Curcumin-nicotinamide cocrystallization with supercritical solvent (CSS): Synthesis, characterization and in vivo antinociceptive and anti-inflammatory activities

Ribas, Marcela M.; Aguiar, Gean Pablo S.; Müller, Liz Girardi; Siebel, Anna Maria; Lanza, Marcelo; Oliveira, J. Vladimir

doi:10.1016/j.indcrop.2019.111537

Cited by 38 publications

(11 citation statements)

References 40 publications

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“…In this method, the solvent causes intermolecular interactions that lead to the nucleation growth and formation of crystals. The benefit of this technique is that it can be performed by eliminating the drying steps ( Ribas et al, 2019 ). Solubility can be altered by adjusting the temperature and pressure conditions (of CO 2 ).…”

Section: Cocrystallization Techniquesmentioning

confidence: 99%

Recent Advances in Pharmaceutical Cocrystals: From Bench to Market

Bandaru¹,

Rout²,

Kenguva³

et al. 2021

Front. Pharmacol.

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The pharmacokinetics profile of active pharmaceutical ingredients (APIs) in the solid pharmaceutical dosage forms is largely dependent on the solid-state characteristics of the chemicals to understand the physicochemical properties by particle size, size distribution, surface area, solubility, stability, porosity, thermal properties, etc. The formation of salts, solvates, and polymorphs are the conventional strategies for altering the solid characteristics of pharmaceutical compounds, but they have their own limitations. Cocrystallization approach was established as an alternative method for tuning the solubility, permeability, and processability of APIs by introducing another compatible molecule/s into the crystal structure without affecting its therapeutic efficacy to successfully develop the formulation with the desired pharmacokinetic profile. In the present review, we have grossly focused on cocrystallization, particularly at different stages of development, from design to production. Furthermore, we have also discussed regulatory guidelines for pharmaceutical industries and challenges associated with the design, development and production of pharmaceutical cocrystals with commercially available cocrystal-based products.

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Section: Cocrystallization Techniquesmentioning

confidence: 99%

Recent Advances in Pharmaceutical Cocrystals: From Bench to Market

Bandaru¹,

Rout²,

Kenguva³

et al. 2021

Front. Pharmacol.

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“…There are plenty of methods to produce co-crystals, e.g., crystallization from solution, from the melt, or via the solid state like grinding procedures. Co-crystals of CUR are quite well documented, it is reported to form co-crystals, for example, with di- and trihydroxybenzenes [ 21 , 22 , 23 , 24 ], nicotinamide [ 25 ], isonicotinamide [ 26 ], cinnamic acid [ 27 ], ascorbic acid [ 28 ], and 4,4′-bipyridine-N,N’-dioxide [ 29 ], but information about co-crystals of BDMC are sparse. In a patent 6 co-crystals with piperazine, caffeine, L-proline, nicotinamide, isonicotinamide and piperidine are reported but not fully proved [ 26 ].…”

Section: Introductionmentioning

confidence: 99%

A Contribution to the Solid State Forms of Bis(demethoxy)curcumin: Co-Crystal Screening and Characterization

et al. 2021

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Bis(demethoxy)curcumin (BDMC) is one of the main active components found in turmeric. Major drawbacks for its usage are its low aqueous solubility, and the challenging separation from other curcuminoids present in turmeric. Co-crystallization can be applied to alter the physicochemical properties of BDMC in a desired manner. A co-crystal screening of BDMC with four hydroxybenzenes was carried out using four different methods of co-crystal production: crystallization from solution by slow solvent evaporation (SSE), and rapid solvent removal (RSR), liquid-assisted grinding (LAG), and crystallization from the melt phase. Two co-crystal phases of BDMC were obtained with pyrogallol (PYR), and hydroxyquinol (HYQ). PYR-BDMC co-crystals can be obtained only from the melt, while HYQ-BDMC co-crystals could also be produced by LAG. Both co-crystals possess an equimolar composition and reveal an incongruent melting behavior. Infrared spectroscopy demonstrated the presence of BDMC in the diketo form in the PYR co-crystals, while it is in a more stable keto-enol form in the HYQ co-crystals. Solubility measurements in ethanol and an ethanol-water mixture revealed an increase of solubility in the latter, but a slightly negative effect on ethanol solubility. These results are useful for a prospective development of crystallization-based separation processes of chemical similar substances through co-crystallization.

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“…Besides, they reported complementary evidence in which in vivo studies in female BALB/c mice showed that CUR nanococrystals had better anticancer effects in a 4T1 orthotopic breast cancer model as compared to F-CUR. Ribas et al [57] reported that supercritical solvents (and no cosolvents) were used to produce their CUR-nicotinamide nanococrystal. The nanosystem showed a higher dissolution rate, in addition to antinociceptive and anti-inflammatory effects.…”

Section: Conventional Nanosystemsmentioning

confidence: 99%

Use of nanosystems to improve the anticancer effects of curcumin

Araya-Sibaja¹,

Salazar‐López²,

Wilhelm-Romero³

et al. 2021

Beilstein J. Nanotechnol.

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Curcumin (CUR) is a phenolic compound that is safe for human consumption. It exhibits chemopreventive, antiproliferative, antiangiogenic, and antimetastatic effects. However, these benefits can be hampered due to the lipophilic nature, rapid metabolism, low bioavailability, and fast elimination of the molecule. Considering this, the present work reviews the use of CUR-based nanosystems as anticancer agents, including conventional nanosystems (i.e., liposomes, nanoemulsions, nanocrystals, nanosuspensions, polymeric nanoparticles) and nanosystems that respond to external stimuli (i.e., magnetic nanoparticles and photodynamic therapy). Previous studies showed that the effects of CUR were improved when loaded into nanosystems as compared to the free compound, as well as synergist effects when it is co-administrated alongside with other molecules. In order to maximize the beneficial health effects of CUR, critical factors need to be strictly controlled, such as particle size, morphology, and interaction between the encapsulating material and CUR. In addition, there is an area of study to be explored in the development of CUR-based smart materials for nanomedical applications. Imaging-guided drug delivery of CUR-based nanosystems may also directly target specific cells, thereby increasing the therapeutic and chemopreventive efficacy of this versatile compound.

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Curcumin-nicotinamide cocrystallization with supercritical solvent (CSS): Synthesis, characterization and in vivo antinociceptive and anti-inflammatory activities

Cited by 38 publications

References 40 publications

Recent Advances in Pharmaceutical Cocrystals: From Bench to Market

Recent Advances in Pharmaceutical Cocrystals: From Bench to Market

A Contribution to the Solid State Forms of Bis(demethoxy)curcumin: Co-Crystal Screening and Characterization

Use of nanosystems to improve the anticancer effects of curcumin

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