Novel curcumin ascorbic acid cocrystal for improved solubility

Pantwalawalkar, Jidnyasa; More, Harinath N.; Bhange, Deu S.; Patil, Udaykumar; Jadhav, Namdeo

doi:10.1016/j.jddst.2020.102233

Cited by 38 publications

(23 citation statements)

References 42 publications

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“…In Physical mixture 2, there were endothermic peaks at 59 • C and 186 • C and an exothermic peak at 254 • C. In contrast, no endothermic (melting) peak of Cur was observed in the DSC thermogram of DG1/Cur-NPs. The reduced intensity of the peak at 188 • C and the appearance of new peaks at 166 • C and 170 • C confirmed the reduced crystallinity of Cur and the formation of a new polymorph during the crystallisation procedure, as reported by Pantwalawalkar [37]. Sadeghi et al reported that the melting peak of Cur disappeared in solid dispersion systems of Cur and PVP, which indicated that Cur was in an amorphous state in the precipitated samples [38].…”

Section: Dsc Analysissupporting

confidence: 72%

Chitosan/Alginate Nanoparticles for the Enhanced Oral Antithrombotic Activity of Clam Heparinoid from the Clam Coelomactra antiquata

et al. 2022

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Chitosan/alginate nanoparticles (DG1-NPs and DG1/Cur-NPs) aiming to enhance the oral antithrombotic activity of clam heparinoid DG1 were prepared by ionotropic pre-gelation. The influence of parameters, such as the concentration of sodium alginate (SA), chitosan (CTS), CaCl2, clam heparinoid DG1, and curcumin (Cur), on the characteristics of the nanoparticles, were investigated. Results indicate that chitosan and alginate can be used as polymer matrices to encapsulate DG1, and nanoparticle characteristics depend on the preparation parameters. Nano-particles should be prepared using 0.6 mg/mL SA, 0.33 mg/mL CaCl2, 0.6 mg/mL CTS, 7.2 mg/mL DG1, and 0.24 mg/mL Cur under vigorous stirring to produce DG1-NPS and DG1/Cur-NPS with small size, high encapsulation efficiency, high loading capacity, and negative zeta potential from approximately −20 to 30 mV. Data from scanning electron microscopy, Fourier-transform infrared spectrometry, and differential scanning calorimetry analyses showed no chemical reaction between DG1, Cur, and the polymers; only physical mixing. Moreover, the drug was loaded in the amorphous phase within the nanoparticle matrix. In the acute pulmonary embolism murine model, DG1-NPs enhanced the oral antithrombotic activity of DG1, but DG1/Cur-NPs did not exhibit higher antithrombotic activity than DG1-NPs. Therefore, the chitosan/alginate nanoparticles enhanced the oral antithrombotic activity of DG1, but curcumin did not further enhance this effect.

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Section: Dsc Analysissupporting

confidence: 72%

Chitosan/Alginate Nanoparticles for the Enhanced Oral Antithrombotic Activity of Clam Heparinoid from the Clam Coelomactra antiquata

et al. 2022

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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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“…However, limited clinical use of CUR relates to di culties in its formulation because of its low solubility and bioavailability in aqueous media (0.6 𝜇g/mL) (Katherine et al, 2018) . Several approaches have also been pursued to increase CUR bioactivity, such as lipophilic matrices (Jäger et al, 2014) , liposomes (Hasan et al, 2014) , nanoparticles (Pandit et al, 2015;Quiñones et al, 2018), nanocapsules (Alippilakkotte and Sreejith, 2018;Pan et al, 2013), bionanoemulsions (Malik et al, 2014) , andMCCs (Dal Magro et al, 2021;Katherine et al, 2018;Pang et al, 2019;Pantwalawalkar et al, 2021;Rathi et al, 2019;Ribas et al, 2019;Sathisaran and Dalvi, 2017). MCCs of CUR have been studied widely in the crystal engineering approach, as shown in Table 1.…”

Section: Curcumin (Cur)mentioning

confidence: 99%

“…MCCs of CUR have been produced conventionally with (Sowa et al, 2014a) Abbreviations: AA, ascorbic acid; 𝛽 -CD, 𝛽 -cyclodextrin; BBB, blood brain barrier; BYP, 4,4'-bipyridine; CA, cinnamic acid; CAF, ca eine; CD, cumulative dissolution; COOH, carboxylic acid; CS, complexation stoichiometry; CUR, curcumin; DSC, di erential scanning calorimetry; DTA, di erential thermal analysis; DX, dextrose; EC, electrostatic charge: FT-IR, Fourier transformation infrared; FT-Raman, Fourier transformation Raman; GEN, genistein; GIT, gastrointestinal tract; HP-𝛽 -CD, hydroxypropyl-𝛽 -cyclodextrin; HSM, hot stage microscopy; INM, isonicotinamide; MA, malonic acid; MYR, myricetin; NM, nicotinamide; NMR, nuclear magnetic resonance; PIP, piperine; PM, physical mixture; PRC, piracetam; PRL, proline; PXRD, powder X-ray di raction; QUE, quercetin; RSV, resveratrol; SA, succinic acid; SAC, saccharine; SCXRD, single-crystal X-ray di raction; SEM, scanning electron microscopy; Smax, maximum solubility; TG, thermogravimetry. solvent evaporation or wet grinding methods (Pantwalawalkar et al, 2021) . formulated CUR with ascorbic acid (AA) cocrystals using the solvent evaporation technique in 0.50-, 0.55-, 0.60-, and 0.65-mole fractions.…”

Section: Curcumin (Cur)mentioning

confidence: 99%

Crystal Engineering Approach in Physicochemical Properties Modifications of Phytochemical

Lutfiyah

Fitriani

Taher

et al. 2022

Sci. Technol. Indones

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Phytochemicals have been used to reduce the risk of diseases and maintain good health and well-being. However, most phytochemicals have a limitation in their physicochemical properties, which can be modified by reforming the shape of the crystals. Therefore, crystal engineering is a promising approach to optimize physicochemical characteristics of the active pharmaceutical ingredients (APIs) in a phytochemical without altering its pharmacological efficacy. Hence, this paper reviews current strategies for the use of crystal engineering to optimize physicochemical properties of phytochemicals, which is followed by the design of the synthesis and characterization of particular phytochemicals, including piperine (PIP), quercetin (QUE), curcumin (CUR), genistein (GEN), and myricetin (MYR). The literature indicates that crystal engineering of multicomponent crystals (MCCs) enhances phytochemical physicochemical properties, including solubility, dissolution rate, stability, and permeability. The MCCs provide a lower lattice energy and noncovalent bonding, which translate into lower melting points and weak intermolecular interactions that generate greater solubility, higher dissolution rate, and better stability of the APIs. Nevertheless, the absence of reported studies of phytochemical crystal engineering leads to a lack of variation in the selection of coformers, methods of preparation, and improvement of physicochemical properties. Therefore, more extensive evaluation of the design and physicochemical characteristics of phytochemicals using MCCs is necessary and manifests the opportunity to enhance the application of phytochemicals in the pharmaceutical industry.

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Novel curcumin ascorbic acid cocrystal for improved solubility

Cited by 38 publications

References 42 publications

Chitosan/Alginate Nanoparticles for the Enhanced Oral Antithrombotic Activity of Clam Heparinoid from the Clam Coelomactra antiquata

Chitosan/Alginate Nanoparticles for the Enhanced Oral Antithrombotic Activity of Clam Heparinoid from the Clam Coelomactra antiquata

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

Crystal Engineering Approach in Physicochemical Properties Modifications of Phytochemical

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