title: Bile acid-cysteamine conjugates: structural properties, gelation, and toxicity evaluation.
abstract: Design, synthesis, and characterization of six novel bile acid-cysteamine conjugates together with investigation of their structural studies, gelation properties, and preliminary toxicity evaluation, are reported. Solid state properties of selected compounds were studied by means of X-ray diffraction and (13)C CPMAS NMR spectroscopy. N-(2-thioethyl)-3α,7α,12α-trihydroxy-5β-cholan-24-amide was shown to exhibit (pseudo)polymorphism, and a single crystal structure of its non-stoichiometric hydrate is reported herein. Cholyl and dehydrocholyl derivatives bearing three functionalities in their steroidal backbone were shown to undergo self-assembly leading to gelation in certain organic solvents. Preliminary morphology studies of the formed gels by scanning electron microscopy (SEM) were performed. The standard model mouse fibroblast cell line together with the MTT and NR tests were utilized for evaluating the toxicity of the prepared compounds. Lithocholyl, ursodeoxycholyl, and dehydrocholyl derivatives turned out to be relatively non-toxic in the conditions studied.
authors: University of Jyväskylä, Department of Chemistry, P.O. Box 35, FI-40014 Jyväskylä, Finland. virpi.noponen@jyu.fi
authors: Virpi
authors: V
authors: Noponen
authors: Heini
authors: H
authors: Belt
authors: Manu
authors: M
authors: Lahtinen
authors: Arto
authors: A
authors: Valkonen
authors: Hannu
authors: H
authors: Salo
authors: Jitka
authors: J
authors: Ulrichová
authors: Adéla
authors: A
authors: Galandáková
authors: Elina
authors: E
authors: Sievänen
mesh_terms: D000577:Amides / Q000737:chemistry / Q000633:toxicity; D000818:Animals; D041702:BALB 3T3 Cells / Q000187:drug effects; D001647:Bile Acids and Salts / Q000737:chemistry*; D019826:Cholic Acid / Q000737:chemistry; D003543:Cysteamine / Q000031:analogs & derivatives / Q000737:chemistry* / Q000633:toxicity; D003840:Deoxycholic Acid / Q000737:chemistry; D005347:Fibroblasts / Q000187:drug effects*; D006860:Hydrogen Bonding; D020128:Inhibitory Concentration 50; D008095:Lithocholic Acid / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D012997:Solvents / Q000737:chemistry; D014580:Ursodeoxycholic Acid / Q000737:chemistry; D014961:X-Ray Diffraction
chemical_list: D000577:Amides; D001647:Bile Acids and Salts; D012997:Solvents; D003840:Deoxycholic Acid; D008095:Lithocholic Acid; D003543:Cysteamine; D014580:Ursodeoxycholic Acid; D019826:Cholic Acid