Preferential solvation of pomalidomide, an anticancer compound, in some binary mixed solvents at 298.15 K

doi:10.1016/j.cjche.2020.07.010

中国化学工程学报 ›› 2020, Vol. 28 ›› Issue (10): 2626-2633.DOI: 10.1016/j.cjche.2020.07.010

• Chemical Engineering Thermodynamics • 上一篇下一篇

Preferential solvation of pomalidomide, an anticancer compound, in some binary mixed solvents at 298.15 K

Mohsen Padervand¹, Shima Naseri¹, Hadi Chahiyan Boroujeni²

1 Department of Chemistry, Faculty of Science, University of Maragheh, Maragheh, Iran;
2 Department of Chemistry and Biology, Farhangian Teacher Training University, Mashhad Branch, Mashhad, Iran

收稿日期:2020-02-18 修回日期:2020-07-04 出版日期:2020-10-28 发布日期:2020-12-03
通讯作者: Mohsen Padervand

Preferential solvation of pomalidomide, an anticancer compound, in some binary mixed solvents at 298.15 K

Mohsen Padervand¹, Shima Naseri¹, Hadi Chahiyan Boroujeni²

1 Department of Chemistry, Faculty of Science, University of Maragheh, Maragheh, Iran;
2 Department of Chemistry and Biology, Farhangian Teacher Training University, Mashhad Branch, Mashhad, Iran

Received:2020-02-18 Revised:2020-07-04 Online:2020-10-28 Published:2020-12-03
Contact: Mohsen Padervand

摘要/Abstract

摘要： Preferential solvation of pomalidomide (PMD) was explored in dimethyl sulfoxide (DMSO)-dimethylformamide (DMF), DMSO-tetrahydrofuran (THF), DMSO-methanol (MeOH), DMSO-isopropanol, DMSO-water, water-DMF, water-THF, water-MeOH, and water-isopropanol binary mixed solvents at 298.15 K. Bosch-Rose model was utilized to determine the electronic transition energies (E_T) and other preferential solvation parameters, describing solute-solute and solute-solvent interactions. We found that λ_max situation shifted with dielectric constant of the pure solvents meaningfully. According to the obtained results, E_T enhanced and λ_max shifted to the lower wavelengths as the percentage of DMSO decreased in the binary mixtures, remarking the important role of DMSO for stabilizing the excited state (π^*) of PMD chromophore via efficient intermolecular solute-solvent interactions. In addition, the aqueous binary systems showed an optimum point for the E_T values as the percentage of water changed in the solutions. The local mole fraction of the solvents in the cybotactic region was also estimated to describe the specific and non-specific interactions in the systems.

关键词: Pomalidomide, Preferential solvation, Bosch-Rose model, Binary solvents

Abstract: Preferential solvation of pomalidomide (PMD) was explored in dimethyl sulfoxide (DMSO)-dimethylformamide (DMF), DMSO-tetrahydrofuran (THF), DMSO-methanol (MeOH), DMSO-isopropanol, DMSO-water, water-DMF, water-THF, water-MeOH, and water-isopropanol binary mixed solvents at 298.15 K. Bosch-Rose model was utilized to determine the electronic transition energies (E_T) and other preferential solvation parameters, describing solute-solute and solute-solvent interactions. We found that λ_max situation shifted with dielectric constant of the pure solvents meaningfully. According to the obtained results, E_T enhanced and λ_max shifted to the lower wavelengths as the percentage of DMSO decreased in the binary mixtures, remarking the important role of DMSO for stabilizing the excited state (π^*) of PMD chromophore via efficient intermolecular solute-solvent interactions. In addition, the aqueous binary systems showed an optimum point for the E_T values as the percentage of water changed in the solutions. The local mole fraction of the solvents in the cybotactic region was also estimated to describe the specific and non-specific interactions in the systems.

Key words: Pomalidomide, Preferential solvation, Bosch-Rose model, Binary solvents

Mohsen Padervand, Shima Naseri, Hadi Chahiyan Boroujeni. Preferential solvation of pomalidomide, an anticancer compound, in some binary mixed solvents at 298.15 K[J]. 中国化学工程学报, 2020, 28(10): 2626-2633.

Mohsen Padervand, Shima Naseri, Hadi Chahiyan Boroujeni. Preferential solvation of pomalidomide, an anticancer compound, in some binary mixed solvents at 298.15 K[J]. Chinese Journal of Chemical Engineering, 2020, 28(10): 2626-2633.

