Fluorinated probes

B. The Fluorine Probe Approach Solution-Phase Structure and... 

IV. FLUORINE-CONTAINING TAXOIDS SAR STUDY AND FLUORINE PROBE APPROACH TO THE IDENTIFICATION OF BIOACTIVE CONFORMATIONS... 

Thus, the fluorine probe approach has proved useful for the conformational analysis of paclitaxel and taxoids in connection with the determination of possible bioactive conformations.77 The previously unrecognized conformer C might be the molecular structure first recognized by the P-tubulin binding site on microtubules. 

C. Determination of the Binding Conformation of Taxoids to Microtubules Using Fluorine Probes... 

We have successfully applied the fluorine probe approach to the estimation of the F-F distance in the microtubule-bound F2-10-Ac-docetaxel (74, SB-T-30021) using the solid-state magic angle spinning (SS MAS) 19F NMR coupled with the radio frequency driven dipolar recoupling (RFDR) technique in our preliminary study.78... 

Chemical synthesis has provided an additional route to peptides containing halogenat-ed amino acids. Early 19F-NMR studies of proteins were performed on semi-synthetic polypeptides prepared by attachment of fluorinated probes to the polypeptide. For example, Heustis and Raftery modified ribonuclease by trifluoroacetylation of Lys residues 1 and 7. They then used 19F-NMR to study conformational changes brought about by the presence of inhibitors200. In his review, Gerig provides several other examples of this strategy187. 

Moreover, combination of a fluorine-containing linker and a fluoro-taxoid may provide fluorine probes for monitoring the internalization and drug release of these conjugates in the tumor cells and tissues by 19F NMR as an alternative method to the use of fluorescence-labeled probes with confocal fluorescence microscopy [69],... 

Rice JW, Weyand EH, Burrill C, et al. 1990. Fluorine probes for investigating the mechanism of activation of indeno(1,2,3-cd)pyrene to a tumorigenic agent. Carcinogenesis 11(11) 1971-1974. 

The C-l Hydroxyl. We examined the role of the C-l hydroxyl in binding the receptor based on the activity of a fluorinated probe. Fluorination of biologically active compounds is useful for studying the... 

Several enzymatic methods in conjunction with conventional organic methods provide new synthetic routes to fluorinated sugars. These new methods allow preparative synthesis of sugars containing the fluorine probe for use in the NMR study of receptor-substrate interactions of enzymes, of cell-surface glycoproteins, and of other systems related to biochemical recognition... 

The consequences of introducing the fluorine probe have to be considered. Replacement of a C-H by a C-F makes the ligand more hydrophobic and hence this can affect binding properties. Evidence so far accumulated indicates that fluorine substitution does not, in general, have a significant influence on the tertiary structure of proteins. 

Use of a fluorine probe eliminates interferences from other common additives... 

Nguyen DM, Frazer A, Rodriguez L, Belfield KD (2010) Selective fluorescence sensing of zinc and mercury ions with hydrophilic 1,2,3-triazoyl fluorine probes. Chem Mater 22 3472-3481... 

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