Hydration behavior of D-calcium pantothenate (vitamin B5) in the presence of sugar-based deep eutectic solvents at different temperatures: experimental and theoretical study | Scientific Reports

Scientific Reports volume 14, Article number: 24805 (2024) Cite this article

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Considerable efforts have been devoted in recent years to enhancing the efficacy medicinal substance, leading to the discovery of innovative drug formulations and delivery techniques. The successful design of these processes necessitates a profound understanding at the molecular level of how these substances interact with biological membranes. Thorough thermodynamic investigations provide invaluable insights into these interactions and aid in selecting suitable compounds for pharmaceutical production. This study aims to determine the density and speed of sound for D-calcium pantothenate in mixtures of water and deep eutectic solvents (DESs), specifically choline chloride/sucrose, choline chloride/ glucose, and choline chloride/ fructose (with 2:1 molar ratio) over a temperature range of 288.15 K to 318.15 K under atmospheric pressure. In order to predict the behavior of molecules, COSMO model (the Conductor-Like Screening Model) offer complementary strengths in quantum chemistry. This approach allows for calculating solvation free energies, making it ideal for predicting properties like solubility, where understanding solvent-solute interactions is crucial. By correlating the measured parameters using standard relationships, important partial molar parameters such as apparent molar volumes and apparent molar isentropic compressibility are calculated. Additionally, apparent molar isobaric expansion, and Hepler’s constant are derived from the density and speed of sound data. The experimental apparent molar volumes, and apparent molar isentropic compressibility data is fitted to the Redlich-Meyer equation to obtain significant quantities such as standard partial molar volume, and partial molar isentropic compression. The comprehensive thermodynamic analysis of this studied system holds immense significance for advancements in the pharmaceutical industry.

In cellular and organ functioning and development, vitamins play a crucial role as organic compounds. They are actively involved in enzymic processes and genetic regulation1. Understanding the physicochemical interactions between vitamins and key biomolecules such as amino acids, proteins, carbohydrates, and lipids is vital for comprehending the pharmacodynamics and pharmacokinetics of these compounds. Furthermore, this knowledge aids in the development of drug formulations within the pharmaceutical industry2,3. To gain deeper insights, researchers conduct comprehensive investigations into the thermophysical properties of vitamins in both water and aqueous media containing essential biomolecules. These studies aim to elucidate the molecular interactions between co-solutes and the hydrophilic and hydrophobic moieties of vitamins. Additionally, they seek to identify the conformational stability of biomolecules within biological systems4,5. Such research contributes to a better understanding of the behavior and interactions of vitamins with biomolecules, further advancing our knowledge of their roles in biological processes and pharmaceutical applications.

D-calcium pantothenate, also known as vitamin B5, plays a crucial role in various biochemical processes within the human body. This vitamin is a water-soluble compound and an integral component of coenzyme A (CoA)6,7. CoA is involved in vital metabolic reactions, including fatty acid synthesis, energy production, and acetylcholine synthesis. In recent years, the combination of vitamins with deep eutectic solvents has garnered considerable attention from researchers and scientists. This unique synergy has shown promising potential in diverse fields, ranging from pharmaceuticals to green chemistry8,9.

DESs are an emerging class of mixtures characterized by significant depressions in melting points compared to those of the neat constituent components. DESs formed through the combination of hydrogen bond donors (HBD) and acceptors (HBA), typically consisting of quaternary ammonium salts and hydrogen bond donors such as alcohols, carboxylic acids, and sugars. They exhibit unique physicochemical properties, including low melting points, non-volatility, and high thermal and chemical stability, making them attractive alternatives to conventional organic solvents in various applications10,11. These solvents have gained significant attention in recent years due to their environmentally friendly nature, biodegradability, and potential for sustainable processes12,13,14. Their tunable properties and ability to dissolve a wide range of compounds have led to their utilization in diverse fields, including catalysis, extraction, electrochemistry, and separation processes. Additionally, their biocompatibility and low toxicity open up possibilities for applications in biotechnology and pharmaceutical industries. The knowledge of volumetric and acoustic of D-calcium pantothenate with DESs is valuable in elucidating the assorted interactions prevailing in their solutions and for improving the design of various processes15.

Physicochemical and thermodynamic investigations are essential tools for understanding the complex nature and various types of molecular interactions in mixtures16,17. Thermodynamic properties, such as volume and compressibility, play a crucial role in elucidating the ionic, hydrophilic, and hydrophobic interactions in different solution media. These properties provide valuable insights into the interactions between solute and solvent molecules in the solution phase18,19. Accordingly, the Conductor-Like Screening Model provides a detailed picture of solute-solvent interactions; By employing this model, scientists have been able to glean significant information about the interplay between some ionic liquids and their environment, leading to more accurate predictions and improved their applications20. However, there is limited knowledge about the contributions of structurally similar DESs that influence the interactions of D-calcium pantothenate and its surroundings concerning temperature. Therefore, in this study, we measured and reported the densities (d) and speeds of sound (u) of D-calcium pantothenate (a derivative of vitamin B5) in water and DESs composed of choline chloride as HBA and sucrose, fructose and glucose as HBD (ChCl/S, ChCl/G, and ChCl/F) aqueous solutions at temperatures ranging from 288.15 K to 318.15 K with a 10 K interval as a function of concentration.

