Using Environment-Sensitive Fluorescent Probes to Characterize Liquid-Liquid Phase Separation in Supersaturated Solutions of Poorly Water Soluble Compounds

Pharmaceutical Research

Volumn 32, Issue 11, 2015, Pages 3660-3673

  Raina, Shweta A ^a,b   Alonzo, David E ^b,c   Zhang, Geoff G Z ^b   Gao, Yi ^b   Taylor, Lynne S ^a  

^a PURDUE UNIVERSITY   (United States)

^b ABBVIE INC   (United States)

^c GILEAD SCIENCES   (United States)

Author keywords

Fluorescence; Phase separation; Supersaturation

Indexed keywords

BENZENE; DIHYDROPYRIDINE DERIVATIVE; FELODIPINE; FLUORESCENT DYE; NIFEDIPINE; PYRENE; TOLUENE; DRUG; SOLUTION AND SOLUBILITY; WATER;

AQUEOUS SOLUTION; ARTICLE; BIREFRINGENCE; CRYSTALLIZATION; FLUORESCENCE; FLUORESCENCE SPECTROSCOPY; PHASE SEPARATION; PRIORITY JOURNAL; SENSITIVITY ANALYSIS; SOLUBILITY; ULTRAVIOLET RADIATION; CHEMICAL STRUCTURE; CHEMISTRY; HIGH THROUGHPUT SCREENING; MEDICINAL CHEMISTRY; PHASE TRANSITION; PROCEDURES; SOLUTION AND SOLUBILITY;

CHEMISTRY, PHARMACEUTICAL; CRYSTALLIZATION; DIHYDROPYRIDINES; FLUORESCENT DYES; HIGH-THROUGHPUT SCREENING ASSAYS; MOLECULAR STRUCTURE; PHARMACEUTICAL PREPARATIONS; PHARMACEUTICAL SOLUTIONS; PHASE TRANSITION; SOLUBILITY; WATER;

EID: 84943580457     PISSN: 07248741     EISSN: 1573904X     Source Type: Journal    
DOI: 10.1007/s11095-015-1725-z     Document Type: Article

References (44)

