NMR spectroscopy in pharmacy

Journal of Pharmaceutical and Biomedical Analysis

Volumn 17, Issue 4-5, 1998, Pages 557-616

  Holzgrabe, Ulrike ^a   Diehl, Bernd W K ^b   Wawer, Iwona ^c  

^a UNIVERSITY OF BONN   (Germany)

^b Spectral Service GmbH   (Germany)

^c MEDICAL UNIVERSITY OF WARSAW   (Poland)

Author keywords

NMR; Pharmacy; Review

Indexed keywords

ANALYTIC METHOD; DRUG FORMULATION; DRUG IMPURITY; DRUG METABOLISM; DRUG SOLUBILITY; DRUG STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REVIEW; STRUCTURE ANALYSIS;

CHEMISTRY, PHARMACEUTICAL; MAGNETIC RESONANCE IMAGING; MAGNETIC RESONANCE SPECTROSCOPY; PHARMACOKINETICS; TISSUE DISTRIBUTION;

EID: 0032145087     PISSN: 07317085     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0731-7085(97)00276-8     Document Type: Review

References (180)

1. [1] K. Wüthrich, Acta Cryst D51 (1995) 249-270.
2. [2] G.A. Neville, T.J. Racey, R.N. Rej, A.S. Perlin, J. Pharm. Sci. 79 (1990) 425-427.
3. [3] G.A. Neville, F. Mori, T.J. Racey, P. Rochon, K.R. Holme, A.S. Perlin, J. Pharm. Sci. 79 (1990) 339-343.
4. [4] G.A. Neville, F. Mori, K.R. Holme, A.S. Perlin, J. Pharm. Sci. 78 (1989) 101-104.
5. [5] U.R. Desai, R.J. Linhardt, J. Pharm. Sci. 84 (1995) 212-215.
6. [6] S. Tachibana, S. Nishiura, S. Ishida, K. Kakehi, S. Honda, Chem. Pharm. Bull. 38 (1990) 2503-2506.
7. [7] B. Casu, M. Guerrini, A. Naggi, G. Torri, L. De-Ambrosi, G. Boveri, S. Gonella, A. Cedro, L. Ferro, E. Lanzarotti, M. Paterno, M. Attolini, M.G. Valle, Arzneim.-Forsch./Drug. Res. 46 (1996) 472-477.
8. [8] F. Nachtmann, G. Atzl, W.D. Roth, Anal. Profiles Drug Subst. 12 (1983) 215-276.
9. [9] K.G. Ludwig-Baxter, R.N. Rej, A.S. Perlin, G.A. Neville, J. Pharm. Sci. 80 (1992) 655-660.
10. [10] G.A. Neville, P. Rochon, R.N. Rej, A.S. Perlin, J. Pharm. Sci. 80 (1991) 239-244.
11. [11] (SSL), Method developed by Spectral Service GmbH, Cologne, Germany, not be published previously.
12. [12] G.L. Silvey, J. Pharm. Sci. 81 (1992) 471-474.
13. [13] A.E. Tonelli, The NMR spectra and the microstructures of polymers, in: Allan H. Fawcett (Ed.), Polymer Spectroscopy, Wiley, Chichester, 1996, pp. 55-95.
14. [14] P.P. Lankhorst, M.M. Foot, M.P.A. de Lange, Pharmacopeial Forum 22 (3) (1996) 2414-2422.
15. [15] G.M. Hanna, C.A. Lau-Cam, J. Pharm. Biomed. Anal. 11 (1993) 855-859.
16. [16] T.A. Schmedake, L.E. Welch, J. Chem. Educ. 73 (1996) 1045-1048.
17. 31P NMR Method, 7th Int. Cong. Phospholipids, Brussels, Belgium, September 1996
18. 31P NMR Method, 7th Int. Cong. Phospholipids, Brussels, Belgium, September 1996
19. [18] J. De Kock, The European Analytical Subgroup of I.L.P.S.: A Joint Effort to Clarify Lecithin and Phospholipid Analysis, Fat Sci. Technol. 95 (9) (1993) 352-355.
