On the properties of a single OPLS-UA model curcumin molecule in water, methanol and dimethyl sulfoxide. Molecular dynamics computer simulation results

Patsahan, T.; Ilnytskyi, Jaroslav; Pizio, Orest

doi:10.5488/cmp.20.23003

Cited by 14 publications

(15 citation statements)

References 37 publications

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“…The viscosity of the MCT oil (assumed to be similar to that of coconut oil) at 55 °C has been reported to be 16 mPa s, while the radius of hydration of curcumin has been reported to be 0.690 nm. 39 This leads to a diffusion coefficient of 2.2 × 10 −11 m 2 s −1 for curcumin in the interior of the oil droplets. Predictions made using the Crank equation show that the rate of transfer of the curcumin molecules from inside the oil droplets to the surrounding water phase (or vice versa) increases as the droplet size decreases (Figure 6).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…The diffusion coefficient can be calculated from the Stokes–Einstein equation Here, k B is Boltzmann’s constant (1.38 × 10 –23 J K –1 ), T is the absolute temperature (328 K), η is the viscosity of the oil phase, and r is the radius of hydration of the curcumin molecule. The viscosity of the MCT oil (assumed to be similar to that of coconut oil) at 55 °C has been reported to be 16 mPa s, while the radius of hydration of curcumin has been reported to be 0.690 nm . This leads to a diffusion coefficient of 2.2 × 10 –11 m 2 s –1 for curcumin in the interior of the oil droplets.…”

Section: Resultsmentioning

confidence: 99%

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Comparison of Emulsion and Nanoemulsion Delivery Systems: The Chemical Stability of Curcumin Decreases as Oil Droplet Size Decreases

Kharat

Aberg

Dai

et al. 2020

J. Agric. Food Chem.

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The water dispersibility, chemical stability, and bioaccessibility of curcumin, a labile hydrophobic nutraceutical, can be enhanced by incorporating it inside the oil droplets of oil-in-water emulsions or nanoemulsions. In these multiphase systems, the curcumin remains relatively stable to degradation when surrounded by oil but degrades rapidly when surrounded by water. We hypothesized that the size of the lipid droplets would therefore impact the stability of encapsulated curcumin by altering the surface area of oil exposed to water. The effect of droplet surface area on the kinetics of curcumin degradation was therefore studied by producing emulsions with different mean droplet diameters (d 32) and therefore different specific surface areas (A S): large (d 32 = 20.9 μm; A S = 300 m2 kg–1); medium (d 32 = 2.53 μm; A S = 2500 m2 kg–1); small (d 32 = 0.26 μm; A S = 24,000 m2 kg–1); and very small (d 32 = 0.083 μm; A S = 80,000 m2 kg–1) emulsions. All the emulsions initially had milky-yellow appearances and were relatively stable to aggregation during the course of the experiments. However, rapid creaming was observed in the large and medium emulsions because of their relatively large droplet size. The emulsions all exhibited some color fading during storage, with the rate of curcumin degradation increasing with decreasing droplet size. For instance, the percentage of curcumin remaining in the emulsions after 17 days storage was 91.4 ± 1.5 > 77.3 ± 6.6 > 66.7 ± 1.9 ≫ 30.6 ± 2.8% for the large, medium, small, and very small emulsions, respectively. The more rapid chemical degradation of the curcumin in the smaller droplets can be attributed to the fact that curcumin exchange between the interior and exterior of the droplets occurs more rapidly as the droplet dimensions decrease. Our results indicate that the droplet size plays a critical role in the degradation of curcumin encapsulated in emulsions, which may have important consequences for the formulation of curcumin-enriched foods and beverages with enhanced bioactivity. In particular, it suggests that emulsions are more effective at chemically stabilizing curcumin than nanoemulsions.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Comparison of Emulsion and Nanoemulsion Delivery Systems: The Chemical Stability of Curcumin Decreases as Oil Droplet Size Decreases

Kharat

Aberg

Dai

et al. 2020

J. Agric. Food Chem.

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“…On the other hand, the gained knowledge would permit to explore complex solutes in mixed solvents tuning with confidence their solubility on solvent composition. Some specific molecules of interest in medicinal chemistry, for example curcumin, are marginally soluble in water, but dissolve well in, e.g., alcohols or dimethylsulfoxide [27][28][29]. Additional comments concerning the methodological difference of our procedure and technical details in comparison with reference [9] are given in the body of the manuscript below.…”

Section: Introductionmentioning

confidence: 99%

Molecular dynamics simulations of the properties of water-methanol mixtures. Effects of force fields

Sánchez¹,

Domínguez²,

Pizio³

2019

Condens. Matter Phys.

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Isothermal-isobaric molecular dynamics simulations are used to examine the microscopic structure and some properties of water-methanol liquid mixture. The TIP4P/2005 and SPC/E water models are combined with the united atom TraPPE and the all-atom force field model for methanol. Our principal focus is to evaluate the quality of predictions of different combinations of model force fields concerning the composition dependence of basic properties of this system. Specifically, we explored the composition effects on density, excess molar volume and excess entropy, as well as on the surface tension and static dielectric constant. In addition, the structural properties are described in terms of the coordination numbers and the average number of hydrogen bonds between molecules of constituent species. Finally, the composition dependence of self-diffusion coefficients of the species is evaluated. All theoretical predictions are tested with respect to experimental data.

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“…The "ball-and-stick" schematic representation of the molecule was already presented in [19,20]. Still, we show it here in figure 2, for the sake of convenience of the reader.…”

Section: Model and Simulation Detailsmentioning

confidence: 99%

Structural aspects of the clustering of curcumin molecules in water. Molecular dynamics computer simulation study

Patsahan¹,

Pizio²

2022

Condens. Matter Phys.

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We explore clustering of curcumin molecules in water by using the OPLS-UA model for the enol conformer of curcumin (J. Mol. Liq., 223, 707, 2016) and the SPC-E water model. With this purpose, solutions of 2, 4, 8, 12, 16 and 20 curcumin molecules in 3000 water molecules are studied by using extensive molecular dynamics computer simulations. Radial distributions for the centers of mass of curcumin molecules are evaluated and the running coordination numbers are analyzed. The formation of clusters on time is elucidated. The internal structure of molecules within the cluster is described by using radial distributions of the elements of the curcumin molecule, the orientation descriptors, the order parameter and the radius of gyration. The self-diffusion coefficient of solute molecules in clusters is evaluated. The distribution of water species around clusters is described in detail. A comparison of our findings with computer simulation results of other authors is performed. A possibility to relate predictions of the model with experimental observations is discussed.

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On the properties of a single OPLS-UA model curcumin molecule in water, methanol and dimethyl sulfoxide. Molecular dynamics computer simulation results

Cited by 14 publications

References 37 publications

Comparison of Emulsion and Nanoemulsion Delivery Systems: The Chemical Stability of Curcumin Decreases as Oil Droplet Size Decreases

Comparison of Emulsion and Nanoemulsion Delivery Systems: The Chemical Stability of Curcumin Decreases as Oil Droplet Size Decreases

Molecular dynamics simulations of the properties of water-methanol mixtures. Effects of force fields

Structural aspects of the clustering of curcumin molecules in water. Molecular dynamics computer simulation study

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