Diamide linked γ-cyclodextrin (γ-CD) dimers are used to capture curcumin and suppress its decomposition in water. In this study, succinamide and urea linked γ-CD dimers joined through the C6(A) carbon on each γ-CD are used. The γ-CD dimers, 66γCD(2)su and 66γCD(2)ur, show a remarkable ability to suppress the decomposition of curcumin and extend its half-life from less than 30 min to greater than 16 h. The 1:1 association of curcumin with 66γCD(2)su and 66γCD(2)ur has high stability constants of 8.7 × 10(6) M(-1) and 2.0 × 10(6) M(-1), respectively. In addition, 2D (1)H NOESY NMR results show specific hydrogen interactions in the association of curcumin with 66γCD(2)su and 66γCD(2)ur, consistent with the cooperative binding of curcumin by both γ-CD annuli of 66γCD(2)su and 66γCD(2)ur. The interactions between curcumin in the linked γ-CD dimers and surfactant micelles were studied using fluorescence spectroscopy. While linked γ-CD dimer-bound curcumin has a negligible fluorescence quantum yield, a significant increase in fluorescence intensity (Φ(fl) > 2%) in the presence of micelles suggests that curcumin is delivered to the micelle. The overall results indicate that the diamide linked γ-CD dimers are highly promising systems for curcumin delivery in vivo due to effective curcumin stabilization.
Ligand-metal interaction between curcumin and Cu(II) in methanol and sodium dodecyl sulfate (SDS) micelles was investigated using fluorescence spectroscopy and transient absorption spectroscopy. The Cu(II) ion exhibits a high efficiency in quenching the fluorescence of curcumin. By quantifying fluorescence quenching as a function of Cu(II) concentration, the complexation constants, K(1) and K(2), for the formation of the 1 : 1 and 1 : 2 Cu(II)-curcumin complexes, [Cu(II)-Cur](+) and [Cu(II)-Cur(2)], have been determined. In methanol, K(1) and K(2) are (1.33 ± 0.47) × 10(8) M(-1) and (6.79 ± 1.77) × 10(5) M(-1), respectively, whereas those in SDS micelles are (9.90 ± 1.68) × 10(5) M(-1) and (1.70 ± 0.48) × 10(6) M(-1), respectively. The transient absorption spectra of curcumin and the Cu(II)-curcumin complexes from 520 nm to 700 nm show a combination of stimulated emission and excited state absorption (ESA). However, the transient absorption signal at 500 nm corresponds to ESA exclusively. For curcumin, the ESA kinetics exhibit two rising components with time constants of 0.9 ps and 8.2 ps in methanol, and 0.5 ps and 2.5 ps in SDS micelles, which are consistent with solvation dynamics of excited state curcumin in these media. In addition, the ESA kinetics show a decay component with a time constant of 125 ps in methanol and 64 ps in SDS micelles, reflecting the excited state intramolecular hydrogen atom transfer of curcumin in these media. The ESA kinetics of the Cu(II)-curcumin complexes exhibit a sharp rise and a fast decay with a time constant of approximately 1 ps in both media due to the strong interaction between Cu(II) and curcumin.
This study investigated compositional changes in red wines resulting from wine alcohol removal by reverse osmosis-vaporative perstraction (RO-EP) and provides insight into the physical and chemical changes in reduced alcohol wine (RAW). Trial 1 involved RO-EP treatment of three wines that were analyzed pre-treatment, post-treatment, and post-treatment with alcohol adjustment (i.e., addition of ethanol to achieve the original alcohol content). Trial 2 involved partial dealcoholization of two wines and analysis of samples collected during RO-EP treatment, i.e., wine in, wine out, retentate, permeate (pre- and post-EP treatment) and strip water. Wine color was analyzed by spectrophotometric methods, while other compositional changes were determined by WineScan, high performance liquid chromatography (HPLC) and gas chromatography–mass spectrometry (GC–MS) analyses. In general, RAWs were slightly more concentrated than pre-treatment wines, which resulted in greater color intensity and increased phenolics and organic acids. However, partial dealcoholization resulted in lower concentrations of some fermentation volatiles, particularly ethyl esters, which may reflect ester hydrolysis following ethanol removal.