20. [19] J. De Kock, The European Analytical Subgroup of I.L.P.S., in: G. Cevc, F. Paltauf (Eds.), Characterization, Metabolism and Novel Biological Applications, AOCS Press, Champaign, pp. 22-28.
21. [20] L.L. Olson, A.P. Cheung, J. Pharm. Biomed. Anal. 8 (1990) 725-728.
22. [21] Pharmeuropa 8 (1986) 232-234.
23. [22] C. Boschetti, G. Fronza, C. Fuganti, P. Grasselli, A.G. Magnone, A. Mele, C. Pellegatta, Arzneim.-Forsch./ Drug Res. 45 (1995) 1217-1221.
24. [23] Pharmeuropa 8 (1996) 521-523.
25. [24] Pharmeuropa 6 (1994) 291.
26. [25] A.F. Casy, G. H Dewar, J. Pharm. Biomed. Anal. 12 (1994) 855-861.
27. [26] J.K. Baker, C.W. Myers, Pharm. Res. 8 (1991) 761-770.
28. [27] A. TM Chan, K.A. Evans, E.A. Belsky, D.J.S. Ditnfeld, A.T. Tsai, A. McPhail, Magn. Res. Chem. 34 (1996) 1025-1030.
29. [28] B.A. Dawson, D.B. Black, G.A. Neville, J. Pharm. Biomed. Anal. 13 (1995) 395-407.
30. [29] G.A. Neville, H.D. Beckstead, D.B. Black, B.A. Dawson, H.F. Shurvell, J. Pharm. Sci. 83 (1994) 1274-1279.
31. [30] B. Vilanova, F. Munoz, J. Donoso, J. Frau, F.G. Blanco, J. Pharm. Sci. 83 (1994) 322-327.
32. [31] E. Inkmann, K.F. Hesse, U. Holzgrabe, Pharmazie 52 (1997) 764-774.
33. [32] G.S. Sadane, A.B. Ghogare, J. Pharm. Sci. 80 (1991) 895-898.
34. [33] S. Görög, G. Balogh, M. Gazdag, J. Pharm. Biomed. Anal. 9 (1991) 829-833.
35. [34] J.A. Dale, D.L. Dull, H.S. Mosher, J. Org. Chem. 34 (1969) 2543-2649.
36. [35] D. Parker, Chem. Rev. 91 (1991) 1441-1457.
37. [36] H.Y. Aboul-Enein, Anal. Lett. 21 (1988) 2155-2163.
38. [37] L.M. Sweeting, D.C. Crans, G.M. Whiteside, J. Org. Chem. 52 (1987) 2273-2276.
39. [38] P.E. Peterson, M. Stepanian, J. Org. Chem. 53 (1988) 1907-1911.
40. [39] G.R. Weisman, in: J.D. Morrison (Ed.), Asymmetric Synthesis, vol. 1, ch. 8, Academic Press, New York, 1983, p. 153-171
41. [40] W.H. Pirkle, D.J. Hoover, Top. Stereochem. 13 (1982) 264-331.
42. [41] B.A. Dawson, S.A. Qureshi, D.B. Black, 33rd Experimental Nuclear Magnetic Resonance Conference, Pacific Grove, CA, 1992
43. [42] C. Dauwe, J. Buddrus, GIT Fachz. Lab. 5 (1994) 517-518.
44. [43] B. Staubach, J. Buddrus, Angew. Chem. 108 (1996) 1443-1445.
45. [44] V. Dinnendahl, U. Fricke, Arzneistoff-Profile, Govi-Verlag, Frankfurt a. M. 1982-1996.
46. [45] G.M. Hanna, C.A. Lau-Cam, Pharm. Res. 7 (1990) 726-729.
47. [46] G.M. Hanna, C.A. Lau-Cam, J. Pharm. Biomed. Anal. 11 (1993) 665-670.
48. [47] P.M. Lacroix, B.A. Dawson, R.W. Sears, D.B. Black, Chirality 6 (1994) 484-491.
