Bile acid alkylamide derivatives as low molecular weight organogelators: systematic gelation studies and qualitative structural analysis of the systems
| Autor: | Miika Löfman, Juha Koivukorpi, Hannu Salo, Elina Sievänen, Virpi Noponen |
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| Rok vydání: | 2011 |
| Předmět: |
Lithocholic acid
medicine.drug_class Surface Properties Electrospray ionization Analytical chemistry Infrared spectroscopy Mass spectrometry Biomaterials Bile Acids and Salts chemistry.chemical_compound Colloid and Surface Chemistry medicine Organic chemistry Fourier transform infrared spectroscopy Particle Size Bile acid Molecular Structure Stereoisomerism Nuclear magnetic resonance spectroscopy Amides Surfaces Coatings and Films Electronic Optical and Magnetic Materials Solvent Molecular Weight chemistry Gels |
| Zdroj: | Journal of colloid and interface science. 360(2) |
| ISSN: | 1095-7103 |
| Popis: | A series of amino- and hydroxyalkyl amides of bile acids have been synthesized and characterized by Fourier transform infrared spectroscopy (FTIR), (1)H and (13)C nuclear magnetic resonance spectroscopy (NMR), as well as electrospray ionization mass spectrometry (ESI-MS) measurements. The ability of the synthesized molecules to promote gel formation was systematically investigated. Out of 396 combinations formed by 11 compounds and 36 different solvents, 22 gel-containing systems were obtained with 1% (w/v) gelator concentration. Apart from one exception, the gelator compounds were lithocholic acid derivatives. This challenges the general trend of bile acid-based physical gelators, according to which the gelation ability of lithocholic acid derivatives is poor. A correlation between the values of Kamlet-Taft parameters and solvent preferences for gelators was observed. The morphologies of the solid and gel structures studied with scanning electron microscopy (SEM) showed variability from fibers to spherical microscale aggregates, the latter of which are unique among bile acid-based organogels. The gels exhibited more complex behavior than was previously established with bile acid derivatives, judging by the microscale diversity present in gelating and non-gelating systems and the tendency for polymorphism. This study underlines the importance of both the molecular and colloidal scale aspects of the gelation phenomenon. |
| Databáze: | OpenAIRE |
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