A combined spectroscopic and crystallographic approach to probing drug-human serum albumin interactions

Bioorganic and Medicinal Chemistry

Volumn 18, Issue 21, 2010, Pages 7486-7496

  Buttar, David ^a   Colclough, Nicola ^a   Gerhardt, Stefan ^a   MacFaul, Philip A ^a   Phillips, Scott D ^b   Plowright, Alleyn ^c   Whittamore, Paul ^a   Tam, Kin ^a   Maskos, Klaus ^d   Steinbacher, Stefan ^d   Steuber, Holger ^d  

^a ASTRAZENECA   (United Kingdom)

^b UNIVERSITY OF ST ANDREWS   (United Kingdom)

^c ASTRAZENECA R AND D   (Sweden)

^d PROTEROS BIOSTRUCTURES GMBH   (Germany)

Author keywords

Albumin; Binding; Crystallography; Drug; Fluorescence; Subdomain IB

Indexed keywords

ACENOCOUMAROL; CHLOROTHIAZIDE; CHLORPROPAMIDE; CLONAZEPAM; CLOXACILLIN; DIAZEPAM; DICOUMAROL; DIFLUNISAL; FATTY ACID; FENBUFEN; FLUFENAMIC ACID; FLURAZEPAM; FUROSEMIDE; GLIBENCLAMIDE; HUMAN SERUM ALBUMIN; IBUPROFEN; INDOMETACIN; ISOXICAM; KETOPROFEN; NAPROXEN; PHENYLBUTAZONE; PHENYTOIN; PINDOLOL; PIROXICAM; SALICYLIC ACID; SULFINPYRAZONE; SULFONAMIDE; TAMOXIFEN; TENOXICAM; UNINDEXED DRUG;

ARTICLE; CRYSTAL STRUCTURE; CRYSTALLOGRAPHY; DRUG PROTEIN BINDING; DRUG STRUCTURE; FLUORESCENCE SPECTROSCOPY; LIPOPHILICITY; PROTEIN DOMAIN;

BINDING SITES; CRYSTALLOGRAPHY, X-RAY; DRUG INTERACTIONS; HUMANS; PHARMACEUTICAL PREPARATIONS; PROTEIN BINDING; PROTEIN STRUCTURE, TERTIARY; SERUM ALBUMIN; SPECTROMETRY, FLUORESCENCE;

EID: 77958021757     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2010.08.052     Document Type: Article

References (64)

