beta-cyclodextrin (CD)

Kenaf (Hibiscus cannabinus L.) seed oil contains high nutrition value, suggesting its potential applications in food and nutraceutical fields. However, the poor water solubility and stability strictly limit its applications. A good physical stability of kenaf seed oil-in-water nanoemulsions stabilised by sodium
caseinate, Tween 20 and b-cyclodextrin complexes were produced using high pressure homogeniser. A simple model of two-stage dynamic in vitro digestion was employed to investigate the releasing rate of bioactive compounds from kenaf seed oil-in-water nanoemulsions, compared to unencapsulated bulk oil. The particles size and structural changes during digestion were also evaluated. Digested nanoemulsions showed good lipid digestion (85.25%), good bioaccessibility of antioxidants (tocopherols and total phenolic contents) and lower degradation rate of phytosterols compared to digested bulk oil. This study provides good information about the characteristic and release behaviour of formulated kenaf seed oil- in-water nanoemulsions, which is important for the future application in food and nutraceutical industries.

The formation of a host-guest inclusion complex
of the antiparasitic drug nitazoxanide (NTZ) with
b-cyclodextrin (b-CD) in aqueous solution has been characterized
by electrochemical methods, cyclic and
differential pulse voltammetry, and UV-Vis absorption
spectroscopy. The nature of the host-guest inclusion complex
between NTZ and b-CD has been elucidated. The
experimental results confirmed the existence of 1:1 inclusion
complex of NTZ with b-CD. The binding constants
describing the extent of formation of the complexes have
been determined, using Benesi-Hildebrand plots, using
voltammetry and UV-Vis spectroscopy. NTZ exhibits an
affinity for b-CD. A special configuration of the complex
has been proposed.

The objectives of the reviews are the collection, concise description, comparison and evaluation of the various chromatographic technologies except liquid chromatography using natural and modified cyclodextrins for the increase the seperation capacity of various chromatographic separation systems.

Kenaf seed oil-in-water nanoemulsions stabilised by sodium caseinate, Tween 20 and-cyclodextrin complexes were produced using high pressure homogeniser. This formulation has been shown to possess good lipid digestion and increased bioaccessibility of tocopherols and total phenolic contents. However, its physicochemical and oxidative stability during storage was unknown. Therefore, the main objectives of this study were to evaluate the effects of three storage temperatures (4 • C ± 2 • C, 25 • C ± 2 • C and 40 • C ± 2 • C) on the physicochemical, oxidative and antioxidant stability of formulated kenaf seed oil-in-water nanoemulsions. The results showed that nanoemulsions stored at 4 • C had maintained the highest stability with the highest zeta-potential value (−36.6 mV), lowest changes of PDI and pH over 12 weeks of storage. It also presented the lowest reduction of polyunsaturated fatty acids (PUFA) over the course of storage period. In contrast, nanoemulsions that stored at 40 • C exhibited lowest stability with the lowest zeta-potential (−27.3 mV). Sediment was observed in 8 weeks of storage and it had the highest reduction of PUFA. Total phenolic contents in nanoemulsions that stored at 4 • C and 25 • C showed decreasing trend during the storage period, except for nanoemulsions that stored at 40 • C showed a significant increase (p < 0.05) in the first week of storage, but subsequently also displayed decreasing trend. The overall results showed that nanoemulsions that stored at 4 • C and 25 • C were stable for up to 8 weeks of storage. Nanoemulsions that stored under accelerated storage temperature of 40 • C were stable for 1 week, which is equivalent to 28 days at room temperature (RT) based on Arrhenius equation. The results of this study could provide better understanding of the storage stability of kenaf seed oil-in-water nanoemulsions under different storage temperatures. It could be served as a predictive model to estimate its shelf-life.

In this study, kenaf (Hibiscus cannabinus L.) seed oil-in-water nanoemulsions stabilized with sodium caseinate, Tween 20 and b-cyclodextrin complexes were produced using high pressure homogenizer. Emulsifying conditions, including concentration of optimized emulsifier mixtures and the addition sequence of b-cyclodextrin (b-CD) were studied. In addition, process parameters, namely homogeniza-tion pressure (16,000e28,000 psi) and homogenization cycles (3e5 cycles) were optimized to produce high physical stability of kenaf seed oil-in-water nanoemulsions. Emulsifier concentration of 10% (w/w) with b-CD on the primary emulsion was successfully optimized, which showed great enhancement on the stability of kenaf seed oil-in-water nanoemulsions to environmental stresses. The optimized process parameters was found to be 28,000 psi for 4 cycles, which produced nanoemulsions with 122.2 nm, 0.147, and À46.6 mV of particle size, PDI, and zeta-potential, respectively. It showed good stability for up to 6 weeks of storage at 25 C ± 2 C. The present study showed that the production of stable kenaf seed oil-in-water nanoemulsions using high pressure homogenizer is feasible and potential for large scale manufacturing.

