Synthesis, Characterization, and Saccharide Binding Studies of Bile Acid − Porphyrin Conjugates

Synthesis and characterization of bile acid-porphyrin conjugates (BAPs) are reported. Binding of saccharides with BAPs in aqueous methanol was studied by monitoring changes in the visible absorption spectral of the porphyrin-moieties. Although these studies clearly showed absorbance changes, suggesting quite high if non-selective binding, the mass spectral studies do not unambiguously support these results.

Novel Porphyrin-cholic Acid Conjugates as Receptors for Biologically Important Anions

Novel Porphyrin-Cholic Acid Conjugates as Receptors for Biologically Important Anions

A series of novel receptors showing high binding affinity in aqueous media for biologically important anions are reported. These naturally chromophoric porphyrin-based receptors contain cholic acids connected via quaternary alkyl ammonium amido linkages.

17O NMR and molecular mechanical studies of arylmethylenemalonaldehydes

The 17O NMR spectra of six different arylmethylenemalonaldehydes were measured for various solvents and temperatures. The 17O NMR chemical shifts and line widths of the carbonyl oxygens of the malonaldehyde fragment show a clear variation in the series of monoaryl compounds studied. The differences between the 17O NMR chemical shifts of the formyl oxygens correlate well with two conformationally dependent 1H–1H and 1H–13C coupling constants for the same compounds. Molecular mechanical calculations were also performed in order to relate the present data with the conformational preferences of the malonaldehyde fragment of the arylmethylenemalonaldehydes.

Porphyrin-bile acid conjugates: from saccharide recognition in the solution to the selective cancer cell fluorescence detection.

This paper describes the preparation and use of conjugates of porphyrins and bile acids as ligands to bind to tumor expressed saccharides. Bile acid-porphyrin conjugates were tested for recognition of saccharides that are typically present on malignant tumor cells. Fluorescence microscopy, in vitro PDT cell killing, and PDT of subcutaneous 4T1 mouse tumors is reported. High selectivity for saccharide cancer markers and cancer cells was observed. This in vivo and in vitro study demonstrated high potential use for these compounds in targeted photodynamic therapy.

1 H,13 C, 19 F NMR, and ESI mass spectral characterization of two geminal difluorosteroids

Two geminal difluorosteroids, 3,3-difluoro-5β-cholan-24-oic acid (1) and 3,3-difluoro-5α-androstan-17-one (2), have been prepared from corresponding ketosteroids with diethylaminosulphurtrifluoride (DAST) treatment in moderate yields. The structures of 1 and 2 have been characterized by 1H, 13C, 19F NMR, and ESI mass spectral techniques. Copyright © 2008 John Wiley & Sons, Ltd.