Diastereoselective synthesis and biological evaluation of new fluorine-containing α-aminophosphonates as anticancer agents and scaffold to human urokinase plasminogen activator inhibitors.

Phosphonate analogues of α-amino acids are increasingly valued for their significant potential in medicinal chemistry. Fluorine is a "magic" element that plays a huge role in modulating the properties of organic compounds. In this work, we combined the two pharmacophores in the synthesis of three series of new α-aminophosphonates.

Structural characterisation and pH-dependent preference of pyrrole cross-link isoforms from reactions of oxoenal with cysteine and lysine side chains as model systems.

In this study, we subjected 5,5-diethoxy-4-oxopent-2-enal (DOPE), a model amino acids cross-linking reagent, to reactions with N-acetylcysteine (Ac-Cys) and N-acetyllysine (Ac-Lys), and identified three pyrrole cross-links. The compounds were isolated and their structures were rigorously determined by spectrometric and spectroscopic methods, including 2D NMR experiments. The use of 2D NMR spectroscopy was crucial to determine the position of the substituents in the pyrrole rings.

Fatty Acids as Potent Modulators of Autophagy Activity in White Adipose Tissue.

A high-fat diet is one of the causative factors of obesity. The dietary profile of fatty acids is also an important variable in developing obesity, as saturated fatty acids are more obesogenic than monounsaturated and polyunsaturated fatty acids. Overweight and obesity are inseparably connected with the excess of adipose tissue in the body, characterized by hypertrophy and hyperplasia of fat cells, which increases the risk of developing metabolic syndrome.

Mechanochemical Synthesis of Fluorinated Imines.

A number of imines, including 12 new compounds, previously not reported in the literature, derived from variously fluorinated benzaldehydes and different anilines or chiral benzylamines were synthesized by a solvent-free mechanochemical method, which was based on the manual grinding of equimolar amounts of the substrates at the room temperature. In a very short reaction time of only 15 min, the method produced the expected products with good-to-excellent yields. The yields were comparable or significantly higher than those reported in the literature for the imines synthesized by other methods.

New insight into the molecular mechanism of protein cross-linking induced by cis-2-butene-1,4-dial, the metabolite of furan: Formation of 2-substituted pyrrole cross-links involving the cysteine and lysine residues.

Furan is an environmental pollutant also present in heat-treated food. The compound is toxic and carcinogenic to rats, and classified as a possible human carcinogen. Mechanisms laying behind the furan carcinogenicity remain unclear, however scientific data indicate the involvement of bioactivation catalysed by cytochrome P450 2E1.