The quantitative structure-activity relationship (QSPR) model was formulated to quantify values of the binding constant (lnK) of a series of ligands to beta-cyclodextrin (β-CD). For this purpose, the multivariate adaptive regression splines (MARSplines) methodology was adopted with molecular descriptors derived from the simplified molecular input line entry specification (SMILES) strings. This approach allows discovery of regression equations consisting of new non-linear components (basis functions) being combinations of molecular descriptors. The model was subjected to the standard internal and external validation procedures, which indicated its high predictive power. The appearance of polarity-related descriptors, such as XlogP, confirms the hydrophobic nature of the cyclodextrin cavity. The model can be used for predicting the affinity of new ligands to β-CD.

Nome: centrocongressiunical password: unical72 IX Congresso Nazionale AIAr Un ponte tra Arte e Scienza: passato, presente e prospettive future Arcavacata di Rende 9-11 Marzo 2016 Mercoledì 9 marzo 8.(a)TecnArt S.r.l. e INFN Torino,(b)Univ. di Torino e INFN Torino,(c)Univ. di Firenze (d)INFNFirenze, (e)WoodIdLab,Torino,(f)Sopr. per i beni e le attività culturali, Patrimonio archeologico, Valle d'Aosta, (g)Archeos S.a.s., Aosta 12.00-12.20

Local anesthetics (LA) are among the most important pharmacological compounds used to attenuate or eliminate pain. However, systemic toxicity is still a limitation for LA application, especially for ester-type drugs, such as tetracaine (TTC) that presents poor chemical stability (due to hydrolysis by plasma esterases). Several approaches have been used to improve LA pharmaceutical properties, including the employment of drug-delivery systems. Here we used beta- cyclodextrin (β-CD) or hydroxypropyl-beta-cyclodextrin (HP-β-CD) to develop two new TTC formulations (TTC:β-CD and TTC:HP-β-CD). The inclusion complexes formation, in a 1:1 stoichiometry, was con rmed by di erential scanning calorimetry, X-ray di raction, UV-VIS absorption and  uorescence. Nuclear magnetic resonance (DOSY experiments) revealed that TTC association with HP-β-CD is stronger (Ka=1200mol/L−1) than with β-CD (Ka=845mol/L−1).
Moreover, nuclear Overhauser e ect (NOE) experiments provided information on the topology of the complexes, where TTC aromatic ring is buried inside the CD hydrophobic cavity. In vitro tests with 3T3  broblast cells culture revealed that complexation decreased TTC cytotoxicity. In addition, the total analgesic e ect of TTC, tested in rats through the infraorbital nerve test, was improved in 36% with TTC:β-CD and TTC:HP-β-CD. In conclusion, these formulations presented potential for future clinical use, by reducing the toxicity and increasing the antinociceptive e ect of tetracaine.

Olive leaf (OLL) extracts contain a high load of antioxidant polyphenols with significant pharmacological potency. In this study, the use of a novel natural deep eutectic solvent enabled the effective extraction of OLL polyphenols and their testing as radical scavengers, in the presence or absence of methyl β-cyclodextrin (m-β-CD), using descriptive kinetics. Testing was extended to include interactions with ascorbic acid—a natural powerful antioxidant—by implementing a response surface methodology. The kinetic study showed that m-β-CD may hinder the radical scavenging effect of OLL extracts, yielding lower stoichiometry upon reaction with the radical probe 2,2-diphenyl-1-picrylhydrazy (DPPH). The extension of the reaction time to determine the total stoichiometry confirmed this effect. As a further concurrence, the interactions of OLL extracts with ascorbic acid showed lower radical scavenging performance in the presence of m-β-CD. These results were discussed on the grounds of the role that m-β-CD may play in similar systems.

