Interaction between naproxen and chemically modified β-cyclodextrins in the liquid and solid state

Mura, Paola; Bettinetti, Giampiero; Melani, Fabrizio; Manderioli, A.

doi:10.1016/0928-0987(95)00025-x

Cited by 57 publications

(30 citation statements)

References 5 publications

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“…There are several reports in the literature using molecular modeling of drugs in HP-β-CyD inclusion complexes (22)(23)(24)(25). Our group has already used the latter's methodological approach, for β-lapachone-HP-β-CyD inclusion complexes considering the degree of substitution of hydroxypropyl (HP) groups in the glucose units of β-CyD (20).…”

Section: Molecular Modeling Of the Inclusion Complexesmentioning

confidence: 99%

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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Section: Molecular Modeling Of the Inclusion Complexesmentioning

confidence: 99%

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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“…Various decoration patterns of substituents are considered (e.g. 1-2-3-4, 1-2-5-6, 1-3-5-7 where numbers indicate the relative position of substitution glucoses) [40,45]. The optimization results do not indicate any significant energy differences on the substituent pattern.…”

Section: Molecular Modeling Of Sfs/hpˇcd-icmentioning

confidence: 96%

“…The initial geometry of ␤-CD was obtained from Cambridge Structural Database [39]. HP␤CD is constructed manually by adding four 2-hydroxypropyl groups on the primary groups of ␤-CD corresponding to a substitution degree per anhydroglucose unit of 0.6 which was compatible with the experiments [40]. The exchange-correlation was treated within Perdew-Burke-Ernzerhof parametrization of the generalized gradient approximation (GGA-PBE) [41] with inclusion of Van der Waals correction [42].…”

Section: Methodsmentioning

confidence: 99%

Sulfisoxazole/cyclodextrin inclusion complex incorporated in electrospun hydroxypropyl cellulose nanofibers as drug delivery system

Aytaç

Sen

Durgun

et al. 2015

Colloids and Surfaces B: Biointerfaces

106

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a b s t r a c tHerein, hydroxypropyl-beta-cyclodextrin (HP␤CD) inclusion complex (IC) of a hydrophobic drug, sulfisoxazole (SFS) was incorporated in hydroxypropyl cellulose (HPC) nanofibers (HPC/SFS/HP␤CD-IC-NF) via electrospinning. SFS/HP␤CD-IC was characterized by DSC to investigate the formation of inclusion complex and the stoichiometry of the complex was determined by Job's plot. Modeling studies were also performed on SFS/HP␤CD-IC using ab initio technique. SEM images depicted the defect free uniform fibers and confirmed the incorporation of SFS/HP␤CD-IC in nanofibers did not alter the fiber morphology. XRD analyses showed amorphous distribution of SFS/HP␤CD-IC in the fiber mat. Release studies were performed in phosphate buffered saline (PBS). The results suggest higher amount of SFS released from HPC/SFS/HP␤CD-IC-NF when compared to free SFS containing HPC nanofibers (HPC/SFS-NF). This was attributed to the increased solubility of SFS by inclusion complexation. Sandwich configurations were prepared by placing HPC/SFS/HP␤CD-IC-NF between electrospun PCL nanofibrous mat (PCL-HPC/SFS/HP␤CD-IC-NF). Consequently, PCL-HPC/SFS/HP␤CD-IC-NF exhibited slower release of SFS as compared with HPC/SFS/HP␤CD-IC-NF. This study may provide more efficient future strategies for developing delivery systems of hydrophobic drugs.

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“…The solvent was evaporated in a rotary evaporator (RV 05S5 from Janke & Kunkel GmbHu.CoKG, Staufen, Germany) at 50-C under vacuum. The presence of residual ammonia was tested using the Nessler test (14,15).…”

Section: Sample Preparationmentioning

confidence: 99%

Dense Gas Processing of Micron-Sized Drug Formulations Incorporating Hydroxypropylated and Methylated Beta-Cyclodextrin

2006

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The ASES was operated under mild conditions and generated micron-sized spherical particles that could be of particular interest in formulations for pulmonary delivery. Particular advantages of the technique are that (1) nontoxic solvents are used, and (2) it is suitable for the processing of thermally labile compounds. The proposed process can create opportunities to improve current administration routes and exploit novel delivery systems for drug formulations incorporating CDs.

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Interaction between naproxen and chemically modified β-cyclodextrins in the liquid and solid state

Cited by 57 publications

References 5 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

Sulfisoxazole/cyclodextrin inclusion complex incorporated in electrospun hydroxypropyl cellulose nanofibers as drug delivery system

Dense Gas Processing of Micron-Sized Drug Formulations Incorporating Hydroxypropylated and Methylated Beta-Cyclodextrin

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