The data obtained from these measurements were then used to calculate various derived thermodynamic parameters, including the apparent molar volume, \({V_\varphi }\), standard partial molar volume, \(V_{\varphi }^{0}\), apparent molar isentropic compression, \({\kappa _\varphi }\), and partial isentropic compression, \(\kappa _{\varphi }^{0}\). These derived thermophysical parameters offer valuable insights into the performance and behavior of solvents during drug manufacturing processes. Understanding the interactions between D-calcium pantothenate and DESs can have significant implications for predicting and optimizing solvent behavior, ultimately contributing to more efficient drug manufacturing processes.

The detailed descriptions of the used chemicals are specified in Table 1. To preparation of solutions double distilled deionized water with a conductivity of 0.055 µS/cm was applied at 298.15 K. Sucrose, glucose, and fructose were dried in vacuum over P2O5 at room temperature for at least 72 h.Other reagents were used without further purifications.

The preparation of all DESs was carried out using an electronic balance with a precision of ± 10−7 kg. The uncertainty in the DES composition, represented by the mole ratio of its constituent ingredients, was found to be within 4 × 10−3. In this research, three type of DESs were prepared using choline chloride as the hydrogen bond acceptor (HBA) and sucrose, glucose, and fructose as the hydrogen bond donor (HBD) in molar ratios of 2:1. The eutectic mixtures were prepared by stirring the two components at 60–80 ºC until a homogeneous transparent liquid was formed21. Subsequently, the mixture was left to cool down to room temperature naturally for further utilization22. The water content of the utilized DESs was determined through Karl-Fischer titration.

For weighing the solutions, an analytical balance (AND, GF202, Japan) with an uncertainty of 10−7 kg was employed. These solutions were then carefully placed inside glass vials, which were securely sealed with parafilm to prevent any potential contamination. The density (d) and speed of sound (u) of the prepared solutions were measured using a vibrating tube densimeter (Anton Paar, DSA 5000 densimeter and speed of sound analyzer). To calibrate the apparatus, dry air at atmospheric pressure and degassed and double-distilled deionized water were utilized. The temperature during the experiments was maintained with a high level of precision, within an uncertainty of 10−3 K.

The measurements of density and speed of sound had uncertainties of 0.15 kg.m−3 and 0.5 m.s−1, respectively. These meticulous measurements and calibrations ensure the accuracy and reliability of the obtained data, allowing for comprehensive and precise analysis of the properties of the prepared solutions.

In this study, we employed density functional theory (DFT) with the Dmol3 program to perform geometry optimizations of sucrose, fructose, glucose and D-calcium pantothenate. The Generalized Gradient Approximation (GGA) with the Vosko-Wilk-Nusair (VWN) functional supplemented by the BP functional (GGA-VWN-BP) was used. This approach replaces the local correlation component of the VWN functional, aligning with established COSMO results in the literature20,23,24.

The experimental densities of D-calcium pantothenate in water and aqueous solutions of DESs (ChCl/S, ChCl/G, and ChCl/F) with different concentrations (0.1, 0.2, and 0.3 mol·kg−1) were investigated at various temperatures (288.15, 298.15, 308.15, and 318.15 K) and are presented in Table 2. In the studied concentration range of DESs, DESs may be converted into their initial materials. Therefore, instead of DES, their mixtures (ChCl/S, ChCl/G, and ChCl/F) are used.

Analysis of the data in Table 2 reveals a consistent trend where the densities increase monotonously with an increase in the concentration of the mixtures (ChCl/S, ChCl/G, and ChCl/F). Moreover, for a fixed D-calcium pantothenate concentration, the densities decrease as the temperature rises. This information indicates the influence of (ChCl/S, ChCl/G, and ChCl/F) concentration and temperature on the densities of the D-calcium pantothenate solutions, providing valuable insights into the behavior of these systems. By using the Eq. (1) apparent molar volumes, \({V_\varphi }\), could be calculated from the experimental density values25,26:

In the investigated solutions, the variables “m” and “M” represent the molalities and molecular mass of D-calcium pantothenate, respectively. Likewise, “d0” and “d” correspond to the densities of the solvent and solutions, respectively. For the ternary systems, the solvent is considered to be a mixture of DES and water. The experimental values of apparent molar volume for D-calcium pantothenate in both pure water and aqueous solutions containing each mixture (ChCl/S, ChCl/G, and ChCl/F) with combined uncertainty of 0.06 × 10−6 m3·mol−1 at various temperatures are documented in Table 3. Furthermore, Fig. 1 displays the plot of apparent molar volumes for D-calcium pantothenate at a fixed molality of each mixture (ChCl/S, ChCl/G, and ChCl/F) (0.3 mol·kg−1) and at a temperature of 298.15 K. From the results, it is evident that the apparent molar volumes increase with the growing concentration of DES and temperature. This observation suggests a direct influence of ChCl/S, ChCl/G, or ChCl/F concentration on the apparent molar volume of D-calcium pantothenate in the studied solutions.

