Characterization of the inclusion interaction between prednisolone and di-O-methyl-β-cyclodextrin: Spectroscopic methods and molecular modeling

Shi, Jie‐Hua; Chen, Ke; Xu, Yan

doi:10.1016/j.molliq.2014.01.023

Cited by 11 publications

(13 citation statements)

References 38 publications

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“…Additionally, the other characteristic peaks of prednisolone at about 1406, 1369, and 1303 cm −1 (δO−H and ωC−H) 63 have disappeared and all these observation can be attributed to the IC formation with HPβCD. 35 On the other hand, broadening, shifting, or disappearance are not detected for the same peaks of prednisolone in the FTIR spectrum of pullulan/ prednisolone nanofibrous webs, confirming the physical mixture of the polymeric matrix and drug molecules (Figure 4b).…”

Section: Resultsmentioning

confidence: 73%

“…For this, prednisolone and the nanofibrous samples are dissolved in DMSO-d 6 to ensure the full dissolution of all components. The characteristic peaks of prednisolone, HPβCD, and pullulan located, respectively, at 5.75−7.50 ppm (H-a,b,c), 35 1.03 ppm (−CH 3 ), 65 and 6.52−6.76 ppm (−OH) 66 have been integrated and proportioned to calculate the approximate prednisolone amount in nanofibrous webs of HPβCD/prednisolone−IC and pullulan/prednisolone. It has been detected from the 1 H-NMR results that the initial prednisolone content (∼10%, w/w), which has been used to prepare the electrospinning solution, has been effectively preserved for both electrospun nanofibrous webs.…”

Section: Resultsmentioning

confidence: 99%

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Orally Fast Disintegrating Cyclodextrin/Prednisolone Inclusion-Complex Nanofibrous Webs for Potential Steroid Medications

et al. 2021

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Prednisolone is a widely used immunosuppressive and anti-inflammatory drug type that suffers from low aqueous solubility and bioavailability. Due to the inclusion complexation with cyclodextrins (CDs), prednisolone's drawbacks that hinder its potential during the administration can be eliminated effectively. Here, we have early shown the electrospinning of free-standing nanofibrous webs of CD/prednisolone inclusion complexes (ICs) in the absence of a polymer matrix. In this study, hydroxypropylbeta-CD (HPβCD) has been used to form ICs with prednisolone and generate nanofibrous webs with a drug loading capacity of ∼10% (w/w). Pullulan/prednisolone nanofibrous webs have been also fabricated as a control sample having the same drug loading (∼10%, w/w). It has been demonstrated that prednisolone has been found in an amorphous state in the HPβCD/prednisolone nanofibrous web due to inclusion complexation, while it has retained its crystal structure in the pullulan/prednisolone nanofibrous web. Therefore, the HPβCD/prednisolone IC nanofibrous web has shown a faster and enhanced release profile and superior disintegration feature in artificial saliva than the pullulan/ prednisolone nanofibrous web. The complexation energy calculated using ab initio modeling displayed a more favorable interaction between HPβCD and prednisolone in the case of a molar ratio of 2:1 than 1:1 (CD: drug). Here, the HPβCD/prednisolone IC nanofibrous web has been developed without using a toxic component or solvent to dissolve drug molecules and boost drug loading in amorphous nature. The investigation of IC nanofibrous webs has been conducted to formulate a promising alternative to the orally disintegrating tablet formulation of prednisolone in the market. The nanofibrous structure and the improved physicochemical properties of prednisolone arising with the complexation might ensure a faster disintegration and onset of action against commercially available and orally disintegrating delivery systems during the desired treatment.

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Section: Resultsmentioning

confidence: 73%

Section: Resultsmentioning

confidence: 99%

Orally Fast Disintegrating Cyclodextrin/Prednisolone Inclusion-Complex Nanofibrous Webs for Potential Steroid Medications

et al. 2021

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“…Molecules 2019, 24, x FOR PEER REVIEW 3 of 15 GSE through hydrogen bonding and Van der Waals forces [26]. The encapsulation efficiency of inclusion complexes was improved at the molar ratio of 1:2, which is maybe due to GSE's ability to adhere to the surface of the inclusion complex.…”