49. [48] B.A. Dawson, D.B. Black, 37th Experimental Nuclear Magnetic Resonance Conference, Pacific Grove, CA, 1996
50. [49] B.A. Dawson, D.B. Black, J. Pharm. Biomed. Anal. 13 (1995) 39-44.
51. [50] C.G. Chavdarian, E.B. Sanders, R.L. Bassfield, J. Org. Chem. 47 (1982) 1069-1073.
52. [51] J.W. Jaroszewski, A. Olsson, J. Pharm. Biomed. Anal. 12 (1994) 295-299.
53. [52] A.F. Casy, TRAC 12 (1993) 185-189.
54. [53] C.A. Marchant, S.K. Branch, J. Pharm. Pharmacol. 42 (1990) P68.
55. [54] T.T. Ndou, S. Mukundan Jr, I.M. Warner, J. Incl. Phenom. 15 (1993) 9-15.
56. [55] M. Wiese, H.-P. Cordes, H. Chi, J.K. Seydel, T. Backensfeld, B.W. Müller, J. Pharm. Sci. 80 (1991) 153-156.
57. [56] A.F. Casy, A.F. Drake, C.R. Ganellin, A.D. Mercer, C. Upton, Chirality 4 (1992) 356-366.
58. [57] J.R. Moyano, M.J. Arias-Blanco, J.M. Gines, A.M. Rabasco, J.I. Perez-Martinez, M. Mor, F. Giordano, J. Pharm. Sci. 86 (1997) 72-75.
59. [58] A.F. Casy, A.D. Cooper, T.M. Jefferies, R.M. Gaskell, D. Greatbanks, R. Pickford, J. Pharm. Biomed. Anal. 9 (1991) 787-792.
60. [59] C.J. Easton, S.F. Lincoln, Chem. Soc. Rev. 1 (1996) 163-170.
61. [60] S.K. Branch, U. Holzgrabe, T.M. Jefferies, H. Mallwitz, M. Matchett, J. Pharm. Biomed. Anal. 12 (1994) 1507-1517.
62. [61] S.K. Branch, U. Holzgrabe, T.M. Jefferies, H. Mallwitz, F.J.R. Oxley, J. Chromatogr. A 758 (1997) 277-292.
63. [62] U. Holzgrabe, H. Mallwitz, S.K. Branch, T.M. Jefferies, M. Wiese, Chirality 9 (1997) 211-219.
64. [63] A. Taylor, D.A.R. Williams, I.D. Wilson, J. Pharm. Biomed. Anal. 9 (1991) 493-496.
65. [64] Y. Kuroda, Y. Suzuki, J. He, T. Kawabata, A. Shibukawa, H. Wada, H. Fujima, Y. Go-oh, E. Imai, T. Nakagawa, J. Chem. Soc., Perkin Trans. 2 (1995) 1749-1759.
66. [65] U. Holzgrabe, M. Thunhorst, Magn. Res. Chem. 36 (1998) 211-216.
67. [66] J.K. Nicholson, I.D. Wilson, Prog. Drug Res. 31 (1987) 428-479.
68. [67] S.K. Branch, A.F. Casy, Prog. Med. Chem. 26 (1989) 355-436.
69. [68] J.R. Everett, K.R. Jennings, G. Woodnutt, M.J. Buckingham, J. Chem. Soc. Chem. Commun. 1 (1984) 894-895.
70. [69] S.C. Connor, J.R. Everett, K.R. Jennings, J.K. Nicholson, G. Woodnutt, J. Pharm. Pharmacol. 46 (1994) 128-134.
71. [70] I.D. Wilson, J. Fromson, I.M. Ismail, J.K. Nicholson, J. Pharm. Biomed. Anal. 5 (1987) 157-163.
72. [71] J.W. Jaroszewski, D. Berenstein, F.A. Slok, P.E. Simonsen, M.K. Agger, J. Pharm. Biomed. Anal. 14 (1996) 543-549.
73. [72] I.D. Wilson, I.M. Ismail, J. Pharm. Biomed. Anal. 4 (1986) 663-665.