The characterization of the original chemical structure and induced changes of micro-and macro-molecules using analytical techniques with concise and detailed outcomes is potentially one of the major challenges for food scientists. To this end, the non-invasive nuclear magnetic resonance (NMR) technique can play a significant role through employment of different NMR methods. The Nuclear Overhauser effect (NOE) and rotating-frame Overhauser effect (ROE) techniques are powerful NMR methods that have attracted great interest because they provide precise information about the three dimensional spatial structure of the molecules, as well as about possible chemical reactions and interactions. Scope and approach In this article, we reviewed the basic principles as well as applications of two NMR techniques: Nuclear Overhauser effect spectroscopy (NOESY) and rotating-frame Overhauser effect spectroscopy (ROESY). Hereby, we focused mainly on the applications and importance of these techniques in food science research. Both the structural (configuration and conformation) changes and the complexes formed by interacting compounds could be better studied using these techniques. Key findings and conclusions The inter-and intra-molecular interactions within food-based ingredient mixtures, as well as configurational and conformational analyses can be more efficiently studied with the aid of NOESY and ROESY. These methods as complementary analysis tools can be exploited for the straightforward elucidation of the spatial proximity of either novel, native or modified compounds. In the future, these techniques may be helpful to better understand the interaction between polymers, such as protein-polysaccharide interactions.

b-cyclodextrin (b-CD) is biocompatible and biodegradable polymer having inherent hydrophobic cavities, thus is widely used as a drug nanocarrier for less water soluble drugs. Naringin is a pharmacologically active important compound however, its therapeutic efficacy is limited due to its unique physicochemical properties including lower aqueous solubility. This study reports improvement in bactericidal potentials of naringin through construction of its nano-formulation using biocompatible b-CD. Naringin loaded b-CD NPs were prepared via solvent evaporation method and characterized using various techniques such as FTIR, UV-visible spectroscopy, AFM, DSC and TGA analysis. Tetrazolium Microplate and AFM assays were used for investigating the bactericidal potential of naringin loaded b-CD NPs. Monodispersed NPs with spherical morphology of 70.00 ± 15.06 nm mean diameter were obtained that possessed net negative surface charge of-18.20 ± 3.24 mV and were highly stable and did not change the chemical nature of the drug in various media. Antibacterial activity of naringin in b-CD NPs significantly enhanced that was authenticated by AFM, showing prominent destructive changes in the bacterial cell's morphology through destabilization of outer membrane of bacterial cells by drug loaded NPs. Results of this study suggest that the b-CD NPs of naringin could be used as a successful formulation for developing more efficacious form of the drug against various bacterial infections.

The role of beta-cyclodextrin (β-CD) in cholesterol removal primarily from mammalian cells and secondly from dairy products has been studied thoroughly in recent years. Although the physicochemical characterization of the inclusion compound of cholesterol in β-CD has been achieved by various methods, no crystal structure has been determined so far. We report here the crystal structure of the inclusion compound of cholesterol in β-CD. The inclusion complex crystallizes in the triclinic space group P1 forming head-to-head dimers which are stacked along the c-axis. One well-defined cholesterol molecule ‘axially’ encapsulated inside the β-CD dimer and 22 water molecules that stabilize the complexes in the crystalline state comprise the asymmetric unit of the structure. The dimers are arranged in an intermediate (IM) channel packing mode in the crystal. Moreover, MD simulations, at 300 and 340 K, based on the crystallographically determined coordinates of the complex show that the formed cholesterol/β-CD inclusion compound remains very stable in aqueous solution at both temperatures.

Propolis is widely recognized for its various therapeutic properties. These are attributed to its rich composition in polyphenols, which exhibit multiple biological properties (e.g., antioxidant, anti-inflammatory, anti-angiogenic). Despite its multiple benefits, oral administration of polyphenols results in low bioavailability at the action site. An alternative to face this problem is the use of biomaterials at nano-micro scale due to its high versatility as carriers and delivery systems of various drugs and biomolecules. The aim of this work is to determine if nPSi-βCD microparticles are a suitable material for the load and controlled release of caffeic acid (CA) and pinocembrin (Pin), two of the main components of a Chilean propolis with anti-atherogenic and anti-angiogenic activity. Polyphenols and nPSi-βCD microparticles cytocompatibility studies were carried out with human umbilical vein endothelial cells (HUVECs). Results from physicochemical characterization demonstrated nPSi-βCD microparticles successfully retained and controlled release CA and Pin. Furthermore, nPSi-βCD microparticles presented cytocompatibility with HUVECs culture at concentrations of 0.25 mg/mL. These results suggest that nPSi-βCD microparticles could safely be used as an alternate oral delivery system to improve controlled release and bioavailability of CA or Pin-and eventually other polyphenols-thus enhancing its therapeutic effect for the treatment of different diseases.

