Updates on contemporary protein binding techniques

Drug Metabolism and Pharmacokinetics

Volumn 24, Issue 4, 2009, Pages 358-364

  Chuang, Victor Tuan Giam ^a   Maruyama, Toru ^b   Otagiri, Masaki ^b,c  

^a CURTIN UNIVERSITY   (Australia)

^b KUMAMOTO UNIVERSITY   (Japan)

^c SOJO UNIVERSITY   (Japan)

Author keywords

Albumin; Binding affinity; Binding site; Protein bindings; Techniques for binding studies

Indexed keywords

BLONANSERIN; DASATINIB; NARATRIPTAN; SORAFENIB;

AFFINITY CHROMATOGRAPHY; BINDING AFFINITY; BINDING SITE; CONFERENCE PAPER; HIGH THROUGHPUT SCREENING; HUMAN; PROTEIN BINDING; SEPARATION TECHNIQUE; SITE DIRECTED MUTAGENESIS; ULTRAFILTRATION;

EID: 70350459449     PISSN: 13474367     EISSN: 18800920     Source Type: Journal    
DOI: 10.2133/dmpk.24.358     Document Type: Conference Paper

References (55)

1. Otagiri, M.: A molecular functional study on the interactions of drugs with plasma proteins. Drug Metabol. Dispos., 20: 309-323 (2005).
2. Otagiri, M., Masuda, K., Imai, T., Imamura, Y. and Yamasaki, M.: Binding of pirprofen to human serum albumin studied by dialysis and spectroscopy techniques. Biochem Pharmacol., 38: 1-7 (1989).
3. Miyoshi, T., Yamamichi, R., Maruyama, T., Takadate, A. and Otagiri, M.: Further characterization of reversal of signs of induced cotton effects of dicumarol derivatives-alpha 1-acid glycoprotein systems by protriptyline., 43: 2161-2167 (1992).
4. Wilting, J., van der Giesen, W. F., Janssen, L. H., Weideman, M. M., Otagiri, M. and Perrin, J. H.: The effect of albumin conformation on the binding of warfarin to human serum albumin. The dependence of the binding of warfarin to human serum albumin on the hydrogen, calcium, and chloride ion concentrations as studied by circular dichroism, fluorescence, and equilibrium dialysis. J. Biol. Chem., 255: 3032-3037 (1980).
5. Kragh-Hansen, U., Dorge, E. and Pedersen, A. O.: Rate-of-dialysis technique: theoretical and practical aspects. Anal Biochem., 340: 145-153 (2005).
6. Kariv, I., Cao, H. and Oldenburg, K. R.: Development of a high throughput equilibrium dialysis method. J. Pharm. Sci., 90: 580-587 (2001).
7. Banker, M. J., Clark, T. H. and Williams. J. A.: Development and validation of a 96-well equilibrium dialysis apparatus for measuring plasma protein binding. J. Pharm. Sci., 92: 967-974 (2003).
8. Waters, N. J., Jones, R., Williams, G. and Sohal, B.: Validation of a rapid equilibrium dialysis approach for the measurement of plasma protein binding. J. Pharm. Sci., 97: 4586-4595 (2008).
9. Bloxam, D. L., Hutson, P. H. and Curzon, G.: A simple apparatus for ultrafiltration of small volumes: application to the measurement of free and albumin-bound tryptophan in plasma. Anal Biochem., 83: 130-142 (1977).
10. Melten, J. W., Wittebrood, A. J., Willems, H. J., Faber, G. H., Wemer, J. and Faber, D. B.: Comparison of equilibrium dialysis, ultrafiltration, and gel permeation chromatography for the determination of free fractions of phenobarbital and phenytoin. J. Pharm. Sci., 74: 692-694 (1985).
11. David, B. M., Tjokrosetio, R. and Ilett, K. F.: Plasma protein binding of disopyramide by equilibrium dialysis and ultrafiltration. Ther. Drug Monit., 5: 81-86 (1983).
12. Barre, J., Chamouard, J. M., Houin, G. and Tillement, J. P.: Equilibrium dialysis, ultrafiltration, and ultracentrifugation compared for determining the plasma-protein-binding characteristics of valproic acid. Clin. Chem., 31: 60-64 (1985).
13. Zlotos, G., Oehlmann, M., Nickel, P. and Holzgrabe. U.: Determination of protein binding of gyrase inhibitors by means of continuous ultrafiltration. J. Pharm. Biomed. Anal., 18: 847-858 (1998).
14. Heinze, A. and Holzgrabe, U.: Determination of the extent of protein binding of antibiotics by means of an automated continuous ultrafiltration method. Int. J. Pharm., 311: 108-112 (2006).
15. Xie, Y., Zhang, D. and Ben-Amotz, D.: Protein-ligand binding detected using ultrafiltration Raman difference spectroscopy. Anal Biochem., 373: 154-160 (2008).
16. Nakai, D., Kumamoto, K., Sakikawa, C., Kosaka, T. and Tokui, T.: Evaluation of the protein binding ratio of drugs by a microscale ultracentrifugation method. J. Pharm. Sci., 93: 847-854 (2004).
