Preparation and Solid-State Characterization of Inclusion Complexes Formed Between Miconazole and Methyl-β-Cyclodextrin

Ribeiro, Andreza Maria; Figueiras, Ana; Santos, Delfim; Veiga, Francisco

doi:10.1208/s12249-008-9143-8

Cited by 93 publications

(42 citation statements)

References 30 publications

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“…6b, b1) is observed as cylindrical spheres. Both structures were in accordance with previous data (28,29). On the other hand, images related to inclusion complex (Fig.…”

Section: Scanning Electron Microscopysupporting

confidence: 92%

Enhanced Antiproliferative Activity of the New Anticancer Candidate LPSF/AC04 in Cyclodextrin Inclusion Complexes Encapsulated into Liposomes

Mendonça

Lira

Rabello³

et al. 2012

AAPS PharmSciTech

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Abstract. LPSF/AC04 (5Z)-[5-acridin-9-ylmethylene-3-(4-methyl-benzyl)-thiazolidine-2,4-dione] is an acridine-based derivative, part of a series of new anticancer agents synthesized for the purpose of developing more effective and less toxic anticancer drugs. However, the use of LPSF/AC04 is limited due to its low solubility in aqueous solutions. To overcome this problem, we investigated the interaction of LPSF/AC04 with hydroxypropyl-β-cyclodextrin (HP-β-CyD) and hydroxypropyl-γ-cyclodextrin (HP-γ-CyD) in inclusion complexes and determine which of the complexes formed presents the most significant interactions. In this paper, we report the physical characterization of the LPSF/AC04-HP-CyD inclusion complexes by thermogravimetric analysis, differential scanning calorimetry, infrared spectroscopy absorption, Raman spectroscopy, 1 HNMR, scanning electron microscopy, and by molecular modeling approaches. In addition, we verified that HP-β-CyD complexation enhances the aqueous solubility of LPSF/AC04, and a significant increase in the antiproliferative activity of LPSF/AC04 against cell lines can be achieved by the encapsulation into liposomes. These findings showed that the nanoencapsulation of LPSF/AC04 and LPSF/AC04-HP-CyD inclusion complexes in liposomes leads to improved drug penetration into the cells and, as a result, an enhancement of cytotoxic activity. Further in vivo studies comparing free and encapsulated LPSF/AC04 will be undertaken to support this investigation.

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“…6b, b1) is observed as cylindrical spheres. Both structures were in accordance with previous data (28,29). On the other hand, images related to inclusion complex (Fig.…”

Section: Scanning Electron Microscopysupporting

confidence: 92%

Enhanced Antiproliferative Activity of the New Anticancer Candidate LPSF/AC04 in Cyclodextrin Inclusion Complexes Encapsulated into Liposomes

Mendonça

Lira

Rabello³

et al. 2012

AAPS PharmSciTech

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“…Powder X-ray diffraction (PXRD) is the commonly used method for the detection of CD complexation either in the powder and microcrystalline states [ 12 ]. The PXRD profiles of the crystalline and non-crystalline RALA-αCD complexes are shown in Figure 3 .…”

Section: Resultsmentioning

confidence: 99%

Structural Analysis of Crystalline R(+)-α-Lipoic Acid-α-cyclodextrin Complex Based on Microscopic and Spectroscopic Studies

Ikuta

Endo

Hosomi

et al. 2015

IJMS

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R(+)-α-lipoic acid (RALA) is a naturally-occurring substance, and its protein-bound form plays significant role in the energy metabolism in the mitochondria. RALA is vulnerable to a variety of physical stimuli, including heat and UV light, which prompted us to study the stability of its complexes with cyclodextrins (CDs). In this study, we have prepared and purified a crystalline RALA-αCD complex and evaluated its properties in the solid state. The results of 1H NMR and PXRD analyses indicated that the crystalline RALA-αCD complex is a channel type complex with a molar ratio of 2:3 (RALA:α-CD). Attenuated total reflection/Fourier transform infrared analysis of the complex showed the shift of the C=O stretching vibration of RALA due to the formation of the RALA-αCD complex. Raman spectroscopic analysis revealed the significant weakness of the S–S and C–S stretching vibrations of RALA in the RALA-αCD complex implying that the dithiolane ring of RALA is almost enclosed in glucose ring of α-CD. Extent of this effect was dependent on the direction of the excitation laser to the hexagonal morphology of the crystal. Solid-state NMR analysis allowed for the chemical shift of the C=O peak to be precisely determined. These results suggested that RALA was positioned in the α-CD cavity with its 1,2-dithiolane ring orientated perpendicular to the plane of the α-CD ring.

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“…[1][2][3][4] The drug/CyD complexes are prepared by various methods and a lot of studies have been reported so far, e.g., kneading, coevaporation, freeze drying, solubility and spray drying methods, etc. [5][6][7] In addition, it has been demonstrated that the preparation methods or the preparation conditions can significantly influence the characteristics of the resulting complexes. [8][9][10] Al-Marzouqi et al reported that benzocaine/b-CyD complexes prepared by the supercritical fluid technology, kneading, co-evaporation, co-grinding or sealedheating methods had different physicochemical properties.…”

mentioning

confidence: 99%

Preparation of Four Types of Coenzyme Q10/.GAMMA.-Cyclodextrin Supramolecular Complexes and Comparison of Their Pharmaceutical Properties

Higashi

Nishimura

Yoshimatsu

et al. 2009

CHEMICAL & PHARMACEUTICAL BULLETIN

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In this study, we prepared four kinds of complexes of Coenzyme Q10 (CoQ10) with gamma-cyclodextrin (gamma-CyD) by the kneading methods and the solubility methods with or without heating, and compared their pharmaceutical properties. Differential scanning calorimetrical curves and powder X-ray diffraction patterns showed that the complexes formed pseudorotaxane-like supramolecular structure, although included free gamma-CyD and CoQ10, when prepared by the kneading method and solubility method without heating. At the preparation process, a heating improved the complexation of CoQ10 with gamma-CyD in the both methods. The dispersion rate of CoQ10 in water increased in the order of CoQ10 alone approximately physical mixture with gamma-CyD<

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Preparation and Solid-State Characterization of Inclusion Complexes Formed Between Miconazole and Methyl-β-Cyclodextrin

Cited by 93 publications

References 30 publications

Enhanced Antiproliferative Activity of the New Anticancer Candidate LPSF/AC04 in Cyclodextrin Inclusion Complexes Encapsulated into Liposomes

Enhanced Antiproliferative Activity of the New Anticancer Candidate LPSF/AC04 in Cyclodextrin Inclusion Complexes Encapsulated into Liposomes

Structural Analysis of Crystalline R(+)-α-Lipoic Acid-α-cyclodextrin Complex Based on Microscopic and Spectroscopic Studies

Preparation of Four Types of Coenzyme Q10/.GAMMA.-Cyclodextrin Supramolecular Complexes and Comparison of Their Pharmaceutical Properties

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