILs with alkyl chains possessing less than ten carbons were active against some specific Candidas and bacteria (mainly S. aureus), and they showed moderate cytotoxicity. The best activity against Gram-positive bacteria was observed for [C4(MIM)2][Pim] toward MRSA. For the DILs described herein, their level of toxicity against C. elegans was lower than that of most of the mono- and dicationic IL analogs with other anions. Our results showed that the presence of carboxylate anions reduces the toxicity of DILs compared to DILs containing halide anions, which is particularly significant to the means of designing biologically active compounds in antimicrobial formulations.

Characterization of a new blackberry cultivar BRS Xingu: Chemical composition, phenolic compounds, and antioxidant capacity in vitro and in vivo.

The cultivar BRS Xingu was launched by EMBRAPA in 2015 with the intention of presenting higher productivity. Due to the lack of studies on this cultivar, the objective was to present the physical-chemical, centesimal, and phenolic composition of the BRS Xingu blackberry, its antioxidant capacity, protection against ROS generation, and compare it with other commercialized cultivars such as Guarani, Tupy, and Xavante. The BRS Xingu was prominent regarding anthocyanin and condensed tannin content and superior to the other cultivars. Moreover, BRS Xingu presented higher antioxidant capacity, protection of C. elegans from ROS generation, and soluble solid content when compared to Tupy, which is the most cultivated variety in the world. In the new cultivar, five anthocyanins, five phenolic acids, and ten non-anthocyanin flavonoids were identified. BRS Xingu is presented as an alternative blackberry with potential for industrialization and in natura consumption.

Impact of Anions on the Partition Constant, Self-Diffusion, Thermal Stability, and Toxicity of Dicationic Ionic Liquids.

Partition constants (KD°), molecular dynamics (T1, T2, and DOSY measurements), thermal stability, and toxicity of dicationic ionic liquids (ILs) were determined. The dicationic ILs derived from 1,n-bis(3-methylimidazolim-1-yl)octane, [BisOct(MIM)2][2X] (in which X = Cl, Br, NO3, SCN, BF4, and NTf2), were evaluated to verify the influence of anion structure on the IL properties. A monocationic IL [Oct(MIM)][Br] was also monitored for comparison. In general, the solubility of the ILs followed the anion free energy of hydration (ΔG°hyd). The thermokinetic and thermodynamic functions of activation of the ILs were determined via thermogravimetric data, and it was observed that polyatomic anions influence the decomposition mechanism of these IL structures. Furthermore, [Oct(MIM)][Br] had a decomposition rate greater than that of the dicationic analogue, and the thermodynamic parameters of activation data corroborate these results. Finally, the dicationic ILs did not indicate toxic effects (LD50 > 40 mM).