synthesis, characterization, and saccharide binding studies of bile acid ？ porphyrin conjugates的合成、表征和糖类结合研究胆汁酸卟啉配合.pdfVIP

Molecules 2007, 12, 13-24 molecules ISSN 1420-3049 Full Paper Synthesis, Characterization, and Saccharide Binding Studies of Bile Acid − Porphyrin Conjugates Juha Koivukorpi 1,†, Elina Sievänen 1,‡, Erkki Kolehmainen 1,* and Vladimír Král 2,3 1 Department of Chemistry, P.O. Box 35, FIN-40014, University of Jyväskylä, Finland; †E-mail: jkkorpi@jyu.fi; ‡E-mail: elvirtan@jyu.fi 2 Institute of Chemical Technology, Technická 5, 166 28 Prague 6, Czech Republic. E-mail: vladimir.kral@vscht.cz 3 Zentiva Ltd., Prague, Czech Republic * Author to whom correspondence should be addressed. E-mail: ekolehma@jyu.fi Received: 17 November 2006; in revised form: 2 January 2007 / Accepted: 4 January 2007 / Published: 5 January 2007 Abstract: 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. Keywords: Bile acids, porphyrin, saccharide, visible spectroscopy, 1H-NMR, ESI MS. Introduction Bile acids possess a large number of applications in pharmaceutical and supramolecular chemistry, as recently reviewed [1]. For example, bile acids are potential carriers for liver specific drugs and they can be used as cholesterol level lowering agents [2]. Bile acids and their derivatives have also been used for treatment of bile acid deficiency a