Apparent molar volume of D-calcium pantothenate, \({V_\varphi }\), versus its molality, m1, in aqueous ChCl/G solutions at T = 298.15 K: ●, binary; ▲, 0.1; ♦, 0.2; ■, 0.3 mol·kg−1.

The following Redlich-Mayer equation was used to obtain the standard partial molar volume, \({V_\varphi }^{0}\)27:

The \({V_\varphi }^{0}\)parameter represents the standard partial molar volume, specifically the partial molar volume at infinite dilution. Empirical parameters Sv and bv are also utilized in this context. Given that solute-solute interactions are negligible under infinite dilution conditions, the standard partial molar volumes offer valuable insights into solute-solvent interactions. In Table 4, we present the values of \({V_\varphi }^{0}\), Sv and bv, along with their corresponding standard deviations. Notably, all values, serving as indicators of solute-solvent interactions, exhibit positive values. Moreover, these values increase with higher concentrations of ChCl/S, ChCl/G, or ChCl/F and at elevated temperatures. This behavior can be attributed to the weaker electrostriction of water and the enhanced interactions between solute and solvent molecules. The larger values observed at higher temperatures likely correspond to the release of solvent molecules into the bulk. The \({V_\varphi }^{0}\)values provide information about the solute–solvent interactions for D-calcium pantothenate in aqueous solutions of DESs as the following order: ChCl/S > ChCl/G > ChCl/F, respectively. This order interpreted that the interactions between D-calcium pantothenate as solute and solvent were strengthened with ChCl/S, ChCl/G, or ChCl/F. The \({V_\varphi }^{0}\) values for D-calcium pantothenate are very close for two ChCl/G, and ChCl/F. This behavior is maybe because of structure and size of studied sugars as HBD. In the case of ternary systems, the positive bv values indicate the dominance of hydrophilic hydrogen-bonding interactions over hydrophobic interactions28,29. These findings shed light on the nature and strength of solute-solvent interactions, particularly in the presence of mixtures of ChCl/S, ChCl/G, or ChCl/F, offering crucial implications for understanding solution behavior and properties.

Temperature dependence of \(V_{\varphi }^{0}\) values can be defined by following equation:

where A, B and C are empirical constants which are calculated by the least-square fitting of standard partial molar volume at studied temperatures30,31.

By differentiating the standard partial molar volume with respect to temperature at constant pressure, the standard apparent molar expansibilities\(E_{\varphi }^{0}\), were computed. The obtained values are presented in Table 5. In the context of aqueous solutions of the studied drug with mixtures of ChCl/S, ChCl/G, or ChCl/F, the values of are consistently positive. This positive expansibility signifies a characteristic property of hydrophobic hydration in such solutions. The presence of hydrophobic groups in the drug molecules leads to an increased volume of the solution relative to pure water, resulting in a positive value for\(E_{\varphi }^{0}\). Consequently, the aqueous mixtures of ChCl/S, ChCl/G, or ChCl/F solutions exhibit an enhanced expansion in volume compared to pure water due to this hydrophobic hydration effect.

The values of \(E_{\varphi }^{0}\) exhibit a positive trend, displaying an increase with both higher concentrations of mixtures of ChCl/S, ChCl/G, or ChCl/F and elevated temperatures. This observation suggests a notable sensitivity of the systems to temperature variations, indicating that molecular motilities are enhanced at higher temperatures32,33.

The thermal expansion coefficient, \(\alpha\), was calculated by the values of the standard partial molar volume, using Eq. (4)34:

The thermal expansion coefficients, denoted as \(\alpha\), have been documented in Table 5 for the examined systems. This parameter serves as a crucial indicator to assess how the solutions respond to changes in temperature. The sign of the second derivative of the volume (\(V_{\varphi }^{0}\)) with respect to temperature allows us to obtain qualitative insights into the solute’s behavior as a structure maker or structure breaker in the solutions. The following expression35 is employed to achieve this analysis:

By analyzing the thermal expansion coefficients and the second derivative of volume with respect to temperature, we can gain valuable information regarding the role of the solute in influencing the solution’s structure and its responsiveness to temperature variations.

The \({({\partial ^2}{V_\varphi }^{0}/\partial {T^2})_p}\)values of the investigated systems are presented in Table 5. According to previous research36, a negative value of \({({\partial ^2}{V_\varphi }^{0}/\partial {T^2})_p}\) suggests a structure-breaking solute, whereas a positive value or one closer to zero indicates a structure-making solute. Our observations reveal that the values of V for aqueous solutions of D-calcium pantothenate tend to be negative and closer to zero. However, as the concentration of mixtures of ChCl/S, ChCl/G, or ChCl/F increases, these values transition to positive values. This behavior implies that the drug, D-calcium pantothenate, predominantly acts as a structure maker in the aqueous mixtures of ChCl/S, ChCl/G, or ChCl/F solutions, influencing their structural characteristics. The results shed light on the solute’s impact on the solution’s structure and offer valuable insights for understanding the behavior of these systems.