1. W.A. Creasey Drug Deposition in Humans: The Basis of Clinical Pharmacology 1979 Oxford University Press Oxford, UK
2. G.L. Trainor Expert Opin. Drug Discov. 2 2007 51
3. T. Peters All About Albumin 1996 Academic Press San Diego
4. K.J. Fehske Biochem. Pharmacol. 30 1981 687
5. K.J. Fehske, U. Schläfer, U. Wollert, and W.E. Müller Mol. Pharmacol. 21 1982 387
6. G. Sudlow, D.J. Birkett, and D.N. Wade Mol. Pharmacol. 11 1975 824
7. X.M. He, and D.C. Carter Nature 358 1992 209
8. J. Ghuman, P.A. Zunszain, I. Petitpas, A.A. Bhattacharya, M. Otagiri, and S. Curry J. Mol. Biol. 353 2005 38
9. S. Wanwimolruk, D.J. Birkett, and P.M. Brooks Mol. Pharmacol. 24 1983 458
10. H. Watanabe, S. Tanase, K. Nakajou, T. Maruyama, U. Kragh-Hansem, and M. Otagiri J. Biochem. 349 2000 813
11. J.R. Simard, P.A. Zunszain, J.A. Hamilton, and S. Curry J. Mol. Biol. 361 2006 336
12. G.M. Pacifici, and A. Viani Clin. Pharmacokinet. 23 1992 449
13. H. Wan, and F. Bergström J. Liq. Chromatorgr. Related Technol. 30 2007 681
14. K. Valko, S. Nunhuck, M.H. Bevan, M.H. Abraham, and D. Reynolds J. Pharm. Sci. 92 2003 2236
15. R.E. Fessey, R.P. Austin, P. Barton, A.M. Davis, and M.C. Wenlock P. Testa, S.D. Krämer, H. Wunderli-Allenspach, G. Folkers, Pharmokinetic Profiling in Drug Research 2006 Wiley-VCH Zürich 119 141
16. B.G. Jenkins, and R.B. Lauffer Mol. Pharmacol. 37 1989 111
17. M. Delfini, C. Bianchetti, M.E. Di Cocco, N. Pescosolido, F. Porecelli, R. Rosa, and G. Rugo Bioorg. Chem. 31 2003 378
18. C. Dufour, and O. Dangles Biochim. Biophys. Acta 1721 2005 164
19. I. Vayá, C.J. Bueno, M.C. Jiménez, and M.A. Miranda ChemMedChem 1 2006 1015
20. C.F. Chignell Ann. N.Y. Acad. Sci. 226 1973 44
21. R.L. Rich, Y.S. Day, T.A. Morton, and D.G. Myszka Anal. Biochem. 296 2001 197
22. Technical note TRK1093, Amersham Biosciences (GE Healthcare).
23. D.E. Epps, T.J. Raub, and F.J. Kézdy Anal. Biochem. 227 1995 342
24. N. Muller, F. Lapicque, E. Drelon, and P. Netter J. Pharm. Pharmacol. 46 1994 300
25. I. Sjöholm, B. Ekman, A. Kober, I. Ljungstedt-Pahlman, B. Seiving, and T. Sjodin Mol. Pharmacol. 16 1979 767
26. K. Yamasaki, T. Maruyama, U. Kragh-Hansen, and M. Otagiri Biochim. Biophys. Acta 1295 1996 147
27. K.F. Brown, and M.J. Crooks Biochem. Pharmacol. 25 1976 1175
28. W.E. Müller, and U. Wollert Naunyn Schmiedebergs Arch. Pharmacol. 280 1973 229
29. H. Mao, P.J. Hajduk, R. Craig, R. Bell, T. Borre, and S.W. Fesik J. Am. Chem. Soc. 123 2001 10429
30. A. Davilas, M. Koupparis, P. Macheras, and G. Valsami J. Pharm. Pharmacol. 58 2006 1467
31. B. Honoré, and R. Brodersen Mol. Pharmacol. 25 1984 137
32. G. Sudlow, D.J. Birkett, and D.N. Wade Mol. Pharmacol. 12 1976 1052
33. S. Kasai, T. Horie, T. Mizuma, and S. Awazu J. Pharm. Sci. 76 1987 387
34. E.M.K. Lui, P.S. Farmer, and C.R. Dean J. Pharm. Sci. 66 1977 950
35. F. Bree, P. Nguyen, E. Albengres, S. Uriem, P. Riant, P.G. Welling, and J.-P. Tillement Biochem. Pharmacol. 38 1989 753
36. M. El-Kemary, M. Gil, and A. Douhal J. Med. Chem. 50 2007 2896
37. M. Lemaire, and J.P. Tillement Biochem. Pharmacol. 31 1982 359
38. I.G. Shah, and D.L. Parsons J. Pharm. Pharmacol. 43 1991 790
39. Birch, A. M Johnstone, C Plowright, A. T Simpson, I Whittamore, P. R. O. PCT Int. Appl., WO 2006082400.
40. Bengtsson, M Larsson, J Nikitidis, G Storm, P Bailey, J. P Griffen, E. J Arnould, J.-C Bird, T. G. C. PCT Int. Appl. WO2006051270.
41. All crystallographic figures were generated using PyMOL: DeLano, W.L. The PyMOL Molecular Graphics System (2002), DeLano Scientific, San Carlos, CA, USA, http://www.pymol.org.
42. PDB ID code 3LU6.
43. PDB ID code 3LU7.
44. PDB ID code 3LU8.
45. P.A. Zunszain, J. Ghuman, A.F. McDonagh, and S. Curry J. Mol. Biol. 381 2008 394
46. Carter, D. C Ho, J. X Wang, Z. International Patent Application WO2005/041895.
47. Carter, D. C Ho, J. X Wang, Z. International Patent Application WO2007/130950.
48. M. Bogdan, A. Pirnau, C. Floare, and C. Bugeac J. Pharm. Biomed. Anal. 47 2008 981
49. J.-S. Mandeville, E. Froehlich, and H.A. Tajmir-Riahi J. Pharm. Biomed. Anal. 49 2009 468
50. S.K. Singh, and N. Kishore J. Pharm. Sci. 97 2008 2362
51. K.S. Joseph, A.C. Moser, S.B.G. Basiaga, J.E. Schiel, and D.S. Hage J. Chromatogr., A 1216 2009 3492
52. Q. Zhang, Y. Huang, R. Zhao, and Y. Chen Biosens. Bioelectron. 24 2008 48
53. C.P. Montgomery, E.J. New, D. Parker, and R.D. Peacock Chem. Commun. 2008 4221
54. N.A. Kratochwil, W. Huber, F. Müller, M. Kansy, and P.R. Gerber Biochem. Pharmacol. 64 2002 1355
55. N.A. Kratochwil, W. Huber, F. Müller, M. Kansy, and P.R. Gerber Curr. Opin. Drug Discov. Dev. 7 2004 507
56. J.R. Votano, M. Parham, M. Hall, L.B. Kier, S. Oloff, and A. Tropsha J. Med. Chem. 49 2006 7169
57. R. Artali, G. Bombieri, L. Calabi, and A. Del Pra Il Farmaco 60 2005 485
58. K. Paal, and A. Shkarupin Bioorg. Med. Chem. 15 2007 7568
59. R. Kiefersauer, M. Than, H. Dobbek, L. Gremer, M. Melero, S. Strobl, J.M. Dias, T. Soulimane, and R. Huber Appl. Cryst. 33 2000 1223
60. M. Kroemer, M.K. Dreyer, and K.U. Wendt Acta Crystallogr., Sect. D 60 2004 1679
61. P. Emsley, and K. Kowtan Acta Crystallogr., Sect. D 60 2004 2126
62. G.N. Murshudov, A.A. Vagin, and E.J. Dodson Acta Crystallogr., Sect. D 53 1997 240
63. M. Winn, M. Isupov, and G.N. Murshudov Acta Crystallogr., Sect. D 57 2001 122
64. R. Laskowski, M. MacArthur, D. Moss, and J. Thornton J. Appl. Crystallogr. 26 1993 283