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Properties of cationic monosubstituted tetraalkylammonium cyclodextrin derivatives - their stability, complexation ability in solution or when deposited on solid anionic surface.

ABSTRACT: The thermal stability of the monosubstituted cationic cyclodextrin (CD) derivatives PEMEDA-?-CD and PEMPDA-?-CD, which differ in their substituent linker length (ethylene and propylene, respectively), was studied via (1)H NMR experiments. PEMPDA-?-CD exhibited higher resistance towards the Hofmann degradation and was chosen as a more suitable host molecule for further studies. Inclusion properties of PEMPDA-?-CD in solution with a series of simple aromatic guests (salicylic acid, p-methoxyphenol and p-nitroaniline) were determined by isothermal titration calorimetry (ITC) and compared to the native ?-CD. Permanently charged cationic CD derivatives were successfully deposited on the anionic solid surface of polymeric Nafion(®) 117 membrane via electrostatic interactions. Deposition kinetics and coverage of the surface were determined by ELSD. Finally, the ability of the CD derivatives bound to the solid surface to encapsulate aromatic compounds from aqueous solution was measured by UV-vis spectroscopy. The obtained results are promising for future industrial applications of the monosubstituted ?-CD derivatives, because the preparation of cationic CD derivatives is applicable in large scale, without the need of chromatographic purification. Their ionic deposition on a solid surface is simple, yet robust and a straightforward process as well.

SUBMITTER: Popr M

PROVIDER: S-EPMC4362307 | biostudies-literature | 2015

REPOSITORIES: biostudies-literature

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Properties of cationic monosubstituted tetraalkylammonium cyclodextrin derivatives - their stability, complexation ability in solution or when deposited on solid anionic surface.

Popr Martin M Filippov Sergey K SK Matushkin Nikolai N Dian Juraj J Jindřich Jindřich J

Beilstein journal of organic chemistry 20150202

The thermal stability of the monosubstituted cationic cyclodextrin (CD) derivatives PEMEDA-β-CD and PEMPDA-β-CD, which differ in their substituent linker length (ethylene and propylene, respectively), was studied via (1)H NMR experiments. PEMPDA-β-CD exhibited higher resistance towards the Hofmann degradation and was chosen as a more suitable host molecule for further studies. Inclusion properties of PEMPDA-β-CD in solution with a series of simple aromatic guests (salicylic acid, p-methoxyphenol ...[more]

PMID: 25815069

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Project description:The goal of the present study was the evaluation of the fatty acid (FA) profile of lipid fraction from dry common beans (Phaseolus vulgaris L.) (CBO) harvested from North-East (NE) and South-West (SW) of Romania and to protect against thermal and oxidative degradation of the contained omega-3 and omega-6 polyunsaturated fatty acid (PUFA) glycerides by ?-cyclodextrin (?-CD) nanoencapsulation, using kneading method. The most abundant FAs in the CBO samples were PUFAs, according to gas chromatography-mass spectrometry (GC-MS) analysis. Linoleic acid (methyl ester) was the main constituent, having relative concentrations of 43.4 (±1.95) % and 35.23 (±0.68) % for the lipid fractions separated from the common beans harvested from the NE and SW of Romania, respectively. Higher relative concentrations were obtained for the omega-3 ?-linolenic acid methyl ester at values of 13.13 (±0.59) % and 15.72 (±0.30) % for NE and SW Romanian samples, respectively. The omega-3/omega-6 ratio consistently exceeds the lower limit value of 0.2, from where the PUFA glyceride mixture is valuable for the human health. This value was 0.32 (±0.02) for the NE samples and significantly higher for the CBO-SW samples, 0.51 (±0.01). These highly hydrophobic mixtures especially consisting of PUFA triglycerides provide ?-CD complexes having higher thermal and oxidative stability. Kneading method allowed obtaining ?-CD/CBO powder-like complexes with higher recovery yields of >70%. Thermal analyses of complexes revealed a lower content of hydration water (3.3-5.8% up to 110°C in thermogravimetry (TG) analysis and 154-347 J/g endothermal effect in differential scanning calorimetry (DSC) analysis) in comparison with the ?-CD hydrate (12.1% and 479.5-480 J/g, respectively). These findings support the molecular inclusion process of FA moieties into the ?-CD cavity. Attenuated total reflectance-Fourier transform infrared spectroscopy (ATR-FTIR) analysis reveals the formation of the ?-CD/CBO inclusion complexes by restricting the vibration and bending of some bonds from the host and guest molecules. Moreover, powder X-ray diffractometry (PXRD) analysis confirm the formation of the host-guest complexes by modifying the diffractograms for ?-CD/CBO complexes in comparison with the ?-CD and ?-CD + CBO physical mixtures. A significant reduction of the level of crystallinity from 93.3 (±5.3) % for ?-CD to 60-60.9% for the corresponding ?-CD/CBO complexes have been determined. The encapsulation efficiency (EE), the profile of FAs, as well as the controlled release of the encapsulated oil have also been evaluated. The EE was >40% in all cases, the highest value being obtained for ?-CD/CBO-SW complex. The SFA content increased, while the unsaturated FA glycerides had lower relative concentrations in the encapsulated CBO samples. It can be emphasized that the main omega-3 FA (namely ?-linolenic acid glycerides) had close concentrations in the encapsulated and raw CBOs (13.13 (±0.59) % and 14.04 (±1.54) % for non-encapsulated and encapsulated CBO-NE samples, 15.72 (±0.30) % and 12.41 (±1.95) % for the corresponding CBO-SW samples, respectively). The overall unsaturated FA content significantly decreased after complexation (from 19.03-19.16% for the raw CBOs to 17.3-17.7% for encapsulated oils in the case of MUFAs, and from 55.7-58.8% to 35.13-43.36% for PUFAs). On the other hand, the omega-3/omega-6 ratio increased by ?-CD nanoencapsulation to 0.51 (±0.07) and 0.76 (0.26) for ?-CD/CBO-NE and ?-CD/CBO-SW complexes, respectively. As a conclusion, the lipid fractions of the Romanian common beans are good candidates for ?-CD complexation and they can be protected against thermal and oxidative degradation in common beans based food products such as functional foods or food supplements using natural CDs.

Dataset Information

Properties of cationic monosubstituted tetraalkylammonium cyclodextrin derivatives - their stability, complexation ability in solution or when deposited on solid anionic surface.

Publications

Properties of cationic monosubstituted tetraalkylammonium cyclodextrin derivatives - their stability, complexation ability in solution or when deposited on solid anionic surface.

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