参考文献

[1] S. Elkinson, P.L. McCormack, Pomalidomide:first global approval, Drugs 73(2013) 595-604.
[2] M. Padervand, M.R. Elahifard, Development of a spectrophotometric method for the measurement of kinetic solubility:economical approach to be used in pharmaceutical companies, Pharm. Chem. J. 51(2017) 511-515.
[3] G.T. Castro, M.A. Filippa, C.M. Peralta, M.V. Davin, M.C. Almandoz, E.I. Gasull, Solubility and preferential solvation of piroxicam in neat solvents and binary systems, Z. Phys. Chem. 232(2018) 257-280.
[4] D.A. Tinjacá, A. Shayanfar, A. Jouyban, F. Martínez, W.E. Acree Jr., Preferential solvation of some antiepileptic drugs in {cosolvent (1)+ water (2)} mixtures at 298.15 K, Phys. Chem. Liq. 56(2018) 646-659.
[5] A. Jouyban, Handbook of Solubility Data for Pharmaceuticals, CRC Press, 2009.
[6] M. Moldovan, A. Lahmar, C. Bogdan, S. Părăuan, I. TOMUŢĂ, M. CRIŞAN, Formulation and evaluation of a water-in-oil cream containing herbal active ingredients and ferulic acid, Clujul Med. 90(2017) 212.
[7] F. Martínez, A. Jouyban, W.E. Acree Jr, Pharmaceuticals solubility is still nowadays widely studied everywhere, Pharm. Sci. 23(1) (2017) 1-2.
[8] Y. Marcus, On the preferential solvation of drugs and PAHs in binary solvent mixtures, J. Mol. Liq. 140(2008) 61-67.
[9] Y. Marcus, Preferential solvation of drugs in binary solvent mixtures, Pharm. Anal. Acta 8(2017) 537.
[10] H.C. Boroujeni, F. Gharib, Solvatochromism and preferential solvation of deferiprone in some water-organic mixed solvents, J. Solut. Chem. 45(2016) 95-108.
[11] A.G. Gilani, V. Taghvaei, E.M. Rufchahi, M. Mirzaei, Tautomerism, solvatochromism, preferential solvation, and density functional study of some heteroarylazo dyes, J. Mol. Liq. 273(2019) 392-407.
[12] A.G. Gilani, M. Salmanpour, T. Ghorbanpour, Solvatochromism, dichroism and excited state dipole moment of azure A and methylene blue, J. Mol. Liq. 179(2013) 118-123.
[13] F. Martínez, A. Jouyban, W.E. Acree Jr., Further numerical analysis on the solubility of ibrutinib in ethanol+ water mixtures at different temperatures, J. Mol. Liq. 218(2016) 35-38.
[14] N. Haq, N.A. Siddiqui, F. Shakeel, Solubility and molecular interactions of ferulic acid in various (isopropanol+ water) mixtures, J. Pharm. Pharmacol. 69(2017) 1485-1494.
[15] A.G. Gilani, M. Moghadam, S. Hosseini, Dielectric study of primary alkanediols (C3, C4, C5) with 1-pentanol isomers, J. Mol. Liq. 231(2017) 27-38.
[16] A. Jouyban, F. Martínez, Modelling the preferential solvation of ferulic acid in {2-propanol (1)+ water (2)} mixtures at 298.15 K, PHARM 23(2017) 330-334.
[17] A. Jouybana, M. Khoubnasabjafari, W.E. Acree Jr, Predicting solubility of anthracene in non-aqueous solvent mixtures using a combination of jouyban-acree and abraham models, Chem. Pharm. Bull. 54(2006) 1124-1130.
[18] A. Martin, J. Newburger, A. Adjei, Extended Hildebrand solubility approach:solubility of theophylline in polar binary solvents, J. Pharm. Sci. 69(1980) 487-491.
[19] W.E. Acree Jr., S.A. Tucker, Thermochemical investigations of hydrogen-bonded solutions part 6. Comparison of mobile order theory versus Kretschmer-Wiebe association model for describing anthracene solubilities in binary hydrocarbon+ alcohol solvent mixtures, Fluid Phase Equilib. 102(1994) 17-29.
[20] N. Lambov, M. Dimitrov, S. Tsankov, Biopharmaceutical study of cross-linked polyethylene oxide hydrogels, Pharmazie 52(1997) 790-792.
