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Abstract(s)
A curcumina é um dos compostos presente no açafrão-da-índia, da planta Curcuma longa. Tem despertado imensa curiosidade na comunidade científica devido às suas diversas atividades biológicas atuando em várias doenças inflamatórias, em vários tipos de cancro, diabetes, entre outras. No entanto, a curcumina, apesar dos seus benefícios, apresenta uma baixa biodisponilidade devido à sua baixa solubilidade em água, ou seja, têm uma má absorção, metabolismo rápido e uma rápida eliminação o que limita significativamente os efeitos terapêuticos da mesma.
De forma a melhorar a solubilidade da curcumina em água e consequentemente as suas propriedades medicinais sintetizaram-se com sucesso diversos derivados curcuminóides utilizando dois métodos de síntese com condições reacionais distintas. Todos os derivados curcuminóides foram caracterizados por técnicas como RMN (1H, 13C, HMQC, COSY), FT-IR, UV-vis e raios-X de cristal único.
Foram efetuados testes antioxidantes de forma a se poder analisar a capacidade antioxidante de cada derivado curcuminóide sintetizado.
Foi necessário, também, estudar a solubilidade dos vários derivados em água, DMSO e meios fisiológicos, como o soro, com vista a estudar os curcuminóides como antidiabético visto que é uma das propriedades da curcumina.
Outra técnica utilizada para melhorar as propriedades físico-químicas de alguns dos compostos sintetizados, nomeadamente, a curcumina e alguns dos derivados curcuminóides, foi a co-cristalização por mecanoquimica, utilizando có-formeros, como o resorcinol, paracetamol, piperazina, entre outros, onde se obteve alguns co-cristais, analisados por raios-X de pós. No entanto, devido à solubilidade de algumas misturas ter aumentado significativamente põe-se a hipótese da existência de misturas eutécticas.
Curcumin is one of the compounds present in the turmeric of the Curcuma longa plant. It has attracted immense curiosity in the scientific community due to its diverse biological activities acting in several inflammatory diseases, in several types of cancer, diabetes, amongst others. However, curcumin has a low bioavailability because of its low solubility in water. Curcumin has poor absorption, rapid metabolism and rapid elimination which significantly limits its therapeutic effects. To improve the solubility of curcumin in water and consequently its medicinal properties, several curcuminoid derivatives have been successfully synthesized using two synthetic methods with different reaction conditions. All the curcuminoid derivatives were characterized by techniques such as NMR (1H, 13C, HMQC, COSY), FT-IR, UV-vis and single crystal X-rays. Antioxidant tests were carried out to analyze the antioxidant capacity of each curcuminoid synthesized. It was also necessary to study the solubility of the various derivatives in water, DMSO and biological environment, such as saline, to study the antidiabetic properties of curcuminoids. Co-crystallization by mechanochemistry was used to improve the physicochemical properties of some of the synthesized compounds, namely curcumin and some curcuminoid derivatives. The co-formers used in the co-crystallization were resorcinol, paracetamol, piperazine, among others. Some crystalline powders were obtained and were analyzed by powder X-rays diffraction. However, the hypothesis is that are eutectic mixtures because the solubility of some blends has increased significantly.
Curcumin is one of the compounds present in the turmeric of the Curcuma longa plant. It has attracted immense curiosity in the scientific community due to its diverse biological activities acting in several inflammatory diseases, in several types of cancer, diabetes, amongst others. However, curcumin has a low bioavailability because of its low solubility in water. Curcumin has poor absorption, rapid metabolism and rapid elimination which significantly limits its therapeutic effects. To improve the solubility of curcumin in water and consequently its medicinal properties, several curcuminoid derivatives have been successfully synthesized using two synthetic methods with different reaction conditions. All the curcuminoid derivatives were characterized by techniques such as NMR (1H, 13C, HMQC, COSY), FT-IR, UV-vis and single crystal X-rays. Antioxidant tests were carried out to analyze the antioxidant capacity of each curcuminoid synthesized. It was also necessary to study the solubility of the various derivatives in water, DMSO and biological environment, such as saline, to study the antidiabetic properties of curcuminoids. Co-crystallization by mechanochemistry was used to improve the physicochemical properties of some of the synthesized compounds, namely curcumin and some curcuminoid derivatives. The co-formers used in the co-crystallization were resorcinol, paracetamol, piperazine, among others. Some crystalline powders were obtained and were analyzed by powder X-rays diffraction. However, the hypothesis is that are eutectic mixtures because the solubility of some blends has increased significantly.
Description
Trabalho final de mestrado para a obtenção do grau de mestre em Engenharia Química e Biológica
Keywords
Curcumina Curcumin Derivados curcuminóides Curcuminoid derivatives Solubilidade Solubility Co-cristalização Co-crystallization Mecanoquimica Mechanochemistry Có-formeros Co-formers
Citation
LOPES, Ana Patrícia Sequeira - Síntese de novos análogos de curcumina com potenciais atividades biológicas. Lisboa: Instituto Superior de Engenharia de Lisboa, 2018. Dissertação de mestrado.
Publisher
Instituto Superior de Engenharia de Lisboa