NMR study of BA/FBA cocrystal confined within mesoporous silica nanoparticles employing thermal solid phase transformation

Journal of Physical Chemistry C

Volumn 119, Issue 16, 2015, Pages 8652-8661

  Skorupska, Ewa ^a   Paluch, Piotr ^a   Jeziorna, Agata ^a   Potrzebowski, Marek J ^a  

^a CENTRE OF MOLECULAR AND MACROMOLECULAR STUDIES   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

MAGIC ANGLE SPINNING; MELTING; MESOPOROUS MATERIALS; MOLECULAR DYNAMICS; NANOPARTICLES; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SILICA;

EQUIMOLAR AMOUNT; FLUORINATED BENZOIC ACIDS; FUTURE APPLICATIONS; MESOPOROUS SILICA NANOPARTICLES; PHYSICAL MIXTURES; SOLID-PHASE TRANSFORMATION; STRUCTURAL CONSTRAINTS; THERMAL TRANSFORMATIONS;

BENZOIC ACID;

EID: 84929095352     PISSN: 19327447     EISSN: 19327455     Source Type: Journal    
DOI: 10.1021/jp5123008     Document Type: Article

References (40)

1. Devadasu, V. R.; Bhardwaj, V.; Kumar, M. N. V.; Can, R. Controversial Nanotechnology Promise Drug Delivery? Chem. Rev. 2013, 113, 1686-1735
2. Alvarez-Lorenzo, C.; Concheiro, A. Smart drug delivery systems: from fundamentals to the clinic Chem. Commun. 2014, 50, 7743-7765
3. Kamaly, N.; Xiao, Z.; Valencia, P. M.; Radovic-Moreno, A. F.; Farokhzad, O. C. Targeted polymeric therapeutic nanoparticles: design, development and clinical translation Chem. Soc. Rev. 2014, 41, 2971-3010
4. Tiwari, G.; Tiwari, R.; Sriwastawa, B.; Bhati, L.; Pandey, S.; Pandey, P.; Bannerjee, S. K. Drug Delivery Systems: An updated review Int. J. Pharm. Invest. 2012, 2, 2-11
5. Slowing, I. I.; Trewyn, B. G.; Giri, S.; Lin, V.S.-Y. Mesoporous Silica Nanoparticles for Drug Delivery and Biosensing Applications Adv. Funct. Mater. 2007, 17, 1225-1236
6. Vadia, N.; Rajput, S. Mesoporous Material, MCM-41: A New Drug Carrier Asian J. Pharm. Clin. Res. 2011, 4, 44-53
7. Skorupska, E.; Jeziorna, A.; Paluch, P.; Potrzebowski, M. J. Ibuprofen in Mesopores of Mobil Crystalline Material 41 (MCM-41): A Deeper Understanding Mol. Pharmaceutics 2014, 11, 1512-1519
8. Charnay, C.; Bégu, S.; Tourné-Péteilh, C.; Nicole, L.; Lerner, D. A.; Devoisselle, J. M. Inclusion of ibuprofen on mesoporus template silica: drug loading and release property Eur. J. Pharm. Biopharm. 2004, 57, 533-540
9. Qian, K. K.; Robin, H.; Bogner, R. H. Application of Mesoporous Silicon Dioxide and Silicate in Oral Amorphous Drug Delivery Systems J. Pharm. Sci. 2012, 101, 444-463
10. Gao, L.; Sun, J.; Zhang, L.; Wang, J.; Ren, B. Influence of different structured channels of mesoporous silicate on the controlled ibuprofen delivery Mater. Chem. Phys. 2012, 135, 786-797
11. Rodríguez-Spong, B.; Price, C. P.; Jayasankar, A.; Matzger, A. J.; Rodríguez-Hornedo, N. General principles of pharmaceutical solid polymorphism: a supramolecular perspective Adv. Drug Delivery Rev. 2004, 56, 241-274
12. Elder, D. P.; Holm, R.; Lopez de Diego, H. Use of pharmaceutical salts and cocrystals to address the issue of poor solubility Int. J. Pharm. 2013, 453, 88-100
13. Yadav, A. V.; Shete, A. S.; Dabke, A. P.; Kulkarni, P. V.; SakhareIndian, S. S. Co-Crystals: A Novel Approach to Modify Physicochemical Properties of Active Pharmaceutical Ingredients J. Pharm. Sci. 2009, 71, 359-370
14. Qiao, N.; Li, M.; Schlindwein, W.; Malek, N.; Davies, A.; Trappitt, G. Pharmaceutical cocrystals: An overview Int. J. Pharm. 2011, 419, 1-11
15. Schultheiss, N.; Newman, A. Pharmaceutical Cocrystals and Their Physicochemical Properties Cryst. Growth Des. 2009, 9, 2950-2967
16. Braga, D.; Maini, L.; Grepioni, F. Mechanochemical preparation of co-crystals Chem. Soc. Rev. 2013, 42, 7638-7648
17. Aitipamula, S.; Chowa, P. S.; Tan, R. B. H. Polymorphism in cocrystals: a review and assessment of its significance CrystEngComm 2014, 16, 3451-3465
