Biocompatible alginate microgel particles as heteronucleants and encapsulating vehicles for hydrophilic and hydrophobic drugs

Crystal Growth and Design

Volumn 14, Issue 4, 2014, Pages 2073-2082

  Eral, Huseyin Burak ^a   López Mejías, Vilmalí ^a   O'Mahony, Marcus ^a   Trout, Bernhard L ^a   Myerson, Allan S ^a   Doyle, Patrick S ^a  

^a Massachusetts Institute of Technology Cambridge   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BIOCOMPATIBILITY; BIOLOGICAL MATERIALS; EMULSIFICATION; EMULSIONS; HYDROPHILICITY; HYDROPHOBICITY; NUCLEATION; SOLUBILITY; WETLANDS;

ACTIVE PHARMACEUTICAL INGREDIENTS; CONFINEMENT EFFECTS; EMULSIFICATION METHODS; EQUILIBRIUM PARTITIONING; HYDROPHILIC AND HYDROPHOBIC; INDUSTRIAL PRACTICES; MICROGEL PARTICLES; NUCLEATION KINETICS;

HYDROGELS;

EID: 84897547454     PISSN: 15287483     EISSN: 15287505     Source Type: Journal    
DOI: 10.1021/cg500250e     Document Type: Article

References (52)

1. Debenedetti, P. G. Metastable Liquids: Concepts and Principles; Princeton University Press: Princeton, NJ, 1996.
2. Mullin, J. W. Crystallization, 4 th ed.; Butterworth-Heinemann: Boston, 2001.
3. Oxtoby, D. W. Nucleation of first-order phase transitions Acc. Chem. Res. 1998, 31 (2) 91-97 (Pubitemid 128474581)
4. Price, C. P.; Grzesiak, A. L.; Matzger, A. J. Crystalline polymorph selection and discovery with polymer heteronuclei J. Am. Chem. Soc. 2005, 127, 5512-5517 (Pubitemid 40569862)
5. Berman, A.; Ahn, D. J.; Lio, A.; Salmeron, M.; Reichert, A.; Charych, D. Total alignment of calcite at acidic polydiacetylene films-Cooperativity at the organic-inorganic interface Science 1995, 269, 515-518
6. Aizenberg, J.; Black, A. J.; Whitesides, G. H. Oriented growth of calcite controlled by self-assembled monolayers of functionalized alkanethiols supported on gold and silver J. Am. Chem. Soc. 1999, 121, 4500-4509
7. Aizenberg, J.; Black, A. J.; Whitesides, G. M. Control of crystal nucleation by patterned self-assembled monolayers Nature 1999, 398, 495-498 (Pubitemid 29177485)
8. Bunker, B. C.; Rieke, P. C.; Tarasevich, B. J.; Campbell, A. A.; Fryxell, G. E.; Graff, G. L.; Song, L.; Liu, J.; Virden, J. W.; Mcvay, G. L. Ceramic thin-film formation on functionalized interfaces through biomimetic processing Science 1994, 264, 48-55 (Pubitemid 24146004)
9. Lee, A. Y.; Lee, I. S.; Dettet, S. S.; Boerner, J.; Myerson, A. S. Crystallization on confined engineered surfaces: A method to control crystal size and generate different polymorphs J. Am. Chem. Soc. 2005, 127, 14982-14983 (Pubitemid 41547338)
10. Carter, P. W.; Ward, M. D. Topographically directed nucleation of organic-crystals on molecular single-crystal substrates J. Am. Chem. Soc. 1993, 115, 11521-11535
11. Gavish, M.; Wang, J. L.; Eisenstein, M.; Lahav, M.; Leiserowitz, L. The role of crystal polarity in alpha-amino-acid crystals for induced nucleation of ice Science 1992, 256, 815-818
12. Hiremath, R.; Basile, J. A.; Varney, S. W.; Swift, J. A. Controlling molecular crystal polymorphism with self-assembled monolayer templates J. Am. Chem. Soc. 2005, 127, 18321-18327 (Pubitemid 43038495)
13. Page, A. J.; Sear, R. P. Heterogeneous nucleation in and out of pores Phys. Rev. Lett. 2006, 97, 065701
14. Page, A. J.; Sear, R. P. Crystallization controlled by the geometry of a surface J. Am. Chem. Soc. 2009, 131, 17550-17551
