The formation of a host-guest inclusion complex system between β-cyclodextrin and baicalin and its dissolution characteristics

Li, Jing; Jiang, Qi; Deng, Peihong; Chen, Qian; Yu, Miao; Shang, Jinsai; Li, Wei

doi:10.1111/jphp.12708

Cited by 39 publications

(17 citation statements)

References 34 publications

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“…On the other hand, the findings obtained from phase solubility diagrams at different temperatures ( Figure 3 (A-1,B-1)) confirmed that the oxyresveratrol solubility in the presence of β-CD and HP-β-CD increased as the temperature increment, which might be attributed to the release of bound water molecules inside the CD cavity at higher temperature [ 26 ]. The K F values of both two CDs decreased with temperature rising, from 1897.54 ± 81.14 M −1 to 197.74 ± 61.29 M −1 and 35,864.72 ± 3415.89 M −1 to 507.61 ± 43.78 M −1 for oxyresveratrol-β-CD and oxyresveratrol-HP-β-CD in 20 °C and 60 °C, respectively ( Figure 3 (A-2,B-2)), different from the previous report [ 27 ]. The results indicated that the tendency to form inclusion was reduced, which might be attributed to the fact that hydrogen bonds are weakened by heating [ 19 , 20 , 21 ].…”

Section: Resultscontrasting

confidence: 75%

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Encapsulation Mechanism of Oxyresveratrol by β-Cyclodextrin and Hydroxypropyl-β-Cyclodextrin and Computational Analysis

Zheng

Zhu

et al. 2017

Molecules

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In this study, the encapsulation mechanism of oxyresveratrol and β-cyclodextrin (β-CD) and hydroxypropyl-β-cyclodextrin (HP-β-CD) was studied. As this research shows, oxyresveratrol and two cyclodextrins (CDs) were able to form inclusion complexes in a 1:1 stoichiometry. However, the interaction with HP-β-CD was more efficient, showing up as higher encapsulation constant (KF) (35,864.72 ± 3415.89 M−1). The KF values exhibited a strong dependence on temperature and pH, which decreased as they increased. From the thermodynamic parameters (ΔH0, ΔS0, and ΔG0) of the oxyresveratrol loaded β-CD (oxyresveratrol-β-CD) and HP-β-CD (oxyresveratrol-HP-β-CD), it could be seen that the complexation process was spontaneous and exothermic, and the main driving forces between oxyrsveratrol and CDs were hydrogen bonding and van der waals force. Besides, molecular docking combined with 1H-NMR were used to explain the most possible mode of interactions between oxyresveratrol and CDs.

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Section: Resultscontrasting

confidence: 75%

“…In general, Δδ H-3 > Δδ H-5 or Δδ H-3 < Δδ H-5 indicated of partial or total inclusion of the guest inside the CD cavity [ 36 , 37 ]. It can be speculated that the guest molecule entered the CD cavity from the wide side and was directed toward the narrow side [ 27 ].…”

Section: Resultsmentioning

confidence: 99%

Encapsulation Mechanism of Oxyresveratrol by β-Cyclodextrin and Hydroxypropyl-β-Cyclodextrin and Computational Analysis

Zheng

Zhu

et al. 2017

Molecules

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“…To gain more insights into the binding mode and binding constants between Diclo and individual CDs, molecular docking between Diclo and α -, β -, γ -, and HP- β -CDs was performed. Molecular docking simulation is the best method to predict drug (guest) orientations, molecular fitting and interactions into/onto the host (CDs) hydrophobic cavity, and hydrophilic rims at the molecular level [ 30 ]. Figure 3 summarizes the molecular docking results.…”

Section: Resultsmentioning

confidence: 99%

Cyclodextrin Enhances Corneal Tolerability and Reduces Ocular Toxicity Caused by Diclofenac

Abdelkader

Fathalla

Moharram

et al. 2018

Oxidative Medicine and Cellular Longevity

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With advances in refractive surgery and demand for cataract removal and lens replacement, the ocular use of nonsteroidal anti-inflammatory drugs (NSAIDs) has increased. One of the most commonly used NSAIDs is diclofenac (Diclo). In this study, cyclodextrins (CDs), α-, β-, γ-, and HP-β-CDs, were investigated with in vitro irritation and in vivo ulceration models in rabbits to reduce Diclo toxicity. Diclo-, α-, β-, γ-, and HP-β-CD inclusion complexes were prepared and characterized and Diclo-CD complexes were evaluated for corneal permeation, red blood cell (RBCs) haemolysis, corneal opacity/permeability, and toxicity. Guest- (Diclo-) host (CD) solid inclusion complexes were formed only with β-, γ-, and HP-β-CDs. Amphipathic properties for Diclo were recorded and this surfactant-like functionality might contribute to the unwanted effects of Diclo on the surface of the eye. Contact angle and spreading coefficients were used to assess Diclo-CDs in solution. Reduction of ocular toxicity 3-fold to16-fold and comparable corneal permeability to free Diclo were recorded only with Diclo-γ-CD and Diclo-HP-β-CD complexes. These two complexes showed faster healing rates without scar formation compared with exposure to the Diclo solution and to untreated groups. This study also highlighted that Diclo-γ-CD and Diclo-HP-β-CD demonstrated fast healing without scar formation.

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“…As a result of the low bioavailability of baicalin, this seriously affected its clinical development, although many new delivery strategies have been designed and developed, including nanonization technology, phospholipid complexes, solid dispersion, inclusion complexes, and micelles (Li B. et al, 2011;Li N. et al, 2011;Yue et al, 2013;Zhang H. et al, 2016;Li et al, 2017). When compared to baicalin alone, modified preparations can improve its dissolution and solubility, which in turn further improve its targeting ability and therapeutic efficacy.…”

Section: Drug Delivery Systemsmentioning

confidence: 99%

Regulatory Mechanisms of Baicalin in Cardiovascular Diseases: A Review

et al. 2020

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Cardiovascular diseases (CVDs) is the leading cause of high morbidity and mortality worldwide, which emphasizes the urgent necessity to develop new pharmacotherapies. In eastern countries, traditional Chinese medicine Scutellaria baicalensis Georgi has been used clinically for thousands of years. Baicalin is one of the main active ingredients extracted from Chinese herbal medicine S. baicalensis. Emerging evidence has established that baicalin improves chronic inflammation, immune imbalance, disturbances in lipid metabolism, apoptosis and oxidative stress. Thereby it offers beneficial roles against the initiation and progression of CVDs such as atherosclerosis, hypertension, myocardial infarction and reperfusion, and heart failure. In this review, we summarize the pharmacological features and relevant mechanisms by which baicalin regulates CVDs in the hope to reveal its application for CVDs prevention and/or therapy.

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The formation of a host-guest inclusion complex system between β-cyclodextrin and baicalin and its dissolution characteristics

Abstract: β-cyclodextrin complex can be used as an effective formulation strategy for development of BCL-loaded delivery system with better therapeutic outcomes.

Cited by 39 publications

References 34 publications

Encapsulation Mechanism of Oxyresveratrol by β-Cyclodextrin and Hydroxypropyl-β-Cyclodextrin and Computational Analysis

Encapsulation Mechanism of Oxyresveratrol by β-Cyclodextrin and Hydroxypropyl-β-Cyclodextrin and Computational Analysis

Cyclodextrin Enhances Corneal Tolerability and Reduces Ocular Toxicity Caused by Diclofenac

Regulatory Mechanisms of Baicalin in Cardiovascular Diseases: A Review

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