Ecotoxicological effects of new C-substituted derivatives of N-phosphonomethylglycine (glyphosate) and their preliminary evaluation towards herbicidal application in agriculture.

In this paper, comparison of ecotoxicological and herbicidal effect of newly synthesized N­[(phosphono)(aryl)methyl]glycines 1a-g (C-substituted glyphosate derivatives) with pure glyphosate (N-phosphonomethylglycine) (2) was demonstrated. All of tested glyphosate derivatives (1a-g) in contrast to glyphosate, were found to be completely safe for oat (Avena sativa) and classified as not harmful for marine bacteria Aliivibrio fischeri. Compounds 1a-g were also found rather harmless to radish (Raphanus sativus) as compared to N-phosphonomethylglycine, but they were moderately toxic against freshwater crustaceans Heterocypris incongruens. One of synthesized compounds, namely N-[(phosphono)(4-hydroxyphenyl)methyl]glycine (1f) was found to possess stronger herbicidal properties against gallant soldier (Galinsoga parviflora) and common sorrel (Rumex acetosa) when compared to pure glyphosate and demonstrated total death of these weeds being ranked 1 in the European Weed Research Council (EWRC) scale. Considering lower phytotoxicity of compound 1f against cultivated plants and tested microorganisms when compared to pure glyphosate, this aminophosphonate may be good candidate for further, more comprehensive study toward its agrochemical application, especially that this active agent demonstrated much stronger herbicidal properties than N-phosphonomethylglycine.

A novel trifluoromethyl 2-phosphonopyrrole analogue inhibits human cancer cell migration and growth by cell cycle arrest at G1 phase and apoptosis.

Pyrroles, an important class of heterocyclic compounds found in naturally occurring products, represent an interesting biologically active scaffold for drug design. Recently we have synthetized a series of five new fluorinated pyrrole derivatives for potential anticancer applications. All new compounds contain a trifluoromethyl and N-benzyl group, but they are different from each other by bearing a phenyl, ethoxycarbonyl or carboxylic moiety, with two of them possessing an additional phosphonyl function. The aim of this study was to evaluate anticancer activity of the new compounds in human lung and breast cancer cells. We found that compound 3, bearing a phosphonyl and phenyl group, was the most effective in attenuating growth of A549 and MCF-7 cells in a dose dependent manner with IC50 36.5 µM ± 1.80 and 27.9 µM ± 1.68, respectively. Compound 3 inhibited cancer cell proliferation by cell cycle arrest at G1 phase as detected by flow cytometry analysis. Furthermore, compound 3 induced apoptosis of A549 cells by activation of caspase-3. Cancer cell migration rate was significantly inhibited when A549 and MCF-7 cells were cultured in the presence of the compound. These results demonstrate that a novel trifluoromethyl-functionalized phosphonopyrrole with a phenyl group might be a promising pyrrole analogue with anticancer potential.

Metal complexation of thiacrown ether macrocycles by electrospray ionization mass spectrometry.

In the present study, electrospray ionization mass spectrometry is used to evaluate the metal-binding selectivities of an array of novel caged macrocycles for mercury(II), lead(II), cadmium(II), and zinc(II) ions. In homogeneous methanol/chloroform solutions as well as extractions of metals from aqueous solution by macrocycles in chloroform, it is found that the type of heteroatom (S, O, N), cavity size, and presence of other substituents influence the metal selectivities. Several of the macrocycles in this study bind mercury ion very selectively and efficiently in the presence of many other metal ions and have an avidity toward mercury that was tunable by the size and combination of heteroatoms in the macrocycle ring and the number of cage groups attached. The extraction mechanism was further investigated by determining the variation in extraction selectivity as a function of the counterions of the mercury salts.