Title: Influence of Cyclodextrin  Complexation Method on the Physical Properties and Dissolution Profile of a BSC Class II Model Drug
Authors: Carmen Popescu1, Cody J. Wiley2, Suresh Potaraju3, Philippe Lefevre4, Liuming Zhou1, Dianne Peterson4, Linda A. Felton2
Affiliations: 
1Roquette America, Inc., 2211 Innovation Dr, Geneva, IL 60134
2University of New Mexico, College of Pharmacy, 2705 Frontier NE, Albuquerque, NM 87131
3
4Roquette Freres, Lestrem,France

Purpose: To evaluate cyclodextrin complexation methods on the physical and dissolution properties of Ibuprofen, a model BCS Class II compound.
Methods: -cyclodextrin (Kleptose®, CD) and three derivatives, two hydroxypropyl--cyclodextrins (Kleptose® HPB, HPBCD, molar degree of substitution 0.62 and Kleptose® HP, HPCD, MS=0.87) and a methylated--cyclodextrin (Crysmeb, MCD, MS=0.57) were used to complex Ibuprofen (an NSAID). Complexation methods included physical blend, kneading, spray drying and lyophilization. Based on previous phase solubility evaluation, ibuprofen displayed an AL solubilization profile and was complexed at a 1:1 molar ratio. The morphology  of the resulting powder was examined by scanning electron microscopy. Bulk and tap density of the powders was also evaluated. Drug content of the resulting powders after complexation was analyzed by HPLC. Efficiency of the production methods was calculated based on percent of theoretical drug content. Capsules containing powder equivalent to 75mg of drug were subjected to USP dissolution testing (pH 7.2 phosphate buffer, apparatus 2, paddles at 50 rpm). The quantity of drug was selected to ensure sink conditions were maintained throughout the dissolution test. Aliquots of the dissolution media were analyzed by HPLC. Dissolution testing was also conducted in 0.1N HCl media.
Results: The physical blend formulations were found to contain between 97.5 and 113% of theoretical quantity of ibuprofen. Kneading resulted in lower drug loading efficiencies, ranging from 85% for B-CD up to 96% for both HP-CD and HPB-CD. Drug loading for spray drying  ranged from 97% for B-CD up to 102% for HP-CD. Particle morphology was dependent on the complexation method. Spray drying produced the smallest particles, irrespective of CD. Interestingly, the particle size of the MCD-drug complex was smaller for the kneaded and lyophilized samples compared to other substituted CDs. Spray dried powders exhibited much lower densities compared to the kneaded material. Drug dissolution in pH 7.2 was rapid for all formulations tested, irrespective of CD, with drug release occurring within 20 minutes.

In our study, the functional features of egg yolk are going to be maintained and a low cholesterol mayonnaise product which is better for the health will be manufactured. Egg yolk cholesterol has been extracted with adsorption to β-CD which is used in food industry by forming a complex with β-CD which reflects a structure of cyclic oligosaccharide. Cholesterol reduced egg yolk used in the production of mayonnaise with different levels of cholesterol reduction (75-85 %) and different levels of xanthan gum (0.5-0.7 %) and egg yolk (4-7.5 %). The effect of cholesterol lowering process on mayonnaise has been examined by analyzing composition, color value, cholesterol level, physicochemical and rheological properties were carried out on the cholesterol reduced mayonnaise and egg yolk.

Our results showed that, the rate of cholesterol in egg yolk has been reduced 83 %. We see that; in comparison with raw and pasteurized egg yolk, cholesterol reduced egg yolk has higher carbohydrate (2.2 %), higher a value, and lower L and b values. The results that are found out as a result of the study will be able to be used in the low cholesterol, functional mayonnaise production in the industry.


Keywords: Egg yolk, Low Cholesterol Functional Mayonnaise, Rheology

The objectives of the reviews are the collection, concise description, comparison and evaluation of the various chromatographic technologies using natural and modified cyclodextrins for the increase the separation capacity of various chromatographic separation systems

The aim of the present study is to histologically evaluate the effect of various grafting materials on the periodontal tissues, and examine the signs of their biodegradation, bony-graft integration and evidence of new bone formation. Materials and Methods: three different nanocomposites were synthesized based on β-Cyclodextrin (β-CD), glycidyl methacrylate (GMA), hydroxyethylmethacrylate (HEMA) and hydroxyapatite (HA). In six healthy mongrel dogs full thickness mucoperiosteal flaps were raised on the buccal aspects to create two-wall intrabony defects at the furcation areas. The mandibular premolars on both sides received the grafting materials. Histological analysis was carried out at 1, 2 and 3 months period. The results revealed the increased proliferation rate of osteoblast cells in the presence of the nano HA fillers inside the prepared nanocomposites. The hydrogel (poly GMA-co-HEMA) used did not enhance bone formation and was not completely resorbed and replaced by bone at the end of the 3 months experiment period. Conclusion: this study demonstrated that these novel nanocomposites, especially the grafted β-CD with the copolymer (GMA-co-HEMA) in presence of the HA nanoparticles possessed a bone forming ability and may serve as a delivery vehicle for osteogenic cells and osteogenic growth factor proteins in the bone development process.