Inhibitory effect of hydroxypropyl methylcellulose acetate succinate on drug recrystallization from a supersaturated solution assessed using nuclear magnetic resonance measurements

Molecular Pharmaceutics

Volumn 10, Issue 10, 2013, Pages 3801-3811

  Ueda, Keisuke ^a   Higashi, Kenjirou ^a   Yamamoto, Keiji ^a   Moribe, Kunikazu ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

1H NMR; HPMC AS; NOESY; Recrystallization inhibition; STD NMR; Supersaturated solution

Indexed keywords

AMIDE; CARBAMAZEPINE; HYDROXYPROPYLMETHYLCELLULOSE ACETATE SUCCINATE; PHENYTOIN; PROTON;

ARTICLE; CHEMICAL STRUCTURE; CRYSTALLIZATION; DRUG SOLUTION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROPHOBICITY; MOLECULAR INTERACTION; NUCLEAR MAGNETIC RESONANCE; NUCLEAR OVERHAUSER EFFECT; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SATURATION TRANSFER DIFFERENCE NUCLEAR MAGNETIC RESONANCE; SUPERSATURATED SOLUTION;

CARBAMAZEPINE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CRYSTALLIZATION; MAGNETIC RESONANCE SPECTROSCOPY; METHYLCELLULOSE; MOLECULAR STRUCTURE; PHENYTOIN;

EID: 84888382217     PISSN: 15438384     EISSN: 15438392     Source Type: Journal    
DOI: 10.1021/mp400278j     Document Type: Article

References (45)

