Design and evaluation of cyclodextrin-based delivery systems to incorporate poorly soluble curcumin analogs for the treatment of melanoma

Michel, Deborah; Chitanda, Jackson M.; Balogh, Réka; Yang, Pin; Singh, Jagbir; Das, Umashankar; El‐Aneed, Anas; Dimmock, Jonathan R.; Verrall, R. E.; Badea, Ildikó

doi:10.1016/j.ejpb.2012.03.016

Cited by 43 publications

(51 citation statements)

References 37 publications

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“…Recently, complexation with cyclodextrins has been reported to enhance the solubility and dissolution rate of itraconazoe (Taupitz et al, 2013), curcumin (Michel et al, 2012), repaglanide (Liu et al, 2014), and myricetin (Yao et al, 2014).…”

Section: Introductionmentioning

confidence: 99%

PREPERATION AND CHARACTERIZATION OF Β-Cyclodextrin INCLUSION COMPLEXES ORAL TABLETS CONTAINING POORLY WATER SOLUBLE GLIMIPIRIDE USING FREEZE DRYING METHOD

Syukri

Fernenda,

Utami

et al. 2015

Indonesian J. Pharm.

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Glimepiride is an oral antidiabetic drugs which is practically insoluble in water. The formation of β-cyclodextrin inclusion complex was able to increase the solubility of glimepiride. This study aim to prepare, characterize and formulation of inclusion complex tablets in order to meet the requirement in Pharmacopeia. The inclusion complex were prepared in a molar ratio of 1:1 and 1:2 by freeze drying method, after that characterized include FTIR spectroscopy and scanning electro microscope (SEM). Further, it was formulated into tablets by direct compression technique using primogel and crospovidone as super disintegrants. The tablets were evaluated include weight uniformity, hardness, friability, disintegration, and dissolution. The dissolution studies of inclusion complex were performed by using USP II apparatus. The result of FTIR and SEM provided evidence of the formation of complexes after utilizing freeze-drying methods. The tablet evaluation containing inclusion complex glimepiride-β cyclodextrin with primogel and cropovidone as disintegrant showed that increased concentration of disintegrant will increase disintegration time of the tablets. All of formulas meet the requirements in the Pharmacopoeia. The inclusion complex of glimepiride-β cyclodextrin successfully used for enhancing the solubility of glimepiride and the tablets meet the requirement in Pharmacopeia.

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Section: Introductionmentioning

confidence: 99%

PREPERATION AND CHARACTERIZATION OF Β-Cyclodextrin INCLUSION COMPLEXES ORAL TABLETS CONTAINING POORLY WATER SOLUBLE GLIMIPIRIDE USING FREEZE DRYING METHOD

Syukri

Fernenda,

Utami

et al. 2015

Indonesian J. Pharm.

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“…10,11 In order to address these drawbacks, formulation approaches using solid dispersion, 12 liposomes, 13 cyclodextrin complexes, 14,15 and nanoparticles have been reported. [16][17][18] Although some progress has been achieved, these approaches have issues of poor drug loading, drug leakage, burst release patterns, and poor physicochemical stability that are unaddressed.…”

Section: Introductionmentioning

confidence: 99%

Entrapment of curcumin into monoolein-based liquid crystalline nanoparticle dispersion for enhancement of stability and anticancer activity

Baskaran¹,

Madheswaran²,

Sundaramoorthy³

et al. 2014

IJN

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Despite the promising anticancer potential of curcumin, its therapeutic application has been limited, owing to its poor solubility, bioavailability, and chemical fragility. Therefore, various formulation approaches have been attempted to address these problems. In this study, we entrapped curcumin into monoolein (MO)-based liquid crystalline nanoparticles (LCNs) and evaluated the physicochemical properties and anticancer activity of the LCN dispersion. The results revealed that particles in the curcumin-loaded LCN dispersion were discrete and monodispersed, and that the entrapment efficiency was almost 100%. The stability of curcumin in the dispersion was surprisingly enhanced (about 75% of the curcumin survived after 45 days of storage at 40°C), and the in vitro release of curcumin was sustained (10% or less over 15 days). Fluorescence-activated cell sorting (FACS) analysis using a human colon cancer cell line (HCT116) exhibited 99.1% fluorescence gating for 5 μM curcumin-loaded LCN dispersion compared to 1.36% for the same concentration of the drug in dimethyl sulfoxide (DMSO), indicating markedly enhanced cellular uptake. Consistent with the enhanced cellular uptake of curcumin-loaded LCNs, anticancer activity and cell cycle studies demonstrated apoptosis induction when the cells were treated with the LCN dispersion; however, there was neither noticeable cell death nor significant changes in the cell cycle for the same concentration of the drug in DMSO. In conclusion, entrapping curcumin into MO-based LCNs may provide, in the future, a strategy for overcoming the hurdles associated with both the stability and cellular uptake issues of the drug in the treatment of various cancers.