15. Ha, J. M.; Wolf, J. H.; Hillmyer, M. A.; Ward, M. D. Polymorph selectivity under nanoscopic confinement J. Am. Chem. Soc. 2004, 126, 3382-3383 (Pubitemid 38366704)
16. Beiner, M.; Rengarajan, G. T.; Pankaj, S.; Enke, D.; Steinhart, M. Manipulating the crystalline state of pharmaceuticals by nanoconfinement Nano Lett. 2007, 7, 1381-1385 (Pubitemid 46834427)
17. Rengarajan, G. T.; Enke, D.; Steinhart, M.; Beiner, M. Stabilization of the amorphous state of pharmaceuticals in nanopores J. Mater. Chem. 2008, 18, 2537-2539 (Pubitemid 351718084)
18. Diao, Y.; Whaley, K. E.; Helgeson, M. E.; Woldeyes, M. A.; Doyle, P. S.; Myerson, A. S.; Hatton, T. A.; Trout, B. L. Gel-induced selective crystallization of polymorphs J. Am. Chem. Soc. 2012, 134, 673-684
19. Diao, Y.; Helgeson, M.; Doyle, P.; Myerson, A.; Hatton, T. A.; Trout, B. Design of polymeric substrates for controlled molecular crystallization Abstr. Pap. Am. Chem. Soc. 2011, 242
20. Diao, Y.; Helgeson, M. E.; Siam, Z. A.; Doyle, P. S.; Myerson, A. S.; Hatton, T. A.; Trout, B. L. Nucleation under soft confinement: Role of polymer-solute interactions Cryst. Growth Des. 2012, 12, 508-517
21. Eral, H. B.; Mugele, F.; Duits, M. H. G. Colloidal dynamics near a particle-covered surface Langmuir 2011, 27, 12297-12303
22. Eral, H. B.; Oh, J. M.; van den Ende, D.; Mugele, F.; Duits, M. H. G. Anisotropic and hindered diffusion of colloidal particles in a closed cylinder Langmuir 2010, 26, 16722-16729
23. Williams, I.; Oguz, E. C.; Bartlett, P.; Lowen, H.; Royall, C. P. Direct measurement of osmotic pressure via adaptive confinement of quasi hard disc colloids Nat. Commun. 2013, 4, 2555
24. Oguz, E. C.; Marechal, M.; Ramiro-Manzano, F.; Rodriguez, I.; Messina, R.; Meseguer, F. J.; Lowen, H. Packing confined hard spheres denser with adaptive prism phases Phys. Rev. Lett. 2012, 109, 218301
25. Suleimanov, Y. V. Surface diffusion of hydrogen on Ni(100) from ring polymer molecular dynamics J. Phys. Chem. C 2012, 116, 11141-11153
26. Diao, Y.; Helgeson, M. E.; Myerson, A. S.; Hatton, T. A.; Doyle, P. S.; Trout, B. L. Controlled nucleation from solution using polymer microgels J. Am. Chem. Soc. 2011, 133, 3756-3759
27. Jackson, C. L.; McKenna, G. B. Vitrification and crystallization of organic liquids confined to nanoscale pores Chem. Mater. 1996, 8, 2128-2137 (Pubitemid 126475402)
28. Augst, A. D.; Kong, H. J.; Mooney, D. J. Alginate hydrogels as biomaterials Macromol. Biosci. 2006, 6, 623-633 (Pubitemid 44329266)
29. Martinsen, A.; Skjakbraek, G.; Smidsrod, O. Alginate as immobilization material. 1. Correlation between chemical and physical-properties of alginate gel beads Biotechnol. Bioeng. 1989, 33, 79-89 (Pubitemid 19010127)
30. Moe, S. T.; Elgsaeter, A.; Skjakbraek, G.; Smidsrod, O. A new approach for estimating the cross-link density of covalently cross-linked ionic polysaccharide gels Carbohydr. Polym. 1993, 20, 263-268 (Pubitemid 23685333)
31. Moe, S. T.; Skjak-Braek, G.; Smidsrod, O. Covalently cross-linked sodium alginate beads Food Hydrocolloids 1991, 5, 119-123
32. Strand, B. L.; Morch, Y. A.; Skjak-Braek, G. Alginate as immobilization matrix for cells Minerva Biotecnol. 2000, 12, 223-233 (Pubitemid 32249217)
33. Takka, S.; Acarturk, F. Calcium alginate microparticles for oral administration: I: effect of sodium alginate type on drug release and drug entrapment efficiency J. Microencapsulation 1999, 16, 275-290 (Pubitemid 29191812)