1. Lipinski, C. Poor aqueous solubility-an industry wide problem in drug discovery. Am. Pharm. Rev. 2002, 5, 82-85.
2. Hauss, D. J. Oral lipid-based formulations. Drugs Pharm. Sci. 2007, 170, 7.
3. Moribe, K.; Fukino, M.; Tozuka, Y.; Higashi, K.; Yamamoto, K. Prednisolone multicomponent nanoparticle preparation by aerosol solvent extraction system. Int. J. Pharmaceutics 2009, 380 (1.2), 201-205.
4. Pongpeerapat, A.; Higashi, K.; Tozuka, Y.; Moribe, K.; Yamamoto, K. Molecular interaction among probucol/PVP/SDS multicomponent system investigated by solid-state NMR. Pharm. Res. 2006, 23 (11), 2566-2574.
5. Higashi, K.; Tozuka, Y.; Moribe, K.; Yamamoto, K. Salicylic acid/gamma-cyclodextrin 2:1 and 4:1 complex formation by sealed-heating method. J. Pharm. Sci. 2010, 99 (10), 4192-4200.
6. Higashi, K.; Ideura, S.; Waraya, H.; Moribe, K.; Yamamoto, K. Incorporation of salicylic acid molecules into the intermolecular spaces of γ-cyclodextrin-polypseudorotaxane. Cryst. Growth Des. 2009, 9 (10), 4243-4246.
7. Itoh, K.; Matsui, S.; Tozuka, Y.; Oguchi, T.; Yamamoto, K. Improvement of physicochemical properties of N-4472. Part II: characterization of N-4472 microemulsion and the enhanced oral absorption. Int. J. Pharmaceutics 2002, 246 (1.2), 75-83.
8. Chiou, W. L.; Riegelman, S. Pharmaceutical applications of solid dispersion systems. J. Pharm. Sci. 1971, 60 (9), 1281-1302.
9. Brouwers, J.; Brewster, M. E.; Augustijns, P. Supersaturating drug delivery systems: the answer to solubility-limited oral bioavailability? J. Pharm. Sci. 2009, 98 (8), 2549-2572.
10. Serajuddin, A. T. Solid dispersion of poorly water-soluble drugs: early promises, subsequent problems, and recent breakthroughs. J. Pharm. Sci. 1999, 88 (10), 1058-1066.
11. Abu-Diak, O. A.; Jones, D. S.; Andrews, G. P. An investigation into the dissolution properties of celecoxib melt extrudates: understanding the role of polymer type and concentration in stabilizing supersaturated drug concentrations. Mol. Pharmaceutics 2011, 8 (4), 1362-1371.
12. Konno, H.; Handa, T.; Alonzo, D. E.; Taylor, L. S. Effect of polymer type on the dissolution profile of amorphous solid dispersions containing felodipine. Eur. J. Pharm. Biopharm. 2008, 70 (2), 493-499.
13. Jung, J. Y.; Yoo, S. D.; Lee, S. H.; Kim, K. H.; Yoon, D. S.; Lee, K. H. Enhanced solubility and dissolution rate of itraconazole by a solid dispersion technique. Int. J. Pharmaceutics 1999, 187 (2), 209-218.
14. Tanno, F.; Nishiyama, Y.; Kokubo, H.; Obara, S. Evaluation of hypromellose acetate succinate (HPMCAS) as a carrier in solid dispersions. Drug Dev. Ind. Pharm. 2004, 30 (1), 9-17.
15. Friesen, D. T.; Shanker, R.; Crew, M.; Smithey, D. T.; Curatolo, W. J.; Nightingale, J. A. Hydroxypropyl methylcellulose acetate succinate-based spray-dried dispersions: an overview. Mol. Pharmaceutics 2008, 5 (6), 1003-1019.
16. Miller, J. M.; Beig, A.; Carr, R. A.; Spence, J. K.; Dahan, A. A win-win solution in oral delivery of lipophilic drugs: supersaturation via amorphous solid dispersions increases apparent solubility without sacrifice of intestinal membrane permeability. Mol. Pharmaceutics 2012, 9 (7), 2009-2016.
17. Ueda, K.; Higashi, K.; Limwikrant, W.; Sekine, S.; Horie, T.; Yamamoto, K.; Moribe, K. Mechanistic differences in permeation behavior of supersaturated and solubilized solutions of carbamazepine revealed by nuclear magnetic resonance measurements. Mol. Pharmaceutics 2012, 9 (11), 3023-3033.
18. Miller, J. M.; Beig, A.; Krieg, B. J.; Carr, R. A.; Borchardt, T. B.; Amidon, G. E.; Amidon, G. L.; Dahan, A. The solubility-permeability interplay: mechanistic modeling and predictive application of the impact of micellar solubilization on intestinal permeation. Mol. Pharmaceutics 2011, 8 (5), 1848-1856.
19. Murray, N. J.; Williamson, M. P.; Lilley, T. H.; Haslam, E. Study of the interaction between salivary proline-rich proteins and a polyphenol by 1H-NMR spectroscopy. Eur. J. Biochem. 1994, 219 (3), 923-935.
20. Tezuka, Y. Nuclear Overhauser effect spectroscopy (NOESY) detection of the specific interaction between substituents in cellulose and amylose triacetates. Biopolymers 1994, 34 (11), 1477-1481.
21. Kim, Y.; Oksanen, D. A.; Massefski, W., Jr.; Blake, J. F.; Duffy, E. M.; Chrunyk, B. Inclusion complexation of ziprasidone mesylate with beta-cyclodextrin sulfobutyl ether. J. Pharm. Sci. 1998, 87 (12), 1560-1567.
22. Lula, I.; Denadai, A. L.; Resende, J. M.; de Sousa, F. B.; de Lima, G. F.; Pilo-Veloso, D.; Heine, T.; Duarte, H. A.; Santos, R. A.; Sinisterra, R. D. Study of angiotensin-(1-7) vasoactive peptide and its beta-cyclodextrin inclusion complexes: complete sequence-specific NMR assignments and structural studies. Peptides 2007, 28 (11), 2199-2210.
