Synthesis and characterization of inclusion complex of the vasodilator drug minoxidil with β-cyclodextrin

Objective:The aim of this work was to investigate the effect of β-cyclodextrin complexation on the solubility and hydrolysis rate of icariin.Material and Methods:The inclusion complex of icariin at the molar ratio of 1:1 was obtained by the dropping method and was characterized by differential scanning calorimetry. The solubility of icariin complex in water at 37°C was 36 times greater than that of free icariin. Enzymatic hydrolysis conditions were tested for the bioconversion of icariin by mono-factor experimental design.Methods:The inclusion complex of icariin at the molar ratio of 1:1 was obtained by the dropping method and was characterized by differential scanning calorimetry. The solubility of icariin complex in water at 37°C was 36 times greater than that of free icariin. Enzymatic hydrolysis conditions were tested for the bioconversion of icariin by mono-factor experimental design.Results:The enzymatic hydrolysis experiment showed that icariin can be transformed into baohuoside I. The optimum conditions determined were as follows: pH 5.0, 50°C, the ratio of cellulase/substrate (0.6), the concentration of icariin 20 mg/ml, and reaction time 12 h. Under these enzymatic conditions, 98.2% transforming rate of baohuoside I from icariin in inclusion complexes was obtained.ConclusionThe aqueous solubility and enzymatic hydrolysis rate of icariin were improved owing to the inclusion complexation.

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“…These results confirm that icariin in complexes exists in the amorphous state. [22] The result is in accordance with the referenced studies. [24]…”

Section: Resultssupporting

confidence: 90%

Effect of β-cyclodextrin complexation on solubility and enzymatic hydrolysis rate of icariin

et al. 2013

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“…This observation indicated that the formation of PAE-HP-b-CD complex retarded the weight loss of PAE during heating. These findings were consistent with the literature, in which the thermal stability of quest molecules was improved when it was complexed with HP-b-CD [29,30].…”

Section: Xrdsupporting

confidence: 93%

Effect of hydroxypropyl-β-cyclodextrin complexation on the aqueous solubility, structure, thermal stability, antioxidant activity, and tyrosinase inhibition of paeonol

Tsao

Tsai

et al. 2011

J Incl Phenom Macrocycl Chem

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The objective of this paper is to study the effect of hydroxypropyl-b-cyclodextrin (HP-b-CD) complexation on the aqueous solubility, structure, thermal stability, antioxidant activity, and tyrosinase inhibition of paeonol (PAE). The inclusion complex (PAE-HP-b-CD complex) of HP-b-CD and PAE was prepared by a freeze-drying method. Phase solubility tests showed that the stability constant of the inclusion complex was about 33.8 M -1 at 25°C. The experimental results of proton nuclear magnetic resonance (H-NMR) spectroscopy, differential scanning calorimetry (DSC) and X-ray diffraction (XRD) suggested that PAE was included by HP-b-CD to form the PAE-HPb-CD complex. Furthermore, the thermogravimetric analysis (TGA) results showed that the thermal stability of PAE was improved when it was complexed with HP-b-CD. Comparing the antioxidant activity of PAE with that of the PAE-HP-b-CD complex at the same concentration revealed that the complex of PAE with HP-b-CD was better able to eliminate radical. Furthermore, the experimental results revealed that the formation of a complex with HP-b-CD increased the water solubility of PAE, improving its apparent inhibitive activity of tyrosinase.

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“…As is already described in the literature, 23 when |Δδ Η3'|.|Δδ Η5'|, the guest inclusion inside the CD cavity is partial, and when |Δδ Η3'|#|Δδ Η5'|, the guest is included more deeply into the cavity. The results (Table 1) showed partial inclusion of CAP in β-CD nanoparticles and total inclusion of CAP in α-CD and HP-β-CD.…”

Section: Results and Discussion Nmrmentioning

confidence: 60%

New formulation of an old drug in hypertension treatment: the sustained release of captopril from cyclodextrin nanoparticles

Azevedo¹,

Tasic²,

Fattori³

et al. 2011

IJN

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Captopril (CAP) was the first angiotensin I-converting enzyme (ACE) inhibitor to be developed and is widely used in hypertension treatment. On the other hand, cyclodextrins (CDs) are cyclic oligosaccharides whose cone-shaped cavity allows formation of noncovalent inclusion complexes with appropriately sized guest molecules, thus modifying guest physical, chemical, and biological properties. Herein, the physicochemical characterization and in vivo ACE inhibition evaluation of seven CAP/CD complexes are reported. The inclusion complexes were prepared by spray-drying, freeze-drying, kneading, or lyophilization methods and characterized by nuclear magnetic resonance, Fourier-transformed infrared spectroscopy, X-ray diffraction, differential scanning calorimetry, and scanning electron microscopy techniques. In vivo assays compared CAP and CAP/CD complex administration (0.5 mg kg −1 or 0.09 mg kg −1 , n = 4–7) to evaluate the ACE inhibition by continuous infusion of angiotensin I (30 ng 50 μL −1 min −1 ) in conscious Wistar rats. The physicochemical analysis demonstrated complete amorphization and complexation between CAP and CDs, indicating the substitution of water molecules inside the CD cavity with CAP. During the infusion of angiotensin I, the administration of all CAP/CD complexes induced a reduction in mean arterial pressure similar to that observed upon CAP administration. The nanoparticles obtained by the kneading method (CAP/α-CD:KM) showed a potent and long-lasting inhibitory activity (∼22 hours) on the angiotensin I pressor effect. The results suggest that the inclusion complex of CAP and α-CD can function as a novel antihypertensive formulation that may improve therapeutic use of CAP by reducing its oral dose administration to once per day, thus providing better quality of life for almost 25% of the world’s population who suffer from hypertension.

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Synthesis and characterization of inclusion complex of the vasodilator drug minoxidil with β-cyclodextrin

Cited by 37 publications

References 16 publications

Effect of β-cyclodextrin complexation on solubility and enzymatic hydrolysis rate of icariin

Effect of β-cyclodextrin complexation on solubility and enzymatic hydrolysis rate of icariin

Effect of hydroxypropyl-β-cyclodextrin complexation on the aqueous solubility, structure, thermal stability, antioxidant activity, and tyrosinase inhibition of paeonol

New formulation of an old drug in hypertension treatment: the sustained release of captopril from cyclodextrin nanoparticles

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