Solubility measurement and thermodynamic modelling of curcumin in twelve pure solvents and three binary solvents at different temperature (T = 278.15–323.15 K)

Cui, Zilong; Liang, Yao; Ye, Jingling; Wang, Zhi; Hu, Yonghong

doi:10.1016/j.molliq.2021.116795

Cited by 21 publications

(11 citation statements)

References 39 publications

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“…The same trends observed for prodan are observed for curcumin, whose Stokes shifts have been measured in 13 different solvents (Patra and Barakat, 2011). In this case, water (Kurien et al, 2007) and alkanes (Cui et al, 2021) represent the outliers due to either their internal resistance to re-arrange, or because of their low polarity and polarization. Instead, the solvents in-between, such as dimethyl sulfoxide (DMSO), THF, and acetonitrile display lower Stokes shifts for curcumin while solubility increases (Cui et al, 2021;Patra and Barakat, 2011).…”

Section: Stokes Shift and Solubilitysupporting

confidence: 64%

“…In this case, water (Kurien et al, 2007) and alkanes (Cui et al, 2021) represent the outliers due to either their internal resistance to re-arrange, or because of their low polarity and polarization. Instead, the solvents in-between, such as dimethyl sulfoxide (DMSO), THF, and acetonitrile display lower Stokes shifts for curcumin while solubility increases (Cui et al, 2021;Patra and Barakat, 2011). This further illustrates that as long as the solvent molecules are capable of polarization and in this way able to accommodate charge re-distribution in the solute, they solvate towards dissolution, while simultaneously not generating a resistance too high to re-orient upon charge movement in the solute, facilitating solubility.…”

Section: Stokes Shift and Solubilitymentioning

confidence: 99%

“…Lignins are not completely comprised of aromatic units, as they also carry aliphatic moieties with different functionalities, and while electrostatic and hydrogen bond interactions have already been mentioned, a type of dispersion interaction has been observed to occur between alkyl and aryl moieties where their close association has been found to display attraction by interchanging electron density via C-H (Danovich et al, 2013). While it seems reasonable to picture a similar situation for parts of the aliphatic lignin moieties with the organic part of the solvent, for such interactions to occur, it is likely necessary that the participating orbitals do not differ substantially in energy levels (Yadav et al, 2020).…”

Section: Polyphenolic Structuresmentioning

confidence: 99%

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Role and importance of solvents for the fractionation of lignocellulosic biomass

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Section: Stokes Shift and Solubilitysupporting

confidence: 64%

Section: Stokes Shift and Solubilitymentioning

confidence: 99%

Section: Polyphenolic Structuresmentioning

confidence: 99%

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Role and importance of solvents for the fractionation of lignocellulosic biomass

Thoresen

Lange

Christakopoulos

et al. 2023

Bioresource Technology

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“…It is known that curcumin is soluble in various solvents [12,13,24]. In particular, in ethanol its solubility is of 10 mg/ml.…”

Section: On the Relation With Experimental Observationsmentioning

confidence: 99%

“…Thus, its delivery to the targets for therapeutic purposes is problematic [11]. In some cases, solvent blends have been used to develop liquid formulations [12,13] with enhanced solubility of curcumin solutes and improved delivery properties. In contrast to water solvent, curcumin is quite soluble in organic solvents such as the DMSO, ethanol and methanol, for example.…”

Section: Introductionmentioning

confidence: 99%

Aspects of the microscopic structure of curcumin solutions with water-dimethylsulfoxide solvent. Molecular dynamics computer simulation study

Patsahan¹,

Pizio²

2023

Condens. Matter Phys.

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We explore some aspects of the microscopic structure of curcumin solutions with water-dimethylsulfoxide solvent of variable composition. Molecular dynamics computer simulations at isobaric-isothermal conditions are used for this purpose. The model consists of the OPLS-UA type model for the enol conformer of curcumin (J. Mol. Liq., 223, 707, 2016), the OPLS model for the dimethylsulfoxide (DMSO) and the SPC/E water model. Radial distributions for the centers of mass of curcumin molecules are evaluated and the corresponding running coordination numbers are analyzed. The disaggregation of curcumin clusters upon increasing the DMSO content in water-DMSO solvent is elucidated. Changes of the distribution of water and DMSO species around curcumin molecules are investigated. A qualitative comparison of our findings with the results of other authors is performed. A possibility to relate predictions of the model with the experimental observations in terms of the so-called critical water aggregation percentage is discussed.

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Enhanced antioxidant properties of novel curcumin derivatives: a comprehensive DFT computational study

Boulmokh,

Belguidoum,

Meddour

et al. 2023

Struct Chem

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Oxidative stress, driven by the accumulation of free radicals and reactive oxygen species (ROS) in the human body, is a key contributor to various diseases. Curcumin, a polyphenolic compound derived from turmeric, has garnered attention for its antioxidant potential. In this context, a recent experimental study by Hao et al. introduced curcumin derivatives with incorporated electron-donating groups (allyl and isopentenyl), aiming to enhance antioxidant activity while circumventing the limitations of traditional curcumin. Building upon this experimental foundation, our study employs computational techniques (DFT) to unravel the molecular mechanisms underpinning the superior antioxidant effects observed in these novel derivatives. We investigated three prominent antioxidant mechanisms: Hydrogen Atom Transfer (HAT), Single Electron Transfer-Proton Transfer (SET-PT), and Sequential Proton Loss Electron Transfer (SPLET). Our results reveal that the allyl and isopentenyl groups play pivotal roles in enhancing the antioxidant properties of the derivatives, as evidenced by reduced bond dissociation energies (BDEs) and favorable proton dissociation energies (PDEs). Moreover, the analysis of Highest Occupied Molecular Orbital (HOMO) and Lowest Unoccupied Molecular Orbital (LUMO) energies indicates their enhanced reactivity as electron donors and acceptors. Notably, the computational investigation of spin densities validates the radical scavenging potential of these derivatives. While curcumin exhibits limitations such as low water solubility, bioavailability, and stability, our ndings suggest that the strategically designed derivatives (especially exhibit superior antioxidant properties, positioning them as promising candidates for further therapeutic applications. This comprehensive study bridges experimental ndings with computational insights to unravel the intricate molecular mechanisms driving the enhanced antioxidant e cacy of the newly developed curcumin derivatives.

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Solubility measurement and thermodynamic modelling of curcumin in twelve pure solvents and three binary solvents at different temperature (T = 278.15–323.15 K)

Cited by 21 publications

References 39 publications

Role and importance of solvents for the fractionation of lignocellulosic biomass

Role and importance of solvents for the fractionation of lignocellulosic biomass

Aspects of the microscopic structure of curcumin solutions with water-dimethylsulfoxide solvent. Molecular dynamics computer simulation study

Enhanced antioxidant properties of novel curcumin derivatives: a comprehensive DFT computational study

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