Inclusion complex of usnic acid with β-cyclodextrin: characterization and nanoencapsulation into liposomes

Lira, Mariane C. B.; Ferraz, Milena Sales; Silva, Dáfila G. V. C. da; Cortés, María Esperanza; Teixeira, Karina Imaculada Rosa; Caetano, N.; Sinisterra, Rubén D.; Ponchel, Gilles; Santos-Magalhães, Nereide Stela

doi:10.1007/s10847-009-9554-5

Cited by 74 publications

(38 citation statements)

References 31 publications

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“…In addition, the antiproliferative activity of curcumin was increased by cyclodextrin complexation and encapsulation into liposomes. Moreover, our recent researches have reported that the solubilization of the anticancer agents usnic acid and β-lapachone with cyclodextrins and their encapsulation into liposomes offer a way to improve drug solubility (19,20).…”

Section: Discussionmentioning

confidence: 99%

“…Preparation of LPSF/AC04-Loaded Liposomes LPSF/AC04-loaded liposomes were prepared using the thin lipid film method (19). Briefly, lipids (SPC, CHOL, and SA, 7:2:1 molar ratio) at a concentration of 42 mM and LPSF/AC04 (0.4-0.8 mg/ml) were dissolved in a mixture of CHCl 3 /MeOH (3:1v/v) under magnetic stirring.…”

Section: Molecular Modeling Of the Inclusion Complexesmentioning

confidence: 99%

“…Moreover, the entrapment of inclusion complexes into drug delivery systems, such as liposomes, can modulate in vivo dissociation of the drug/CyD complex, thereby contributing to improvements in the pharmacokinetic profile, chemical stability, and therapeutic efficacy of the drugs (16)(17)(18)(19)(20). The main purpose of inclusion complex-loaded liposomes is to combine the advantages of cyclodextrins as increasing agents of drug solubility with those of liposomes as drug targeting agents.…”

Section: Introductionmentioning

confidence: 99%

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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: Discussionmentioning

confidence: 99%

Section: Molecular Modeling Of the Inclusion Complexesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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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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“…Glutamine-loaded liposomes were prepared using the modified thin-lipid-film method (24). Briefly, lipids consisting of soya phosphatidylcholine and cholesterol, with or without stearylamine, a positive charged lipid, were dissolved in a mixture of CHCl 3 :MeOH (3:1 v/v) under magnetic stirring.…”

Section: Preparation Of Glutamine-loaded Conventional Liposomesmentioning

confidence: 99%

“…The drug EE% was determined using the ultrafiltration/ ultracentrifugation technique with Ultrafree ® units (Millipore Corporation, Bedford, MA, USA) (24). Liposomal samples (400 μl) were inserted into the filtration unit and subjected to centrifugation (Ultracentrifuge KT-20000, Kubota, Japan) at 8776×g for 1 h at 4°C.…”

Section: Physicochemical Characterization Of Glutamine-loaded Conventmentioning

confidence: 99%

Glutamine-Loaded Liposomes: Preliminary Investigation, Characterization, and Evaluation of Neutrophil Viability

et al. 2015

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Abstract. Glutamine has received attention due to its ability to ameliorate the immune system response. Once conventional liposomes are readily recognized and captured by immune system cells, the encapsulation of glutamine into those nanosystems could be an alternative to reduce glutamine dosage and target then to neutrophils. Our goals were to nanoencapsulate glutamine into conventional liposomes (Gln-L), develop an analytical high-performance liquid chromatography (HPLC) method for its quantification, and evaluate the viability of neutrophils treated with Gln-L. Liposomes were prepared using the thin-film hydration technique followed by sonication and characterized according to pH, mean size, zeta potential, and drug encapsulation efficiency (EE%). We also aimed to study the effect of liposomal constituent concentrations on liposomal characteristics. The viability of neutrophils was assessed using flow cytometry after intraperitoneal administration of free glutamine (Gln), Gln-L, unloaded-liposome (UL), and saline solution as control (C) in healthy Wistar rats. The selected liposomal formulation had a mean vesicle size of 114.65±1.82 nm with a polydispersity index of 0.30±0.00, a positive surface charge of 36.30±1.38 mV, and an EE% of 39.49±0.74%. The developed chromatographic method was efficient for the quantification of encapsulated glutamine, with a retention time at 3.8 min. A greater viability was observed in the group treated with glutamine encapsulated compared to the control group (17%), although neutrophils remain viable in all groups. Thus, glutamine encapsulated into liposomes was able to increase the number of viable neutrophils at low doses, thereby representing a promising strategy for the treatment of immunodeficiency conditions.

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Delivering Herbal Drugs Using Nanotechnology

Manasa¹,

Shivananjappa²

2023

Advances in Novel Formulations for Drug Delivery

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Inclusion complex of usnic acid with β-cyclodextrin: characterization and nanoencapsulation into liposomes

Cited by 74 publications

References 31 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

Glutamine-Loaded Liposomes: Preliminary Investigation, Characterization, and Evaluation of Neutrophil Viability

Delivering Herbal Drugs Using Nanotechnology

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