Reversible binding of celecoxib and valdecoxib with human serum albumin using fluorescence spectroscopic technique

Pharmacological Research

Volumn 54, Issue 2, 2006, Pages 77-84

  Seedher, Neelam ^a   Bhatia, Sonu ^a  

^a PANJAB UNIVERSITY   (India)

Author keywords

Celecoxib; Fluorescence spectroscopy; Human serum albumin; Interaction; Valdecoxib

Indexed keywords

8 ANILINO 1 NAPHTHALENESULFONIC ACID; CELECOXIB; DANSYLSARCOSINE PIPERIDINIUM SALT; HUMAN SERUM ALBUMIN; NONSTEROID ANTIINFLAMMATORY AGENT; OXYGEN; PHENOL; PIPERIDINE DERIVATIVE; TRYPTOPHAN; TYROSINE; UNCLASSIFIED DRUG; VALDECOXIB;

ANALYTIC METHOD; ARTICLE; BINDING AFFINITY; BINDING SITE; DRUG PROTEIN BINDING; FLUORESCENCE SPECTROSCOPY; HYDROGEN BOND; HYDROPHOBICITY; LIPOPHILICITY; MOLECULAR PROBE; PHOTOCHEMICAL QUENCHING; PRIORITY JOURNAL; THERMODYNAMICS;

ANILINO NAPHTHALENESULFONATES; ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; FLUORESCENT DYES; HYDROGEN-ION CONCENTRATION; ISOXAZOLES; MOLECULAR STRUCTURE; PROTEIN BINDING; PYRAZOLES; SERUM ALBUMIN; SPECTROMETRY, FLUORESCENCE; STRUCTURE-ACTIVITY RELATIONSHIP; SULFONAMIDES; TEMPERATURE; THERMODYNAMICS;

EID: 33745815121     PISSN: 10436618     EISSN: 10961186     Source Type: Journal    
DOI: 10.1016/j.phrs.2006.02.008     Document Type: Article

References (46)

