Dataset Information

ITC and NMR Analysis of the Encapsulation of Fatty Acids within a Water-Soluble Cavitand and its Dimeric Capsule.

ABSTRACT: We report here NMR and ITC studies of the binding of ionizable guests (carboxylate acids) to a deep-cavity cavitand. These studies reveal that the shortest guests favored 1:1 complex formation, but the longer the alkyl chain the more the 2:1 host-guest capsule is favored. For intermediate-sized guests, the equilibrium between these two states is controlled by pH; at low values the capsule containing the carboxylic acid guest is favored, whereas as the pH is raised deprotonation of the guest favors the 1:1 complex. Interestingly, for one host-guest pair the energy required to de-cap the 2:1 capsular complex and form the 1:1 complex is sufficient to shift the pKa of the guest by ~ 3-4 orders of magnitude (4.1-5.4 kcal mol-1). The two largest guests examined form stable 2:1 capsules, with in both cases the guest adopting a relatively high energy J-shaped motif. Furthermore, these 2:1 complexes are sufficiently stable that at high pH guest deprotonation occurs without de-capping of the capsule.

SUBMITTER: Wang K

PROVIDER: S-EPMC4792523 | biostudies-literature | 2016

REPOSITORIES: biostudies-literature

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ITC and NMR Analysis of the Encapsulation of Fatty Acids within a Water-Soluble Cavitand and its Dimeric Capsule.

Wang Kaiya K Sokkalingam Punidha P Gibb Bruce C BC

Supramolecular chemistry 20151015 1-2

We report here NMR and ITC studies of the binding of ionizable guests (carboxylate acids) to a deep-cavity cavitand. These studies reveal that the shortest guests favored 1:1 complex formation, but the longer the alkyl chain the more the 2:1 host-guest capsule is favored. For intermediate-sized guests, the equilibrium between these two states is controlled by pH; at low values the capsule containing the carboxylic acid guest is favored, whereas as the pH is raised deprotonation of the guest favo ...[more]

PMID: 26997853

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Project description:The nutritional quality of animal products is strongly related to their fatty acid content and composition. Nowadays, attention is paid to the possibility of producing healthier foods of animal origin by intervening in animal feed. In this field, the use of condensed tannins as dietary supplements in animal nutrition is becoming popular due to their wide range of biological effects related, among others, to their ability to modulate the rumen biohydrogenation and biofortify, through the improvement of the fatty acids profile, the derivate food products. Unfortunately, tannins are characterized by strong astringency and low bioavailability. These disadvantages could be overcome through the microencapsulation in protective matrices. With this in mind, the optimal conditions for microencapsulation of a polyphenolic extract rich in condensed tannins by spray drying using a blend of maltodextrin (MD) and gum Arabic (GA) as shell material were investigated. For this purpose, after the extract characterization, through spectrophotometer assays and ultra-high-performance liquid chromatography-quadrupole time-of-flight (UHPLC-QTOF) mass spectrometry, a central composite design (CCD) was employed to investigate the combined effects of core:shell and MD:GA ratio on the microencapsulation process. The results obtained were used to develop second-order polynomial regression models on different responses, namely encapsulation yield, encapsulation efficiency, loading capacity, and tannin content. The formulation characterized by a core:shell ratio of 1.5:5 and MD:GA ratio of 4:6 was selected as the optimized one with a loading capacity of 17.67%, encapsulation efficiency of 76.58%, encapsulation yield of 35.69%, and tannin concentration of 14.46 g/100 g. Moreover, in vitro release under varying pH of the optimized formulation was carried out with results that could improve the use of microencapsulated condensed tannins in animal nutrition for the biofortification of derivates.

Dataset Information

ITC and NMR Analysis of the Encapsulation of Fatty Acids within a Water-Soluble Cavitand and its Dimeric Capsule.

Publications

ITC and NMR Analysis of the Encapsulation of Fatty Acids within a Water-Soluble Cavitand and its Dimeric Capsule.

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