Complexation of tauro- and glyco-conjugated bile salts with α-cyclodextrin and hydroxypropyl-α-cyclodextrin studied by affinity capillary electrophoresis and molecular modelling

Journal of Separation Science

Volumn 34, Issue 22, 2011, Pages 3221-3230

  Holm, René ^a   Schönbeck, Christian ^a,b   Askjær, Sune ^a   Jensen, Henrik ^c   Westh, Peter ^b   Østergaard, Jesper ^c  

^a H LUNDBECK A S   (Denmark)

^b ROSKILDE UNIVERSITY   (Denmark)

^c UNIVERSITY OF COPENHAGEN   (Denmark)

Author keywords

Cyclodextrin; Bile salts; Biological surfactants; Complexation; Structure analysis

Indexed keywords

ADDITIVE CONCENTRATIONS; AFFINITY CAPILLARY ELECTROPHORESIS; AQUEOUS SOLUBILITY; BACK GROUND ELECTROLYTE; BILE SALTS; CONJUGATED BILE SALTS; CURRENT RATIOS; DRUG SUBSTANCES; GLYCOCHENODEOXYCHOLATE; MEDIUM EFFECT; MOBILITY SHIFT; SIDE-CHAINS; SMALL INTESTINE; SOLUBILISATION; STABILITY CONSTANTS; STRUCTURE ANALYSIS; TAUROCHOLATE;

BODY FLUIDS; CAPILLARY ELECTROPHORESIS; COMPLEXATION; CYCLODEXTRINS; MOLECULAR MODELING; ORGANIC POLYMERS; SOLUBILITY; SURFACE ACTIVE AGENTS;

SALTS;

ALPHA CYCLODEXTRIN; BILE SALT; ELECTROLYTE; GLYCOCHENODEOXYCHOLIC ACID; GLYCOCHOLIC ACID; GLYCODEOXYCHOLIC ACID; HYDROXYPROPYL ALPHA CYCLODEXTRIN; PROSTAGLANDIN A1; TAUROCHENODEOXYCHOLIC ACID; TAUROCHOLIC ACID; TAURODEOXYCHOLIC ACID; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; CAPILLARY ELECTROPHORESIS; MOLECULAR MODEL; PRIORITY JOURNAL; SOLUBILIZATION; VISCOSITY;

ALPHA-CYCLODEXTRINS; ANIMALS; BILE ACIDS AND SALTS; DOGS; ELECTROPHORESIS, CAPILLARY; HUMANS; KINETICS; MODELS, MOLECULAR; RATS;

CANIS FAMILIARIS; INDICATOR MINOR; RATTUS;

EID: 81755183000     PISSN: 16159306     EISSN: 16159314     Source Type: Journal    
DOI: 10.1002/jssc.201100479     Document Type: Article

References (76)