74. [73] J.R. Bales, D.P. Higham, I. Howe, J.K. Nicholson, P.J. Sadler, Clin. Chem. 30 (1984) 1631-1636; S.K. Branch, L.J. Notorianni, M.L. Sitanggang, J. Pharm. Pharmacol. 38(Suppl.) 115P (1986); M.L. Sitanggang, Thesis, Bath, UK, 1988; T.D. Spurway, K.P.R. Gartland, A. Warrander, R. Pickford, J.K. Nicholson, I.D. Wilson, J. Pharm. Biomed. Anal. 8(Suppl) (1990) 969-973.
75. [73] J.R. Bales, D.P. Higham, I. Howe, J.K. Nicholson, P.J. Sadler, Clin. Chem. 30 (1984) 1631-1636; S.K. Branch, L.J. Notorianni, M.L. Sitanggang, J. Pharm. Pharmacol. 38(Suppl.) 115P (1986); M.L. Sitanggang, Thesis, Bath, UK, 1988; T.D. Spurway, K.P.R. Gartland, A. Warrander, R. Pickford, J.K. Nicholson, I.D. Wilson, J. Pharm. Biomed. Anal. 8(Suppl) (1990) 969-973.
76. [73] J.R. Bales, D.P. Higham, I. Howe, J.K. Nicholson, P.J. Sadler, Clin. Chem. 30 (1984) 1631-1636; S.K. Branch, L.J. Notorianni, M.L. Sitanggang, J. Pharm. Pharmacol. 38(Suppl.) 115P (1986); M.L. Sitanggang, Thesis, Bath, UK, 1988; T.D. Spurway, K.P.R. Gartland, A. Warrander, R. Pickford, J.K. Nicholson, I.D. Wilson, J. Pharm. Biomed. Anal. 8(Suppl) (1990) 969-973.
77. [73] J.R. Bales, D.P. Higham, I. Howe, J.K. Nicholson, P.J. Sadler, Clin. Chem. 30 (1984) 1631-1636; S.K. Branch, L.J. Notorianni, M.L. Sitanggang, J. Pharm. Pharmacol. 38(Suppl.) 115P (1986); M.L. Sitanggang, Thesis, Bath, UK, 1988; T.D. Spurway, K.P.R. Gartland, A. Warrander, R. Pickford, J.K. Nicholson, I.D. Wilson, J. Pharm. Biomed. Anal. 8(Suppl) (1990) 969-973.
78. [74] I.D. Wilson, J.K. Nicholson, Anal. Chem. 59 (1987) 2830-2832.
79. [75] G.C. Leo, W.-N. Wu, J. Pharm. Biomed. Anal. 10 (1992) 607-613.
80. [76] P.J.D. Foxall, J.A. Parkinson, I.H. Sadler, J.C. Lindon, J.K. Nicholson, J. Pharm. Biomed. Anal. 11 (1993) 21-31.
81. [77] M.-C. Malet-Martino, R. Martino, A. Lopez, J.-P. Beteille, M. Bon, J. Bernadou, J.-P. Armand, Cancer Chemoth. Pharmacol. 13 (1984) 31-35.
82. [78] M.-C. Malet-Martino, J.-P. Armand, A. Lopez, J. Bernadou, J.-P. Beteille, M. Bon, R. Martino, Cancer Res. 46 (1986) 2105-2112.
83. [79] W.E. Hull, R.E. Port, R. Herrmann, B. Britsch, W. Kunz, Cancer Res. 48 (1988) 1680-1688.
84. [80] D. Meynial, A. Lopez, M.-C. Malet-Martino, L.S. Hoffmann, R. Martino, J. Pharm. Biomed. Anal. 6 (1988) 47-59.
85. [81] J.R. Everett, K. Jennings, G. Woodnutt, J. Pharm. Pharmacol. 37 (1985) 869-873.
86. [82] J.R. Everett, K. Jennings, G. Woodnutt, J. Pharm. Biomed. Anal. 7 (1989) 397-403.
87. [83] F.Y.K. Ghauri, C.A. Blackledge, I.D. Wilson, J.K. Nicholson, J. Pharm. Biomed. Anal. 8 (1990) 939-944.
