ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Preferential solvation and solvation shell composition of sunitinib malate, an anti-tumor compound, in some binary mixed solvents at 298.15 K

Mohsen Padervand, Shima Naseri, and Sima Hajiahmadi

Department of Chemistry, Faculty of Science, University of Maragheh, Maragheh, Iran

E-mail: mohsenpadervand@gmail.com

Received: 30 July 2020  Accepted: 18 September 2020

Abstract:

Preferential solvation of sunitinib malate (STM) was investigated in the binary mixtures of water, ethanol, ethylene glycol (EG), and propylene carbonate (PC) solvents at 298.15 K. Similar to its pharmaceutical formulation steps, dimethyl sulfoxide (DMSO) was used as the base solvent during our experiments. Bosch–Rose model was utilized to estimate the electronic transition energies, E_T, and other preferential solvation parameters, demonstrating solute–solvent and solute–solute interactions. Shifting λ_max situation with respect to the dielectric constant of the pure solvents was carefully monitored indicating that STM had the lowest λ_max in water and PC among HBD and HBA solvents, respectively. Moreover, E_T showed positive deviation with respect to ideality for ethanol–EG, ethanol–PC, and ethanol–DMSO binary systems while negative deviation was obtained for the others which was explainable based on the model assumptions. According to the results, STM molecules preferred to be solvated by PC, ethanol, EG, and DMSO solvent molecules rather than water in the binary mixtures of the aforementioned solvents, meaning that the presence of water in the cybotactic region is least probable compared to the others. Based on the local mole fractions, the abundance of pure solvents and/or complex solvent molecules in the cybotactic region around the solute was discussed in detail, illustrating the specific and non-specific interactions between solute and solvent molecules.

Keywords: Sunitinib malate; Bosch–Rose model; Preferential salvation; Mixed solvents

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-020-01367-z

Chemical Papers 75 (3) 939–950 (2021)