23. Parmar, A.; Singh, K.; Bahadur, A.; Marangoni, G.; Bahadur, P. Interaction and solubilization of some phenolic antioxidants in Pluronic® micelles. Colloids Surf., B: Biointerfaces 2011, 86 (2), 319-326.
24. Macura, S.; Ernst, R. R. Elucidation of cross relaxation in liquids by two-dimensional N.M.R. spectroscopy. Mol. Phys. 1980, 41 (1), 95-117.
25. Angulo, J.; Enriquez-Navas, P. M.; Nieto, P. M. Ligand-receptor binding affinities from saturation transfer difference (STD) NMR spectroscopy: the binding isotherm of STD initial growth rates. Chemistry 2010, 16 (26), 7803-7812.
26. Tatami, A.; Hon, Y. S.; Matsuo, I.; Takatani, M.; Koshino, H.; Ito, Y. Analyses of carbohydrate binding property of lectin-chaperone calreticulin. Biochem. Biophys. Res. Commun. 2007, 364 (2), 332-337.
27. Wang, Y. S.; Liu, D.; Wyss, D. F. Competition STD NMR for the detection of high-affinity ligands and NMR-based screening. Magn. Reson. Chem. 2004, 42 (6), 485-489.
28. Murphy, D.; Rodriguez-Cintron, F.; Langevin, B.; Kelly, R. C.; Rodriguez-Hornedo, N. Solution-mediated phase transformation of anhydrous to dihydrate carbamazepine and the effect of lattice disorder. Int. J. Pharmaceutics 2002, 246 (1-2), 121-134.
29. Kadam, Y.; Yerramilli, U.; Bahadur, A. Solubilization of poorly water-soluble drug carbamezapine in pluronic micelles: effect of molecular characteristics, temperature and added salt on the solubilizing capacity. Colloids Surf., B: Biointerfaces 2009, 72 (1), 141-147.
30. Park, S. H.; Choi, H. K. The effects of surfactants on the dissolution profiles of poorly water-soluble acidic drugs. Int. J. Pharmaceutics 2006, 321 (1-2), 35-41.
31. Ould-Ouali, L.; Arien, A.; Rosenblatt, J.; Nathan, A.; Twaddle, P.; Matalenas, T.; Borgia, M.; Arnold, S.; Leroy, D.; Dinguizli, M.; Rouxhet, L.; Brewster, M.; Preat, V. Biodegradable self-assembling PEG-copolymer as vehicle for poorly water-soluble drugs. Pharm. Res. 2004, 21 (9), 1581-1590.
32. Kochoyan, M.; Leroy, J. L.; Gueron, M. Proton exchange and base-pair lifetimes in a deoxy-duplex containing a purine-pyrimidine step and in the duplex of inverse sequence. J. Mol. Biol. 1987, 196 (3), 599-609.
33. Zhao, D.; Moore, J. S. Synthesis and self-association of an iminecontaining m-phenylene ethynylene macrocycle. J. Org. Chem. 2002, 67 (11), 3548-3554.
34. Ding, X.; Stringfellow, T. C.; Robinson, J. R. Self-association of cromolyn sodium in aqueous solution characterized by nuclear magnetic resonance spectroscopy. J. Pharm. Sci. 2004, 93 (5), 1351-1358.
35. Hasegawa, A.; Taguchi, M.; Suzuki, R.; Miyata, T.; Nakagawa, H.; Sugimoto, I. Supersaturation mechanism of drugs from solid dispersions with enteric coating agents. Chem. Pharm. Bull. 1988, 36 (12), 4941-4950.
36. Kubota, N. Effect of impurities on the growth kinetics of crystals. Cryst. Res. Technol. 2001, 36 (8-10), 749-769.
37. Somasundaran, P.; Krishnakumar, S. Adsorption of surfactants and polymers at the solid-liquid interface. Colloids Surf., A 1997, 123-124 (0), 491-513.
38. Anwar, J.; Boateng, P. K.; Tamaki, R.; Odedra, S. Mode of action and design rules for additives that modulate crystal nucleation. Angew. Chem., Int. Ed. 2009, 48 (9), 1596-1600.
39. Gordon, S. L.; Wuethrich, K. Transient proton-proton Overhauser effects in horse ferrocytochrome c. J. Am. Chem. Soc. 1978, 100 (22), 7094-7096.
40. Yuan, H. Z.; Cheng, G. Z.; Zhao, S.; Miao, X. J.; Yu, J. Y.; Shen, L. F.; Du, Y. R. Conformational dependence of Triton X-100 on environment studied by 2D NOESY and 1H NMR relaxation. Langmuir 2000, 16 (7), 3030-3035.
41. Kumar, A.; Wagner, G.; Ernst, R. R.; Wuethrich, K. Buildup rates of the nuclear Overhauser effect measured by two-dimensional proton magnetic resonance spectroscopy: implications for studies of protein conformation. J. Am. Chem. Soc. 1981, 103 (13), 3654-3658.
42. Neuhaus, D.; Williamson, M. P. The nuclear Overhauser effect in structural and conformational analysis; VCH: New York, NY, 1989; p xxii.
43. Ilevbare, G. A.; Liu, H.; Edgar, K. J.; Taylor, L. S. Impact of polymers on crystal growth rate of structurally diverse compounds from aqueous solution. Mol. Pharmacol. 2013, 10 (6), 2381-2393.
44. Parmar, A. V.; Bahadur, A.; Kuperkar, K.; Bahadur, P. PEO-PPO based star-block copolymer T904 as pH responsive nanocarriers for quercetin: Solubilization and release study. Eur. Polym. J. 2013, 49 (1), 12-21.
45. Cheng, Y.; Li, Y.; Wu, Q.; Zhang, J.; Xu, T. Generationdependent encapsulation/electrostatic attachment of phenobarbital molecules by poly(amidoamine) dendrimers: Evidence from 2DNOESY investigations. Eur. J. Med. Chem. 2009, 44 (5), 2219-2223.