88. [84] E. Holmes, B.C. Sweatman, M.E. Bollard, C.A. Blackledge, C.R. Beddell, I.D. Wilson, J.C. Lindon, J.K. Nicholson, Xenobiotics 25 (1995) 1269-1281.
89. [85] M. Tugnait, F.Y. Ghauri, J.K. Nicholson, K. Borner, I. D. Wilson, Bioanalytical Approaches, vol. 22, ch. 48, 1992, pp. 291-296.
90. [86] U. Holzgrabe, S.K. Branch, Magn. Res,. Chem. 31 (1994) 192-196.
91. [87] K.E. Wade, I.D. Wilson, J.A. Troke, J.K. Nicholson, J. Pharm. Biomed. Anal. 8 (1990) 401-410.
92. [88] M. Spraul, M. Hofmann, I.D. Wilson, E. Lenz, J.K. Nicholson, J.C. Lindon, J. Pharm. Biomed. Anal. 11 (1993) 1009-1015.
93. [89] N.E. Preece, J.K. Nicholson, J.A. Timbrell, Biochem. Pharmacol. 41 (1991) 1319-1324.
94. [90] D. Busse, F.W. Busch, F. Bohnenstengel, M. Eichbaum, P. Fischer, J. Opalinska, K. Schumacher, E. Schweizer, H.K. Kroemer, J. Clin. Oncol. 15 (1997) 1885-1896.
95. [91] M.J. Basker, S.C. Finch, J.W. Tyler, J. Pharm. Biomed. Anal. 8 (1990) 573-576.
96. [92] D.A. Ryan, J.K.M. Sanders, G.C. Curtis, H. Hughes, J. Pharm. Biomed. Anal. 13 (1995) 723-734.
97. [93] D.A. Ryan, J.K.M. Sanders, G.C. Curtis, H. Hughes, J. Pharm. Biomed. Anal. 13 (1995) 735-745.
98. [94] P.J.D. Foxall, M. Spraul, R.D. Farrant, J.C. Lindon, G.H. Neild, J.K. Nicholson, J. Pharm. Biomed. Anal. 11 (1993) 267-276.
99. [95] J.K. Nicholson, P.J.D. Foxall, M. Spraul, R.D. Farrant, J.C. Lindon, Anal. Chem. 67 (1995) 793-811.
100. [96] M. Spraul, J.K. Nicholson, M.J. Lynch, J.C. Lindon, J. Pharm. Biomed. Anal. 12 (1994) 613-618.
101. [97] M. Liu, J.K. Nicholson, J.C. Lindon, Anal. Chem. 68 (1996) 3370-3376.
102. [98] P.E. McGowan, J. Reglinski, R. Wilson, J.J. Walker, S. Wisdom, J.H. McKillop, J. Pharm. Biomed. Anal. 11 (1993) 629-632.
103. [99] B.C. Sweatman, R.D. Farrant, E. Holmes, F.Y. Ghauri, J.K. Nicholson, J.C. Lindon, J. Pharm. Biomed. Anal. 11 (1993) 651-664.
104. [100] M.J. Lynch, J. Masters, J.P. Pryor, J.C. Lindon, M. Spraul, P.J.D. Foxall, J.K. Nicholson, J. Pharm. Biomed. Anal. 12 (1994) 5-19.
105. [101] M. Spraul, M. Hofmann, J.C. Lindon, J.K. Nicholson, I.D. Wilson, in: E. Reid, H.M. Hill, I.D. Wilson (Eds.), Biofluid and Tissue Analysis for Drugs, Including Hypolipidaemics: Methodology Surveys in Bioanalysis of Drug, vol. 23, Royal Society of Chemistry, 1994, pp. 21-32.
106. [102] M. Hofmann, M. Spraul, R. Streck, I.D. Wilson, A. Rapp, Laborpraxis no. 10, 1993, p. 1/2; M. Thiele, M. Biernacki, M. Spraul, M. Hofmann, Bruker brochure LC NMR
107. [102] M. Hofmann, M. Spraul, R. Streck, I.D. Wilson, A. Rapp, Laborpraxis no. 10, 1993, p. 1/2; M. Thiele, M. Biernacki, M. Spraul, M. Hofmann, Bruker brochure LC NMR
108. [103] J.C. Lindon, J.K. Nicholson, I.D. Wilson, Adv. Chromatogr. 36 (1996) 315-382.
