The fluorous effect in biomolecular applications

Abstract

From being a niche area only a few decades ago, fluorous chemistry has gained momentum and is, nowadays, a fervent area of research. It has brought forth, in fact, numerous applicative innovations that stretch among different fields: from catalysis to separation science, from supramolecular to materials and analytical chemistry. Recently, the unique features of perfluorinated compounds have reached the attention of the biochemists' audience. This tutorial review introduces the basic concepts of fluorous chemistry and illustrates its main biomolecular applications. Special attention has been given to fluorous microarrays and their combination with Mass-Spectroscopy (MS) techniques, to protein properties modification by the introduction of local fluorous domains, and to the most recent applications of (19)F-Magnetic Resonance Imaging ((19)F-MRI).

Per- and polyfluorinated substances (PFASs): Environmental challenges

“…carboxylic acid-and phospholipidbased F-surfactants or even FnHm diblocks (Table 1)) readily form sturdy insoluble monolayers on water with high collapse pressures, their 4-or 6-carbon homologues generally fail to form stable molecular films [382]. The self-assembling capacity, packing organization, formation of ordered liquid condensed phases, and viscoelastic properties of interfacial surfactant films are also extremely sensitive to F-chain length [383][384][385][386][387]. 6:2 F-telomer sulfonates were deemed less effective than PFOS for hard-metal plating by the United Nations Environment Programme (UNEP), which encouraged research for better performing substitutes [388].…”

Nanoemulsions in Medicine

“…161,162 Second, 19 F has high natural abundance (100%), and 19 F has a resonant frequency, NMR sensitivity, and signal-to-noise ratio 94%, 83% and 89%, respectively, that of 1 H. Together with the lack of background 19 F-MRI signals, this makes 19 F-MRI uniquely sensitive and an attractive tool for diagnostics. 163 Perfluorocarbon NEs have found several unique uses in providing MRI contrast agents. Tracking cells in vivo is a challenging and yet crucial challenge in utilizing cell therpeutics.…”

A synthetically modified hydrophobin showing enhanced fluorous affinity

“…Protein fluorination strategies have to date mainly relied on the introduction of selectively fluorinated amino acids, typically leucines, in the protein primary structure [20][21][22][23][24][25][26][27]. An alternative approach consists of the site-specific derivatization with fluorous tags by covalently binding FC residues to peptides and proteins, mainly for immobilization, separation, and enrichment purposes [28][29][30][31].…”