Sulfadiazine/hydroxypropyl-β-cyclodextrin host–guest system: Characterization, phase-solubility and molecular modeling

Araújo, Márcia Valéria Gaspar de; Vieira, Elze Kelly Barbosa; Lázaro, Gilderman Silva; Conegero, Leila S.; Almeida, Luís Eduardo; Barreto, Ledjane Silva; Costa, Nivan B. da; Gimenez, Iara F.

doi:10.1016/j.bmc.2008.03.057

Cited by 54 publications

(14 citation statements)

References 38 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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“…FST exhibited a sharp endothermic peak at 344.58 C corresponding to its melting point (Liu et al, 2014) (Supplementary Figure S2(b)) while pure HPbCD showed a broad endothermic peak in between 50 and 80 C due to the release of water molecules (de Araújo et al, 2008). The physical mixture of FST-HPbCD (FHPM) showed a broad endotherm for HPbCD at around 80 C and a slight shift in the peak of FST indicating no or a very less interaction.…”

Section: Preparation and Characterization Of Fhicmentioning

confidence: 99%

Enhanced oral bioavailability and anticancer efficacy of fisetin by encapsulating as inclusion complex with HPβCD in polymeric nanoparticles

et al. 2017

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Fisetin (FST), a potent anticancer phytoconstituent, exhibits poor aqueous solubility and hence poor bioavailability. The aim of the present study is to improve the oral bioavailability of FST by encapsulating into PLGA NPs (poly-lactide-co-glycolic acid nanoparticles) as a complex of HPbCD (hydroxyl propyl beta cyclodextrin) and to assess its anti-cancer activity against breast cancer cells. FST-HPbCD inclusion complex (FHIC) was prepared and the supramolecular complex formation was characterized by FTIR, DSC, PXRD and 1 H NMR. FHIC encapsulated PLGA nanoparticles (FHIC-PNP) were prepared and were studied for in vitro anticancer activity, cellular uptake, apoptosis and reactive oxygen species generation in MCF-7 human breast cancer cells. Comparative bioavailability of FST was determined after oral administration in C57BL6 mice as pure FST and FHIC-PNP. The results revealed that FHIC-PNP not only enhanced the anti-cancer activity and apoptosis of FST against MCF-7 cells but also improved its oral bioavailability, as demonstrated by increased peak plasma concentration and total drug absorbed.

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“…It exhibits a truncated-cone shape with a hydrophobic inner and a hydrophilic outer surface, capable of including molecules to form inclusion complexes, and enhancing properties such as solubility, bioavailability and stability. Therefore, previous reports demonstrated that the formation of complex between several sulfonamides and CDs exhibited improved aqueous solubility compared to that of the free drugs, [8][9][10][11] and thus may have implication on its therapeutic applicability.…”

Section: Introductionmentioning

confidence: 99%

Complexation of Sulfonamides With β-Cyclodextrin Studied by Experimental and Theoretical Methods

Zoppi

Quevedo

Delrivo

et al. 2010

Journal of Pharmaceutical Sciences

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Sulfadiazine/hydroxypropyl-β-cyclodextrin host–guest system: Characterization, phase-solubility and molecular modeling

Cited by 54 publications

References 38 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

Enhanced oral bioavailability and anticancer efficacy of fisetin by encapsulating as inclusion complex with HPβCD in polymeric nanoparticles

Complexation of Sulfonamides With β-Cyclodextrin Studied by Experimental and Theoretical Methods

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