1. Tachibana T, Nakamura A. A methode for preparing an aqueous colloidal dispersion of organic materials by using water-soluble polymers: dispersion ofΒ-carotene by polyvinylpyrrolidone. Kolloid-ZuZPolymere. 1965;203:130-3.
2. Aisha AFA, Ismail Z, Abu-salah KM, Majid AMSA. Solid dispersions of α-mangostin improve its aqueous solubility through self-assembly of nanomicelles. J Pharm Sci. 2012;101:815-25.
3. Friesen DT, Shanker R, Crew M, Smithey DT, Curatolo WJ, Nightingale JAS. Hydroxypropyl methylcellulose acetate succinate-based spray-dried dispersions: an overview. Mol Pharmaceutics. 2008;5:1003-19.
4. Alonzo DE, Gao Y, Zhou D, Mo H, Zhang GG, Taylor LS. Dissolution and precipitation behavior of amorphous solid dispersions. J Pharm Sci. 2011;100:3316-31.
5. Kanzer J, Hupfeld S, Vasskog T, Tho I, Hölig P, Mägerlein M, et al. In situ formation of nanoparticles upon dispersion of melt extrudate formulations in aqueous medium assessed by asymmetrical flow field-flow fractionation. J Pharm Biomed Anal. 2010;53:359-65.
6. Müllertz A, Ogbonna A, Ren S, Rades T. New perspectives on lipid and surfactant based drug delivery systems for oral delivery of poorly soluble drugs. J Pharm Pharmac. 2010;62:1622-36.
7. Pacheco LF, Carmona-Ribeiro AM. Effects of synthetic lipids on solubilization and colloid stability of hydrophobic drugs. J Colloid Interf Sci. 2003;258:146-54.
8. Sassene PJ, Knopp MM, Hesselkilde JZ, Koradia V, Larsen A, Rades T, et al. Precipitation of a poorly soluble model drug during in vitro lipolysis: characterization and dissolution of the precipitate. J Pharm Sci. 2010;99:4982-91.
9. Hsieh Y-L, Box K, Taylor LS. Assessing the impact of polymers on the pH-induced precipitation behavior of poorly water-soluble compounds using synchrotron wide angle X-ray scattering. J Pharm Sci. 2014;103:2724-35.
10. Hsieh Y-L, Ilevbare G, Van Eerdenbrugh B, Box K, Sanchez-Felix M, Taylor L. pH-induced precipitation behavior of weakly basic compounds: determination of extent and duration of supersaturation using potentiometric titration and correlation to solid state properties. Pharm Res. 2012;29:2738-53.
11. Coan KED, Shoichet BK. Stoichiometry and physical chemistry of promiscuous aggregate-based inhibitors. J Am Chem Soc. 2008;130:9606-12.
12. Zhang F, Roosen-Runge F, Sauter A, Roth R, Skoda MWA, Jacobs R, et al. The role of cluster formation and metastable liquid-liquid phase separation in protein crystallization. Faraday Discuss. 2012;159:313-25.
13. Veesler S, Lafferrère L, Garcia E, Hoff C. Phase transitions in supersaturated drug solution. Org Process Res Dev. 2003;7:983-9.
14. Raina SA, Zhang GGZ, Alonzo DE, Wu J, Zhu D, Catron ND, et al. Enhancements and limits in drug membrane transport using supersaturated solutions of poorly water-soluble drugs. J Pharm Sci. 2014;103:2736-48.
15. S.A. Raina, G.G.Z. Zhang, D.E. Alonzo, J. Wu, D. Zhu, N.D. Catron, Y. Gao, L.S. Taylor. Impact of Solubilizing Additives on Supersaturation and Membrane Transport of Drugs. Pharm Res (2015). doi: 10.1007/s11095-015-1712-4
16. Raina SA, Eerdenbrugh BV, Alonzo DE, Mo H, Zhang GGZ, Gao Y, et al. Trends in the precipitation and crystallization behavior of supersaturated aqueous solutions of poorly water-soluble drugs assessed using synchrotron radiation. J Pharm Sci. 2015;104:1981-92.
17. Frank KJ WU, Rosenblatt KM, Hölig P, Rosenberg J, Mägerlein M, Fricker G, et al. The amorphous solid dispersion of the poorly soluble ABT-102 forms nano/microparticulate structures in aqueous medium: impact on solubility. Int J Nanomed. 2012;7:5757-68.
18. Frank KJ, Westedt U, Rosenblatt KM, Hölig P, Rosenberg J, Mägerlein M, et al. What is the mechanism behind increased permeation rate of a poorly soluble drug from aqueous dispersions of an amorphous solid dispersion? J Pharm Sci. 2014;103:1779-86.
19. Wang J, Matayoshi E. Solubility at the molecular level: development of a critical aggregation concentration (CAC) assay for estimating compound monomer solubility. Pharm Res. 2012;29:1745-54.
20. Taboada P, Attwood D, Ruso JM, Garcia M, Mosquera V. Static and dynamic light scattering study on the association of some antidepressants in aqueous electrolyte solutions. Phys Chem Chem Phys. 2000;2:5175-9.
