Characterization of the inclusion complex of zerumbone with hydroxypropyl-β-cyclodextrin

Eid, Eltayeb E M; Abdul, Ahmad Bustamam; Suliman, Fakhr Eldin O.; Sukari, Mohd Aspollah; Abdullah, Rasedee; Fatah, Safa S.

doi:10.1016/j.carbpol.2010.10.033

Cited by 120 publications

(57 citation statements)

References 39 publications

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“…It has been demonstrated when a molecule forms an inclusion complex with a cyclodextrin, there is a shifting or a disappearance of the melting point peak 18,19 . Figure 4 presents the DSC diagrams of EB, 1:1 physical mixture and inclusion complexes.…”

Section: 3-differential Scanning Calorimetrymentioning

confidence: 99%

“…However, the XRD patterns of the co-evaporated and spray dried complexes showed a complete absence of crystalline peaks, suggesting the formation of a new structure, in which EB probably is included in the hydrophobic cavity of HP-β-CD. It is described that a lack of crystallinity is indicative of the formation of an inclusion complex [18][19][20] . 3.6.-Maximum solubility of the inclusion complexes at pH 8 EB is a basic drug whose solubility is reduced at higher pH, and this characteristic can be a drawback when the drug is administered to salmons through medicated foods.…”

Section: 4-ft-ir Spectroscopymentioning

confidence: 99%

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Preparation and Characterization of the Emamectin Benzoate/Hydroxypropyl-B-Cyclodextrin Inclusion Complex

Torres¹,

Villa²,

González³

et al. 2011

J. Chil. Chem. Soc.

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The objective of this study was to prepare an inclusion complex of the insecticide emamectin benzoate (EB) with hydroxypropyl-β-cyclodextrin (HP-β-CD) by co-evaporation and spray drying methods. The complexation of both compounds was evaluated on the aqueous and solid state using phase solubility diagrams, differential scanning calorimetry (DSC), X-Ray diffraction (XRD), Fourier transform infrared spectroscopy (FT-IR) and scanning electron microscopy (SEM). The aqueous solubility of the inclusion complexes at pH 8 had a 2-fold increase respect to the drug alone and dissolution profiles showed a rise in the dissolution rate. These results suggest that the use of HP-β-CD could be an interesting alternative to enhance the bioavailability of EB in salmons.Key Words: Emamectin benzoate, cyclodextrin, inclusion complex, salmon.e-mail: cvonples@udec.cl 1.-INTRODUCTIONEmamectin benzoate, (4′'R)-4″-deoxy-4″-(methylamino)avermectin b1 benzoate, is one of the most widely used compounds in the salmon industry. Chemically, is a semisynthetic derivative of avermectins (Figure 1), which shows insecticide properties against the sea lice (Lepeophteirus salmonis), an ectoparasite that infests farmed salmons [1][2][3] . Unfortunately, it has been demonstrated that the efficacy of anti-infective treatments in salmons and trouts is low because is very difficult to control the dosage in medicated foods, which results in high intra-inter variability in plasma concentrations of the agents used [4][5][6] Of the approaches considered for improvement of the accuracy in the administration of EB, Glover et al. demonstrated that the intraperitoneal injection of the drug in farmed salmons resulted in higher and more predictable concentrations, but there are constraints that have relation with the manipulation of individual specimens 7 . From a point of view of the drug, one of the factors that influence the bioavailability of active compounds in living systems are their physicochemical properties like the solubility, which is often the limiting step in the absorption process. EB is a compound that has an erratic bioavailability and poor water solubility, which depends on the pH of the aqueous medium. At pH higher than 7, the solubility is drastically reduced and this is a relevant issue, because the intestinal pH of some fish can reach values of 7 -9 8 . Actually, the salmon industry is concerned about the need for optimize the therapeutic regimes, and one way to achieve predictable drug concentrations in plasma and tissues (taking into account the low and pH dependent solubility of EB) after an oral dose of a drug is improving its aqueous solubility with the use of cyclodextrins [9][10][11][12] . Of all the cyclodextrins used, hydroxypropyl-β-cyclodextrin (HP-β-CD) has been the most studied, because of its toxicological profile and better aqueous solubility [13][14][15] . Since there is no evidence of previous research, the aim of this work is to study the possibility of form an inclusion complex of EB and HP-β-CD, characterizing the...

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Section: 3-differential Scanning Calorimetrymentioning

confidence: 99%

Section: 4-ft-ir Spectroscopymentioning

confidence: 99%

Preparation and Characterization of the Emamectin Benzoate/Hydroxypropyl-B-Cyclodextrin Inclusion Complex

Torres¹,

Villa²,

González³

et al. 2011

J. Chil. Chem. Soc.

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“…This allows the construction of three-dimensional models of drug-CD complexes, visualization of structural integrity, and intra-and intermolecular interactions (Seridi, Boufelfel, 2011;Leila et al, 2011;Eid et al, 2011;Ge et al, 2011;Mishur et al, 2011).…”

Section: Formation Of Inclusion Complexesmentioning

confidence: 99%

Cyclodextrins and ternary complexes: technology to improve solubility of poorly soluble drugs

Miranda

Martins

Veiga

et al. 2011

Braz. J. Pharm. Sci.