The partial molar volume of transfer, \({\Delta _{tr}}\mathop V\nolimits_{\varphi }^{0}\), for D-calcium pantothenate from water to the aqueous mixtures of ChCl/S, ChCl/G, or ChCl/F solutions have been calculated as37:

The \({\Delta _{tr}}\mathop V\nolimits_{\varphi }^{0}\) values of the studied solutions are reported in Table 4. The values of \(V_{\varphi }^{0}\) for binary (D-calcium pantothenate + water) was taken from reference38. These \({\Delta _{tr}}\mathop V\nolimits_{\varphi }^{0}\) values demonstrate a positive trend at all temperatures and exhibit an increase with the growing concentration of each mixture of ChCl/S, ChCl/G, or ChCl/F. The interactions between the solute, D-calcium pantothenate, and the co-solute, mixtures of ChCl/S, ChCl/G, or ChCl/F, in the ternary solutions (D-calcium pantothenate + (ChCl/S, ChCl/G, or ChCl/F) + water) encompass several possibilities: (i) ion-hydrophilic and hydrophilic-hydrophilic interactions between ions of D-calcium pantothenate and the polar groups of ChCl/S, ChCl/G, or ChCl/F; (ii) hydrophobic interactions between ions of D-calcium pantothenate and the non-polar groups of ChCl/S, ChCl/G, or ChCl/F; (iii) hydrophobic-hydrophobic interactions between the alkyl groups of the drug and the hydrophobic groups of ChCl/S, ChCl/G, or ChCl/F; and (iv) hydrophilic-hydrophobic interactions between the cation and anion components of D-calcium pantothenate and the hydrophilic groups of mixtures of ChCl/S, ChCl/G, or ChCl/F.

According to the co-sphere overlap model39,40, two types of interactions, namely, ion-hydrophilic and hydrophilic-hydrophilic interactions, result in positive effects on the \({\Delta _{tr}}\mathop V\nolimits_{\varphi }^{0}\) values, while the other types lead to negative transfer volumes. The presence of positive \({\Delta _{tr}}\mathop V\nolimits_{\varphi }^{0}\) values suggests that hydrophilic interactions between the COOH and CH2OH groups predominate over other types of interactions, and this trend becomes more pronounced with increasing concentrations of each mixtures of ChCl/S, ChCl/G, or ChCl/F41,42.

The findings indicate the significance of hydrophilic interactions in influencing the volumetric behavior of the solutions and provide valuable insights into the molecular interactions occurring in these systems.

Experimentally measured speeds of sound, u, for D-calcium pantothenate in water and aqueous solutions of mixtures of ChCl/S, ChCl/G, or ChCl/F at different temperatures are listed in Table 2. The Laplace–Newton’s equation43 was used to obtain the isentropic compressibility value, \({\kappa _s}\) by following equation:

The overall isentropic compressibility (\({\kappa _s}\)) of a system is composed of two components: \({\kappa _{s1}}\)to solvent intrinsic and \({\kappa _{s2}}\) to solute intrinsic. The former is associated with the compression of the solvent, which can be either water or aqueous solutions of mixtures of ChCl/S, ChCl/G, or ChCl/F. The latter, \({\kappa _{s1}}\) (solute intrinsic), accounts for the compression layer of solute molecules influenced by the surrounding solvent molecules occupying the empty spaces around the solute. Notably, at low concentrations of D-calcium pantothenate, the dominant contribution to the overall \({\kappa _{s1}}\) value is attributed to \({\kappa _s}\) (solvent intrinsic)44. As the concentration of mixtures of ChCl/S, ChCl/G, or ChCl/F increases, lower values of \({\kappa _s}\) are observed. This behavior can be attributed to the disruption of the three-dimensional structure of water caused by the formation of hydrogen bonds around the D-calcium pantothenate molecules. Consequently, this phenomenon leads to a reduction in the compression of water molecules within the bulk solution. The interplay between solvent and solute molecules and their respective compressibility contributions influences the overall isentropic compressibility of the system. These findings highlight the complex nature of molecular interactions within the solution and their impact on its compressibility behavior.

The apparent molar isentropic compressibility, (\({\kappa _\varphi }\)) is obtained from the Eq. (8):

where \({\kappa _{s0}}\), and \({\kappa _s}\) are isentropic compressibility values of the solvent and solutions, respectively. The calculated \({\kappa _\varphi }\)values with combined uncertainty of 0.02 × 10−14 m3∙mol∙Pa−1 for investigated systems are given in Table 2. Also, the apparent molar isentropic compressibility values for D-calcium pantothenate in the aqueous solutions of mixtures of ChCl/S, ChCl/G, or ChCl/F with concentration of 0.3 mol.kg−1 of each ChCl/S, ChCl/G, or ChCl/F at 298.15 K are represented in Fig. 2. As can be seen from Table 2, the values of apparent molar isentropic compressibility increase with increasing of temperature and concentration of studied mixtures of ChCl/S, ChCl/G, or ChCl/F. The variation of apparent molar isentropic compressibility with molality of D-calcium pantothenate can be presented by using the Eq. (9):

