Hydroxypropyl-β-cyclodextrin as an effective carrier of curcumin – piperine nutraceutical system with improved enzyme inhibition properties

Stasiłowicz, Anna; Tykarska, Ewa; Lewandowska, Kornelia; Kozak, Maciej; Miklaszewski, Andrzej; Kobus‐Cisowska, Joanna; Szymanowska, Daria; Plech, Tomasz; Jenczyk, Jacek; Cielecka‐Piontek, Judyta

doi:10.1080/14756366.2020.1801670

Cited by 32 publications

(29 citation statements)

References 64 publications

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“…Piperine also increases the bioavailability of the substances [ 20 , 21 ]. For the more complex piperine-CD systems, where additionally curcumin was added, an improvement in important physicochemical properties was also noted to improve their bioavailability [ 4 ]. The modification of silybin bioavailability with strong hepatoprotective potential, but the use limited by low bioavailability was studied by Xiaoli Bi et al A combination of silybin (50 mg/kg) and piperine (50 mg/kg) was administered to rats.…”

Section: Resultsmentioning

confidence: 99%

“…Based on both studies’ efflux ratios, it can be concluded that piperine is not much involved in active transport [ 23 , 24 ]. However, there are no preformulation studies that would cause modifications to piperine’s permeability across the blood–brain barrier beyond our previous studies in combination with curcumin and cyclodextrin [ 4 ].…”

Section: Resultsmentioning

confidence: 99%

“…Then, 5 mg powdered samples were placed in hermetically enclosed aluminum cells next to their as the reference sample and heated at a scanning rate of 5 K min −1 from 294 to 295 °C in a helium atmosphere with a flow rate of 40 mL min −1 . The experimental procedure and data processing details were identical to those described by us for other pharmaceutical compounds [ 4 , 32 ].…”

Section: Methodsmentioning

confidence: 99%

“…Despite the proven multidirectional effects of piperine, its use is limited by low water solubility (40 mg/L at 18 °C) [ 2 ]. Piperine alleviates the bioavailability of other active substances according to inhibition of metabolizing CYP450 enzymes, particularly CYP3A4, CYP2C9, and CYP1A2, stimulation of amino acid transporters in the lining of the intestine, and inhibition of P -glycoprotein [ 3 , 4 ]. However, piperine itself has poor bioavailability.…”

Section: Introductionmentioning

confidence: 99%

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Combinations of Piperine with Hydroxypropyl-β-Cyclodextrin as a Multifunctional System

Stasiłowicz

Rosiak

Tykarska

et al. 2021

IJMS

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Piperine is an alkaloid that has extensive pharmacological activity and impacts other active substances bioavailability due to inhibition of CYP450 enzymes, stimulation of amino acid transporters and P-glycoprotein inhibition. Low solubility and the associated low bioavailability of piperine limit its potential. The combination of piperine with 2-hydroxypropyl-β-cyclodextrin (HP-β-CD) causes a significant increase in its solubility and, consequently, an increase in permeability through gastrointestinal tract membranes and the blood–brain barrier. X-ray powder diffraction (XRPD), differential scanning calorimetry (DSC), Fourier-transform infrared spectroscopy (FT-IR), nuclear magnetic resonance (NMR) were used to characterize interactions between piperine and HP-β-CD. The observed physicochemical changes should be combined with the process of piperine and CD system formation. Importantly, with an increase in solubility and permeability of piperine as a result of interaction with CD, it was proven to maintain its biological activity concerning the antioxidant potential (2,2-diphenyl-1-picryl-hydrazyl-hydrate assay), inhibition of enzymes essential for the inflammatory process and for neurodegenerative changes (hyaluronidase, acetylcholinesterase, butyrylcholinesterase).

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Combinations of Piperine with Hydroxypropyl-β-Cyclodextrin as a Multifunctional System

Stasiłowicz

Rosiak

Tykarska

et al. 2021

IJMS

Self Cite

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“…The angular range was 3° to 50° with a step size of 0.017° and counting rate of 15 s/step. OriginPro 8 was used to analyze the acquired data [ 14 , 15 ].…”

