Ionization constants and ionization profiles

Comprehensive Medicinal Chemistry II

Volumn 5, Issue , 2006, Pages 357-397

  Comer, J E A ^a  

^a Sirius Analytical Instruments Ltd   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84906444395     PISSN: None     EISSN: None     Source Type: Book    
DOI: None     Document Type: Chapter

References (82)

1. Sørensen, S. P L. Biochem Z. 1909, 21-131.
2. Kusalik, P. G.; Svishchev, I. M. Science 1994, 265, 1219-1221.
3. Marshall, W L.; Frank, E. U. J. Phys. Chem. Ref. Data 1981, 10, 295-304.
4. Smith, W; Martell, A. E. Critical Stability Constants.; Plenum Press: New York, 1974-1989; Vols 4-6.
5. Ackermann, T Z. Elektrochemie 1958, 62, 411-419.
6. Sillén, L. G.; Martell, A. E. Stability Constants. Special Publication No. 17; The Chemical Society: London, UK, 1964.
7. Sillén, L. G.; Martell, A. E. Stability Constants. Special Publication No. 25; The Chemical Society: London, UK, 1971.
8. Butler, J. N. Ionic Equilibrium, Solubility and pH Calculations; John Wiley: New York, 1998.
9. Albert, A.; Serjeant, E. P. The Determination of Ionization Constants; 3rd ed.; Chapman and Hall: London, UK, 1984.
10. Comer, J.; Tam, K. Lipophilicity Profiles: Theory and Measurement. In Pharmacokinetic Optimization in Drug Research: Biological, Physicochemical and Computational Strategies; Testa, B., van de Waterbeemd, H., Folkers, G., Guy, R., Eds.; VHCA: Zurich, Switzerland, 2001, pp 275-304.
11. Avdeef, A. Curr. Topics Med. Chem. 2001, 1, 277-351.
12. Wells, J. I. Pharmaceutical Preformulation; Ellis Horwood: London, UK, 1988.
13. Cunderikov, B.; Kaalhus, O.; Cunderlik, R.; Mateasik, A.; Moan, J.; Kongshaug, M. Photochem. Photobiol. 2004, 79, 242-247.
14. Stephens, C. R.; Murai, K.; Brunings, K. J.; Woodward, R. B. J. Am. Chem. Soc 1956, 78, 4155-4157.
15. Rigler, N. E.; Bag, S. P; Leyden, D. E.; Sudmeier, J. L.; Reilley, C. N. Anal. Chem. 1965, 37, 872-875.
16. Castro, J. L.; Collins, I.; Russell, M. G. N.; Watt, A. P.; Sohal, B.; Rathbone, D.; Beer, M. S.; Stanton, J. A. J. Med. Chem. 1998, 41, 2667-2670.
17. Schmitt, L.; Schlewer, G.; Spiess, B. Biochim. Biophys. Acta 1991, 1075, 139-140.
18. Presland, J. P.; Strange, P. G. Biochem. Pharmacol. 1991, 41, R9-R12.
19. D'Souza, U. M.; Strange, P. G. Biochem. Soc. Trans. 1992, 20, 146S.
20. Castro, J. L.; Broughton, H. B.; Russell, M. G. N.; Rathbone, D.; Watt, A. P; Ball, R. G.; Chapman, K. L.; Patel, S.; Smith, A. J.; Marshall, G. R.; Matassa, V G. J. Med. Chem. 1997, 40, 2491-2501.
21. Sheldon, R. S.; Hill, R. J.; Taouis, M.; Wilson, L. M. Mol. Pharmacol. 1991, 39, 609-614.
22. Srinivas, M.; Hopperstad, M. G.; Spray, D. C. Proc. Natl. Acad. Sei. USA 2001, 98, 10942-10947.
23. Porcar, I.; Codoner, A.; Gomez, C. M.; Abad, C.; Campos, A. J. Pharm. Sei. 2003, 92, 45-57.
24. Austin, R. P.; Davis, A. M.; Manners, C. N. J. Pharm. Sei. 1995, 84, 1180-1183.
25. Avdeef, A.; Box, K. J.; Comer, J. E. A.; Hibbert, C.; Tam, K. Y Pharm. Res. 1998, 15, 209-215.
