Drug delivery systems: Study of inclusion complex formation for ternary caffeine– β -cyclodextrin–water mixtures from apparent molar volume values at 298.15 K and 310.15 K

Santos, Cecília I.A.V.; Teijeiro, C.; Ribeiro, Ana C.F.; Rodrigues, Daniela F. S. L.; Romero, Carmen M.; Esteso, Miguel A.

doi:10.1016/j.molliq.2016.08.035

Cited by 25 publications

(29 citation statements)

References 36 publications

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“…7). Comparison with experimental data [70][71][72][73] shows that MARTINI tends to underestimate the density of saccharide solutions by up to 10% at high solute concentrations ( fig. 7A, B).…”

Section: G Validation Of the Proposed Modificationsmentioning

confidence: 94%

See 1 more Smart Citation

Overcoming the Limitations of the MARTINI Force Field in Simulations of Polysaccharides

Schmalhorst

Deluweit²,

Scherrers³

et al. 2017

J. Chem. Theory Comput.

101

144

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Polysaccharides (carbohydrates) are key regulators of a large number of cell biological processes. However, precise biochemical or genetic manipulation of these often complex structures is laborious and hampers experimental structure-function studies. Molecular Dynamics (MD) simulations provide a valuable alternative tool to generate and test hypotheses on saccharide function. Yet, currently used MD force fields often overestimate the aggregation propensity of polysaccharides, affecting the usability of those simulations. Here we tested MARTINI, a popular coarse-grained (CG) force field for biological macromolecules, for its ability to accurately represent molecular forces between saccharides. To this end, we calculated a thermodynamic solution property, the second virial coefficient of the osmotic pressure (B). Comparison with light scattering experiments revealed a nonphysical aggregation of a prototypical polysaccharide in MARTINI, pointing at an imbalance of the nonbonded solute-solute, solute-water, and water-water interactions. This finding also applies to smaller oligosaccharides which were all found to aggregate in simulations even at moderate concentrations, well below their solubility limit. Finally, we explored the influence of the Lennard-Jones (LJ) interaction between saccharide molecules and propose a simple scaling of the LJ interaction strength that makes MARTINI more reliable for the simulation of saccharides.

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Section: G Validation Of the Proposed Modificationsmentioning

confidence: 94%

“…Note the different scaling of the x-axis in every panel. Experimental data were taken from references denoted [P][70], [C][71], [F][72], and [S][73].…”

mentioning

confidence: 99%

Overcoming the Limitations of the MARTINI Force Field in Simulations of Polysaccharides

Schmalhorst

Deluweit²,

Scherrers³

et al. 2017

J. Chem. Theory Comput.

101

144

View full text Add to dashboard Cite

show abstract

“…However, the β-CD concentration does not seem to affect the concentration of caffeine in the extract and it can be observed that the highest C Caf was obtained in the absence of cyclodextrin. The inclusion complex formation of caffeine has already been studied [25] and the usage of cyclodextrin has been proposed for the decaffeination process [26]. In complicated extracts, it is difficult to figure out which specific compounds form complexes [13].…”

Section: Discussionmentioning

confidence: 99%

Green Extracts from Coffee Pulp and Their Application in the Development of Innovative Brews

et al. 2020

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Coffee pulp, a by-product of coffee production, contains valuable compounds such as caffeine and chlorogenic acid with high antiradical activity. In this study, aqueous solutions of β-cyclodextrin (β-CD) were used as a non-conventional solvent for the extraction of targeted compounds from coffee pulp. The parameters of β-CD concentration (Cβcd), liquid-to-solid ratio (L/S), and temperature (T) were evaluated based on the antiradical activity (AAR) and the caffeine content (CCaf). The optimum operational conditions were found to be Cβcd: 9.25 mg/mL, L/S: 30 mL/g and T: 80 °C. The sensory profiles of brews prepared with coffee and coffee pulp with or without cyclodextrin were studied with quantitative descriptive analysis. The brew from the by-product had fruity, botanic, sweet and sourness sensory properties, and cyclodextrin was found to be able to affect the overall taste of the brew.

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“…delivery profile from guar-gum films, alginate beads and GfB compared with a control solution of free caffeine (2 mg/mL).The higher flux of caffeine from control solution crossed the dialysis membrane occurred in the first 15 min, indicating that caffeine flux easily occurred from the inside of the dialysis membrane to the outside, following Fick's first law. Caffeine is a small (194.194 g.mol -1 ), highly hydrophilic (2.16E04 mg/L) molecule and a fast efflux from the dialysis membrane was predictable[47,48]. Release profile of caffeine content in control solution was almost linear in the first 60 min, approaching a zero-order release kinetics and reaching a plateau from 60 min till the end of the release study.…”

mentioning

confidence: 99%

Incorporation of beads into oral films for buccal and oral delivery of bioactive molecules

Castro

Sousa

Magalhães

et al. 2018

Carbohydrate Polymers

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The association of alginate beads and guar-gum films in a single delivery system was idealized to promote a more effective buccal and oral delivery of bioactive molecules. A response surface method (experimental design approach) was performed to obtain optimal formulations of alginate beads to be incorporated into guar gum oral films as combined buccal and oral delivery systems for caffeine delivery. The combined formulation was further characterized regarding physicochemical properties, drug release, cell viability and buccal permeability. Beads average size, determined by dynamic light scattering (DLS), was of 3.37 ± 6.36 μm. Film thickness was set to 62 μm. Scanning electron microscopy micrographs revealed that beads were evenly distributed onto the film matrix and beads size was in accordance to data obtained from DLS analysis. Evaluation of Fourier-transform infrared spectra did not indicate the formation of new covalent bonds between the matrix of guar-gum films, alginate beads and caffeine. In vitro release assays by dialysis membrane allowed understanding that the combination of guar-gum films and alginate beads assure a slower release of caffeine when compared with the delivery profile of free caffeine from alginate beads or guar-gum films alone. MTT assay, performed on human buccal carcinoma TR146 cell line, allowed concluding that neither guar-gum film, alginate beads nor guar-gum film incorporated into alginate beads significantly compromised cell viability after 12 h of exposure. As demonstrated by in vitro permeability assay using TR146 human buccal carcinoma cell lines, combination of guar-gum films and alginate beads also promoted a slower release and, thus, lower apparent permeability (1.15E-05 ± 3.50E-06) than for caffeine solution (2.68E-05 ± 7.30E-06), guar-gum film (3.12E-05 ± 4.70E-06) or alginate beads (2.01E-05 ± 3.90E-06). The conjugation of alginate beads within an orodispersible film matrix represents an effective oral/buccal delivery system that induces a controlled release along with an enhanced intimate contact with cell layers that may promote higher in vivo bioavailability of carried drugs.

show abstract

Drug delivery systems: Study of inclusion complex formation for ternary caffeine– β -cyclodextrin–water mixtures from apparent molar volume values at 298.15 K and 310.15 K

Cited by 25 publications

References 36 publications

Overcoming the Limitations of the MARTINI Force Field in Simulations of Polysaccharides

Overcoming the Limitations of the MARTINI Force Field in Simulations of Polysaccharides

Green Extracts from Coffee Pulp and Their Application in the Development of Innovative Brews

Incorporation of beads into oral films for buccal and oral delivery of bioactive molecules

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