Apparent molar isentropic compressibility of D-calcium pantothenate, \({K_\varphi }\), versus its molality, m1, in aqueous ChCl/G solutions at T = 298.15 K: ●, binary; ▲, 0.1; ♦, 0.2; ■, 0.3 mol·kg−1.

where \(\kappa _{\varphi }^{0}\), is partial molar isentropic compressibility, \({S_k}\) and \({b_k}\) have the empirical and similar meaning as in Eq. 2 for apparent molar volumes. The values of \(\kappa _{\varphi }^{0}\), \({S_k}\) and \({b_k}\) are given for the studied solutions along with standard deviations at the experimental temperatures in Table 6. The small \({b_k}\) values rather than \(\kappa _{\varphi }^{0}\) predict that solute-solute interactions are negligible in comparison to solute–solvent interactions. The \(\kappa _{\varphi }^{0}\) values increase from negative values towards positive values by increasing the ChCl/S, ChCl/G, or ChCl/F concentration and temperature. By increasing mixtures of ChCl/S, ChCl/G, or ChCl/F concentration the formation of ion-pairs cause to suppressed the electrostatic interactions between D-calcium pantothenate and water molecules which leads to become more compressible than that at lower concentration45. The \(\kappa _{\varphi }^{0}\)values for D-calcium pantothenate in aqueous solutions of different DESs have similar order with \(V_{\varphi }^{0}\)and confirm the volumetric results: ChCl/S,> ChCl/G > ChCl/F, respectively.

Partial molar isentropic compressibility of transfer, \({\Delta _{tr}}\kappa _{\varphi }^{0}\), for water and the aqueous solutions of DESs have been calculated using the following equation:

The values of \({\Delta _{tr}}\mathop \kappa \nolimits_{\varphi }^{0}\) for studied solutions are represented in Table 6. The values of \(\kappa _{\varphi }^{0}\) for binary (D-calcium pantothenate + water) was taken from reference38. The sign of \({\Delta _{tra}}\mathop \kappa \nolimits_{\varphi }^{0}\) is positive in the studied systems and these values increase with a rise in the concentration of mixtures of ChCl/S, ChCl/G, or ChCl/F. Positive values of \(\mathop \kappa \nolimits_{\varphi }^{0}\) for D-calcium pantothenate illustrates the dominance of the head charged groups N+ and COO– of DESs with the ions of D-calcium pantothenate which increase with a rise in the concentration of mixtures of ChCl/S, ChCl/G, or ChCl/F. This behavior which observed for partial molar isentropic compressibility of transfer, are in good agreement with volumetric results and supports them.

The σ-profile is a crucial concept in COSMO-based thermodynamics, representing the charge distribution on a molecule’s surface. It acts as a unique fingerprint, indicating the likelihood of finding specific charge density values in segmented segments. COSMO models, such as COSMO-RS and COSMO-SAC, utilize σ-profiles to predict thermodynamic properties and molecule-environment interactions.

These profiles are obtained through computational methods, primarily employing density functional theory (DFT) calculations, which can be computationally expensive. The utilization of the GGA VWN-BP function in Dmol3, as suggested by the developer. In this study, COSMO results were obtained through DFT calculations using the Dmol3 module of Materials Studio (Biovia, Materials Studio 2023). The molecule geometry was optimized using GGA (VWN-BP). Figure 3 presents the optimized structures of the molecules and the corresponding σ-profiles, for the studied molecules including choline chloride, glucose, fructose, sucrose, and calcium pantothenate. Additionally, Table 7 provides the cavity volume and cavity surface area results besides the HOMO and LUMO energy of the compounds from Dmol3 energy optimization calculations. These σ-profiles show that calcium pantothenate and choline chloride as ionic species show most negative and positive values due to the density of electron in the positive region with higher σ-profiles with higher intensity and vice versa for positive charge distribution in the negative region. The carbohydrates show negative and positive distributions around the 0 screen charge density. Choline chloride has the smallest cavity volume and surface area compared to the other molecules, suggesting a more compact solute. It also has the least negative dielectric (hydration) energy after calcium pantothenate, indicating a stronger interaction with the solvent compared to the other molecules. These results are compatible with the results are obtained in the previous sections. The results suggest that calcium pantothenate exhibits a different hydration behavior compared to the studied molecules (sucrose, fructose, glucose, and choline chloride). Smaller cavity volume and surface area, along with its less negative dielectric energy, indicate a more compact solute with weaker H-bonding interactions with the solvent. On the other hand, the studied molecules have larger cavity volumes and surface areas, stronger dielectric energies, and can form more intricate H-bond interactions with the solvent.

Optimized structure of (a) sucrose, (b) fructose, (c) glucose, (d) choline chloride, d) Calcium pantothenate, and (e) σ- profiles of these molecules.

This research study focused on investigating the thermodynamic properties of D-calcium pantothenate (also known as vitamin B5), an essential micronutrient, in aqueous solutions of three DESs comprising choline chloride as the hydrogen bond acceptor (HBA) and sucrose, fructose, and glucose as the hydrogen bond donors (HBDs) (with molar ratio of 2:1) at concentrations of 0.1, 0.2, and 0.3 mol·kg−1 at different temperatures.