109. [104] L. Griffiths, Anal. Chem. 67 (1995) 4091-4095.
110. [105] M. Spraul, M. Hofmann, P. Dvortsak, J.K. Nicholson, I.D. Wilson, Anal. Chem. 65 (1993) 327-330.
111. [106] I.D. Wilson, J.K. Nicholson, M. Hofmann, M. Spraul, J.C. Lindon, J. Chromatogr. 617 (1993) 324-328.
112. [107] M. Spraul, M. Hofmann, J.C. Lindon, R.D. Farrant, M.J. Seddon, J.K. Nicholson, I.D. Wilson, NMR Biomed. 7 (1994) 295-303.
113. [108] M. Spraul, M. Hofmann, J.C. Lindon, J.K. Nicholson, I.D. Wilson, Anal. Proc. 30 (1993) 390-392.
114. [109] U.G. Sidelmann, C. Gavaghan, H.A.J. Carless, R.D. Farrant, J.C. Lindon, I.D. Wilson, J.K. Nicholson, Anal. Chem. 67 (1995) 3401-3404.
115. [110] U.G. Sidelmann, C. Gavaghan, H.A.J. Carless, M. Spraul, M. Hofmann, J.C. Lindon, I.D. Wilson, J.K. Nicholson, Anal. Chem. 67 (1995) 4441-4445.
116. [111] U.G. Sidelmann, E.M. Lenz, M. Spraul, M. Hofmann, J. Troke, P.N. Sanderson, J.C. Lindon, I.D. Wilson, J.K. Nicholson, Anal. Chem. 68 (1996) 106-110.
117. [112] E.M. Lenz, D. Greatbanks, I.D. Wilson, M. Spraul, M. Hofmann, J. Troke, J.C. Lindon, J.K. Nicholson, Anal. Chem. 68 (1996) 2832-2837.
118. [113] J.K. Roberts, R.J. Smith, J. Chromatogr. A 677 (1994) 385-389.
119. [114] K. Albert, G. Schlotterbeck, U. Braumann, H. Händel, M. Spraul, G. Krack, Angew. Chem. 107 (1995) 1102-1104.
120. [115] B. Behnke, G. Schlotterbeck, U. Tallarek, S. Strohschein, L.-H. Tseng, T. Keller, K. Albert, E. Bayer, Bayer, Anal. Chem. 68 (1996) 1110-1115.
121. [116] A.E. Mutlib, J.T. Strupczewski, S.M. Chesson, Drug Metab. Dispos. 23 (1995) 951-964.
122. [117] J.P. Shockcor, S.E. Unger, I.D. Wilson, P.J.D. Foxall, J.K. Nicholson, J.C. Lindon, Anal. Chem. 68 (1996) 4431-4435.
123. [118] K. Albert, U. Braumann, L.-H. Tseng, G. Nicholson, E. Bayer, M. Spraul, M. Hofmann, C. Dowle, M. Chippendale, Anal. Chem. 66 (1994) 3042-3046.
124. [119] U. Braumann, L.-H. Tseng, K. Albert, M. Spraul, GIT 38 (1994) 77-79.
125. [120] S.A. Korhammer, A. Bernreuther, Fresenius J. Anal. Chem. 35 (1996) 131-135.
126. [121] U. Braumann, H. Händel, K. Albert, R. Ecker, M. Spraul, Anal. Chem. 34 (1995) 930-935.
127. [122] S. Johnson, E.D. Morgan, I.D. Wilson, M. Spraul, M. Hofmann, J. Chem. Soc. Perkin Trans. 1 (1994) 1499-1502.
128. [123] A.C. Olivieri, L. Frydman, L.E. Diaz, J. Magn. Reson. 75 (1987) 50-62.