21. Van Eerdenbrugh B, Alonzo DE, Taylor LS. Influence of particle size on the ultraviolet spectrum of particulate-containing solutions: implications for in-situ concentration monitoring using UV/Vis fiber-optic probes. Pharm Res. 2011;28:1643-52.
22. Sugano K, Kato T, Suzuki K, Keiko K, Sujaku T, Mano T. High throughput solubility measurement with automated polarized light microscopy analysis. J Pharm Sci. 2006;95:2115-22.
23. Qi S, Roser S, Edler K, Pigliacelli C, Rogerson M, Weuts I, et al. Insights into the role of polymer-surfactant complexes in drug solubilisation/stabilisation during drug release from solid dispersions. Pharm Res. 2013;30:290-302.
24. Gao X, Huang Y, Makhov AM, Epperly M, Lu J, Grab S, et al. Nanoassembly of surfactants with interfacial drug-interactive motifs as tailor-designed drug carriers. Mol Pharmaceutics. 2012;10:187-98.
25. Giannetti AM, Koch BD, Browner MF. Surface plasmon resonance based assay for the detection and characterization of promiscuous inhibitors. J Med Chem. 2008;51:574-80.
26. Abbou Oucherif K, Raina S, Taylor LS, Litster JD. Quantitative analysis of the inhibitory effect of HPMC on felodipine crystallization kinetics using population balance modeling. CrystEngComm. 2013;15:2197-205.
27. Raina SA, Alonzo DE, Zhang GGZ, Gao Y, Taylor LS. Impact of polymers on the crystallization and phase transition kinetics of amorphous nifedipine during dissolution in aqueous media. Mol Pharmaceutics. 2014;11:3565-76.
28. Baird JA, Van Eerdenbrugh B, Taylor LS. A classification system to assess the crystallization tendency of organic molecules from undercooled melts. J Pharm Sci. 2010;99:3787-806.
29. Ilevbare GA, Taylor LS. Liquid-liquid phase separation in highly supersaturated aqueous solutions of poorly water-soluble drugs: implications for solubility enhancing formulations. Cryst Growth Des. 2013;13:1497-509.
30. Hoffman JD. Thermodynamic driving force in nucleation and growth processes. J Chem Phys. 1958;29:1192-3.
31. Murdande SB, Pikal MJ, Shanker RM, Bogner RH. Solubility advantage of amorphous pharmaceuticals: I. A thermodynamic analysis. J Pharm Sci. 2010;99:1254-64.
32. Murdande SB, Pikal MJ, Shanker RM, Bogner RH. Solubility advantage of amorphous pharmaceuticals, part 3: Is maximum solubility advantage experimentally attainable and sustainable? J Pharm Sci. 2011;100:4349-56.
33. Murdande S, Pikal M, Shanker R, Bogner R. Solubility advantage of amorphous pharmaceuticals: II. Application of quantitative thermodynamic relationships for prediction of solubility enhancement in structurally diverse insoluble pharmaceuticals. Pharm Res. 2010;27:2704-14.
34. Alonzo D, Zhang GZ, Zhou D, Gao Y, Taylor L. Understanding the behavior of amorphous pharmaceutical systems during dissolution. Pharm Res. 2010;27:608-18.
35. Ndouand TT, von Wandruszka R. Pyrene fluorescence in premicellar solutions: the effects of solvents and temperature. J Lumin. 1990;46:33-8.
36. Chandar P, Somasundaran P, Turro NJ. Fluorescence probe investigation of anionic polymer-cationic surfactant interactions. Macromolecules. 1988;21:950-3.
37. Goddard ED, Turro NJ, Kuo PL, Ananthapadmanabhan KP. Fluorescence probes for critical micelle concentration determination. Langmuir. 1985;1:352-5.
38. Zana R, Yiv S, Strazielle C, Lianos P. Effect of alcohol on the properties of micellar systems: I. Critical micellization concentration, micelle molecular weight and ionization degree, and solubility of alcohols in micellar solutions. J Colloid Interf Sci. 1981;80:208-23.
39. Jensen KHR, Rekling JC. Development of a no-wash assay for mitochondrial membrane potential using the styryl Dye DASPEI. J Biomol Screen. 2010;15:1071-81.
40. Lakowicz JR. Principles of fuorescence spectroscopy. New York: Springer; 2006.
41. Marini A, Muñoz-Losa A, Biancardi A, Mennucci B. What is solvatochromism? J Phys Chem B. 2010;114:17128-35.
42. Pávez P, Encinas MV. Photophysics and photochemical studies of 1,4-dihydropyridine derivatives. Photochem Photobiol. 2007;83:722-9.
43. Fasani E, Dondi D, Ricci A, Albini A. Photochemistry of 4-(2-nitrophenyl)-1,4-dihydropyridines. Evidence for electron transfer and formation of an intermediate. Photochem Photobiol. 2006;82:225-30.
44. Van Eerdenbrugh B, Raina S, Hsieh Y-L, Augustijns P, Taylor L. Classification of the crystallization behavior of amorphous active pharmaceutical ingredients in aqueous environments. Pharm Res. 2014;31:969-82.