Hydroxypropyl-β-cyclodextrin-complexed naringenin by solvent change precipitation for improving anti-inflammatory effect in vivo

Gratieri, Taís; Pinho, Ludmila A.G.; Oliveira, Marlange Almeida; Barreto, Lívia Cristina Lira de Sá; Marreto, Ricardo Neves; Silva, Izabel C.; Gelfuso, Guilherme M.; Quintans, Jullyana de Souza Siqueira; Quintans‐Júnior, Lucindo José; Cunha-Filho, Marcílio

doi:10.1016/j.carbpol.2019.115769

Cited by 34 publications

(13 citation statements)

References 36 publications

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“…The increase in pharmacological activity for API with a different mechanism of action after their introduction into CD cavities, confirmed by the results of in vivo studies were reported, eg, for antimicrobial activity cefuroxime axetil, for the anti-inflammatory activity of naringenin and for reduction of arterial pressure by valsartan. [50][51][52] In our previous studies, we also confirmed that an increase in the analgesic effect for sumatriptan after introduction into CD structures was possible. 23 Other studies confirming the beneficial impact of CD systems on the analgesic effect were also obtained in the case of ketoprofen, where antipyretic, analgesic and anti-inflammatory effects increased, and in the mice study for meloxicam, where the elevated API serum levels maximized its analgesic activity.…”

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confidence: 85%

The Inclusion of Tolfenamic Acid into Cyclodextrins Stimulated by Microenvironmental pH Modification as a Way to Increase the Anti-Migraine Effect

Stasiłowicz

Tykarska

Rosiak

et al. 2021

JPR

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Purpose The poorly soluble nonsteroidal anti-inflammatory drug (NSAID), tolfenamic acid (TA), was studied to maximize its solubility, permeability through biological membranes, and pharmacological activity. Methods A mixture with magnesium stearate (MS) – microenvironment pH-modifier was prepared, as well as systems additionally containing incorporating substances methyl-β-cyclodextrin (M-β-CD) and 2-hydroxypropyl-β-cyclodextrin (HP-β-CD). The identification of TA-MS-CD systems was confirmed using experimental methods: X-ray powder diffraction (XRPD) and Fourier transform infrared spectroscopy (FT-IR) with the theoretical support. Apparent solubility study was performed using the paddle apparatus, while in vitro gastrointestinal tract (GIT) and blood-brain barrier (BBB) permeability were conducted by using PAMPA (Parallel Artificial Membrane Permeability Assay). The in vivo part of the study used the mouse nitroglycerin (NTG)-induced migraine pain model. Results From practically insoluble substance, TA in TA-MS-M-β-CD system dissolved up to 80.13% ± 2.77%, and in TA-MS-HP-β-CD up to 92.39% ± 3.25% in 180 minutes. An increase in TA permeability was also obtained in the TA-MS-M-β-CD and TA-MS-HP-β-CD systems through GIT membranes (P app values 2.057 x 10 −5 cm s −1 and 2.091 x 10 −5 cm s −1 , respectively) and through BBB (P app values 3.658 x 10 −5 cm s −1 and 3.629 x 10 −5 cm s −1 , respectively). The enlargement of the solubility and permeability impacted analgesia. The dose 25 mg/kg of both TA-MS-HP-β-CD and TA-MS-M-β-CD was almost equally effective and only slightly less effective than the dose 50 mg/kg of pure TA. Both TA-MS-HP-β-CD and TA-MS-M-β-CD used at 50 mg/kg more effectively attenuated tactile allodynia in NTG-treated mice than the same dose of pure TA. None of TA forms influenced heat hyperalgesia. Conclusion Increasing solubility of TA caused an increase of its analgesic effect in an animal model of migraine pain.