129. [124] L.B. Alemany, D.M. Grant, R.J. Pugmire, T.D. Alger, K.W. Zilm, J. Am. Chem. Soc. 105 (1983) 2133-2142.
130. [125] H. Saito, M. Yokoi, M. Aida, M. Kodama, T. Oda, Y. Sato, Magn. Reson. Chem. 26 (1988) 155-161.
131. [126] R.K. Harris, Analyst 110 (1985) 649-655.
132. [127] D.G. Retwitsch, M.A. Jacintha, C.R. Dybowski, Anal. Chim. Acta 283 (1993) 1033-1049.
133. [128] A. Jurkiewicz, G.E. Maciel, Anal. Chem. 67 (1995) 2188-2194.
134. [129] R. Suryanarayanan, T.S. Wiedmann, Pharm. Res. 7 (1990) 184-187.
135. [130] P. Gao, Pharm. Res. 13 (1996) 1095-1104.
136. [131] H.G. Brittain, S.J. Bogdanowich, D.E. Bugay, J. DeVincentis, G. Lewen, A.W. Newman, Pharm. Res 8 (1991) 963-973.
137. [132] D.E. Bugay, Pharm. Res. 10 (1993) 317-327.
138. [133] S.R. Byrn, G. Gray, R.R. Pfeiffer, J. Frye, J. Pharm. Sci. 74 (1985) 565-568.
139. [134] R.A. Fletton, R.K. Harris, A.M. Kenwright, R.W. Lancaster, K.J. Packer, N. Sheppard, Spectrochim. Acta 43A (1987) 1111-1120.
140. [135] R.K. Harris, B.J. Say, R.R. Yeung, R.A. Fletton, R.W. Lancaster, Spectrochim. Acta 45A (1989) 465-469.
141. [136] R.K. Harris, A.M. Kenwright, B.J. Say, R.R. Yeung, R.A. Fletton, R.W. Lancaster, G.L. Hardgrove, Spectrochim. Acta 46A (1990) 927-935.
142. [137] S.R. Byrn, P.A. Sutton, B. Tobias, J. Frye, P. Main, J. Am. Chem. Soc. 110 (1988) 1609-1614.
143. [138] K. Raghavan, A. Dwivedi, G.C. Campbell, E. Johnston, D. Levorse, J. McCauley, M. Hussain, Pharm. Res. 10 (1993) 900-904.
144. [139] C. Doherty, P. York, Int. J. Pharm. 47 (1988) 141-155.
145. [140] J.J. Gerber, J.G. vanderWatt, A.P. Lötter, Int. J. Pharm. 73 (1991) 137-145.
146. [141] R.G. Ball, M.W. Baum, J. Org. Chem. 57 (1992) 801-803.
147. [142] E.B. Vadas, P. Toma, G. Zografi, Pharm. Res. 8 (1991) 148-155.
148. [143] H.G. Brittain, K.R. Morris, D.E. Bugay, A.B. Thakur, A.T.M. Serajuddin, J. Pharm. Biomed. Anal. 11 (1993) 1063-1069.
149. [144] A.B. Thakur, K. Morris, J.A. Grosso, K. Himes, J.K. Thottathil, R.L. Jerzewski, D.A. Wadke, J.T. Cartensen, Pharm. Res. 10 (1993) 800-809.
150. [145] H. Martinez, S.R. Byrn, R.R. Pfeiffer, Pharm. Res. 7 (1990) 147-153.
151. [146] J. Fattah, J.M. Twyman, S.J. Heyes, D.J. Watkin, A.J. Edwards, K. Proust, Ch.M. Dobson, J. Am. Chem. Soc. 115 (1993) 5636-5650.
152. [147] C. Chang, L.E. Diaz, F. Morin, D.M. Grant, Magn. Res. Chem. 24 (1986) 768-771.
153. [148] L.E. Diaz, L. Frydman, A.C. Olivieri, B. Frydman, Anal. Lett. 20 (1987) 1657-1666.
154. [149] N.R. Jagannathan, Current Science 56 (1987) 827-830.