1. Szejtli, J., Cyclodextrin Technology, Kluwer Academic Publishers, Dordrecht 1988.
2. Szejtli, J., in:, Szejtli, J., Osa, T., (Eds.), Cyclodextrins, 1st Edn, Elsevier Science Ltd, Oxford 1996, pp. 189-204.
3. Szejtli, J., J. Incl. Phenom. Macrocycl. Chem. 2005, 52, 1-11.
4. Carrier, R. L., Miller, L. A., Ahmed, I., J. Control. Rel. 2007, 123, 78-99.
5. Davis, M. E., Brewster, M. E., Nat. Rev. Drug Disc. 2004, 3, 1023-1035.
6. Brewster, M. E., Loftsson, T., Adv. Drug Del. Rev. 2007, 59, 645-666.
7. Loftsson, T., Brewster, M. E., Masson, M., Am. J. Drug Del. 2004, 2, 175-261.
8. Szejtli, J., Med. Res. Rev. 1994, 14, 353-386.
9. Rajewski, R. A., Stella, V. J., J. Pharm. Sci. 1996, 85, 1142-1169.
10. Uekama, K., Otagiri, M., Crit. Rev. Ther. Drug 1987, 3, 1-40.
11. Challa, R., Ahuja, A., Ali, J., Khar, R. K., AAPS PharmSciTech. 2005, 6, E329-E357.
12. Arima, H., Hirayama, F., Okamoto, C. T., Uekama, K., Recent Res. Devel. Chem. Pharm. 2002, 2, 155-193.
13. Thompson, D. O., Crit. Rev. Ther. Drug 1997, 14, 1-104.
14. Uekama, K., Chem. Pharm. Bull. 2004, 52, 900-915.
15. Lina, B. A. R., Bär, A., Regul. Toxicol. Pharmacol. 2004, 39, S14-S26.
16. Lina, B. A. R., Bär, A., Regul. Toxicol. Pharmacol. 2004, 39, S27-S33.
17. Uekama, K., Hirayama, F., Arima, H., J. Incl. Phenom. Macrocycl. Chem. 2006, 56, 3-8.
18. Ono, N., Hirayama, F., Arima, H., Uekama, K., Rytting, J. H., J. Incl. Phenom. Macrocycl. Chem. 2003, 44, 93-96.
19. Ghorab, M. K., Adeyeye, M. C., J. Pharm. Sci. 2003, 98, 1690-1697.
20. Alvaro, D., Cantatore, A., Attili, A. F., Gianni Corrandini, S., De Luca, C., Minervini, G., Di Base, A., Angelico, M., Comp. Biochem. Physiol. 1986, 83B, 551-554.
21. Cabrer, P. R., Alvarez-Parrilla, E., Al-Soufi, W., Meijide, F., Núñez, E. R., Tato, J. V., Supramol. Chem. 2003, 15, 33-43.
22. Cabrer, P. R., Alvarez-Parrilla, E., Meijide, F., Seijas, J. A., Núñez, E. R., Tato, J. V., Langmuir 1999, 15, 5489-5495.
23. Abadie, C., Hug, M., Kübli, C., Gains, N., Biochem. J. 1994, 229, 725-730.
24. Tan, X., Lindenbaum, S., Int. J. Pharm. 1991, 74, 127-135.
25. Miyajima, K., Yokoi, M., Komatsu, H., Nakagaki, M., Chem. Pharm. Bull. 1986, 34, 1395-1398.
26. González-Gaitano, G., Compostizo, A., Sánchez-Martin, L., Tardajos, G., Langmuir 1997, 13, 2235-2241.
27. Tan, Z. J., Zhu, X. X., Brown, G. R., Langmuir 1994, 10, 5488-5495.
28. Cooper, A., Nutley, M. A., Camilleri, P., Anal. Chem. 1998, 70, 5024-5028.
29. Holm, R., Nicolajsen, H. V., Hartvig, R. A., Westh, P., Østergaard, J., Electrophoresis 2007, 28, 3745-3752.
30. Holm, R., Hartvig, R. A., Nicolajsen, H. V., Westh, P., Østergaard, J., J. Incl. Phenom. Macrocycl. Chem. 2008, 61, 161-169.
31. Østergaard, J., Jensen, H., Holm, R., J. Sep. Sci. 2009, 32, 1712-1721.
32. Heegaard, N. H. H., Electrophoresis 2009, 30, S229-S239.
33. Winzor, D. J., Anal. Biochem. 2008, 383, 1-17.
34. Tanaka, Y., Terabe, S., J. Chromatogr. B 2002, 768, 81-92.
35. Uselova-Vcelakova, K., Zuskova, I., Gas, B., Electrophoresis 2007, 28, 2145-2152.
36. Vespalec, R., Bocek, P., J. Chromatogr. A 2000, 875, 431-445.
37. Britz-McKibbin, P., Chen, D. D. Y., Electrophoresis 2002, 23, 880-888.