26. Ermondi, G.; Lorenti, M.; Caron, G. J. Med. Chem. 2004, 47, 3949-3961.
27. Shore, P A.; Brodie, B. B.; Hogben, C. A. J. Pharmacol. Exp. Ther. 1957, 119, 361-369.
28. Camenisch, G.; Folkers, G.; van de Waterbeemd, H. Pharm. Acta Helv. 1996, 71, 309-327.
29. Nagahara, N.; Tavelin, S.; Artursson, P. J. Pharm. Sci. 2004, 93, 2972-2984.
30. Kimura, T; Nakayama, T; Kurosaki, Y; Suzuki, Y; Arimoto, S.; Hayatsu, H. Jpn. J. Cancer Res. 1985, 76, 272-277.
31. Avdeef, A. Absorption and Drug Development. Solubility, Permeability and Charge State; Wiley-Interscience: Hoboken, NJ, 2003.
32. Gobry, V; Bouchard, G.; Carrupt, P. A.; Testa, B.; Girault, H. H. Helv. Chim. Acta 2000, 83, 1465-1474.
33. Hägele, G.; Holzgrabe, U. pH-Dependent NMR Measurements. In NMR Spectroscopy in Drug Development and Analysis; Holzgrabe, U., Wawer, I., Diehl, B., Eds.; Wiley-VCH: Weinheim, Germany, 1999, pp 61-76.
34. Acharya, P; Cheruku, P; Chatterjee, S.; Acharya, S.; Chattopadhyaya, J. J. Am. Chem. Soc. 2004, 126, 2862-2869.
35. Abe, H.; Nakanishi, H. J. Peptide Sei. 2003, 9, 177-186.
36. Kahyaoglu, A.; Jordan, F Protein Sei. 2002, 11, 965-973.
37. Ermondi, G.; Caron, G.; Bouchard, G.; van Balen, G. P.; Pagliara, A.; Grandi, T; Carrupt, P. A.; Fruttero, R.; Testa, B. Helv. Chim. Acta 2001, 84, 360-374.
38. Tam, K. Y; Quéré, L. Anal Sei. 2001, 17, 1203-1208.
39. Espinosa, S.; Bosch, E.; Roseés, M. J. Chromatogr. A. 2002, 947, 47-58.
40. Espinosa, S.; Bosch, E.; Rosées, M. J. Chromatogr. A. 2002, 945, 83-96.
41. Shoskes, D. A. Can. J. Urol. 2001, 8, 24-28.
42. Nangia, A.; Andersen, P H.; Berner, B.; Maibach, H. I. Contact Dermatitis 1996, 34, 237-242.
43. Skopp, G.; Potsch, L. Int. J. Legal Med. 1999, 112, 213-221.
44. de la Torre, R.; Farre, M.; Navarro, M.; Pacifici, R.; Zuccaro, P; Pichini, S. Clin. Pharmacokinet. 2004, 43, 157-185.
45. Newton, D. W; Kluza, R. B. Drug Inteil. Clin. Pharm. 1978, 12, 546-554.
46. Box, K.; Bevan, C.; Comer, J.; Hill, A.; Allen, R.; Reynolds, D. Anal. Chem. 2003, 75, 883-892.
47. Dressman, J. B.; Amidon, G. L.; Reppas, C.; Shah, V. P. Pharm. Res. 1998, 15, 11-22.
48. Avdeef, A. Assessment of Distribution-pH Profiles. In Lipophilicity in Drug Action; Pliska, V, Testa, B., van de Waterbeemd, H., Eds.; VCH: Weinheim, Germany, 1995, pp 109-139.
49. Slater, B. ; McCormack, A. ; Avdeef, A. ; Comer, J. E. J. Pharm. Sei. 1994, 83, 1280-1283.
50. Streng, W H. ; Hsi, S. K. ; Helms, P E. ; Tan, H. G. J. Pharm. Sei. 1984, 73, 1679-1684.
51. Streng, W. H.; Tan, H. G. H. Int. J. Pharm. 1985, 25, 135-145.
52. Ozturk, S. S.; Palsson, B. O.; Dressman, J. B. Pharm. Res. 1988, 5, 272-282.
53. Avdeef, A. Pharm. Pharmacol. Commun. 1998, 4, 165-178.
54. Stuart, M.; Box, K. Anal. Chem. 2005, 77, 983-990.
55. Avdeef, A.; Comer, J. E. A.; Thomson, S. J. Anal. Chem. 1993, 65, 42-49.
56. Takács-Novák, K.; Box, K. J.; Avdeef, A. Int. J. Pharm. 1997, 151, 235-248.
57. Rived, F; Canals, I.; Bosch, E.; Rosës, M. Anal. Chim. Acta 2001, 439, 315-333.
