RESUMEN
Four novel bile acid ethyl amides were synthetized using a well-known method. All the four compounds were characterized by IR, SEM, and X-ray crystal analyses. In addition, the cytotoxicity of the compounds was tested. Two of the prepared compounds formed organogels. Lithocholic acid derivative 1 formed hydrogels as 1% and 2% (w/v) in four different aqueous solutions. This is very intriguing regarding possible uses in biomedicine.
Asunto(s)
Amidas/química , Materiales Biocompatibles/química , Hidrogeles/química , Ácido Litocólico/química , Células 3T3 , Animales , Materiales Biocompatibles/síntesis química , Materiales Biocompatibles/toxicidad , Ácido Litocólico/síntesis química , Ácido Litocólico/toxicidad , Ratones , Modelos Moleculares , Conformación Molecular , Agua/químicaRESUMEN
The synthesis and gelation properties of a picolinic acid conjugated bile acid derivative in the presence of metal salts along with the stimuli-responsiveness of the systems are reported. The gels are formed in the presence of Cu(2+) ions in the solvent systems composed of 30-50% of organic solvent (MeOH, acetonitrile, or acetone) in water. The gels respond to various stimuli: they can be formed upon sonication or shaking, and their gel-sol transformation can be triggered by a variety of chemical species. NMR, MS, and SEM techniques are exploited in order to gain a deeper insight on the self-assembled systems.
Asunto(s)
Amidas/síntesis química , Ácidos y Sales Biliares/química , Cobre/química , Geles/síntesis química , Amidas/química , Geles/química , Estructura Molecular , Ácidos Picolínicos/químicaRESUMEN
It was shown that 5-chloro-8-hydroxyquinoline, an antituberculosis agent, gels aqueous alcohol solutions efficiently. Thermal stability and gel-to-sol transition temperature of 1% gel in CD3OD/D2O (2:1) was studied by ¹H-NMR. Fibrous structures of four xerogels have been characterized by scanning electron microscope.
RESUMEN
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-5ß-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.
Asunto(s)
Ácidos y Sales Biliares/química , Cisteamina/química , Fibroblastos/efectos de los fármacos , Amidas/química , Amidas/toxicidad , Animales , Células 3T3 BALB/efectos de los fármacos , Ácido Cólico/química , Cisteamina/análogos & derivados , Cisteamina/toxicidad , Ácido Desoxicólico/química , Enlace de Hidrógeno , Concentración 50 Inhibidora , Ácido Litocólico/química , Espectroscopía de Resonancia Magnética , Ratones , Solventes/química , Ácido Ursodesoxicólico/química , Difracción de Rayos XRESUMEN
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.
Asunto(s)
Amidas/química , Ácidos y Sales Biliares/química , Amidas/síntesis química , Ácidos y Sales Biliares/síntesis química , Geles/síntesis química , Geles/química , Estructura Molecular , Peso Molecular , Tamaño de la Partícula , Estereoisomerismo , Propiedades de SuperficieRESUMEN
Three oxo-derivatives of bile acid methyl esters have been used as starting compounds in the preparation of novel bile acid monoketals with 1,2-benzenediol (catechol) and 2,3-naphthalenediol, as well as mono- and diketals with pentaerythritol. Monoketals of pentaerythritol showed a tendency to form thermoreversible gels in many aromatic solvents and the methyl lithocholate derivative proved to be a supergelator able to form a gel with t-butylbenzene at a concentration as low as 0.5% w/v. Whereas the naphthalenediol ketals formed film-type materials in the studied solvents, the catechol ketals underwent rapid crystallization into X-ray quality single crystals. Single crystal X-ray structures of the catechol ketals have been determined. The monoketal obtained from methyl-3,7,12-trioxo-5beta-cholan-24-oate (dehydrocholate) revealed to have an unusual packing pattern in its solid state compared to other bile acid derivatives reported in the literature. The synthesis of diketals from pentaerythritol furnished a mixture of two diastereomers which, in the case of the methyl lithocholate derivative, have been separated and the X-ray crystal structure of one isomer resolved.
RESUMEN
OBJECTIVE: To evaluate skeletal and dentoalveolar changes induced by the eruption guidance appliance in the early mixed dentition. MATERIALS AND METHODS: Pre- and posttreatment cephalometric radiographs of 115 consecutively treated children, 62 boys and 53 girls, were compared with those obtained from a control group of 104 children, 52 boys and 52 girls. Pretreatment radiographs were taken at the deciduous-mixed dentition interphase (T1) and after full eruption of all permanent incisors and first molars (T2). The mean age of the children in both groups was 5.1 years at T1 and 8.4 years at T2. RESULTS: A significant difference between the groups at T2 was found in the mandibular length, midfacial length, and maxillomandibular differential. The increase in mandibular length was 11.1 mm in the treatment group and 7.2 mm in the control group. No differences were found in measurements of maxillary position or size. There was a significant shift toward a Class I relationship in the treatment group. Labial tipping and linear protrusion of the mandibular incisors was evident in the treatment group at T2. There was no effect on the inclination or position of the maxillary incisors. CONCLUSIONS: Occlusal correction was achieved mainly through changes in the dentoalveolar region of the mandible. In addition, the appliance enhanced condylar growth resulting in a clinically significant increase in mandibular length. No effect was observed on maxillary position, maxillary size, inclination or protrusion of the maxillary incisors, or facial height.