Through the analysis of volumetric and acoustic properties, strong interactions were observed between D-calcium pantothenate and the studied DESs, predominantly characterized by hydrophilic-hydrophilic interactions between the solute and solvent. The Helper’s constant, \({({\partial ^2}{V_\varphi }^{0}/\partial {T^2})_p}\), demonstrated the structure-making nature of D-calcium pantothenate in the aqueous solutions of the mentioned DESs. Overall, the findings indicate that the addition of DESs to aqueous solutions of D-calcium pantothenate leads to the release of water molecules from the solute’s hydration layer. As a result, the interactions between D-calcium pantothenate and DESs become more pronounced and strengthened. These insights contribute to a better understanding of the behavior and interactions of D-calcium pantothenate in aqueous ChCl/S, ChCl/G, or ChCl/F solutions, offering valuable implications for potential applications in various fields.

All data generated or analysed during this study are included in this article.

Ayranci, G., Sahin, M. & Ayranci, E. Volumetric properties of ascorbic acid (vitamin C) and thiamine hydrochloride (vitamin B1) in dilute HCl and in aqueous NaCl solutions at (283.15, 293.15, 298.15, 303.15, 308.15, and 313.15)K. J. Chem. Thermodyn. 39, 1620–1631 (2007).

Article ADS Google Scholar

Bhattacharya, D. M. et al. Investigation of volumetric and acoustic properties of procainamide hydrochloride in aqueous binary and (water + amino acid) ternary mixtures at different temperatures. J. Chem. Eng. Data 62, 4083–4092 (2017).

Article Google Scholar

Khatun, M. R., Islam, M. M., Rima, F. R. & Islam, M. N. Apparent molar volume, adiabatic compressibility, and critical micelle concentration of flucloxacillin sodium in aqueous NaCl solutions at different temperatures. J. Chem. Eng. Data 61, 102–113 (2016).

Article Google Scholar

Bhattacharya, D. M., Dhondge, S. S. & Zodape, S. P. Solvation behaviour of an antihelmintic drug in aqueous solutions of sodium chloride and glucose at different temperatures. J. Chem. Thermodyn. 101, 207–220 (2016).

Article ADS Google Scholar

Singla, M., Kumar, H. & Jindal, R. Solvation behaviour of biologically active compounds in aqueous solutions of antibacterial drug Amoxicillin at different temperatures. J. Chem. Thermodyn. 76, 100–115 (2014).

Article ADS Google Scholar

Ping, L. Determination of D-calcium pantothenate and D-biotin in premixed feeds by ultrahigh-performance liquid chromatography. Acta Agriculturae Shanghai. 26, 124–126 (2010).

Google Scholar

Liu, L. et al. D-Calcium pantothenate-derived porous carbon: carbonization mechanism and application in aqueous Zn-ion hybrid capacitors. J. Mater. Chem. A. 11, 14311–14319 (2023).

Article ADS Google Scholar

Shekaari, H., Ghaffari, F. & Mokhtarpour, M. Volumetric, ultrasonic properties of thiamine hydrochloride drug in aqueous solutions of choline-based deep eutectic solvents at different temperatures. Chin. J. Chem. Eng. 62, 21–30 (2023).

Ghaffari, F., Zafarani-Moattar, M. T. & Shekaari, H. Aqueous biphasic systems created with choline chloride-fructose natural deep eutectic solvents and polypropylene glycol 400 and usage of these systems for extraction of some commonly used drugs. Fluid. Phase. Equilibria. 555, 113348 (2022).

Article Google Scholar

Hansen, B. B. et al. Deep eutectic solvents: a review of fundamentals and applications. Chem. Rev. 121, 1232–1285 (2021).

Article PubMed Google Scholar

Abranches, D. O. & Coutinho, J. A. P. Everything you wanted to know about deep eutectic solvents but were afraid to be told. Annual Rev. Chem. Biomol. Eng. 14, 141–163 (2023).

Article Google Scholar

Zafarani-Moattar, M. T., Shekaari, H. & Ghaffari, F. Evaluation of solute-solvent interaction and phase separation for aqueous polymers solutions containing choline chloride/D-sucrose natural deep eutectic solvent through vapor-liquid equilibria, volumetric and acoustic studies. J. Chem. Thermodyn. 142, 105963 (2020).

Article Google Scholar

Shekaari, H., Zafarani-Moattar, M. T., Mokhtarpour, M. & Faraji, S. Osmotic coefficients of gabapentin drug in aqueous solutions of deep eutectic solvents: experimental measurements and thermodynamic modeling. J. Chem. Eng. Data. 68, 1663–1672 (2023).

Article Google Scholar

Thomas, F. & Kayser, O. Natural deep eutectic solvents enhance cannabinoid biotransformation. Biochem. Eng. J. 180, 108380 (2022).

