Catalyzed and non-catalyzed synthesis of bioactive monastrol

The bioactive 3,4-dihydropyrimidin-2(1H)-thione derivative known as Monastrol was synthesized under catalyzed and non-catalyzed conditions through the Biginelli multicomponent reaction under solvent-free conditions. The use of two Lewis acids (FeCl3 and CuCl2) and two Brønsted acids (HCl and CF3COOH) as catalysts improved the reaction yields of the transformation compared with the non-catalyzed reaction. The experiments investigated catalysis and its role, the importance of multicomponent reactions and their green features, and the application of these concepts to the synthesis of a biologically important structure

Poli-líquidos iônicos e complexos solúveis de Eu3+ e Tb3+ : bioimageamento celular seletivo

Este trabalho apresenta a síntese, caracterização e aplicação de complexos ionicamente marcados de európio (III) e térbio (III) como sondas fluorescentes em ensaios de bioimageamento. Estes novos complexos foram obtidos a partir de um líquido iônico de função específica (inédito) e sua posterior polimerização. De acordo com os dados de calorimetria diferencial de varredura e análises termogravimétricasos complexos apresentaram-se termicamente mais estáveis quando comparados com seus monómeros precursores e respectivos polímeros ausente de metais. Outras técnicas de caracterização, como RMN, ATR-FTIR, fluorescência e cromatografia de permeação em gel confirmou a síntese bem sucedida de complexos marcados ionicamente e seus polímeros. As análises de FTIR-ATR e fluorescência sugerem que clusters de água auto-organizadas suprimem a emissão de luz dos complexos. Na verdade, o baixo rendimento quântico de fluorescência é uma consequência do acoplamento vibrônico das moléculas de água. Todos os complexos foram submetidos a experimentos de imagem celular. Os resultados forneceram evidências de que estes complexos foram eficazes e seletivos na distinção das diferentes organelas dentro da célula. Alguns dos complexos (VAIEu) foram seletivos para os endossomos precoces e tardios, enquanto outros (VAITb) associaram ao retículo endoplasmático. Além disso, VAIEu-βdicetona acumulou em vesículas citoplasmáticas, PVAIEu associado com lisossomos, complexos PVAITb foram seletivos para retículo endoplasmático e PVAIEu-βdicetona apresentou associação para vesículas e endossomos, tanto precoces e tardios. _____________________________________________________________________________________________ ABSTRACTThis work presents the synthesis, characterization, and the application of ionically tagged complexes of europium(III) and terbium(III) as fluorescent probes in cellular bio imaging. These new complexes were obtained from an ionic liquid of specific function and their post polymerization. According to thermogravimetric and differential scanning calorimetrydata the polymerized complexes were thermally more stable than the precursor monomers and respective polymers absent of metals. In particular, the glass transition temperature was higher in metaled polymerized complexes. Other characterization techniques, namely NMR H1 and C13, FTIR-ATR, fluorescence and gel permeation chromatography confirmed the successful synthesis ofionically tagged complexes and their polymers. FTIR-ATR and fluorescence analysis suggest that self-organized water clusters suppress the light emission of ionically tagged complexes and their polymers. In fact, the low quantum yield of fluorescence is a consequence of the vibronic coupling with water molecules. All complexes were submitted to experiments of cellular imaging. Results provided evidence that these complexes were effective and selective in the distinction of different organelles within the cell. Some of the complexes (VAIEu) were selective for early and late endosomes, while others (VAITb) were associated with the endoplasmic reticulum. Moreover, VAIEu-βdiketoneaccumulated in cytoplasmic vesicles, PVAIEu associated with lysosomes, PVAITb complexes were selective for endoplasmic reticulum and PVAIEu-βdiketonepresented association to vesicles and endosomes, both early and late