18. Steed, J. W. The role of co-crystals in pharmaceutical design Trends Pharmacol. Sci. 2013, 34, 185-193
19. Gdaniec, M.; Jankowski, W.; Milewska, M. J.; Poński, T. Supramolecular Assemblies of Hydrogen-Bonded Carboxylic Acid Dimers Mediated by Phenyl-Pentafluorophenyl Stacking Interactions Angew. Chem. 2003, 115, 4033-4036
20. Skorupska, E.; Jeziorna, A.; Kazmierski, S.; Potrzebowski, M. J. Recent progress in solid-state NMR studies of drugs confined within drug delivery systems Solid State Nucl. Magn. Reson. 2014, 57-58, 2-16
21. Liu, S.-F.; Schmidt-Rohr, K. High-Resolution Solid-State 13C NMR of Fluoropolymers Macromolecules 2001, 34, 8416-8418
22. Suzuki, K.; Martineau, C.; Fink, G.; Steuernagel, S.; Teulelle, F. Hartmann-Hahn 2D-map to optimize the RAMP-CPMAS NMR experiment for pharmaceutical materials Magn. Reson. Chem. 2012, 50, 159-168
23. Hahn, E. L. Spin echoe Phys. Rev. 1950, 80, 580-594
24. Cory, G.; Ritchey, W. M. Suppression of signals from the probe in bloch decay spectra J. Magn. Reson. 1988, 80, 128-132
25. Azais, T.; Hartmeyer, G.; Quignard, S.; Laurent, G.; Babonneau, F. Solution State NMR Techniques Applied to Solid State Samples: Characterization of Benzoic Acid Confined in MCM-41 J. Phys. Chem. C 2010, 114, 8884-8891
26. Brown, S. P. Applications of high-resolution 1H solid-state NMR Solid State Nucl. Magn. Reson. 2012, 41, 1-27
27. Brown, S. P. Probing proton-proton proximities in the solid state Prog. Nucl. Magn. Reson. 2007, 50, 199-251
28. Chu, P. J.; Potrzebowski, M. J.; Scott, A. I.; Gao, Y. Conformational studies of N -benzoyl- l -phenylalanine by combined rotation and multiple-pulse spectroscopy proton nuclear magnetic resonance J. Am. Chem. Soc. 1990, 112, 881-883
29. Van Rossum, B.-J.; Foerster, H.; de Groot, H. J. M. High-field and high-speed CP-MAS 13C NMR heteronuclear dipolar-correlation spectroscopy of solids with frequency-switched Lee-Goldburg homonuclear decoupling J. Magn. Reson. 1997, 124, 516-519
30. Pickard, C. J.; Mauri, F. All-electron magnetic response with pseudopotentials: NMR chemical shifts Phys. Rev. B 2001, 63, 245101
31. Yates, J. R.; Pickard, C. J.; Mauri, F. Calculation of NMR chemical shifts for extended systems using ultrasoft pseudopotentials Phys. Rev. B 2007, 76, 024401
32. Miller, J. M. Fluorine-19 magic-angle spinning NMR Prog. Nucl. Magn. Reson. Spectrosc. 1996, 255-281
33. Chen, H.; Viel, S.; Ziarelli, F.; Peng, L. 19F NMR: a valuable tool for studying biological events Chem. Soc. Rev. 2013, 42, 7971-7982 and references cited therein.
34. Feike, M.; Demco, D. E.; Graf, R.; Gottwald, J.; Hafner, S.; Spiess, H. W. Broadband Multiple-Quantum NMR Spectroscopy J. Magn. Reson., Ser. A 1996, 122, 214-221
35. Azaïs, T.; Tourné-Péteilh, C.; Aussenac, F.; Baccile, N.; Coelho, C.; Devoisselle, J.-M.; Babonneau, F. Solid-State NMR Study of Ibuprofen Confined in MCM-41 Material Chem. Mater. 2006, 18, 6382-6390
36. Wu, D.; Hwang, S.-J.; Zones, S. I.; Navrotsky, A. Guest-host interactions of a rigid organic molecule in porous silica frameworks Proc. Natl. Acad. Sci. U.S.A. 2014, 111, 1720-1725
37. Spiess, H. W. Molecular dynamics of solid polymers as revealed by deuteron NMR Colloid Polym. Sci. 1983, 261, 193-209
38. Jelinski, L. W. In High Resolution NMR of Synthetic Polymers in Bulk; Komoroski, R. A., Ed.; Verlag Chemie: New York, 1986.
39. Spiess, H. W. Deuteron NMR-a new tool for studying chain mobility and orientation in polymers Adv. Polym. Sci. 1985, 61, 23-58
40. Potrzebowski, M. J.; Wasiak, J.; Ciesielski, W.; Klinowski, J. 1H/2H-Dimethyl Sulfone as a Convenient Standard for Setting the Hartmann-Hahn Match in 1H-2H CP/MAS NMR J. Magn. Reson., Ser. A 1995, 114, 70-72