Inclusion complexes of cannabidiol with β-cyclodextrin and its derivative: Physicochemical properties, water solubility, and antioxidant activity

Li, Hang; Chang, Senlin; Chang, Tanran; You, Ying; Wang, Xiaodong; Wang, Liwei; Yuan, Xiaofan; Tan, Minghui; Wang, Peidong; Xu, Pengwei; Gao, Weibo; Zhao, Qingsheng; Zhao, Bing

doi:10.1016/j.molliq.2021.116070

Cited by 78 publications

(51 citation statements)

References 49 publications

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“…CBD also exhibits a wide range of anti-tumor activities, which can induce programmed death of different types of cancer cells according to reports ( Olea-Herrero et al, 2009 ; Aviello et al, 2012 ; Pacher, 2013 ; Fonseca et al, 2018 ; Yang et al, 2020 ), including human prostate cancer, human breast carcinoma, human glioblastoma, human cervical cancer, human lung cancer, lymphocytic, and monocytic leukemias, endometrial cancer, pancreatic cancer. However, the poor water solubility and specificity of CBD severely limits its application in the medical field ( Li et al, 2021 ). Therefore, it is of great significance to improve the solubility and specificity of CBD.…”

Section: Introductionmentioning

confidence: 99%

Self-Assembly System Based on Cyclodextrin for Targeted Delivery of Cannabidiol

Zhu

Zhang

et al. 2021

Front. Chem.

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Cannabidiol (CBD) is one specific kind of the cannabinoid in Cannabis sativa L with a wide range of pharmacological activities. However, the poor water solubility and specificity of CBD limits its application in pharmaceutical field. For solving these problems, in this work, we successfully prepared a targeted carrier by grafting biotin (BIO) onto ethylenediamine-β-Cyclodextrin (EN-CD) in a single step to generate a functionalized supramolecule, named BIO-CD. Subsequently, an amantadine-conjugated cannabinoids (AD-CBD) was prepared and self-assembled with the BIO-CD. A series of methods were used to characterize the inclusion behavior and physicochemical properties of AD-CBD and BIO-CD. The results showed that AD-CBD entered the cavity of BIO-CD and formed a 1:1 host-guest inclusion complex. MTT assay and confocal laser scanning microscopy (CLSM) revealed that the targeting effect and anticancer activity of AD-CBD/BIO-CD inclusion complex against three human cancer cell lines were higher than BIO-CD, AD-CBD and free CBD. Moreover, the inclusion complex could release drugs under weakly acidic conditions. These results demonstrated that AD-CBD/BIO-CD inclusion complex possess excellent targeted and anticancer activity, which is hopeful to be applied in clinic as a new therapeutic approach.

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Section: Introductionmentioning

confidence: 99%

Self-Assembly System Based on Cyclodextrin for Targeted Delivery of Cannabidiol

Zhu

Zhang

et al. 2021

Front. Chem.

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“…In the case of pure HEC, CBD is adsorbed into the cryogel walls, whereas in the β-CD-modified carriers, a fraction of the CBD (47-52%) is embedded inside the β-CD cavities in the form of the inclusion "host-guest" complex. CBD spontaneously forms an inclusion complex with β-CD at a 1:1 stoichiometric ratio; this process is endothermic, and the apparent stability constants of the complex are relatively high (Ks = 315) [12]. Hence, a higher β-CD concentration leads to an increased fraction of tightly bounded cannabidiol.…”

Section: Discussionmentioning

confidence: 99%

“…This gap is certainly not insurmountable with conventional drug delivery platforms and dosing schedules. On these grounds, numerous drug delivery systems for cannabidiol based on nanocarriers or nanocomposite materials, such as self-emulsifying systems, nano-spheres, micelles, and inclusion complexes have been developed [11][12][13][14][15][16]. Since the oral route of administration for CBD has been associated with poor bioavailability, other more effective routes for sustained therapeutic delivery of CBD have been evaluated.…”

