Fabrication and Characterization of Antifungal Hydroxypropyl-β-Cyclodextrin/Pyrimethanil Inclusion Compound Nanofibers Based on Electrospinning

Gao, Shuang; Feng, Weiwei; Sun, Han; Zong, Lei; Li, Xiaoming; Zhao, Li‐Xia; Ye, Fei; Fu, Ying

doi:10.1021/acs.jafc.2c01866

Cited by 32 publications

(8 citation statements)

References 51 publications

(70 reference statements)

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“…Cuminaldehyde and isoeugenol inclusion complexes with M-β-CD prepared in aqueous solution and in a solid state via the ultrasonication method increased the solubility ten and twelve times, respectively [ 47 ]. In studies on electrospinning, the water solubility of pyrimethanil was enhanced due to the inclusion of compound nanofibers preparation with HP-β-CD, whilst the solubility of difenoconazole was increased about five times in a 10 mM solution of HP-β-CD [ 48 , 49 ].…”

Section: Resultsmentioning

confidence: 99%

Cyclodextrin Derivatives as Promising Solubilizers to Enhance the Biological Activity of Rosmarinic Acid

et al. 2022

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Rosmarinic acid (RA) is a natural antioxidant with neuroprotective properties; however, its preventive and therapeutic use is limited due to its slight solubility and poor permeability. This study aimed to improve RA physicochemical properties by systems formation with cyclodextrins (CDs): hydroxypropyl-α-CD (HP-α-CD), HP-β-CD, and HP-γ-CD, which were prepared by the solvent evaporation (s.e.) method. The interactions between components were determined by X-ray powder diffraction (XRPD), differential scanning calorimetry (DSC) and Fourier Transform infrared spectroscopy (FTIR). The sites of interaction between RA and CDs were suggested as a result of in silico studies focused on assessing the interaction between molecules. The impact of amorphous systems formation on water solubility, dissolution rate, gastrointestinal (GIT) permeability, and biological activity was studied. RA solubility was increased from 5.869 mg/mL to 113.027 mg/mL, 179.840 mg/mL, and 194.354 mg/mL by systems formation with HP-α-CD, HP-β-CD, and HP-γ-CD, respectively. During apparent solubility studies, the systems provided an acceleration of RA dissolution. Poor RA GIT permeability at pH 4.5 and 5.8, determined by parallel artificial membrane permeability assay (PAMPA system), was increased; RA–HP-γ-CD s.e. indicated the greatest improvement (at pH 4.5 from Papp 6.901 × 10−7 cm/s to 1.085 × 10−6 cm/s and at pH 5.8 from 5.019 × 10−7 cm/s to 9.680 × 10−7 cm/s). Antioxidant activity, which was determined by DPPH, ABTS, CUPRAC, and FRAP methods, was ameliorated by systems; the greatest results were obtained for RA–HP-γ-CD s.e. The inhibition of acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) was increased from 36.876% for AChE and 13.68% for BChE to a maximum inhibition of the enzyme (plateau), and enabled reaching IC50 values for both enzymes by all systems. CDs are efficient excipients for improving RA physicochemical and biological properties. HP-γ-CD was the greatest one with potential for future food or dietary supplement applications.

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Section: Resultsmentioning

confidence: 99%

Cyclodextrin Derivatives as Promising Solubilizers to Enhance the Biological Activity of Rosmarinic Acid

et al. 2022

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“…The benzene ring on GA interacted with active sites Ala199 and Ala408 by Pi interactions. These hydrogen bond interactions were the most important forces between Pv and GA, enhancing the strength of the noncovalent bonds during the interaction. − These interactions enabled Pv to form a stable complex with GA, stabilizing the spatial conformation of the GA and Pv complexes . In conclusion, the above molecular docking studies provided a reasonable explanation for the interaction between Pv and GA and provided evidence for the conclusion that noncovalent complexes exhibit better antioxidant properties.…”

Section: Resultsmentioning

confidence: 63%

Covalent and Noncovalent Complexation of Phosvitin and Gallic Acid: Effects on Protein Functionality and In Vitro Digestion Properties

Jiang

Zhong

et al. 2022

J. Agric. Food Chem.

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To investigate the effects of different binding modes on the structure, function, and digestive properties of the phosvitin (Pv) and gallic acid (GA) complex, Pv was covalently and noncovalently combined with different concentrations of GA (0.5, 1.5, and 2.5 mM). The structural characterization of the two Pv–GA complexes was performed by Fourier transform infrared, circular dichroism, and LC–MS/MS to investigate the covalent and noncovalent binding of Pv and GA. In addition, the microstructure of the two Pv–GA complexes was investigated by super-resolution microscopy and transmission electron microscopy. The particle size and zeta potential results showed that the addition of GA increased the particle size and the absolute potential of Pv. The determination of protein digestibility, polyphenol content, SH and S–S group levels, sodium dodecyl sulfate-polyacrylamide gel electrophoresis, and antioxidant capacity of the digests indicated that noncovalent complexes had greater antioxidant and protective effects on polyphenols. Molecular docking revealed that GA was conjugated with Pv through hydrogen bond interactions.

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“…More specifically, the diameter of the β-CDs cavity offers the most suitable size for different compounds [ 35 , 36 ]. Although β-CDs show a lower water solubility compared to other natural and derivative cyclodextrins [ 37 , 38 , 39 ], they are considered a perfect tool in environmental remediation processes for their low cost [ 40 ]. In light of these considerations, it is worthwhile to characterize β-CDs inclusion complex with different pesticides further.…”

Section: Introductionmentioning

confidence: 99%

Inclusions of Pesticides by β-Cyclodextrin in Solution and Solid State: Chlorpropham, Monuron, and Propanil

et al. 2023

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Persistence and degradation are important factors in determining the safe use of such synthetic products, and numerous studies have been addressed to develop pesticide remediation methods aimed at ameliorating these features. In this frame, the use of different cyclodextrins (CDs) molecules has attracted considerable attention due to their well-known non-toxic nature, limited environmental impact, and capability to reduce the environmental and health risks of pesticides. CDs appear to be a valuable tool for the elimination of pesticides from polluted areas as well as for better pesticide formulations that positively influence their hydrolysis or degradation. The present work investigates the interaction between β-cyclodextrins and three commonly used pesticides (i.e., chlorpropham, monuron, and propanil) both in solution and in the solid state by means of UV-Vis, FT-IR, and X-ray powder diffractometry. We show that such interactions result in all three cases in the formation of inclusion complexes with a 1:1 stoichiometry and binding constants (Kb) of 369.9 M−1 for chlorpropham, 292.3 M−1 for monuron, and 298.3 M−1 for propanil. We also report the energy-minimized structures in silico for each complex. Our data expand and complement the available literature data in indicating CDs as a low-cost and very effective tool capable of modulating the properties that determine the environmental fate of pesticides.

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Fabrication and Characterization of Antifungal Hydroxypropyl-β-Cyclodextrin/Pyrimethanil Inclusion Compound Nanofibers Based on Electrospinning

Cited by 32 publications

References 51 publications

Cyclodextrin Derivatives as Promising Solubilizers to Enhance the Biological Activity of Rosmarinic Acid

Cyclodextrin Derivatives as Promising Solubilizers to Enhance the Biological Activity of Rosmarinic Acid

Covalent and Noncovalent Complexation of Phosvitin and Gallic Acid: Effects on Protein Functionality and In Vitro Digestion Properties

Inclusions of Pesticides by β-Cyclodextrin in Solution and Solid State: Chlorpropham, Monuron, and Propanil

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