155. [150] P.J. Saindon, N.S. Cauchon, P.A. Sutton, C. Chang, G.E. Peck, S.R. Byrn, Pharm. Res. 10 (1993) 197-203.
156. [151] G.E. Maciel, W. Kolodziejski, M.S. Bertran, B.E. Dale, Macromolecules 15 (1982) 686-687.
157. [152] M.J. Gidley, S.M. Bociek, J. Am. Chem. Soc. 110 (1988) 3820-3829.
158. [153] K.R. Morgan, R.H. Furneaux, R.A. Stanley, Carbohydr. Res. 235 (1992) 15-22.
159. [154] S.J. Heyes, N.J. Clayden, Ch.M. Dobson, Carbohydr. Res. 233 (1992) 1-14.
160. [155] L.E. Diaz, F. Morin, C.L. Mayne, D.M. Grant, C. Chang, Magn. Reson. Chem. 24 (1986) 167-170.
161. [156] M. Herve, J. Hirschinger, P. Granger, P. Gilard, A. Deflandre, N. Goetz, Biochim. Biophys. Acta 1204 (1994) 19-27.
162. [157] S. Ando, I. Ando, A. Shoji, T. Ozaki, J. Am. Chem. Soc. 110 (1988) 3380-3386.
163. [158] A. Shoji, S. Ando, S. Kuroki, I. Ando, G.A. Webb, in: G.A. Webb (Ed.), Annual Reports on NMR Spectroscopy, vol. 28, Academic Press, New York, 1993, pp. 55-98
164. [159] I. Wawer, A, Zielinska, Solid-State NMR, in press
165. [160] G. Nebgen, D. Gross, V. Lehmann, F. Müller, J. Pharm. Sci. 84 (1995) 283-291.
166. [161] A.R. Rajabi-Siahboomi, R.W. Bowtell, P. Mansfield, M.C. Davies, C.D. Melia, Pharm. Res. 13 (1996) 376-380.
167. [162] A. Haase, MAGMA 2 (1994) 157-160.
168. [163] L. Parnetti, D.T. Lowenthal, O. Presciutti, G.P. Pelliccioli, R. Palumbo, G. Gobbi, P. Chiarini, B. Palumbo, R. Tarducci, U. Senin, J. Am. Geriatr. Soc. 44 (1996) 133-138.
169. [164] B. Borah, M.D. Francis, K. Hovancik, J.T. Boyce, N.M. Szeverenyi, J. Rheumatol. 22 (1995) 855-862.
170. [165] A.C. Silva, W. Zhang, D.S. Williams, A.P. Koretsky, Magn. Reson. Med. 33 (1995) 209-214.
171. [166] Y. Xu, P. Tang, W. Zhang, L. Firestone, P.M. Winter, Anestesiology 83 (1995) 766-774.
172. [167] C.A. Bramch, J.A. Helpern, J.R. Ewing, K.M. Welch, Magn. Reson. Med. 20 (1991) 151-157.
173. [168] R.J. Maxwell, T.A. Frenkiel, D.R. Newell, C. Bauer, J.R. Griffiths, Magn. Reson. Med. 17 (1991) 189-196.
174. [169] U. Noth, L.J. Jager, J. Lutz, A. Haase, Magn. Reson. Imag. 12 (1994) 149-153.
175. [170] L.J. Jager, U. Noth, A. Haase, J. Lutz, Adv. Exp. Med. Biol. 361 (1994) 129-134.
176. [171] N. Beckmann, I. Turkay, J. Seelig, U. Keller, Biochemistry 30 (1991) 6362-6366.
177. [172] K. Kanamori, B.D. Ross, Biochem. J. 305 (1995) 329-336.
178. [173] J.D. Bell, Spectroscopy Europe 8 (1996) 18-24.
179. [174] P.C. Dagnelie, D.K. Menon, I.J. Cox, J.D. Bell, J. Sargentoni, G.A. Coutts, J. Urenjak, R.A. Iles, Clin. Sci. Colch. 83 (1992) 183-190.
180. [176] D.J. Craik, K.J. Nielsen, K.A. Higgins, Annu. Rev. Spectrosc. 32 (1996) 143-213.