Article Google Scholar

Abedi, R., Shekaari, H., Mokhtarpour, M. & Faraji, S. Determination of osmotic coefficients and activity coefficients of calcium d-pantothenate, cefazolin sodium, and ceftriaxone sodium drugs in aqueous solutions of amino acids by using vapor pressure osmometry at 310.15 K. J. Chem. Thermodyn. 181, 107024 (2023).

Article Google Scholar

Dhondge, S. S., Zodape, S. P. & Parwate, D. V. Volumetric and viscometric studies of some drugs in aqueous solutions at different temperatures. J. Chem. Thermodyn. 48, 207–212 (2012).

Article ADS Google Scholar

Pal, A. & Soni, S. Volumetric properties of Glycine in Aqueous solutions of some Sulfa drugs at (288.15, 298.15, and 308.15) K. J. Chem. Eng. Data. 58, 18–23 (2013).

Article Google Scholar

Singh, V. et al. Solvation behavior of monosaccharides in aqueous protic ionic liquid solutions: volumetric, calorimetric and NMR spectroscopic studies. Fluid. Phase. Equilibria. 421, 24–32 (2016).

Article Google Scholar

Torres, D. R., Blanco, L. H., Martínez, F. & Vargas, E. F. Apparent Molal volumes of Lidocaine – HCl and Procaine – HCl in aqueous solution as a function of temperature. J. Chem. Eng. Data. 52, 1700–1703 (2007).

Article Google Scholar

Thermodynamic Properties of Binary Mixtures Containing Ionic Liquid 1-Butyl-3-methylimidazolium Thiocyanate and Ethanolamines at Different Temperatures: Measurement and PC-SAFT Modeling. J. Chem. Eng. Datahttps://doi.org/10.1021/acs.jced.3c00374.

Xu, K., Wang, Y., Huang, Y., Li, N. & Wen, Q. A green deep eutectic solvent-based aqueous two-phase system for protein extracting. Anal. Chim. Acta. 864, 9–20 (2015).

Article PubMed Google Scholar

Mohan, M., Naik, P. K., Banerjee, T., Goud, V. V. & Paul, S. Solubility of glucose in tetrabutylammonium bromide based deep eutectic solvents: experimental and molecular dynamic simulations. Fluid. Phase. Equilibria. 448, 168–177 (2017).

Article Google Scholar

Klamt, A. Conductor-like screening model for real solvents: a new approach to the quantitative calculation of solvation phenomena (ACS Publications, 2002). https://doi.org/10.1021/j100007a062, https://pubs.acs.org/doi/pdf/10.1021/j100007a062.

COSMO-RS - Google Books. https://www.google.com/books/edition/_/750C7V5e_s4C?hl=en&gbpv=1&pg=PP1&dq=COSMO-RS+from+Quantum+Chemistry+to+Fluid+Phase+Thermodynamics+and+Drug+Design.+By+A.+Klamt.+Elsevier:+Amsterdam,+The+Netherlands,+2005.+246+pp.+$US+165.+ISBN+0-444-51994-7+%7C+Request+PDF.+https://www.researchgate.net/publication/244465398_COSMO-RS_from_Quantum_Chemistry_to_Fluid_Phase_Thermodynamics_and_Drug_Design_By_A_Klamt_Elsevier_Amsterdam_The_Netherlands_2005_246_pp_US_165_ISBN_0-444-51994-7+ (accessed+2024-07-26).

Kikuchi, M., Sakurai, M. & Nitta, K. Partial molar volumes and adiabatic compressibilities of amino acids in Dilute Aqueous solutions at 5, 15, 25, 35, and 45.degree.C (ACS Publications, 2002). https://doi.org/10.1021/je00020a045.

Taherinia, R., Ghaffari, F., Shekaari, H. & Mokhtarpour, M. Thermophysical properties of acetaminophen in aqueous solutions of protic ionic liquids based on ethanolamine at T = 288.15–318.15 K. J. Chem. Eng. Data 68, 1525–1533 (2023).

Ananthaswamy, J. & Atkinson, G. Thermodynamics of concentrated electrolyte mixtures. 4. Pitzer-Debye-Hueckel limiting slopes for water from 0 to 100.degree.C and from 1 atm to 1 kbar (ACS Publications, 2002). https://doi.org/10.1021/je00035a027.

Pal, A. & Kumar, S. Viscometric and volumetric studies of some amino acids in binary aqueous solutions of urea at various temperatures. J. Mol. Liq. 109, 23–31 (2004).

Article Google Scholar

Behboudi, M. R., Zafarani-Moattar, M. T., Shekaari, H. & Ghaffari, F. Effect of choline-based ionic liquids on thermodynamic and transport properties of aqueous diphenhydramine hydrochloric acid solutions. J. Mol. Liq. 337, 116431 (2021).

Article Google Scholar

Jamal, M. A., Khosa, M. K., Rashad, M., Mansha, A. & Naqvi, S. A. R. Volumetric and acoustic behavior of sodium cyclamate in aqueous system from 293.15 K to 318.15 K. J. Solut. Chem. 45, 1009–1020 (2016).

