NMR spectroscopy and imaging studies of pharmaceutical tablets made of starch

Carbohydrate Polymers

Volumn 75, Issue 3, 2009, Pages 369-379

  Thérien Aubin, Héloïse ^a   Zhu, X X ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

13C CP MAS NMR spectroscopy; Drug release; NMR imaging; Starch

Indexed keywords

BIOPOLYMERS; DRUG PRODUCTS; MAGNETIC RESONANCE IMAGING; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYSACCHARIDES;

13C CP/MAS NMR SPECTROSCOPY; CONTROLLED DRUG RELEASES; CONTROLLED RELEASE SYSTEMS; CROSSLINKED; DRUG RELEASE; DRUG RELEASES; HIGH AMYLOSES; HUMAN BODIES; HYDROPHILIC MATRIXES; MODIFIED STARCHES; NMR IMAGING; NMR SPECTROSCOPIES; PHARMACEUTICAL TABLETS; SOLID STATES; SUSTAINED RELEASES;

STARCH;

EID: 57349102913     PISSN: 01448617     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carbpol.2008.08.010     Document Type: Review

References (85)

1. Alfrey T.J., Gurnee E.F., and Lloyd W.G. Diffusion in glassy polymers. Journal of Polymer Science, Part C: Polymer Symposia 12 (1966) 249-261
2. 13 C CP/MAS solid state NMR. Carbohydrate Polymers 58 (2004) 383-389
3. 13 C CP/MAS NMR studies on aging of starch in white bread. Journal of Agricultural and Food Chemistry 51 5 (2003) 1242-1248
4. Baille W.E., Malveau C., Zhu X.X., and Marchessault R.H. NMR imaging of high-amylose starch tablets. 1. Swelling and water uptake. Biomacromolecules 3 1 (2002) 214-218
5. Barsby T.L., Donald A.M., and Frazier P.J. Starch: Advances in structure and function (2001), The Royal Society of Chemistry, Cambridge
6. 1 H NMR and MRI methods. European Journal of Pharmaceutics and Biopharmaceutics 59 2 (2005) 299-306
7. Blaszczak W., Valverde S., and Fornal J. Effect of high pressure on the structure of potato starch. Carbohydrate Polymers 59 3 (2005) 377-383
8. Bogracheva T.Y., Morris V.J., Ring S.G., and Hedley C.L. The granular structure of C-type pea starch and its role in gelatinization. Biopolymers 45 4 (1998) 323-332
9. Bogracheva T.Y., Wang Y.L., and Hedlery C.L. The effect of water content on the ordered/disordered structures in starches. Biopolymers 58 (2001) 247-259
10. Bowtell R., Sharp J.C., Peters A., Mansfield P., Rajabi-Siahboomi A.R., Davies M.C., and Melia C.D. NMR microscopy of hydrating hydrophilic matrix pharmaceutical tablets. Magnetic Resonance Imaging 12 2 (1994) 361-364
11. Buleon A., Colonna P., Planchot V., and Ball S. Starch granules: Structure and biosynthesis. International Journal of Biological Macromolecules 23 2 (1998) 85-112
12. Bulpin P.V., Welsh E.J., and Morris E.R. Physical characterization of amylose-fatty acid complexes in starch granules and in solution. Starch/Staerke 34 10 (1982) 335-339
13. Cartilier, L., Ungur, M., Chebli, C. (2006). Tablet formulation for sustained drug release comprising a starch derivative matrix. International Patent Office, Pat. No. WO 2006/066399.
14. Case S.E., Capitani T., Whaley J.K., Shi Y.C., Trzasko P., Jeffcoat R., et al. Physical properties and gelation behavior of a low-amylopectin maize starch and other high-amylose maize starches. Journal of Cereal Science 27 3 (1998) 301-314
15. Chauve G., Ravenelle F., and Marchessault R.H. Comparative imaging of a slow-release starch excipient tablet: Evidence of membrane formation. Carbohydrate Polymers 70 8 (2007) 61-67
16. Chebli C., Moussa I., Buczkowski S., and Cartilier L. Substituted amylose as a matrix for sustained drug release. Pharmaceutical Research 16 9 (1999) 1436-1440
17. 12. Biomacromolecules 5 3 (2004) 971-976
18. Chowdhury M.A., Hill D.J.T., Whittaker A.K., Braden M., and Patel M.P. NMR imaging of the diffusion of water at 310 K into semi-IPNs of PEM and poly(HEMA-co-THFMA) with and without chlorhexidine diacetate. Biomacromolecules 5 4 (2004) 1405-1411
19. Crank J. The mathematics of diffusion (1979), Clarendon Press, Oxford
20. Crank J., and Park G.S. Diffusion in polymers (1968), Academic Press, London
