10.3987/COM-10-S(E)102
The research aimed to synthesize antioxidant flavonoid derivatives, specifically quercetin-caffeic acid and quercetin-curcumin conjugates, to prevent age-related macular degeneration (AMD). The study sought to enhance the antioxidative properties of the naturally occurring plant antioxidant quercetin by linking it with other plant antioxidants, caffeic acid and curcumin. The researchers designed and synthesized quercetin derivatives connected to these natural products via an appropriate linker, expecting the resulting compounds to have increased chemical stability and antioxidative activities. The study concluded with the successful synthesis of new types of antioxidants, quercetin/caffeic acid derivative 7 and quercetin/curcumin derivative 11, and planned to further compare their antioxidant properties with other known antioxidants, with ongoing studies on their activity against A2E photooxidation.
10.1016/j.bmc.2005.03.054
The study focuses on the synthesis and biological evaluation of aromatic enones related to curcumin, a natural product derived from turmeric with known anti-cancer and anti-angiogenic properties. The researchers aimed to develop curcumin analogs with potential as angiogenic inhibitors, targeting the process of new blood vessel formation that is crucial for tumor growth and metastasis. A series of structurally related compounds were synthesized, utilizing a substituted chalcone backbone, and tested for their ability to inhibit endothelial cell growth in vitro using the SVR cell proliferation assay. The chemicals used in the study included various substituted aromatic aldehydes, ketones, and enone derivatives, which served as the building blocks for the synthesized curcumin analogs. These compounds were designed to retain the electrophilic nature of curcumin's central β-diketone component, which is believed to contribute to its biological activity. The purpose of these chemicals was to create a range of compounds that could potentially match or exceed curcumin's ability to inhibit angiogenesis, providing new leads for developing anti-cancer drugs.
10.1021/ol702370m
The research describes the synthesis of monofunctional curcumin derivatives, a "clicked" curcumin dimer, and a PAMAM dendrimer-curcumin conjugate for therapeutic applications. The purpose of this study was to overcome the poor water and plasma solubility of curcumin, a bioactive compound found in turmeric, which possesses antioxidant, anticancer, anti-inflammatory, and anti-Alzheimer's disease properties. The researchers developed a synthetic methodology to produce curcumin conjugates with water-soluble polymers and targeting proteins, potentially enhancing curcumin's therapeutic efficacy. Key chemicals used in the process include curcumin, glutaric anhydride, amino-PEG azide, 1,3-dicyclohexylcarbodiimide (DCC), propargyl bromide, K2CO3, and copper(II) sulfate with sodium ascorbate for the "click" reaction. The study concluded that the monofunctional curcumin derivatives retained biological activity, efficiently labeled and dissolved amyloid fibrils, and the curcumin dimer selectively destroyed human neurotumor cells, making it a promising drug candidate. The conjugates were also expected to exhibit the EPR effect, enhancing their potential therapeutic applications.
10.1039/b812018h
The research focuses on the annular tautomerism of curcuminoid NH-pyrazoles, which are derivatives of curcumin, the principal curcuminoid found in turmeric. The purpose of the study was to determine and discuss the structure, tautomerism, and possible proton transfer in the solid state of six NH-pyrazoles using a combination of X-ray crystallography and 13C/15N NMR spectroscopy. The research concluded that the most abundant tautomer in solution coincides with the tautomer present in the solid state for compounds 4, 5, and 8, and that none of the compounds displayed solid-state proton transfer (SSPT). The study also found that compound 5 is an exception to the rule of similarity between solution and solid state, existing in the solid state as a 66% 5a/34% 5b mixture and in HMPA as a 35% 5a/65% 5b mixture. The chemicals used in the process included various NH-pyrazole derivatives, such as (E)-3,5-bis[b-(4-hydroxy-3-methoxyphenyl)-ethenyl]-1H-pyrazole (3), (E)-3(5)-[b-(4-hydroxy-3-methoxyphenyl)-ethenyl]-5(3)-methyl-1H-pyrazole (4), and others, which were synthesized from corresponding β-diketones and hydrazine hydrate in acetic acid. The researchers also utilized solvents like DMSO-d6 and HMPA-d18 for NMR studies and CH2Cl2/hexane/EtOH mixtures for recrystallization of the compounds.
10.1016/j.foodchem.2014.05.094
This research aimed to enhance the solubility of curcumin, a nutraceutical with limited water solubility, by forming an inclusion complex with β-cyclodextrin. The study employed phase solubility analysis, 1H and 2D ROESY NMR spectroscopy, and molecular modeling to investigate the interaction topology and geometry between curcumin and β-cyclodextrin. The results demonstrated a linear increase in curcumin solubility with increasing β-cyclodextrin concentration, confirming the formation of a 1:1 or 1:2 inclusion complex. The research concluded that the hydrophobic aromatic rings of curcumin were covered by the cavity of β-cyclodextrin, which enhanced its aqueous solubility.
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