Mesoscale Modeling Approach to Study the Dispersion and the Solubility of Flavonoids in Organic Solvents

Industrial and Engineering Chemistry Research

Volumn 57, Issue 37, 2018, Pages 12519-12530

  Slimane, Manel ^a   Ghoul, Mohamed ^a   Chebil, Latifa ^a  

^a UNIVERSITÉ DE LORRAINE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONITRILE; DISPERSIONS; PHASE SEPARATION; PHENOLS; SOLUBILITY; SOLVENTS;

FLORY-HUGGINS INTERACTION PARAMETER; ISO-PROPANOLS; MAIN GROUP; MESO-SCALE MODELING; MESOSCALE MODEL SIMULATION; MICROSCOPIC OBSERVATIONS; ORDER PARAMETER; TERT-AMYL ALCOHOLS;

FLAVONOIDS;

EID: 85053715727     PISSN: 08885885     EISSN: 15205045     Source Type: Journal    
DOI: 10.1021/acs.iecr.8b02321     Document Type: Article

References (31)

1. Arora, A.; Nair, M. G.; Strasburg, G. M. Antioxidant activities of isoflavones and their biological metabolites in a liposomal system. Arch. Biochem. Biophys. 1998, 356 (2), 133-141, 10.1006/abbi.1998.0783
2. Burda, S.; Oleszek, W. Antioxidant and antiradical activities of flavonoids. J. Agric. Food Chem. 2001, 49 (6), 2774-2779, 10.1021/jf001413m
3. Pietta, P. G. Flavonoids as antioxidants. J. Nat. Prod. 2000, 63 (7), 1035-1042, 10.1021/np9904509
4. Rice-Evans, C. A.; Bagchi, D. Nutritional proanthocyanidins, flavonoids, and related phenols. Antioxid. Redox Signaling 2001, 3 (6), 939-940, 10.1089/152308601317203486
5. Di Carlo, G.; Mascolo, N.; Izzo, A. A.; Capasso, F. Flavonoids: Old and new aspects of a class of natural therapeutic drugs. Life Sci. 1999, 65 (4), 337-353, 10.1016/S0024-3205(99)00120-4
6. Middleton, E.; Kandaswami, C.; Theoharides, T. C. The effects of plant flavonoids on mammalian cells: Implications for inflammation, heart disease, and cancer. Pharmacol. Rev. 2000, 52 (4), 673-751
7. Chebil, L.; Bouroukba, M.; Gaiani, C.; Charbonel, C.; Khaldi, M.; Engasser, J. M.; Ghoul, M. Elucidation of the kinetic behavior of quercetin, isoquercitrin, and rutin solubility by physicochemical and thermodynamic investigations. Ind. Eng. Chem. Res. 2013, 52 (4), 1464-1470, 10.1021/ie3029202
8. Chebil, L.; Chipot, C.; Archambault, F.; Humeau, C.; Engasser, J. M.; Ghoul, M.; Dehez, F. Solubilities Inferred from the Combination of Experiment and Simulation. Case Study of Quercetin in a Variety of Solvents. J. Phys. Chem. B 2010, 114 (38), 12308-12313, 10.1021/jp104569k
9. Chebil, L.; Humeau, C.; Anthoni, J.; Dehez, F.; Engasser, J. M.; Ghoul, M. Solubility of flavonoids in organic solvents. J. Chem. Eng. Data 2007, 52 (5), 1552-1556, 10.1021/je7001094
10. Dai, X. X.; Shi, X. Y.; Wang, Y. G.; Qiao, Y. J. Solubilization of saikosaponin a by ginsenoside Ro biosurfactant in aqueous solution: Mesoscopic simulation. J. Colloid Interface Sci. 2012, 384, 73-80, 10.1016/j.jcis.2012.06.018
11. Otto, D. P.; Otto, A.; de Villiers, M. M. Experimental and mesoscale computational dynamics studies of the relationship between solubility and release of quercetin from PEG solid dispersions. Int. J. Pharm. 2013, 456 (2), 282-292, 10.1016/j.ijpharm.2013.08.039
12. Chansuna, M.; Pimpha, N.; Vao-soongnern, V. Mesoscale simulation and experimental studies of self-assembly behavior of a PLA-PEG-PLA triblock copolymer micelle for sustained drug delivery. J. Polym. Res. 2014, 21, 6, 10.1007/s10965-014-0452-1
13. Li, Y. M.; Xu, G. Y.; Chen, A. M.; Yuan, S. L.; Cao, X. R. Aggregation between xanthan and nonyphenyloxypropyl beta-hydroxyltrimethylammonium bromide in aqueous solution: MesoDyn simulation and binding isotherm measurement. J. Phys. Chem. B 2005, 109 (47), 22290-22295, 10.1021/jp0528414
14. Ramos-Rodríguez, D. A.; Rodríguez-Hidalgo, M. R.; Soto-Figueroa, C.; Vicente, L. Molecular and mesoscopic study of ionic liquids and their use as solvents of active agents released by polymeric vehicles. Mol. Phys. 2010, 108 (5), 657-665, 10.1080/00268971003657094