58. Comer, J. E. A.; Avdeef, A.; Box, K. J. Am. Lab. 1995, 4, 36C-361.
59. Morgan, M. E.; Liu, K.; Anderson, B. D. J. Pharm. Sei. 1998, 87, 238-245.
60. Allen, R. I.; Box, K. J.; Comer, J. E. A.; Peake, C.; Tam, K. Y J. Pharm. Biomed. Anal. 1998, 17, 699-712.
61. Tam, K. Y; Takács-Novák, K. Anal. Chim. Acta 2001, 434, 157-167.
62. Takács-Novák, K.; Tam, K. Y J. Pharm. Biomed. Anal. 2000, 21, 1171-1182.
63. Comer, J. E. A. High Throughput Measurement of log D and pKa. In Drug Bioavailability. Estimation of Solubility, Permeability and Bioavailability; Artursson, P, Lennernas, H., van de Waterbeemd, H., Eds.; Wiley-VCH: Weinheim, Germany, 2003, pp 21-45.
64. Gluck, S. J.; Steele, K. P; Benko, M. H. J. Chromatogr. A 1996, 745, 117-125.
65. Caliaro, G. A.; Herbots, A. A. J. Pharm. Biomed. Anal. 2001, 26, 427-434.
66. Wan, H.; Holmen, A.; Nagard, M.; Lindberg, W J. Chromatogr. A 2002, 979, 369-377.
67. Poole, S. K.; Patel, S.; Dehring, K.; Workman, H.; Poole, C. F J. Chromatogr. A 2004, 1037, 445-454.
68. Sjöberg, H.; Karami, K.; Beronius, P; Sundelöf, L. Int. J. Pharm. 1996, 141, 63-70.
69. Peck, C. C.; Benet, L. Z. J. Pharm. Sei. 1978, 67, 12-16.
70. Hansen, J. B.; Hafliger, O. J. Pharm. Sei. 1983, 72, 429-431.
71. Vazquez, J. L.; Berlanga, M.; Merino, S.; Domenech, O.; Vinas, M.; Montero, M. T; Hernandez-Borrell, J. Photochem. Photobiol 2001, 73, 14-19.
72. Saurina, J.; Hernandez-Cassou, S.; Tauler, R.; Izquierdo-Ridorsa, A. Anal. Chim. Acta 2000, 408, 135-143.
73. Perrin, D. D.; Dempsey, B.; Serjeant, E. PKa Prediction for Organic Acids and Bases; Chapman and Hall: London, UK, 1981.
74. Hammett, L. P. Chem. Rev. 1935, 17, 125-136.
75. Taft, R. W, Jr. Separation of Polar, Steric and Resonance Effects in Reactivity. In Steric Effects in Organic Chemistry; Newman, M. S., Ed.; John Wiley: New York, 1956, pp 556-675.
76. Clark, J.; Perrin, D. D. Q. Rev. 1964, 18, 295-320.
77. Biggs, A. I.; Robinson, R. A.; J. Chem. Soc. London 1961, 338-393.
78. Sirius Analytical Instruments Sirius Technical Application Notes 1; Sirius Analytical Instruments: Forest Row, UK, 1994.
79. Sirius Analytical Instruments Sirius Technical Application Notes 2; Sirius Analytical Instruments: Forest Row, UK, 1995.
80. Sirius Analytical Instruments. Unpublished data, 2005.
81. Loeuillet-Ritzler, F; Faller, B. High-Throughput pKa with the Sirius Profiler SGA Using a Co-Solvent Approach. In Pharmacokinetic Profiling in Drug Research; Testa, B., Krämer, S. D., Wunderli-Allenspach, H., Folkers, G., Eds.; VHCA: Zürich, Switzerland, 2006, Poster A19 (CD).
82. Kenseth, J.; Bastin, A.; Gossett, K.; Prog, H. High Throughput Determination of pKa Values of Soluble and Insoluble Compounds Using Multiplexed Capillary Electrophoresis with Absorbance Detection. In Pharmacokinetic Profiling in Drug Research; Testa, B., Kramer, S. D., Wunderli-Allenspach, H., Folkers, G., Eds.; VHCA: Züurich, Switzerland, 2006, Poster Session A, 3 (on CD).