21. Deval F., Crini G., Bertini S., Morin-Crini N., Badot P.M., Verbrel J., et al. Characteization of crosslinked starch materials with spectrocopic techniques. Journal of Applied Polymer Science 93 (2004) 2650-2663
22. Dumoulin Y., Alex S., Szabo P., Cartilier L., and Mateescu M.A. Crosslinked amylose as matrix for drug controlled release. X-Ray and FT-IR structural analysis. Carbohydrate Polymers 37 4 (1998) 361-370
23. Dumoulin, Y., Carriere, F., Ingenito, A. (1998b). Industrial manufacture of crosslinked amylose in aqueous media, useful as an slow-release excipient. International Patent Office, Pat. No. WO 98/35992.
24. Flory P.J. Principles of polymer chemistry (1953), Cornell University Press, Ithaca
25. Frisch H.L. Sorption and transport in glassy-polymers. Polymer Engineering and Science 20 1 (1980) 2-13
26. Fyfe C.A., and Blazek-Welsh A.I. Quantitative NMR imaging study of the mechanism of drug release from swelling hydroxypropyl Me cellulose tablets. Journal of Controlled Release 68 3 (2000) 313-333
27. Fyfe C.A., and Blazek A.I. Investigation of hydrogel formation from hydroxypropylmethylcellulose (HPMC) by NMR spectroscopy and NMR imaging techniques. Macromolecules 30 20 (1997) 6230-6237
28. Gidley M.J. Molecular mechanisms underlying amylose aggregation and gelation. Macromolecules 22 1 (1989) 351-358
29. 13 C CP/MAS NMR study. Journal of the American Chemical Society 107 (1985) 7040-7044
30. 13 C chemical shifts. Journal of the American Chemical Society 110 12 (1988) 3820-3829
31. Hopkinson I., Jones R.A.L., Black S., Lane D.M., and McDonald P.J. Fickian and case II diffusion of water into amylose: A stray field NMR study. Carbohydrate Polymers 34 1-2 (1997) 39-47
32. Horigane A.K., Naito S., Kurimoto M., Irie K., Yamada M., Motoi H., et al. Moisture distribution and diffusion in cooked spaghetti studied by NMR imaging and diffusion model. Cereal Chemistry 83 3 (2006) 235-242
33. Horigane A.K., Takahashi H., Maruyama S., Ohtsubo K., and Yoshida M. Water penetration into rice grains during soaking observed by gradient echo magnetic resonance imaging. Journal of Cereal Science 44 3 (2006) 307-316
34. Imberty A., Buleon A., Vinh T., and Perez S. Recent advances in knowledge of starch structure. Starch/Staerke 43 10 (1991) 375-384
35. Imberty A., Chanzy H., Perez S., Buleon A., and Tran V. The double-helical nature of the crystalline part of A-starch. Journal of Molecular Biology 201 2 (1988) 365-378
36. Immel S., and Lichtenthaler F.W. The hydrophobic topographies of amylose and its blue iodine complex. Starch/Staerke 52 1 (2000) 1-8
37. Joensson, M., Gustavsson, N.O., Laakso, T., Reslow, M. (2002). Biodegradable controlled release microparticles containing amylopectin-based starch of reduced molecular weight. International Patent Office, Pat. No. WO 2002/028370.
38. Kasai M., Lewis A.R., Ayabe S., Hatae K., and Fyfe C.A. Quantitative NMR imaging study of the cooking of japonica and indica rice. Food Research International 40 8 (2007) 1020-1029
39. Kojima M., and Nakagami H. Investigation of water mobility and diffusivity in hydrating micronized low-substituted hydroxypropyl cellulose, hydroxypropylmethyl cellulose, and hydroxypropyl cellulose matrix tablets by magnetic resonance imaging (MRI). Chemical & Pharmaceutical Bulletin 50 12 (2002) 1621-1624
40. Kowalczuk J., Tritt-Goc J., and Pislewski N. The swelling properties of hydroxypropyl methyl cellulose loaded with tetracycline hydrochloride: Magnetic resonance imaging study. Solid State Nuclear Magnetic Resonance 25 1-3 (2004) 35-41
41. Le Bail P., Morin F.G., and Marchessault R.H. Characterization of a crosslinked high amylose starch excipient. International Journal of Biological Macromolecules 26 (1999) 193-200
42. Lefevre, P., Fuertes, P., Quettier, C. (2001). Excipients and disintegrants based on starch and their manufacture. European Patent Office, Pat. No. EP 1106646.
43. Lenaerts, V., Beck, R. H. F., Van Bogaert, E., Chouinard, F., Hopcke, R., & Desevaux, C. (2003). Crosslinked high amylose starch having functional groups as a matrix for the slow release of pharmaceutical agents. US Patent Office, Pat. No. US 6,607,748.