[21] E. Ruckenstein, I. Shulgin, Solubility of drugs in aqueous solutions:part 1. Ideal mixed solvent approximation, Int. J. Pharm. 258(2003) 193-201.
[22] W.E. Acree Jr., J.H. Rytting, Solubility in binary solvent systems III:predictive expressions based on molecular surface areas, J. Pharm. Sci. 72(1983) 292-296.
[23] A.R. Katritzky, D.C. Fara, H. Yang, K. Tämm, T. Tamm, M. Karelson, Quantitative measures of solvent polarity, Chem. Rev. 104(2004) 175-198.
[24] A.G. Gilani, M. Yazdanbakhsh, N. Mahmoodi, M. Moghadam, E. Moradi, Solvatochromism and dichroism of fluorinated azoquinolin-8-ol dyes in liquid and liquid crystalline solutions, J. Mol. Liq. 139(2008) 72-79.
[25] C. Reichardt, T. Welton, Solvents and Solvent Effects in Organic Chemistry, John Wiley & Sons, 2011.
[26] M. Panigrahi, S. Dash, S. Patel, B.K. Mishra, Preferential solvation of styrylpyridinium dyes in binary mixtures of alcohols with hexane, dioxane, and dichloromethane, J. Phys. Chem. B 115(2010) 99-108.
[27] F.M. Testoni, E.A. Ribeiro, L.A. Giusti, V.G. Machado, Merocyanine solvatochromic dyes in the study of synergistic effects in mixtures of chloroform with hydrogenbond accepting solvents, Spectrochim. Acta A Mol. Biomol. Spectrosc. 71(2009) 1704-1711.
[28] M. Rosés, U. Buhvestov, C. Ràfols, F. Rived, E. Bosch, Solute-solvent and solvent-solvent interactions in binary solvent mixtures. Part 6. A quantitative measurement of the enhancement of the water structure in 2-methylpropan-2-ol-water and propan-2-ol-water mixtures by solvatochromic indicators, J. Chem. Soc. Perkin Trans. 2(1997) 1341-1348.
[29] R.D. Skwierczynski, K.A. Connors, Solvent effects on chemical processes. Part 7. Quantitative description of the composition dependence of the solvent polarity measure ET (30) in binary aqueous-organic solvent mixtures, J. Chem. Soc. Perkin Trans. 2(1994) 467-472.
[30] Y. Marcus, The use of chemical probes for the characterization of solvent mixtures. Part 2. Aqueous mixtures, J. Chem. Soc. Perkin Trans. 2(1994) 1751-1758.
[31] J. Ortega, C. Ràfols, E. Bosch, M. Rosés, Solute-solvent and solvent-solvent interactions in binary solvent mixtures. Part 3. The ET (30) polarity of binary mixtures of hydroxylic solvents, J. Chem. Soc. Perkin Trans. 2(1996) 1497-1503.
[32] F. Naderi, A. Farajtabar, F. Gharib, Solvatochromic and preferential solvation of fluorescein in some water-alcoholic mixed solvents, J. Mol. Liq. 190(2014) 126-132.
[33] A. Duereh, Y. Sato, R.L. Smith Jr., H. Inomata, Analysis of the cybotactic region of two renewable lactone-water mixed-solvent systems that exhibit synergistic KamletTaft basicity, J. Phys. Chem. B 120(2016) 4467-4481.
[34] J.A. Riddick, W.B. Bunger, T.K. Sakano, Organic Solvents:Physical Properties and Methods of Purification, Wiley-Interscience, 1986.
[35] T. Bevilaqua, T.F. Gonçalves, C.d.G. Venturini, V.G. Machado, Solute-solvent and solvent-solvent interactions in the preferential solvation of 4-[4-(dimethylamino) styryl]-1-methylpyridinium iodide in 24 binary solvent mixtures, Spectrochim. Acta A Mol. Biomol. Spectrosc. 65(2006) 535-542.
[36] T. Clark, J.S. Murray, P. Lane, P. Politzer, Why are dimethyl sulfoxide and dimethyl sulfone such good solvents? J. Mol. Model. 14(2008) 689-697.

Preferential solvation of pomalidomide, an anticancer compound, in some binary mixed solvents at 298.15 K

Preferential solvation of pomalidomide, an anticancer compound, in some binary mixed solvents at 298.15 K

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