38. Jiang, C. X., Armstrong, D. W., Electrophoresis 2010, 31, 17-27.
39. Rundlett, K. L., Amstrong, D. W., Electrophoresis 1997, 18, 2194-2202.
40. Lemesle-Lamache, V., Taverna, M., Wouessidjewe, D., Duchene, D., Ferrier, D., J. Chromatogr. A 1996, 735, 321-331.
41. Shibukawa, A., Lloyd, D. K., Wainer, I. W., Chromatographia 1993, 35, 419-429.
42. Penn, S. G., Bergström, E. T., Knights, I., Liu, G., Ruddick, A., Goodall, D. M., J. Phys. Chem. 1995, 99, 3875-3880.
43. Peng, X., Bebault, G. M., Sacks, S. L., Chen, D. D. Y., Can. J. Chem. 1997, 75, 507-517.
44. Wren, S. A. C., Rowe, R. C., J. Chromatogr. A 1992, 603, 235-241.
45. Bartak, P., Bednar, P., Kubcek, L., Lämmerhofer, M., Lindner, W., Stransky, Z., Anal. Chim. Acta 2004, 506, 105-113.
46. Ehala, S., Makrlik, E., Toman, P., Kasicka, V., Electrophoresis 2010, 31, 702-708.
47. Ehala, S., Toman, P., Makrlik, E., Kasicka, V., J. Chromatogr. A 2009, 1216, 7927-7931.
48. Ehala, S., Dybal, J., Makrlik, E., Kasicka, V., J. Sep. Sci. 2009, 45, 597-604.
49. Penn, S. G., Bergström, E. T., Goodall, D. M., Anal. Chem. 1994, 66, 2866-2873.
50. Kawaoka, J., Gomez, F. A., J. Chromatogr. B 1998, 715, 203-210.
51. Schipper, B. J., Ramstad, T., J. Pharm. Sci. 2005, 94, 1528-1537.
52. Rekharsky, M. V., Inoue, Y., Chem. Rev. 1998, 98, 1875-1917.
53. Wallingford, R. A., Ewing, A. G., Adv. Chromatogr. 1989, 29, 1-76.
54. Rundlett, K. L., Armstrong, D. W., J. Chromatogr. A 1996, 721, 173-186.
55. Chen, W., Chang, C-E., Gilson, M. K., Biophys. J. 2004, 87, 3035-3049.
56. Chang, C. E., Gilson, M. K., J. Am. Chem. Soc. 2004, 126, 13156-13164.
57. Molecular Operating Environment (MOE), version 2006.08 [computer program], Montreal, Quebec, Canada 2002.
58. Chang, C. E., Chen, W., Gilson, M. K., Proc. Natl. Acad. Sci. USA 2007, 104, 1534-1539.
59. Halgren, T. A., J. Comput. Chem. 1996, 17, 490-519.
60. Halgren, T. A., J. Comput. Chem. 1996, 17, 520-552.
61. Halgren, T. A., J. Comput. Chem. 1996, 17, 553-586.
62. Halgren, T. A., Nachbar, R. B., J. Comput. Chem. 1996, 17, 587-615.
63. Halgren, T. A., J. Comput. Chem. 1996, 17, 616-641.
64. Halgren, T. A., J. Comput. Chem. 1999, 20, 720-729.
65. Halgren, T. A., J. Comput. Chem. 1999, 20, 730-748.
66. Kalantzi, L., Goumas, K., Kalioras, V., Abrahamsson, B., Dressman, J. B., Reppas, C., Pharm. Res. 2006, 23, 165-176.
67. Kok, W. T., Chromatographia 2000, 51, S24-S27.
68. Bowser, M. T., Chen, D. D. Y., Anal. Chem. 1998, 70, 3261-3270.
69. Loftsson, T., Másson, M., Brewster, M. E., J. Pharm. Sci. 2004, 93, 1091-1099.
70. Connors, K. A., J. Pharm. Sci. 1995, 84, 843-848.
71. Ollila, F., Pentikäinen, O. T., Forss, S., Johnson, M. S., Slotte, J. P., Langmuir 2001, 17, 7107-7111.
72. Holm, R., Shi, W., Hartvig, R. A., Askjær, S., Madsen, J. C., Westh, P., Phys. Chem. Chem. Phys. 2009, 11, 5070-5078.
73. Holm, R., Madsen, J. C., Shi, W., Larsen, K. L., Städe, L. W., Westh, P., J. Incl. Phenom. Macrocycl. Chem. 2011, 69, 201-211.
74. Connors, K. A., Chem. Rev. 1997, 97, 1325-1357.
75. Larsen, K. L., Aachmann, F. L., Wimmer, R., Stella, V. J., Kjølner, U. M., J. Pharm. Sci. 2005, 94, 507-515.
76. van Ommen, B., De Bie, A. T. H. J., Bär, A., Regul. Toxicol. Pharmacol. 2004, 39, S57-S66.