44. Lenaerts, V., Chouinard, F., Mateescu, M. A., & Ispas-Szabo, P. (2002). Crosslinked high amylose starch having functional groups as a matrix for the slow release of pharmaceutical agents. US Patent Office, Pat. No. US 6,419,957.
45. Lenaerts V., Dumoulin Y., and Mateescu M.A. Controlled release of theophylline from crosslinked amylose tablets. Journal of Controlled Release 15 1 (1991) 39-46
46. Lenaerts V., Moussa I., Dumoulin Y., Mebsout F., Chouinard F., Szabo P., et al. Crosslinked high amylose starch for controlled release of drugs: Recent advances. Journal of Controlled Release 53 1-3 (1998) 225-234
47. Lin J.H., Wang S.W., and Chang Y.H. Effect of molecular size on gelatinization thermal properties before and after annealing of rice starch with different amylose contents. Food Hydrocolloids 22 1 (2008) 156-163
48. Malveau C., Baille W.E., Zhu X.X., and Marchessault R.H. NMR imaging of high-amylose starch tablets. 2. Effect of tablet size. Biomacromolecules 3 6 (2002) 1249-1254
49. Mateescu, M. A., Lenaerts, V., & Dumoulin, Y. (1992). Use of crosslinked amylose as a matrix for slow-release oral pharmaceutical compositions. US Patent Office, Pat. No. US 5,456,921.
50. Miles M.J., Morris V.J., Orford P.D., and Ring S.G. The roles of amylose and amylopectin in the gelation and retrogradation of starch. Carbohydrate Research 135 2 (1985) 271-281
51. Morgan K.R., Furneaux R.H., and Larsen N.G. Solid-state NMR studies on the structures of starch granules. Carbohydrate Research 276 (1995) 387-399
52. 13 C CP/MAS NMR spectroscopy of the transformations of wheat starch associated with the making and staling of bread. Carbohydrate Research 235 (1992) 15-22
53. Morrison W.R., Tester R.F., and Gidley M.J. Properties of damaged starch granules. II. Crystallinity, molecular order and gelatinization of ball-milled starches. Journal of Cereal Science 19 3 (1994) 209-217
54. Moussa I.S., and Cartilier L.H. Characterization of moving fronts in crosslinked amylose matrixes by image analysis. Journal of Controlled Release 42 1 (1996) 47-55
55. O'Neil M.J. The Merck index: An encyclopedia of chemicals, drugs, and biologicals (2006), Merck & Co, Whitehouse Station, NJ
56. 13 C CP/MAS NMR. International Journal of Biological Macromolecules 29 2 (2001) 127-136
57. 13 C CP/MAS NMR spectroscopy 1: Spectral decomposition. Carbohydrate Polymers 39 (1999) 327-339
58. 13 C CP MAS NMR and enzymatic degradation study. Journal of Agricultural and Food Chemistry 47 10 (1999) 4060-4063
59. Pope, D. G., & Royce, A. E. (1987). Multilayer drug delivery device with alternate layers of drug in swellable material and spacers, for intermittent delivery of drugs. European Patent Office, Pat. No. EP 246819.
60. Primo-Martin C., van Nieuwenhuijzen N.H., Hamer R.J., and van Vliet T. Crystallinity changes in wheat starch during the bread-making process: Starch crystallinity in the bread crust. Journal of Cereal Science 45 2 (2007) 219-226
61. Rajabi-Siahboomi A.R., Bowtell R.W., Mansfield P., Davies M.C., and Melia C.D. Structure and behavior in hydrophilic matrix sustained release dosage forms: 4. Studies of water mobility and diffusion coefficients in the gel layer of HPMC tablets using NMR imaging. Pharmaceutical Research 13 3 (1996) 376-380
62. Rajabi-Siahboomi A.R., Bowtell R.W., Mansfield P., Henderson A., Davies M.C., and Melia C.D. Structure and behavior in hydrophilic matrix sustained-release dosage forms: 2. NMR-imaging studies of dimensional changes in the gel layer and core of HPMC tablets undergoing hydration. Journal of Controlled Release 31 2 (1994) 121-128
63. Ravenelle F., and Rahmouni M. Contramid: High-amylose starch for controlled drug delivery. In: Marchessault R.H., Ravenelle F., and Zhu X.X. (Eds). Polysaccharides for Drug Delivery and Pharmaceutical Applications (2006), ACS Symposium Series, New York 79-104
