Enhancement of the oral bioavailability of isopropoxy benzene guanidine though complexation with hydroxypropyl-β-cyclodextrin

Lu, Yixing; Yang, Liuye; Zhang, Wanying; Xie, Shiting; Zhao, Fei; Peng, Xianfeng; Qin, Zhan-Fen; Zeng, Dongping; Zeng, Zhenling

doi:10.1080/10717544.2022.2118400

Cited by 7 publications

(2 citation statements)

References 28 publications

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“…The BS diagram indicates an initial increase in apparent solubility, followed by a plateau evolution and the diagram is B I if the complex formed is insoluble. 28 The diagram o β-CD appears linear or concentrations below 10 mM. Our result is similar to that of Savic et al who found an AL-type diagrams with β-CD and HP β-CD.…”

Section: Study Of Phase Solubilitysupporting

confidence: 92%

Potential of Native Cyclodextrins and L-Lysine for Enhancing Ellagic Acid Aqueous Solubility

Nyamba,

Sombie,

Lechanteur

et al. 2024

IJDDT

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This study aimed to examine the influence of β cyclodextrin (βCD) and γ cyclodextrin (γCD) alone and in combination with L-lysine on ellagic acid (EA) solubility. Indeed, complexation with cyclodextrins can be used to improving the solubility of drugs poorly soluble in water such as EA. EA is a Biopharamceutical Classification System (BCS) IV bioactive polyphenol with numerous therapeutic activities, including antimalarial activities. However, its unfavorable physicochemical properties limit its therapeutic use. Therefore, after a phase solubility study, we successfully prepared EA-βCD and γ CD binary solid complexes using the freeze-drying technique. Methods including proton nuclear magnetic resonance (1H-NMR) analysis and fourier-transform infrared (FTIR) spectroscopy were used to characterize the inclusion behaviors of the complexes of EA with cyclodextrins both in solution and solid forms. The results of the phase solubility study indicated Ap-type diagrams of EA with the two cyclodextrins (CDs). The solubility of EA was multiplied by 9.92 and 2.98 in the presence of γCD and βCD respectively. Moreover, the complexes characterization by FTIR spectroscopy revealed the involvement of the C=O and EA OH groups in the interaction with the CDs. The results of NMR spectroscopic characterization revealed that the formation of EA inclusion complexes with βCD was partial. However, these results did not indicate the appearance of EA inclusion complexes with γCD. These relatively modest results in terms of increased EA solubility, obtained with cyclodextrins, prompted us to use a third compound, l-lysine, to enhance CDs complexation. Thus, the formation of ternary complexes led to a very significant increase EA solubility. Indeed, the incorporation of EA into EA-L-lysine-βCD and γ CD complexes increased its water solubility at pH 7.4 by a factor of 555 and 663, respectively.

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Section: Study Of Phase Solubilitysupporting

confidence: 92%

Potential of Native Cyclodextrins and L-Lysine for Enhancing Ellagic Acid Aqueous Solubility

Nyamba,

Sombie,

Lechanteur

et al. 2024

IJDDT

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“…α-CD and γ-CD exhibited a series of strong and sharp diffraction peaks, indicating that these two natural CDs existed in crystalline form ( Figure 3 A,C). In contrast, HP-β-CD was amorphous, displaying a diffuse halo pattern, as shown in Figure 3 B [ 38 ]. In the diffraction patterns of three CRT/CD PMs, peaks derived from the CRT crystal and three natural CDs were observed, which could be a simple superposition of the drug and each CD.…”

Section: Resultsmentioning

confidence: 99%

Preparation of trans-Crocetin with High Solubility, Stability, and Oral Bioavailability by Incorporation into Three Types of Cyclodextrins

Liu,

Xiao,

Zang

et al. 2023

Pharmaceutics

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Crocetin (CRT), an active compound isolated from saffron, exhibits several pharmacological activities, including anti-tumor and immune-regulatory activities, and is effective against myocardial ischemia and coronary heart disease; however, its low stability and solubility limit its clinical application. Therefore, we investigated CRT inclusion complexes (ICs) with three cyclodextrins—α-CD, HP-β-CD, and γ-CD—suitable for oral administration prepared using an ultrasonic method. Fourier transform infrared spectroscopy and powder X-ray diffraction indicated that the crystalline state of CRT in ICs disappeared, and intermolecular interactions were observed between CRT and CDs. 1H nuclear magnetic resonance and phase solubility studies confirmed CRT encapsulation in the CD cavity and the formation of ICs. In addition, we observed the morphology of ICs using scanning electron microscopy. All ICs showed a high drug encapsulation efficiency (approximately 90%) with 6500–10,000 times better solubilities than those of the pure drug. CRT showed rapid dissolution, whereas pure CRT was water-insoluble. The formation of ICs significantly improved the storage stability of CRT under heat, light, and moisture conditions. Further, the peak time of CRT in rats significantly decreased, and the relative bioavailability increased by approximately 3–4 times. In addition, the oral bioavailability of CRT IC was evaluated. Notably, the absorption rate and degree of the drug in rats were improved. This study illustrated the potential applications of CRT/CD ICs in the food, healthcare, and pharmaceutical industries, owing to their favorable dissolution, solubility, stability, and oral bioavailability.

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Delivery of soluble ethinylestradiol complex by pH‐responsive core‐shell composite hydrogel capsules

Gong

Jiang

Gao

et al. 2023

J of Applied Polymer Sci

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Ethinylestradiol (EE) is a potent estrogen widely used to treat diseases such as breast cancer, prostate cancer, and menopausal syndrome. The poor aqueous solubility of EE leads to erratic oral absorption, resulting in suboptimal plasma levels. Developing a formulation to enhance the solubility of EE in the gastrointestinal tract would be beneficial to increase the bioavailability of EE. Thereafter, we prepare diethylenetriamine-β-cyclodextrin/ethinylestradiol (DETA-β-CD/EE) complex, aiming to increase the solubility of EE in water, and design and prepare core-shell composite hydrogel capsules with aldocellulose and hydroxyethyl cellulose as the core and sodium alginate as the shell. The stability, swelling, drug release behavior and biocompatibility of the core-shell hydrogel capsules are carefully investigated. And the results show that the prepared hydrogel capsules have the controlled and sustained release ability of soluble DETA-β-CD/ EE, can achieve pH-responding to intestinal fluid, and are non-toxic to normal human cells.

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Enhancement of the oral bioavailability of isopropoxy benzene guanidine though complexation with hydroxypropyl-β-cyclodextrin

Cited by 7 publications

References 28 publications

Potential of Native Cyclodextrins and L-Lysine for Enhancing Ellagic Acid Aqueous Solubility

Potential of Native Cyclodextrins and L-Lysine for Enhancing Ellagic Acid Aqueous Solubility

Preparation of trans-Crocetin with High Solubility, Stability, and Oral Bioavailability by Incorporation into Three Types of Cyclodextrins

Delivery of soluble ethinylestradiol complex by pH‐responsive core‐shell composite hydrogel capsules

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