1. Kragh-Hansen U., Chuang V.T.G., and Otagiri M. Practical aspects of the ligand-binding and enzymatic properties of human serum albumin. Biol Pharm Bull 25 (2002) 695-704
2. Lin J.H., Cocchetto D.M., and Duggan D.E. Protein binding as a primary determinant of the clinical pharmacokinetic properties of non-steroidal antiinflammatory drugs. Clin Pharmacokinet 12 (1987) 402-432
3. Fichtl B., Nieciecki A., and Walter K. Tissue binding versus plasma binding of drugs: general principles and pharmacokinetic consequences. Adv Drug Res 20 (1991) 117-166
4. Levy R.H., and Moreland T.A. Rationale for monitoring free drug levels. Clin Pharmacokinet 9 Suppl. 1 (1984) 1-9
5. Rowland M. Plasma protein binding and therapeutic drug monitoring. Ther Drug Monit 2 (1980) 29-37
6. Rahman M.H., Maruyama T., Okada T., Yamasaki K., and Otagiri M. Study of interaction of carprofen and its enantiomers with human serum albumin-I. Mechanism of binding studied by dialysis and spectroscopic methods. Biochem Pharmacol 46 (1993) 1721-1731
7. Russeva V., and Mihailova D. Binding of phenylbutazone to human serum albumin. Arzneim-Forsch/Drug Res 49 (1999) 255-258
8. Afifi N.N. Using difference spectrophotometry to study the influence of different ions and buffer systems on drug protein binding. Drug Develop Ind Pharm 5 (1999) 735-743
9. Trivedi V.D., Vorum H., Honore B., and Qasim M.A. Molecular basis of indomethacin-human serum albumin interaction. J Pharm Pharmacol 51 (1999) 591-600
10. Seedher N., and Bhatia S. Mechanism of interaction of non-steriodal anti-inflammatory drugs meloxicam and nimesulide with serum albumin. J Pharm Biomed Anal 39 (2005) 257-262
11. Oravkova J., Bohs B., and Lindner W. Drug-protein binding studies. New trends in analytical and experimental methodology. J Chromatogr B 677 (1996) 1-28
12. Epps D.E., Raub T.J., Caiolfa V., Chiari A., and Zamai M. Determination of the affinity of drugs towards serum albumin by measurement of the quenching of the intrinsic trytophane fluorescence of the protein. J Pharm Pharmacol 51 (1999) 41-48
13. Job P. Formation and stability of inorganic complexes in solution. Ann Chim 9 (1928) 113-203
14. Ward L.D. Measurement of ligand binding to proteins by fluorescence spectroscopy. Methods in Enzymol 117 (1985) 400-414
15. Weber G., and Young L.B. Fragmentation of bovine serum albumin by pepsin. I. The origin of the acid expansion of the albumin molecule. J Biol Chem 239 (1964) 1415-1423
16. 1-acid glycoprotein and human serum albumin. Int J Pharm 59 (1990) 137-143
17. Martin B.K. Potential effect of the plasma proteins on drug distribution. Nature 207 (1965) 274-276
18. Neault J.F., Novetta-Delen A., Arakawa H., Malonga H., and Tajmir-Riahi H.A. The effect of Aspirin-HSA complexation on protein secondary structure. Can J Chem 78 (2000) 291-296
19. Laznicek M., and Laznickova A. The effect of lipophilicity on the protein binding and blood cell uptake of some acidic drugs. J Pharm Biomed Anal 13 (1995) 823-828
20. Deschamps-Labat L., Pehourcq F., Jagou M., and Bannwarth B. Relationship between lipophilicity and binding to human serum albumin of arylpropionic acid non-steroidal anti-inflammatory drugs. J Pharm Biomed Anal 16 (1997) 223-229
21. Lien E.J., and Wang P.H. Lipophilicity, molecular weight, and drug action: reexamination of parabolic and bilinear models. J Pharm Sci 69 (1980) 648-650
22. Seedher N., and Kanojia M. Correlation between physico-chemical properties and protein binding of phenothiazine derivatives. Indian J Pharm Sci 62 (2000) 441-446
23. Ross P.D., and Subramanian S. Thermodynamics of protein association reactions. Forces contributing to stability. Biochemistry 20 (1981) 3096-3102
24. Plaizier-Vercammen J.E., and De Neve R.E. Interaction of povidone with aromatic compounds III: thermodynamics of the binding equilibria and interaction forces in buffer solutions at varying pH values and varying dielectric constant. J Pharm Sci 71 (1982) 552-556
25. Seedher N., Singh B., and Singh P. Mode of interaction of metronidazole with bovine serum albumin. Indian J Pharm Sci 61 (1999) 143-148
26. Zhivkova Z.D., and Russeva V.N. Thermodynamic characterization of the binding process of sulindac to human serum albumin. Arznemittel-Forschung 53 (2003) 53-56
27. Jun H.W., and Ruenitz P.C. Interaction of tricyclic antipsychotic and antidepressant drugs with 1-anilino-8-naphthalenesulfonic acid. J Pharm Sci 67 (1978) 861-863
28. Thumser A.E.A., Buckland A.G., and Wilton D.C. Monoacylglycerol binding to human serum albumin: evidence that monooleyglycerol binds at the dansylsarcosine site. J Lipid Res 39 (1998) 1033-1038
29. Sudlow G., Birkett D.J., and Wade D.N. The characterization of two specific drug binding sites on human serum albumin. Mol Pharmacol 11 (1975) 824-832
30. Seedher N. In vitro study of the mechanism of interaction of trifluoperazine dihydrochloride with bovine serum albumin. Indian J Pharm Sci 62 (1999) 16-20
31. Sudlow G., Birkett D.J., and Wade D.N. Further characterization of specific drug binding sites on human serum albumin. Mol Pharmacol 12 (1976) 1052-1061
32. Kasai S., Horie T., Mizuma T., and Awazu S. Fluorescence energy transfer study of the relationship between the lone tryptophan residue and drug binding sites in human serum albumin. J Pharm Sci 76 (1987) 387-392
33. Sugio S., Kashima A., Mochizuki S., Noda M., and Kobayashi K. Crystal structure of human serum albumin at 2.5 Å resolution. Protein Eng 12 (1999) 439-446
34. He X.M., and Carter D.C. Atomic structure and chemistry of human serum albumin. Nature 358 (1992) 209-215
35. 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 aryl propionic acid NSAID containing a benzophenone moiety. Biochim Biophys Acta 1434 (1999) 18-30
36. Wanwimolruk S., Birkett D.J., and Brooks P.M. Structural requirements for drug binding to site II on human serum albumin. Mol Pharmacol 24 (1983) 458-463
37. 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 (1989) 1-7
38. 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 (2000) 813-819
39. Fasano M., Curry S., Terreno E., Galliano M., Fanali G., Narciso P., et al. The extraordinary ligand binding properties of human serum albumin. IUBMB Life 57 (2005) 787-796
40. Eftink M.R., and Ghiron C.A. Fluorescence quenching studies with proteins. Anal Biochem 114 (1981) 199-227
41. Lehrer S.S. Solute perturbation of fluorescence. The quenching of the tryptophyl fluorescence of model compounds and of lysozyme by iodide ion. Biochemistry 10 (1971) 3254-3263
42. Friedman M.L., Schlueter K.T., Kirley T.L., and Halstall H.B. Fluorescence quenching of human orosomucoid. Biochem J 232 (1985) 863-867
43. Cui F.L., Fan J., Li W., Fan Y.C., and Hu Z.D. Fluorescence Spectroscopic studies on 5-aminosalicylic acid and zinc 5-aminosalicylate interaction with human serum albumin. J Pharm Biomed Anal 34 (2004) 189-197
44. Campbell I.D., and Dwek R.A. Biological Spectroscopy (1984), The Benjamin/Cummings Publishing Company Inc, London p. 108-9
45. Maruthamuthu M., and Kishore S. Heterotropic binding of alclofenac and dansylsarcosine to bovine serum albumin. Proc Indian Acad Sci (Chem Sci) 103 (1991) 173-183
46. Wilting J., Van der Giesen W.F., and Janssen L.H.M. The effect of chloride on the binding of warfarin to albumin as a function of pH. Biochem Pharmacol 30 (1981) 1025-1031