64. Robyt J.F. Essentials of Carbohydrate Chemistry (1998), Springer, New York
65. Rowe R.C., Sheskey P.J., and Weller P.J. Handbook of pharmaceutical excipients (2003), Pharmaceutical Press, London
66. Rudnic, E. M., McCarty, J. A., & Belenduik, G. W. (1996). Sustained-release drug delivery system comprising a highly soluble pharmaceuticals. US Patent Office, Pat. No. US 5,484,608.
67. Russo M.A.L., Strounina E., Waret M., Nicholson T., Truss R., and Halley P.J. A study of water diffusion into a high-amylose starch blend: The effect of moisture content and temperature. Biomacromolecules 8 1 (2007) 296-301
68. Shi Y.-C., Capitani T., Trzasko P., and Jeffcoat R. Molecular structure of a low-amylopectin starch and other high-amylose maize starches. Journal of Cereal Science 27 3 (1998) 289-299
69. 1 relaxation of epichlorohydrin crosslinked high amylose starch excipient. Starch/Staerke 52 6-7 (2000) 186-195
70. Shogren R.L., Thompson A.R., Felker F.C., Harryokuru R.E., Gordon S.H., Greene R.V., et al. Polymer compatibility and biodegradation of starch poly(ethylene-co-acrylic acid) polyethylene blends. Journal of Applied Polymer Science 44 11 (1992) 1971-1978
71. Smits A.L.M., Kruiskamp P.H., van Soest J.J.G., and Vliegenthart J.F.G. The influence of various small plasticisers and malto-oligosaccharides on the retrogradation of (partly) gelatinised starch. Carbohydrate Polymers 51 4 (2003) 417-424
72. 13 C CP/MAS NMR. Biomacromolecules 8 3 (2007) 885-891
73. Te Wierik G.H.P., Eissens A.C., Bergsma J., Arends-Scholte A.W., and Lerk C.F. A new generation of starch products as excipient in pharmaceutical tablets. II. High surface area retrograded pregelatinized potato starch products in sustained-release tablets. Journal of Controlled Release 45 1 (1997) 25-33
74. Thérien-Aubin H., Baille W.E., Zhu X.X., and Marchessault R.H. Imaging of high-amylose starch tablets. 3. Initial diffusion and temperature effect. Biomacromolecules 6 (2005) 3367-3372
75. 13 C NMR spectroscopy. Carbohydrate Research 342 11 (2007) 1525-1529
76. Thérien-Aubin H., and Zhu X.X. Water diffusion in drug delivery systems made of high-amylose starch as studied by NMR imaging. In: Marchessault R.H., Ravenelle F., and Zhu X.X. (Eds). Polysaccharides for drug delivery and pharmaceutical applications (2006), ACS Symposium Series, New York 105-120
77. Therien-Aubin H., Zhu X.X., Moorefield C.N., Kotta K., and Newkome G.R. Effect of ionic binding on the self-diffusion of anionic dendrimers and hydrophilic polymers in aqueous systems as studied by pulsed gradient NMR techniques. Macromolecules 40 10 (2007) 3644-3649
78. Thérien-Aubin H., Zhu X.X., Ravenelle F., and Marchessault R.H. Membrane formation and drug loading effects in high amylose starch tablets studied by NMR imaging. Biomacromolecules 9 (2008) 1248-1254
79. Tritt-Goc J., Kowalczuk J., and Pislewski N. Magnetic resonance imaging study of the transport phenomena of solvent into the gel layer of hypromellose matrices containing tetracycline hydrochloride. Journal of Pharmacy and Pharmacology 55 11 (2003) 1487-1493
80. 13 C CP/MAS NMR. Macromolecules 19 (1986) 1030-1034
81. Whistler R.L., BeMiller J.N., and Paschall E.F. Starch: Chemistry and technology (1984), Academic Press, Orlando
82. Wu H.-C.H., and Sarko A. Packing analysis of carbohydrates and polysaccharides. IX. The double-helical molecular structure of crystalline A-amylose. Carbohydrate Research 61 (1978) 27-40
83. Wu H.-C.H., and Sarko A. Packing analysis of carbohydrates and polysaccharides. VIII. The double-helical molecular structure of crystalline B-amylose. Carbohydrate Research 61 (1978) 7-25
84. Zhang, Y., Xiao, C., Bindzus, W., & Green, V. (2006). Tablet excipient based on starch. US Patent Office, Pat. No. US 2006/008521.
85. Ziegler G.R., MacMillan B., and Balcom B.J. Moisture migration in starch molding operations as observed by magnetic resonance imaging. Food Research International 36 4 (2003) 331-340