Section: Introductionmentioning

confidence: 99%

Polysaccharide Cryogels Containing β-Cyclodextrin for the Delivery of Cannabidiol

et al. 2021

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Cannabidiol (CBD) has attracted increasing interest due to its therapeutic potential for treating numerous diseases. However, CBD is very lipophilic and has very unfavorable pharmacokinetics and low bioavailability. Efforts are focused on developing drug delivery systems for enhanced solubilization and therapeutic activity of CBD. Here, we report the preparation of original super-macroporous cryogels from 2-hydroxyethyl cellulose (HEC) and β-cyclodextrin (β-CD) designed for the topical delivery of CBD. The cryogels were synthesized by photochemical crosslinking in a frozen aqueous system, purified, and then loaded with CBD. The effect of HEC/β-CD mass ratio (100:0; 50:50; 40:60 and 20:80) in the reaction mixture on the reaction efficiency, physico-mechanical properties of cryogels, drug release profile, and antineoplastic potential were evaluated in detail. The cryogels showed a bi-phasic release behavior: initial burst release in the first 3 hours followed by slower drug release which can be beneficial in the treatment of cutaneous neoplastic diseases.

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“…Cyclodextrins are water-soluble cyclic oligo-saccharides with a truncated cone-structure possessed a hydrophobic cavity and hydrophilic outer surface border [1]. Recently, the guesthost cyclodextrin complex formations were examined for many and different ligands like for example: remdesivir [2], water-soluble betulin derivatives [3], thiabendazole [4], ethinyloestradiol [5], bis(1,10-phenanthroline) silver (I) salicylate [6], oncocalyxone A [7], or β-cyclodextrinenhanced Eu 3+ luminescence aggregates with bright red fluorescence of Eu 3+ convenient for environmental detection system [8] and many others [9][10][11][12]. Reactions involving cyclodextrins are still important to the separation [13,14] and food industry [15][16][17] or other kinds of industries [18,19], but mostly to drug delivery systems for various applications in the field of medical biomaterials for example in the technology of polymers to get artificial abdominal wall prosthesis textile with improved biological and antibiotic delivery properties [20].…”

Section: Introductionmentioning

confidence: 99%

Thermodynamic Studies of Interactions between Sertraline Hydrochloride and Randomly Methylated β-Cyclodextrin Molecules Supported by Circular Dichroism Spectroscopy and Molecular Docking Results

Belica-Pacha

Daśko

Buko

et al. 2021

IJMS

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The interaction between sertraline hydrochloride (SRT) and randomly methylated β-cyclodextrin (RMβCD) molecules have been investigated at 298.15 K under atmospheric pressure. The method used—Isothermal Titration Calorimetry (ITC) enabled to determine values of the thermodynamic functions like the enthalpy (ΔH), the entropy (ΔS) and the Gibbs free energy (ΔG) of binding for the examined system. Moreover, the stoichiometry coefficient of binding (n) and binding/association constant (K) value have been calculated from the experimental results. The obtained outcome was compared with the data from the literature for other non-ionic βCD derivatives interacting with SRT and the enthalpy-entropy compensation were observed and interpreted. Furthermore, the connection of RMβCD with SRT was characterized by circular dichroism spectroscopy (CD) and complexes of βCD derivatives with SRT were characterized through the computational studies with the use of molecular docking (MD).

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Inclusion complexes of cannabidiol with β-cyclodextrin and its derivative: Physicochemical properties, water solubility, and antioxidant activity

Cited by 78 publications

References 49 publications

Self-Assembly System Based on Cyclodextrin for Targeted Delivery of Cannabidiol

Self-Assembly System Based on Cyclodextrin for Targeted Delivery of Cannabidiol

Polysaccharide Cryogels Containing β-Cyclodextrin for the Delivery of Cannabidiol

Thermodynamic Studies of Interactions between Sertraline Hydrochloride and Randomly Methylated β-Cyclodextrin Molecules Supported by Circular Dichroism Spectroscopy and Molecular Docking Results

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