15. Coveney, P. V. Modeling structure and properties in mesoscale fluid systems. Mesoscale Phenomena In Fluid Systems 2003, 861, 206-226, 10.1021/bk-2003-0861.ch013
16. Fan, C. F.; Olafson, B. D.; Blanco, M.; Hsu, S. L. Application of molecular simulation to derive phase diagrams of binary mixtures. Macromolecules 1992, 25 (14), 3667-3676, 10.1021/ma00040a010
17. Flory, P. J. Thermodynamics for high polymer solutions. J. Chem. Phys. 1942, 10, 51, 10.1063/1.1723621
18. Flory, P. J. Introduction to branched molecules. Ann. N. Y. Acad. Sci. 1953, 57 (4), 327-331, 10.1111/j.1749-6632.1953.tb36406.x
19. Hoogerbrugge, P. J.; Koelman, J. Simulating microscopic hydrodynamic phenomena with dissipative particle dynamics. Europhys. Lett. 1992, 19 (3), 155-160, 10.1209/0295-5075/19/3/001
20. Connolly, M. L. Solvent-accessible surfaces of proteins and nucleic-acids. Science 1983, 221 (4612), 709-713, 10.1126/science.6879170
21. Groot, R. D.; Warren, P. B. Dissipative particle dynamics: Bridging the gap between atomistic and mesoscopic simulation. J. Chem. Phys. 1997, 107 (11), 4423-4435, 10.1063/1.474784
22. Fraaije, J.; vanVlimmeren, B. A. C.; Maurits, N. M.; Postma, M.; Evers, O. A.; Hoffmann, C.; Altevogt, P.; GoldbeckWood, G. The dynamic mean-field density functional method and its application to the mesoscopic dynamics of quenched block copolymer melts. J. Chem. Phys. 1997, 106 (10), 4260-4269, 10.1063/1.473129
23. Maurits, N. M.; Fraaije, J. Application of free energy expansions to mesoscopic dynamics of copolymer melts using a Gaussian chain molecular model. J. Chem. Phys. 1997, 106 (16), 6730-6743, 10.1063/1.473670
24. Guo, Q. Y.; Knight, P. T.; Wu, J.; Mather, P. T. Blends of paclitaxel with POSS-based biodegradable polyurethanes: morphology, miscibility, and specific interactions. Macromolecules 2010, 43 (11), 4991-4999, 10.1021/ma100662x
25. Pajula, K.; Taskinen, M.; Lehto, V. P.; Ketolainen, J.; Korhonen, O. Predicting the formation and stability of amorphous small molecule binary mixtures from computationally determined Flory-Huggins interaction parameter and phase diagram. Mol. Pharmaceutics 2010, 7 (3), 795-804, 10.1021/mp900304p
26. Luo, Z. L.; Jiang, J. W. pH-sensitive drug loading/releasing in amphiphilic copolymer PAE-PEG: Integrating molecular dynamics and dissipative particle dynamics simulations. J. Controlled Release 2012, 162 (1), 185-193, 10.1016/j.jconrel.2012.06.027
27. Abou-Rachid, H.; Lussier, L. S.; Ringuette, S.; Lafleur-Lambert, X.; Jaidann, M.; Brisson, J. On the correlation between miscibility and solubility properties of energetic plasticizers/polymer blends: Modeling and simulation studies. Propellants, Explos., Pyrotech. 2008, 33 (4), 301-310, 10.1002/prep.200700211
28. Luo, Z. L.; Jiang, J. W. Molecular dynamics and dissipative particle dynamics simulations for the miscibility of poly(ethylene oxide)/poly(vinyl chloride) blends. Polymer 2010, 51 (1), 291-299, 10.1016/j.polymer.2009.11.024
29. Wu, H.; Xin, Y. Molecular dynamics and MesoDyn simulations for the miscibility of polyvinyl alcohol/polyvinyl pyrrolidone blends. Plast., Rubber Compos. 2017, 46 (2), 69-76, 10.1080/14658011.2017.1280642
30. Yang, J. Q.; Zhang, X. L.; Gao, P.; Gong, X. D.; Wang, G. X. Molecular dynamics and dissipative particle dynamics simulations of the miscibility and mechanical properties of GAP/DIANP blending systems. RSC Adv. 2014, 4 (79), 41934-41941, 10.1039/C4RA04236K
31. Mu, D.; Li, J. Q.; Feng, S. Y. MesoDyn simulation study on the phase morphologies of Miktoarm PEO-b-PMMA copolymer doped by nanoparticles. Mol. Phys. 2013, 111 (5), 687-695, 10.1080/00268976.2012.741722