Article Google Scholar

Romero, C. M. & Negrete, F. Effect of temperature on partial molar volumes and viscosities of aqueous solutions of α-dl-aminobutyric acid, dl-norvaline and dl-norleucine. Phys. Chem. Liq. 42, 261–267 (2004).

Article Google Scholar

Maham, Y., Teng, T. T., Mather, A. E. & Hepler, L. G. Volumetric properties of (water + diethanolamine) systems. Can. J. Chem. 73, 1514–1519 (1995).

Article Google Scholar

Ali, A. & Shahjahan, S. Volumetric and viscometric behaviour of some amino acids and their Group contributions in Aqueous tetramethylammonium bromide at different temperatures. Z. für Phys. Chem. 222, 1519–1532 (2008).

Article Google Scholar

Shekaari, H., Kazempour, A. & Ghasedi-Khajeh, Z. Structure-making tendency of ionic liquids in the aqueous d-glucose solutions. Fluid. Phase. Equilibria. 316, 102–108 (2012).

Article Google Scholar

Munde, M. M. & Kishore, N. Volumetric properties of Aqueous 2-Chloroethanol solutions and volumes of transfer of some amino acids and peptides from water to aqueous 2-chloroethanol solutions. J. Solution Chem. 32, 791–802 (2003).

Article Google Scholar

Roy, M. N., Dakua, V. K., Sinha, B., Partial Molar & Volumes viscosity B-coefficients, and adiabatic compressibilities of sodium molybdate in aqueous 1,3-dioxolane mixtures from 303.15 to 323.15 K. Int. J. Thermophys. 28, 1275–1284 (2007).

Article ADS Google Scholar

Yan, Z., Geng, R., Gu, B., Pan, Q. & Wang, J. Densities, electrical conductances, and spectroscopic properties of glycyl dipeptide + ionic liquid ([C12mim]Br) + water mixtures at different temperatures. Fluid. Phase. Equilibria. 367, 125–134 (2014).

Article Google Scholar

Thermodynamic study of calcium. d-pantothenate drug in the presence of aqueous solutions including some amino acids: volumetric and compressibility properties - ScienceDirect. https://www.sciencedirect.com/science/article/abs/pii/S0021961422002567.

Iqbal, M. J. & Chaudhry, M. A. Effect of temperature on volumetric and viscometric properties of some non-steroidal anti-inflammatory drugs in aprotic solvents. J. Chem. Thermodyn. 42, 951–956 (2010).

Article ADS Google Scholar

Banipal, T. S., Singh, G. & Lark, B. S. Partial molar volumes of transfer of some amino acids from water to aqueous glycerol solutions at 25°C. J. Solution Chem. 30, 657–670 (2001).

Article Google Scholar

Bahadur, I. & Deenadayalu, N. Apparent molar volume and apparent molar isentropic compressibility for the binary systems {methyltrioctylammoniumbis(trifluoromethylsulfonyl)imide + ethyl acetate or ethanol} at different temperatures under atmospheric pressure. Thermochim. Acta. 566, 77–83 (2013).

Article Google Scholar

Mishra, A. K. & Ahluwalia, J. C. Apparent molal volumes of amino acids, N-acetylamino acids, and peptides in aqueous solutions (ACS Publications, 2002). https://doi.org/10.1021/j150645a021.

Fortin, T. J., Laesecke, A., Freund, M. & Outcalt, S. Advanced calibration, adjustment, and operation of a density and sound speed analyzer. J. Chem. Thermodyn. 57, 276–285 (2013).

Article ADS Google Scholar

Shekaari, H., Zafarani-Moattar, M. T. & Ghaffari, F. Volumetric, acoustic and conductometric studies of acetaminophen in aqueous ionic liquid, 1-Octyl-3-methylimidazolium Bromide at T = 293.15-308.15 K. Phys. Chem. Res. 4, 119–141 (2016).

Google Scholar

Sadeghi, R. & Goodarzi, B. Apparent molar volumes and isentropic compressibilities of transfer of l-alanine from water to aqueous potassium di-hydrogen citrate and tri-potassium citrate at T =(283.15 to 308.15) K. J. Mol. Liq. 141, 62–68 (2008).

Article Google Scholar

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This research is supported by a postdoctoral grant of the University of Tabriz (No: SAD/3900-14001224).

Department of Physical Chemistry, University of Tabriz, Tabriz, Iran

Nadia Beladi, Fariba Ghaffari, Behrang Golmohammadi & Shekaari Hemayat

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H. Shekaari supervision and writerN. Beladi experimental worksF. Ghaffari investigation and writerB. Golmohammadi validation.

Correspondence to Shekaari Hemayat.

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Beladi, N., Ghaffari, F., Golmohammadi, B. et al. Hydration behavior of D-calcium pantothenate (vitamin B5) in the presence of sugar-based deep eutectic solvents at different temperatures: experimental and theoretical study. Sci Rep 14, 24805 (2024). https://doi.org/10.1038/s41598-024-75905-0

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Received: 15 June 2024

Accepted: 09 October 2024

Published: 22 October 2024

DOI: https://doi.org/10.1038/s41598-024-75905-0

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