17. Shibukawa, A., Kuroda, Y. and Nakagawa, T.: High-performance frontal analysis for drug-protein binding study. J. Pharm. Biomed. Anal., 18: 1047-1055 (1999).
18. Hage, D. S. and Austin, J.: High-performance affinity chromatography and immobilized serum albumin as probes for drug-and hormone-protein binding. J. Chromatogr. B. Biomed. Sci. Appl., 739: 39-54 (2000).
19. Kim, H. S. and Wainer, I. W.: Rapid analysis of the interactions between drugs and human serum albumin (HSA) using high-performance affinity chromatography (HPAC). J. Chromatogr. B. Biomed. Sci. Appl., 870: 22-26 (2008).
20. Theodoridis, G.: Application of solid-phase microextraction in the investigation of protein binding of pharmaceuticals. J. Chromatogr. B. Biomed. Sci. Appl., 830: 238-244 (2006).
21. Musteata, F. M. and Pawliszyn, J.: Study of ligand-receptor binding using SPME: investigation of receptor, free, and total ligand concentrations. J. Proteom. Res., 4: 789-800 (2005).
22. Vuckovic, D. and Pawliszyn, J.: Automated study of ligand-receptor binding using solid-phase microextraction. J. Pharm. Biomed. Anal., (2009) in press.
23. Otagiri, M. and Perrin, J. H.: Circular dichroic investigations of the binding of salicylate and related compounds to human serum albumin. Biochem. Pharmacol., 26: 283-288 (1977).
24. Yamasaki, K., Rahman, M. H., Tsutsumi, Y., Maruyama, T., Ahmed, S., Kragh-Hansen, U. and Otagiri, M.: Circular dichroism simulation shows a site-II-to-site-I displacement of human serum albumin-bound diclofenac by ibuprofen. AAPS PharmSciTech., 1: E12 (2000).
25. Otagiri, M., Fleitman, J. S. and Perrin, J. H.: Investigations into the binding of phenprocoumon to albumin using fluorescence spectroscopy. J. Pharm. Pharmacol., 32: 478-482 (1980).
26. Yamasaki, K., Miyoshi, T., Maruyama, T., Takadate, A. and Otagiri, M.: Characterization of region Ic in site I on human serum albumin. Microenvironmental analysis using fluorescence spectroscopy. Biol. Pharm. Bull., 17: 1656-1662 (1994).
27. Yamasaki, K., Maruyama, T., Yoshimoto, K., Tsutsumi, Y., Narazaki, R., Fukuhara, A., Kragh-Hansen, U. and Otagiri, M.: Interactive binding to the two principal ligand binding sites of human serum albumin: effect of the neutral-to-base transition. Biochim. Biophy. Acta., 1432: 313-323 (1999).
28. Moore, J. M.: NMR techniques for characterization of ligand binding: utility for lead generation and optimization in drug discovery. Biopolymers., 51: 221-243 (1999).
29. Clarkson, J. and Campbell, I. D.: Studies of protein-ligand interactions by NMR. Biochemical Society Transactions., 31: 1006-1009 (2003).
30. Fielding, L., Rutherford, S. and Fletcher. D.: Determination of protein-ligand binding affinity by NMR: observations from serum albumin model systems. Magn. Reson. Chem., 43: 463-470 (2005).
31. Frostell-Karlsson, A., Remaeus, A., Roos, H., Andersson, K., Borg, P., Hamalainen, M. and Kalsson, R.: Biosensor analysis of the interaction between immobilized human serum albumin and drug compounds for prediction of human serum albumin binding levels. J. Med. Chem., 43: 1986-1992 (2000).
32. Rich, R. L., Day, Y. S., Morton, T. A. and Myszka. D. G.: High-resolution and high-throughput protocols for measuring drug/human serum albumin interactions using BIACORE. Anal. Biochem., 296: 197-207 (2001).
33. Ahmad, A., Ramakrishnan, A., McLean, M. A. and Breau, A. P.: Use of surface plasmon resonance biosensor technology as a possible alternative to detect differences in binding of enantiomeric drug compounds to immobilized albumins. Biosen. Bioelectr., 18: 399-404 (2003).
34. Kosa, T., Maruyama, T., Sakai, N., Yonemura, N., Yahara, S. and Otagiri. M.: Species differences of serum albumins: III. Analysis of structural characteristics and ligand binding properties during N-B transitions. Pharm. Res., 15: 592-598 (1998).
35. Celej, M. S,, Dassie, S. A., Gonzalez, M., Bianconi, M. L. and Fidelio, G. D.: Differential scanning calorimetry as a tool to estimate binding parameters in multiligand binding proteins. Anal. Biochem., 350: 277-284 (2006).