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confidence: 85%

The Inclusion of Tolfenamic Acid into Cyclodextrins Stimulated by Microenvironmental pH Modification as a Way to Increase the Anti-Migraine Effect

Stasiłowicz

Tykarska

Rosiak

et al. 2021

JPR

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“…Talking about stability, Tais et al applied MD simulations and docking studies to predict the most stable stoichiometric inclusion complex of naringenin with cyclodextrin (CD) [ 42 ]. Their main goal was to enhance the solubility of this poorly water soluble drug -and hence its dissolution rate- by high encapsulation inside CD with minimum dissociation rate.…”

Section: MD Simulations and Dockingmentioning

confidence: 99%

Evolution of the Computational Pharmaceutics Approaches in the Modeling and Prediction of Drug Payload in Lipid and Polymeric Nanocarriers

et al. 2021

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This review describes different trials to model and predict drug payload in lipid and polymeric nanocarriers. It traces the evolution of the field from the earliest attempts when numerous solubility and Flory-Huggins models were applied, to the emergence of molecular dynamic simulations and docking studies, until the exciting practically successful era of artificial intelligence and machine learning. Going through matching and poorly matching studies with the wet lab-dry lab results, many key aspects were reviewed and addressed in the form of sequential examples that highlighted both cases.

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“…The use of cyclodextrins (CD), which are cyclic oligosaccharides obtained from the intramolecular transglycolation of starch, presents itself as an alternative to improve the solubility of molecules ( Praphanwittaya et al, 2020 ). This is attributed to its conical spatial structure with the orientation of hydroxy groups to the outside confer unique physical–chemical properties, being capable of being solubilized in aqueous medium and at the same time encapsulating hydrophobic molecules inside its cavity ( Gratieri et al, 2020 ).…”

Section: Introductionmentioning

confidence: 99%

Inclusion complex of clausenidin with hydroxypropyl-β-cyclodextrin: Improved physicochemical properties and anti-colon cancer activity

Al-Abboodi

Al-Sheikh

Eid

et al. 2021

Saudi Pharmaceutical Journal

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The long-term objective of the present study was to prepare, physicochemically characterize and determine the anticancer of clausenidin/hydroxypropyl-β-cyclodextrin (Clu/HPβCD) inclusion complex. We used differential scanning calorimetry, X-ray diffractometer, fourier transform infrared spectroscopy, ultraviolet–visible spectrophotometer and 13 C and 1 H nuclear magnetic resonance followed by in vitro anticancer assays. The orientation and intermolecular interactions of Clausenidin within cyclodextrin cavity were also ascertained by molecular docking simulation accomplished by AutoDock Vina. The guest molecule was welcomed by the hydrophobic cavity of the host molecule and sustained by hydrogen bond between host/guest molecules. The constant drug release with time, and increased solubility were found after successful complexation with HPβCD as confirmed by physicochemical characterizations. Clausenidin had greater cytotoxic effect on colon cancer HT29 cells when incorporated into HPβCD cavity than dissolved in DMSO. Also, from a comparison of cell viability between normal and cancer cells, a reduced side effect was observed. The Clu/HPβCD inclusion complex triggered reactive oxygen species-mediated cytotoxicity in HT29 cells. The inclusion complex-treated HT29 cells showed cell cycle arrest and death by apoptosis associated with caspases activation. The presence of HPβCD seems to aid the anticancer activity of clausenidin.

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Hydroxypropyl-β-cyclodextrin-complexed naringenin by solvent change precipitation for improving anti-inflammatory effect in vivo

Cited by 34 publications

References 36 publications

The Inclusion of Tolfenamic Acid into Cyclodextrins Stimulated by Microenvironmental pH Modification as a Way to Increase the Anti-Migraine Effect

The Inclusion of Tolfenamic Acid into Cyclodextrins Stimulated by Microenvironmental pH Modification as a Way to Increase the Anti-Migraine Effect

Evolution of the Computational Pharmaceutics Approaches in the Modeling and Prediction of Drug Payload in Lipid and Polymeric Nanocarriers

Inclusion complex of clausenidin with hydroxypropyl-β-cyclodextrin: Improved physicochemical properties and anti-colon cancer activity

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