Encompassment of isoeugenol in 2-hydroxypropyl-β-cyclodextrin using ultrasonication: Characterization, antioxidant and antibacterial activities

Siva, S.; Li, Changzhu; Cui, Haiying; Lin, Lin

doi:10.1016/j.molliq.2019.111777

Cited by 38 publications

(15 citation statements)

References 44 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…XRD is proposed as a useful approach to determining crystal states of the test substances, in which the new generations or changes of characteristic peaks represent the formation of the complex [ 38 , 39 ]. Figure 1 b presents the XRD spectra of α-CD, MTPITC-α-CD, CS, and CS-MTPITC-α-CD.…”

Section: Resultsmentioning

confidence: 99%

Functional Chitosan-Based Composite Film Incorporated with 3-(Methylthio) Propyl Isothiocyanate/α-Cyclodextrin Inclusion Complex for Chicken Meat Preservation

Liu

et al. 2022

Polymers

View full text Add to dashboard Cite

The 3-(Methylthio) propyl isothiocyanate (MTPITC)-loaded inclusion complex prepared by α-cyclodextrin (α-CD) was incorporated into chitosan (CS) film to fabricate a packaging material for fresh chicken meat preservation. Scanning electron microscope images indicated homogenous dispersion of the MTPITC-α-CD in CS polymer. Fourier-transform infrared and X-ray diffraction techniques revealed that MTPITC-α-CD was incorporated into the CS film matrix by the physical interactions. The introduction of MTPITC-α-CD improved the UV-vis light-blocking ability, with a slight loss of transparency. Although the water solubility and water vapor barrier capacity were not significantly influenced by the addition of MTPITC-α-CD, the antioxidant attribute was significantly enhanced. The CS-MTPITC-α-CD film displayed obvious and sustained suppressive effects against Salmonella typhimurium, with the inhibition zone diameters of 14.7 mm at 12 h and 7.3 mm at 24 h, respectively. Moreover, the quality index analysis indicated that the CS-MTPITC-α-CD film-wrapped fresh chicken, during refrigerated storage, exhibited better preservative efficacy than the control groups, with the total viable counts of 6.5 Log CFU/g, total volatile base nitrogen of 8.4 mg/100 g, pH of 6.6, thiobarbituric acid-reactive substances of 0.2 mg/kg, and the sensory score of 5 at day 16. Collectively, these results suggest that CS-MTPITC-α-CD film is a prospective packaging candidate for delaying the quality deterioration of chicken meat.

show abstract

Section: Resultsmentioning

confidence: 99%

Functional Chitosan-Based Composite Film Incorporated with 3-(Methylthio) Propyl Isothiocyanate/α-Cyclodextrin Inclusion Complex for Chicken Meat Preservation

Liu

et al. 2022

Polymers

View full text Add to dashboard Cite

show abstract

“…The value of

Δ

G is −4.14 kcal mol −1 . Negative

Δ

G indicates that EE enter the hydrophobic cavity of DETA‐β‐CD spontaneously, indicating that there is higher affinity energy between the two molecules [43–44] . According to the results of phase solubility studies, EE and DETA‐β‐CD combine with each other through host and guest encapsulation cooperation, forming a stable inclusion complex DETA‐β‐CD/EE to a large extent, suggesting a self‐assembly solubilization system of EE was established.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Characterization of Water Soluble Diethylenetriamine‐β‐Cyclodextrin/Ethinylestradiol Inclusion Complex