34. Lipinski, C. A.; Lombardo, F.; Dominy, B. W.; Feeney, P. J. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings Adv. Drug Delivery Rev. 2012, 64, 4-17
35. Inoue, T.; Chen, G. H.; Hoffman, A. S.; Nakamae, K. A hydrophobically modified bioadhesive polymeric carrier for controlled drug delivery to mucosal surfaces J. Bioact. Compat. Polym. 1998, 13, 50-64 (Pubitemid 28069858)
36. Gou, M. L.; Li, X. Y.; Dai, M.; Gong, C. Y.; Wang, X. H.; Xie, Y.; Deng, H. X.; Chen, L. J.; Zhao, X.; Qian, Z. Y.; Wei, Y. Q. A novel injectable local hydrophobic drug delivery system: Biodegradable nanoparticles in thermo-sensitive hydrogel Int. J. Pharm. 2008, 359, 228-233
37. Jeong, B.; Bae, Y. H.; Kim, S. W. Drug release from biodegradable injectable thermosensitive hydrogel of PEG-PLGA-PEG triblock copolymers J. Controlled Release 2000, 63, 155-163 (Pubitemid 30046951)
38. Mason, T. G.; Wilking, J. N.; Meleson, K.; Chang, C. B.; Graves, S. M. Nanoemulsions: formation, structure, and physical properties J. Phys.: Condens. Matter 2006, 18, R635-R666 (Pubitemid 44508561)
39. McClements, D. J. Crystals and crystallization in oil-in-water emulsions: Implications for emulsion-based delivery systems Adv. Colloid Interface Sci. 2012, 174, 1-30
40. McClements, D. J. Nanoemulsions versus microemulsions: terminology, differences, and similarities Soft Matter 2012, 8, 1719-1729
41. An, H. Z.; Helgeson, M. E.; Doyle, P. S. Nanoemulsion composite microgels for orthogonal encapsulation and release Adv. Mater. 2012, 24, 3838-3844
42. Jagadeesan, D.; Nasimova, I.; Gourevich, I.; Starodubtsev, S.; Kumacheva, E. Microgels for the encapsulaption and stimulus-responsive release of molecules with distinct polarities Macromol. Biosci. 2011, 11, 889-896
43. Josef, E.; Zilberman, M.; Bianco-Peled, H. Composite alginate hydrogels: An innovative approach for the controlled release of hydrophobic drugs Acta Biomater. 2010, 6, 4642-4649
44. Turco, G.; Donati, I.; Grassi, M.; Marchioli, G.; Lapasin, R.; Paoletti, S. Mechanical spectroscopy and relaxometry on alginate hydrogels: A comparative analysis for structural characterization and network mesh size determination Biomacromolecules 2011, 12, 1272-1282
45. Larson, R. The Structure and Rheology of Complex Fluids; Oxford University Press: New York, 1999.
46. Gardel, M. L.; Shin, J. H.; MacKintosh, F. C.; Mahadevan, L.; Matsudaira, P.; Weitz, D. A. Elastic behavior of cross-linked and bundled actin networks Science 2004, 304, 1301-1305 (Pubitemid 38697422)
47. Flory, P. J. Principles of Polymer Chemistry; Oxford University Press: Ithaca, NY, 1953.
48. Chan, A. W.; Whitney, R. A.; Neufeld, R. J. Kinetic controlled synthesis of pH-responsive network alginate Biomacromolecules 2008, 9, 2536-2545
49. Jamzad, S.; Fassihi, R. Role of surfactant and pH on dissolution properties of fenofibrate and glipizide-A technical note AAPS PharmSciTech 2006, 7, E33
50. Diao, Y.; Harada, T.; Myerson, A. S.; Hatton, T. A.; Trout, B. L. The role of nanopore shape in surface-induced crystallization Nat. Mater. 2011, 10, 867-871
51. Diao, Y.; Helgeson, M.; Myerson, A.; Hatton, T. A.; Doyle, P.; Trout, B. Rational design of polymeric nucleants for controlling nucleation Abstr. Pap. Am. Chem. Soc. 2011, 241
52. Fryd, M. M.; Mason, T. G. Advanced nanoemulsions Annu. Rev. Phys. Chem. 2012, 63, 493-518