Purpose -The purpose of this paper is to propose a "Fit" manufacturing paradigm for industry so that manufacturing companies can become economically sustainable and can operate effectively in a global competitive market. The proposed Fit paradigm is aimed at providing a new manufacturing management perspective to both academics and industrialists. Design/methodology/approach -The Fit paradigm is developed and proposed as a new manufacturing management strategy towards creating economically sustainable manufacturing organisations. Fit is a theoretical development using the principles of existing manufacturing paradigms along with new and innovative management concepts to create a sustainable approach to manufacturing. Findings -Manufacturing strategies such as lean and agility allow companies to deliver bottom-line savings in production terms although their effectiveness depends upon the volume and demand profile of their products. The trend towards mass customisation requires companies to provide personalised products and services at mass production prices. This now places a further burden on companies and therefore a holistic manufacturing framework must be developed in order to ensure that the factory of the future is able to meet this new demand. This paper proposes a fit manufacturing paradigm which integrates the manufacturing efficiencies achieved through lean and agility with the need to break into new markets through effective marketing and product innovation strategies to achieve long term economic sustainability. The small scale application of the approach in a case company shows that the initial results to be positive when measured against a fit index which is developed within this paper. Originality/value -The development of a fit paradigm aimed at tackling directly the issues of economic sustainability is proposed and is considered by the authors as one of a kind. Fit will also provide a framework for the implementation of sustainable manufacturing operations within organisations.
Diamide linked γ-cyclodextrin (γ-CD) dimers are proposed as molecular-scale delivery agents for the anticancer agent curcumin. N,N'-Bis(6(A)-deoxy-γ-cyclodextrin-6(A)-yl)succinamide (66γCD2su) and N,N'-bis(6(A)-deoxy-γ-cyclodextrin-6(A)-yl)urea (66γCD2ur) markedly suppress the degradation of curcumin by forming a strong 1:1 cooperative binding complexes. The results presented in this study describe the potential efficacy of 66γCD2su and 66γCD2ur for intracellular curcumin delivery to cancer cells. Cellular viability assays demonstrated a dose-dependent antiproliferative effect of curcumin in human prostate cancer (PC-3) cells that was preserved by the curcumin-66γCD2su complex. In contrast, delivery of curcumin by 66γCD2ur significantly delayed the antiproliferative effect. We observed similar patterns of gene regulation in PC-3 cells for curcumin complexed with either 66γCD2su or 66γCD2ur in comparison to curcumin alone, although curcumin delivered by either 66γCD2su or 66γCD2ur induces a slightly higher up-regulation of heme oxygenase-1. Highlighting their nontoxic nature, neither 66γCD2su nor 66γCD2ur carriers alone had any measurable effect on cell proliferation or candidate gene expression in PC-3 cells. Finally, confocal fluorescence imaging and uptake studies were used to demonstrate the intracellular delivery of curcumin by 66γCD2su and 66γCD2ur. Overall, these results demonstrate effective intracellular delivery and action of curcumin when complexed with 66γCD2su and 66γCD2ur, providing further evidence of their potential applications to deliver curcumin effectively in cancer and other treatment settings.
Molecular tweezers were synthesised by using a microwave accelerated alkene plus cyclobutane epoxide reaction between norbornyl appended porphyrin moieties and a diepoxide functionalised phenyl diimide spacer. The tweezers contain several rotational degrees of freedom; about the porphyrin with respect to the norbornyl linker, and between the two norbornyl backbone sections. The ability of ZnII metallated tweezer 1 to complex 1,4‐diazabicyclo[2.2.2]octane (DABCO) was studied by UV/Vis and 1H NMR spectroscopy and multivariate global spectral analysis. The system was found to form a strong 1:1 intramolecular complex (1:DABCO) with an association constant of K11 = 8.1 × 107 M–1, transforming to a 1:2 open complex [1:(DABCO)2] with K12 = 2.7 × 109 M–2 at high concentrations of DABCO.
A close correllation between molecular-level interactions and macroscopic characteristics of polymer networks exists. The characteristics of the polymeric hydrogels assembled from β-cyclodextrin (β-CD) and adamantyl (AD) substituted poly(acrylate)s can be tailored through selective host-guest complexation between β-CD and AD substituents and their tethers. Dominantly, steric effects and competitive intra- and intermolecular host-guest complexation are found to control poly(acrylate) isomeric inter-strand linkage in polymer network formation. This understanding of the factors involved in polymeric hydrogel formation points the way towards the construction of increasingly sophisticated biocompatible materials.
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