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“…4,24 Among these structures, NC 2067 ( Figure 1B) has demonstrated high in vitro cell toxicity toward melanoma and colon cancer cell lines. 3,25 Its high log P value of 4.6 26 and the presence of aromatic ring moieties in its structure suggest that NC 2067 is a good candidate for encapsulation by CD. Beta cyclodextrin-gemini surfactant (CDgemini surfactant) is a novel carrier composed of CD attached by an ester or amide linker to a cationic gemini surfactant ( Figure 1C and D, respectively).…”

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confidence: 99%

“…While they show strong in vitro anticancer activity toward different cancer cell lines, [3][4][5][6][7][8][9] their lipophilicity (high log P value) is a limitation for in vivo applications. Various nanotechnology-based drug delivery systems, such as liposomes, 10,11 solid lipid nanoparticles, 6,12,13 polymer-based nanoparticles 7,14,15, and mesoporous nanoparticles, 16 have been developed to encapsulate curcumin and its analogs so as to enhance solubilization and deliver them to cancerous cells.…”

mentioning

confidence: 99%

“…Beta cyclodextrin-gemini surfactant (CDgemini surfactant) is a novel carrier composed of CD attached by an ester or amide linker to a cationic gemini surfactant ( Figure 1C and D, respectively). They were synthesized in order to create a suitable substitute for a solubilizing agent, 3 hypothesizing that the hydrophobic CD cavity can accommodate NC 2067 while the gemini surfactant tail possibly could contribute to a supramolecular association that would enhance diffusion into biomembranes.…”

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confidence: 99%

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Characterization of the host–guest complex of a curcumin analog with β-cyclodextrin and β-cyclodextrin–gemini surfactant and evaluation of its anticancer activity

Poorghorban¹,

Das²,

Alaidi³

et al. 2015

IJN

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Background Curcumin analogs, including the novel compound NC 2067, are potent cytotoxic agents that suffer from poor solubility, and hence, low bioavailability. Cyclodextrin-based carriers can be used to encapsulate such agents. In order to understand the interaction between the two molecules, the physicochemical properties of the host–guest complexes of NC 2067 with β-cyclodextrin (CD) or β-cyclodextrin–gemini surfactant (CDgemini surfactant) were investigated for the first time. Moreover, possible supramolecular structures were examined in order to aid the development of new drug delivery systems. Furthermore, the in vitro anticancer activity of the complex of NC 2067 with CDgemini surfactant nanoparticles was demonstrated in the A375 melanoma cell line. Methods Physicochemical properties of the complexes formed of NC 2067 with CD or CDgemini surfactant were investigated by synchrotron-based powder X-ray diffraction, Fourier-transform infrared spectroscopy, and thermogravimetric analysis. Synchrotron-based small- and wide-angle X-ray scattering and size measurements were employed to assess the supramolecular morphology of the complex formed by NC 2067 with CDgemini surfactant. Lastly, the in vitro cell toxicity of the formulations toward A375 melanoma cells at various drug-to-carrier mole ratios were measured by cell viability assay. Results Physical mixtures of NC 2067 and CD or CDgemini surfactant showed characteristics of the individual components, whereas the complex of NC 2067 and CD or CDgemini surfactant presented new structural features, supporting the formation of the host–guest complexes. Complexes of NC 2067 with CDgemini surfactants formed nanoparticles having sizes of 100–200 nm. NC 2067 retained its anticancer activity in the complex with CDgemini surfactant for different drug-to-carrier mole ratios, with an IC 50 (half-maximal inhibitory concentration) value comparable to that for NC 2067 without the carrier. Conclusion The formation of host–guest complexes of NC 2067 with CD or CDgemini surfactant has been confirmed and hence the CDgemini surfactant shows good potential to be used as a delivery system for anticancer agents.

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Design and evaluation of cyclodextrin-based delivery systems to incorporate poorly soluble curcumin analogs for the treatment of melanoma

Cited by 43 publications

References 37 publications

PREPERATION AND CHARACTERIZATION OF Β-Cyclodextrin INCLUSION COMPLEXES ORAL TABLETS CONTAINING POORLY WATER SOLUBLE GLIMIPIRIDE USING FREEZE DRYING METHOD

PREPERATION AND CHARACTERIZATION OF Β-Cyclodextrin INCLUSION COMPLEXES ORAL TABLETS CONTAINING POORLY WATER SOLUBLE GLIMIPIRIDE USING FREEZE DRYING METHOD

Entrapment of curcumin into monoolein-based liquid crystalline nanoparticle dispersion for enhancement of stability and anticancer activity

Characterization of the host–guest complex of a curcumin analog with β-cyclodextrin and β-cyclodextrin–gemini surfactant and evaluation of its anticancer activity

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Design and evaluation of cyclodextrin-based delivery systems to incorporate poorly soluble curcumin analogs for the treatment of melanoma

Cited by 43 publications

References 37 publications

PREPERATION AND CHARACTERIZATION OF Β-Cyclodextrin INCLUSION COMPLEXES ORAL TABLETS CONTAINING POORLY WATER SOLUBLE GLIMIPIRIDE USING FREEZE DRYING METHOD

PREPERATION AND CHARACTERIZATION OF Β-Cyclodextrin INCLUSION COMPLEXES ORAL TABLETS CONTAINING POORLY WATER SOLUBLE GLIMIPIRIDE USING FREEZE DRYING METHOD

Entrapment of curcumin into monoolein-based liquid crystalline nanoparticle dispersion for enhancement of stability and anticancer activity

Characterization of the host&ndash;guest complex of a curcumin analog with &beta;-cyclodextrin and &beta;-cyclodextrin&ndash;gemini surfactant and evaluation of its anticancer activity

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Characterization of the host–guest complex of a curcumin analog with β-cyclodextrin and β-cyclodextrin–gemini surfactant and evaluation of its anticancer activity