Gong

et al. 2022

ChemistrySelect

View full text Add to dashboard Cite

Ethinylestradiol (EE), is widely used to treat conditions such as breast cancer, prostate cancer and climacteric syndrome. However, due to the low water solubility of EE, the bioavailability of EE is low. Herein, to improve the bioavailability of EE, a hydrosoluble cyclodextrin drug carrier system, diethylenetriamine‐β‐cyclodextrin/ethinylestradiol (DETA‐β‐CD/EE) was prepared. High performance liquid chromatography (HPLC), fourier transform infrared (FTIR), 2D rotating frame overhauser effect spectroscopy (ROESY) spectrum and scanning electron microscope (SEM) were used to characterize the DETA‐β‐CD/EE. HPLC test showed that DETA‐β‐CD was the optimal host molecule, which can improve the solubility of EE to 496 mg L−1. Phase solubility indicated the formation of a soluble inclusion complex with 1 : 1 stoichiometry. In terms of practical application, the solubility and stability of DETA‐β‐CD/EE in blood was proved by dissolution rate studies. Overall, by the encapsulation in polysaccharide DETA‐β‐CD, the water solubility of EE is increased by 100 times. The establishment of hydrosoluble cyclodextrin drug carrier system provides support for the sustained release system or large dose drug delivery.

show abstract

“…βCD, HPβCD, and 4-sulfobutylated βCD (SBβCD) could effectively complex a nonsteroidal anti-inflammatory drug, salicyl salicylate (salsalate), using 60 W of 24 kHz sonication [ 48 ]. The preparation of HPβCD complexes of cumin aldehyde [ 49 ] and isoeugenol [ 50 ] used 60 W horn-type 20 kHz US irradiation and was significantly more effective than classic methods of the native form of host molecules. Resveratrol is a naturally occurring pharmacologically active and light- and oxygen-sensitive antioxidant.…”

Section: Discussionmentioning

confidence: 99%

Toward a Greener World—Cyclodextrin Derivatization by Mechanochemistry

Jicsinszky

Cravotto

2021

Molecules

View full text Add to dashboard Cite

Cyclodextrin (CD) derivatives are a challenge, mainly due to solubility problems. In many cases, the synthesis of CD derivatives requires high-boiling solvents, whereas the product isolation from the aqueous methods often requires energy-intensive processes. Complex formation faces similar challenges in that it involves interacting materials with conflicting properties. However, many authors also refer to the formation of non-covalent bonds, such as the formation of inclusion complexes or metal–organic networks, as reactions or synthesis, which makes it difficult to classify the technical papers. In many cases, the solubility of both the starting material and the product in the same solvent differs significantly. The sweetest point of mechanochemistry is the reduced demand or complete elimination of solvents from the synthesis. The lack of solvents can make syntheses more economical and greener. The limited molecular movements in solid-state allow the preparation of CD derivatives, which are difficult to produce under solvent reaction conditions. A mechanochemical reaction generally has a higher reagent utilization rate. When the reaction yields a good guest co-product, solvent-free conditions can be slower than in solution conditions. Regioselective syntheses of per-6-amino and alkylthio-CD derivatives or insoluble cyclodextrin polymers and nanosponges are good examples of what a greener technology can offer through solvent-free reaction conditions. In the case of thiolated CD derivatives, the absence of solvents results in significant suppression of the thiol group oxidation, too. The insoluble polymer synthesis is also more efficient when using the same molar ratio of the reagents as the solution reaction. Solid reactants not only reduce the chance of hydrolysis of multifunctional reactants or side reactions, but the spatial proximity of macrocycles also reduces the length of the spacing formed by the crosslinker. The structure of insoluble polymers of the mechanochemical reactions generally is more compact, with fewer and shorter hydrophilic arms than the products of the solution reactions.

show abstract

Encompassment of isoeugenol in 2-hydroxypropyl-β-cyclodextrin using ultrasonication: Characterization, antioxidant and antibacterial activities

Cited by 38 publications

References 44 publications

Functional Chitosan-Based Composite Film Incorporated with 3-(Methylthio) Propyl Isothiocyanate/α-Cyclodextrin Inclusion Complex for Chicken Meat Preservation

Functional Chitosan-Based Composite Film Incorporated with 3-(Methylthio) Propyl Isothiocyanate/α-Cyclodextrin Inclusion Complex for Chicken Meat Preservation

Synthesis and Characterization of Water Soluble Diethylenetriamine‐β‐Cyclodextrin/Ethinylestradiol Inclusion Complex

Toward a Greener World—Cyclodextrin Derivatization by Mechanochemistry

Contact Info

Product

Resources

About