36. Jelesarov, I. and Bosshard, H. R.: Isothermal titration calorimetry and differential scanning calorimetry as complementary tools to investigate the energetics of biomolecular recognition. J. Mol. Recognit., 12: 3-18 (1999).
37. Celej, M. S., Dassie, S. A., Freire, E., Bianconi, M. L. and Fidelio, G. D.: Ligand-induced thermostability in proteins: thermodynamic analysis of ANS-albumin interaction. Biochim. Biophys Acta., 1750: 122-133 (2005).
38. Muramoto, K. and Ramachandran, J.: Identification of the corticotropin binding domain of bovine serum albumin by photoaffinity labeling. Biochemistry., 20: 3380-3385 (1981).
39. Eckenhoff, R. G. and Shuman. H.: Halothane binding to soluble proteins determined by photoaffinity labeling. Anesthesiology, 79: 96-106 (1993).
40. Chuang, V. T., Kuniyasu, A., Nakayama, H., Matsushita, Y., Hirono, S. and Otagiri. M.: Helix 6 of subdomain III A of human serum albumin is the region primarily photolabeled by ketoprofen, an arylpropionic acid NSAID containing a benzophenone moiety. Biochim. Biophys Acta., 1434: 18-30 (1999).
41. Kaneko, K., Fukuda, H., Chuang, V. T., Yamasaki, K., Kawahara, K., Nakayama, H., Suenaga, A., Maruyama, T. and Otagiri, M.: Subdomain IIIA of dog albumin contains a binding site similar to site II of human albumin. Drug Metabol. Dispos., 36: 81-86 (2008).
42. Chuang, V. T. and Otagiri, M.: How do fatty acids cause allosteric binding of drugs to human serum albumin? Pharm Res., 19: 1458-1464 (2002).
43. Watanabe, H., Tanase, S., Nakajou, K., Maruyama, T., Kragh-Hansen, U. and Otagiri. M.: Role of arg-410 and tyr-411 in human serum albumin for ligand binding and esterase-like activity. Biochem. J., 349: 813-819 (2000).
44. Watanabe, H., Kragh-Hansen, U., Tanase, S., Nakajou, K., Mitarai, M., Iwao, Y., Maruyama, T. and Otagiri, M.: Conformational stability and warfarin-binding properties of human serum albumin studied by recombinant mutants. Biochem. J., 357: 269-274 (2001).
45. Kragh-Hansen, U., Watanabe, H., Nakajou, K., Iwao, Y. and Otagiri. M.: Chain length-dependent binding of fatty acid anions to human serum albumin studied by site-directed mutagenesis. J. Mol. Biol., 363: 702-712 (2006).
46. Ho, J. X., Holowachuk, E. W., Norton, E. J., Twigg, P. D. and Carter, D. C.: X-ray and primary structure of horse serum albumin (Equus caballus) at 0.27-nm resolution. E J Biochem/FEBS., 215: 205-212 (1993).
47. Curry, S., Mandelkow, H., Brick, P. and Franks, N.: Crystal structure of human serum albumin complexed with fatty acid reveals an asymmetric distribution of binding sites. Nature Stru. Biology., 5: 827-835 (1998).
48. Petitpas, I., Bhattacharya, A. A., Twine, S., East, M. and Curry, S.: Crystal structure analysis of warfarin binding to human serum albumin: anatomy of drug site I. J. Biol. Chem., 276: 22804-22809 (2001).
49. Bhattacharya, A. A., Grune, T. and Curry, S.: Crystallographic analysis reveals common modes of binding of medium and longchain fatty acids to human serum albumin. J. Mol. Biol., 303: 721-732 (2000).
50. Bhattacharya, A. A., Curry, S. and Franks, N. P.: Binding of the general anesthetics propofol and halothane to human serum albumin. High resolution crystal structures. J. Biol. Chem., 275: 38731-38738 (2000).
51. Eckenhoff, R. G., Petersen, C. E., Ha, C. E. and Bhagavan, N. V.: Inhaled anesthetic binding sites in human serum albumin. J. Biol. Chem., 275: 30439-30444 (2000).
52. Petersen, C. E., Ha, C. E., Curry, S. and Bhagavan, N. V.: Probing the structure of the warfarin-binding site on human serum albumin using site-directed mutagenesis. Proteins., 47: 116-125 (2002).
53. Simard, J. R., Zunszain, P. A., Ha, C. E., Yang, J. S., Bhagavan, N. V., Petitpas, I., Curry, S. and Hamilton, J. A.: Locating high-affinity fatty acid-binding sites on albumin by x-ray crystallography and NMR spectroscopy. PNAS., 102: 17958-17963 (2005).
54. Schuhmacher, J., Buhner, K. and Witt-Laido, A.: Determination of the free fraction and relative free fraction of drugs strongly bound to plasma proteins. J. Pharm. Sci., 89: 1008-1021 (2000).
55. Schuhmacher, J., Kohlsdorfer, C., Buhner, K., Brandenburger, T. and Kruk, R.: High-throughput determination of the free fraction of drugs strongly bound to plasma proteins. J. Pharm. Sci., 93: 816-830 (2004).