Section: Ftir Spectramentioning

confidence: 99%

“…The results indicated that the HP-β-CD/GSE inclusion complex had the best effect at the molar ratio of 1:0.5. This probably occurs as the hydrophobic cavity of HP-β-CD molecule had enough space to encapsulate and interact with GSE through hydrogen bonding and Van der Waals forces [26]. The encapsulation efficiency of inclusion complexes was improved at the molar ratio of 1:2, which is maybe due to GSE's ability to adhere to the surface of the inclusion complex.…”

Section: Introductionmentioning

confidence: 99%

Preparation and Characterisation of Polyphenol-HP-β-Cyclodextrin Inclusion Complex that Protects Lamb Tripe Protein against Oxidation

Lidan

Liu

et al. 2019

Molecules

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Grape seed extract (GSE) displays strong antioxidant activity, but its instability creates barriers to its applications. Herein, three HP-β-CD/GSE inclusion complexes with host–guest ratios of 1:0.5, 1:1, and 1:2 were successfully prepared by co-precipitation method to improve stability. Successful embedding of GSE in the HP-β-CD cavity was confirmed by fourier-transform infrared spectroscopy (FTIR), X-ray diffraction (XRD), differential scanning calorimetry (DSC), and scanning electron microscopy (SEM) analyses. The Autodock Tools 1.5.6 was used to simulate the three-dimensional supramolecular structure of the inclusion complex of 2-hydroxypropyl-β-cyclodextrin and grape seed extract (HP-β-CD/GSE) by molecular docking. The MALDI-TOF-MS technology and chemical database Pubchem, and structural database PDB were combined to reconstitute the three-dimensional structure of target protein. The binding mode of the HP-β-CD/GSE inclusion complex to target protein was studied at the molecular level, and the antioxidant ability of the resulting HP-β-CD/GSE inclusion complexes was investigated by measuring 2,2-diphenyl-1-picrylhydrazyl (DPPH) free radical scavenging. The effects of HP-β-CD/GSE on myofibrillar protein from lamb tripe were also investigated under oxidative conditions. The positions and interactions of the binding sites of HP-β-CD/GSE inclusion complexes and target protein receptors were simulated by molecular docking. The results showed that HP-β-CD/GSE inclusion complexes were successfully prepared, optimally at a molar ratio of 1:2. At low (5 μmol/g) to medium (105 μmol/g) concentrations, HP-β-CD/GSE inclusion complexes decreased the carbonyl content, hydrophobicity, and protein aggregation of myofibrillar protein from lamb tripe, and increased the sulphydryl content. Furthermore, high concentration (155 μmol/g) of HP-β-CD/GSE inclusion complexes promoted protein oxidation.

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“…Having a shape like truncated cone with a hydrophilic external surface and a hydrophobic central cavity, CDs are capable of creating inclusion complexes with various molecules by including them into the cavity [6,7,8,9,10]. The driving forces for complex formation are van der Waals, hydrophobic or hydrogen bond interactions [11,12].…”

Section: Introductionmentioning

confidence: 99%

NMR Study on the Inclusion Complexes of β-Cyclodextrin with Isoflavones

et al. 2016

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Abstract:The structure of the inclusion complexes of β-cyclodextrin (β-CD) with daidzein and daidzin in D 2 O were investigated using NMR spectroscopy. For the β-CD and daidzein system, two types of 1:1 complexes were formed with the daidzein deeply inserted into the CD cavity with different orientations. For the β-CD/daidzin system, a 1:1 complex was formed with the flavonoid part of daidzin entering the CD cavity from the wide rim. The inclusion complexes determined by NMR were constructed using molecular docking. Furthermore, the mixture of puerarin, daidzein and daidzin, which are the major isoflavonoid components present in Radix puerariae, was analyzed by diffusion-ordered spectroscopy (DOSY) alone and upon addition of β-CD in order to mimic chromatographic conditions and compare their binding affinities.

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Characterization of the inclusion interaction between prednisolone and di-O-methyl-β-cyclodextrin: Spectroscopic methods and molecular modeling

Cited by 11 publications

References 38 publications

Orally Fast Disintegrating Cyclodextrin/Prednisolone Inclusion-Complex Nanofibrous Webs for Potential Steroid Medications

Orally Fast Disintegrating Cyclodextrin/Prednisolone Inclusion-Complex Nanofibrous Webs for Potential Steroid Medications

Preparation and Characterisation of Polyphenol-HP-β-Cyclodextrin Inclusion Complex that Protects Lamb Tripe Protein against Oxidation

NMR Study on the Inclusion Complexes of β-Cyclodextrin with Isoflavones

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