Section: Methodsmentioning

confidence: 99%

Structural Polymorphism of Sorafenib Tosylate as a Key Factor in Its Solubility Differentiation

et al. 2021

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The presence of active pharmaceutical ingredients (APIs) in the forms of different polymorphic states can induce differences in their physicochemical properties. In the case of poorly soluble APIs, like the oncological drug sorafenib tosylate, small variations in solubility may result in large bioavailability differences. The control of its therapeutic dose is crucial from the effective pharmacotherapy point of view and the reduction of side effects. Therefore, this study aimed to assess the influence of sorafenib tosylate polymorphic forms on its solubility and, consequently, permeability, based on passive diffusion through membranes simulating the gastrointestinal tract (GIT) conditions. In the first part of the work, two crystalline forms of sorafenib tosylate were identified using the X-ray powder diffraction, FT-IR, and Raman spectroscopy. Subsequently, solubility studies were carried out. Both forms of sorafenib tosylate were insoluble in 0.1 N hydrochloric acid (HCl), in acetate buffer (pH 4.5), and in phosphate buffer (pH 6.8). Solubility (mg/mL) of form I and III of sorafenib tosylate in 0.1 N HCl + 1.0% SDS was 0.314 ± 0.006 and 1.103 ± 0.014, respectively, in acetate buffer pH 4.5 + 1.0% SDS it was 2.404 ± 0.012 and 2.355 ± 0.009, respectively, and in phosphate buffer pH 6.8 + 1.0% SDS it was 0.051 ± 0.005 and 1.805 ± 0.023, respectively. The permeability study was assessed using the parallel artificial membrane permeability assay (PAMPA) model. The apparent permeability coefficient (Papp—cm s−1) of form I and III in pH 1.2 was 3.01 × 10−5 ± 4.14 × 10−7 and 3.15 × 10−5 ± 1.89 × 10−6, respectively, while in pH 6.8 it was 2.72 × 10−5 ± 1.56 × 10−6 and 2.81 × 10−5 ± 9.0 × 10−7, respectively. Changes in sorafenib tosylate concentrations were determined by chromatography using the high-performance liquid chromatography (HPLC)–DAD technique. As a result of the research on the structural polymorphism of sorafenib tosylate, its full spectral characteristics and the possibility of using FT-IR and Raman spectroscopy for the study of polymorphic varieties were determined for the first time, and the HPLC method was developed, which is appropriate for the assessment of sorafenib solubility in various media. The consequences of various physicochemical properties resulting from differences in the solubility of sorafenib tosylate polymorphs are important for pre-formulation and formulation studies conducted with its participation and for the safety of oncological sorafenib therapy.

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Preclinical studies of the antitumor effect of curcumin‐loaded polymeric nanocapsules: A systematic review and meta‐analysis

Oliveira

Stein

Andrade

et al. 2022

Phytotherapy Research

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Curcumin, a plant-derived compound, has various well-known biological effects (antiinflammatory, antioxidant, antitumor, among others) as well as some important limitations for formulators, such as poor water solubility and low oral bioavailability. Its nanoencapsulation is reported to overcome these drawbacks and to improve its in vivo efficacy. Here, data from preclinical in vivo studies evaluating the antitumor efficacy of curcumin-loaded polymeric nanocapsules are collected, analyzed, and discussed as a systematic review. Meta-analyses are performed to assess the contribution of this nanoencapsulation compared with nonencapsulated curcumin. Eighteen studies (116 animals) meet the inclusion criteria. The evidence that curcumin-loaded polymeric nanocapsules inhibits tumor growth (SMD: À3.03; 95% CI: À3.84, À2.21; p < 0.00001) and decreases tumor weight (SMD: À3.96; 95% CI: À6.22, À1.70; p = 0.0006) in rodents is established, regardless of the solid tumor model. To assess the quality of the studies included in the review a bias risk analysis was performed using the SYRCLE's RoB tool. Therefore, encapsulation in polymeric nanocapsules represents an important tool to improve the antitumor effects of curcumin, and this systematic review paves the way for future clinical studies and the translation of curcumin formulations into novel nanomedicines for human cancer treatment.

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Hydroxypropyl-β-cyclodextrin as an effective carrier of curcumin – piperine nutraceutical system with improved enzyme inhibition properties

Cited by 32 publications

References 64 publications

Combinations of Piperine with Hydroxypropyl-β-Cyclodextrin as a Multifunctional System

Combinations of Piperine with Hydroxypropyl-β-Cyclodextrin as a Multifunctional System

Structural Polymorphism of Sorafenib Tosylate as a Key Factor in Its Solubility Differentiation

Preclinical studies of the antitumor effect of curcumin‐loaded polymeric nanocapsules: A systematic review and meta‐analysis

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