151

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Cyclodextrins (CDs) are cyclic oligosaccharides composed of D-glucopyranoside units linked by glycosidic bonds. Their main property is the ability to modify the physicochemical and biological characteristics of low-soluble drugs through the formation of drug:CD inclusion complexes. Inclusion complexation requires that host molecules fit completely or partially within the CD cavity. This adjustment is directly related to the physicochemical properties of the guest and host molecules, easy accommodation of guest molecules within the CD cavity, stoichiometry, therapeutic dose, and toxicity. However, dosage forms may achieve a high volume, depending on the amount of CD required. Thus, it is necessary to increase solubilization efficiency in order to use smaller amounts of CD. This can be achieved by adding small amounts of water-soluble polymers to the system. This review addresses aspects related to drug complexation with CDs using water-soluble polymers to optimize the amount of CD used in the formulation in order to increase drug solubility and reduce dosage form volume. Uniterms:Cyclodextrins. Ternary complexes. Drugs/complexation. Water-soluble polymers/use. Drugs/ solubility. Inclusion complexe.Ciclodextrinas (CDs) são oligossacarídeos cíclicos, compostos por unidades D-glicopiranosídicas ligadas entre si por meio de ligações glicosídicas e sua principal propriedade está na capacidade de alterar as características físico-químicas e biológicas de fármacos com baixa solubilidade por meio da formação de complexos de inclusão fármaco:CD. Para a formação dos complexos de inclusão a molécula hospedeira necessita ajustar-se total ou parcialmente no interior da cavidade da CD, onde este ajuste está diretamente ligado a propriedades físico-químicas da molécula hóspede e hospedeira, facilidade de alojamento da molécula hóspede no interior da cavidade da CD, estequiometria, dose terapêutica e toxicidade. No entanto, as formas farmacêuticas podem atingir um elevado volume, em função da quantidade de CD requerida, sendo necessário aumentar sua eficiência de solubilização para que seja possível utilizar menores quantidades das mesmas. Isso pode ser obtido com a inclusão de pequenas quantidades de polímeros hidrossolúveis ao sistema. Nessa revisão, são abordados aspectos relacionados à complexação de fármacos com ciclodextrinas empregando-se polímeros hidrossolúveis para otimização da quantidade de CD utilizada na formulação, com a finalidade de aumentar a solubilidade do fármaco e reduzir o volume das preparações.Unitermos: SCiclodextrinas. Complexos ternários. Fármacos/complexação. Polímeros hidrossolúveis/ uso. Fármacos/solubilidade. Complexos de inclusão.

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“…FTIR spectra of the inclusion complex and those for pure compounds as well as the physical mixture are shown in corresponding to C=O stretching vibration shifted to 1752 cm -1 and the intensity decreased. The observed changes in the FTIR spectra of LIG complexed with HP-b-CD are due to a restriction of the vibration of the LIG molecule upon its encapsulation into the HP-b-CD cavity (23). Therefore, the FTIR spectroscopy result indicated that the inclusion complex of LIG with HP-b-CD was obtained.…”

Section: Ftir Spectroscopymentioning

confidence: 81%

Complexation of Z-ligustilide with hydroxypropyl-β-cyclodextrin to improve stability and oral bioavailability

Liu

Zhao

et al. 2014

Acta Pharmaceutica

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Radix Angelica sinensis, known as Danggui and mainly spread in Gansu and Sichuan provinces of China, has been used for a long time as a traditional Chinese medicine to treat cardiovascular and cerebrovascular diseases (1, 2) as well as a common food supplement to reinforce vital energy (3, 4). Modern phytochemical studies have shown that LIG (Fig. 1) is the main lipophilic component of Danggui (1). Our previous studies have shown that LIG had neuroprotective effects on some models of diseases associated with cerebral ischemia. Treatment with LIG could significantly improve behavioral deficits and dose-dependently reduce cerebral infarct volumes after focal cerebral ischemia in rats (1, 5). It could also prevent chronically hypoperfused cognitive deficits and brain damage in rats induced by permanent ligation of both common carotid arteries (6). A recent study has shown that LIG has a neuroprotective effect on Alzheimer's disease, cognitive impairment and neuropathological changes induced by bilateral intracerebroven- To improve the stability and oral bioavailability of Z-ligustilide (LIG), the inclusion complex of LIG with hydroxypropyl-b-cyclodextrin (HP-b-CD) was prepared by the kneading method and characterized by UV-Vis spectroscopy, differential thermal analysis (DTA) and Fourier transform infrared (FTIR) spectroscopy. LIG is capable of forming an inclusion complex with HP-b-CD and the stoichiometry of the complex was 1:1. Stability of the inclusion complex against temperature and light was greatly enhanced compared to that of free LIG. Further, oral bioavailability of LIG and the inclusion complex in rats were studied and the plasma drug concentration-time curves fitted well with the non-compartment model to estimate the absolute bioavailability, which was 7.5 and 35.9 %, respectively. In conclusion, these results show that LIG/HP-b-CD complexation can be of great use for increasing the stability and biological efficacy of LIG.

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Characterization of the inclusion complex of zerumbone with hydroxypropyl-β-cyclodextrin

Cited by 120 publications

References 39 publications

Preparation and Characterization of the Emamectin Benzoate/Hydroxypropyl-B-Cyclodextrin Inclusion Complex

Preparation and Characterization of the Emamectin Benzoate/Hydroxypropyl-B-Cyclodextrin Inclusion Complex

Cyclodextrins and ternary complexes: technology to improve solubility of poorly soluble drugs

Complexation of Z-ligustilide with hydroxypropyl-β-cyclodextrin to improve stability and oral bioavailability

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