Stereoselective binding of human serum albumin

Chirality

Volumn 18, Issue 3, 2006, Pages 159-166

  Chuangl, Victor Tuan Giam ^a,b   Otagiri, Masaki ^a  

^a KUMAMOTO UNIVERSITY   (Japan)

^b UNIVERSITI KEBANGSAAN MALAYSIA   (Malaysia)

Author keywords

Allosteric interaction; Binding site; Human serum albumin; Stereoselective binding; Subdomain

Indexed keywords

1 CHLORO 1,2,2 TRIFLUOROISOBUTANE; ANESTHETIC AGENT; BUTANE; CARPROFEN; DIAZEPAM; DICARBOXYLIC ACID; ETODOLAC; FENOPROFEN; FLURBIPROFEN; HALOTHANE; HEPARIN DERIVATIVE; HETEROCYCLIC COMPOUND; HUMAN SERUM ALBUMIN; IBUPROFEN; INDOPROFEN; ISOFLURANE; KETOPROFEN; LONG CHAIN FATTY ACID; LORAZEPAM; NONSTEROID ANTIINFLAMMATORY AGENT; OCTANOIC ACID; PHENYLBUTAZONE; PIRPROFEN; PROPOFOL; UNCLASSIFIED DRUG; UREMIC TOXIN; WARFARIN;

ALLOSTERISM; CONFERENCE PAPER; CONFORMATIONAL TRANSITION; CRYSTAL STRUCTURE; DRUG BINDING SITE; DRUG DISPOSITION; DRUG PROTEIN BINDING; ENANTIOMER; FIRST PASS EFFECT; HUMAN; HYDROPHILICITY; KIDNEY CLEARANCE; METABOLIC CLEARANCE RATE; PRIORITY JOURNAL; PROTEIN BINDING; PROTEIN CONFORMATION; PROTEIN DOMAIN; STEREOCHEMISTRY; X RAY DIFFRACTION;

BINDING SITES; HUMANS; MODELS, MOLECULAR; PROTEIN BINDING; PROTEIN CONFORMATION; SERUM ALBUMIN; STEREOISOMERISM;

EID: 33644681693     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.20237     Document Type: Conference Paper

References (42)

1. Crom WR. Effect of chirality on pharmacokinetics and pharmacodynamics. Am J Hosp Pharm 1992;49(9 Suppl 1):S9-S14.
2. Cordato DJ, Mather LE, Herkes GK. Stereochemistry in clinical medicine: a neurological perspective. J Clin Neurosci 2003;10:649-654.
3. Kim KA, Shon JH, Park JY, Yoon YR, Kim MJ, Yun DH, Kim MK, Cha IJ, Hyun MH, Shin JG. Enantioselective disposition of lansoprazole in extensive and poor metabolizers of CYP2C19. Clin Pharmacol Ther 2002;72:90-99.
4. Fitos I, Visy J, Simonyi M. Species-dependency in chiral-drug recognition of serum albumin studied by chromatographic methods. J Biochem Biophys Methods 2002;54:71-84.
5. Walle UK, Walle T, Bai SA, Olanoff LS. Stereoselective binding of propranolol to human plasma, alpha 1-acid glycoprotein, and albumin. Clin Pharmacol Ther 1983;34(6):718-723.
6. Seideman P, Lohrer F, Graham GG, Duncan MW, Williams KM, Day RO. The stereoselective disposition of the enantiomers of ibuprofen in blood, blister and synovial fluid. Br J Clin Pharmacol 1994;38(3):221-227.
7. Lapicque F, Muller N, Payan E, Dubois N, Netter P. Protein binding and stereoselectivity of nonsteroidal anti-inflammatory drugs. Clin Pharmacokinet 1993;25:115-123.
8. Peters Jr T. All about albumin: biochemistry, genetics, and medical applications. Orlando, FL: Academic Press; 1996.
9. Carter DC, Ho JX. Structure of serum albumin. Adv Protein Chem 1994;45:153-203.
10. Curry S, Mandelkow H, Brick P, Franks N. Crystal structure of human serum albumin complexed with fatty acid reveals an asymmetric distribution of binding sites. Nat Struct Biol 1998;5:827-835.
11. Kragh-Hansen U, Chuang VT, Otagiri M. Practical aspects of the ligand-binding and enzymatic properties of human serum albumin. Biol Pharm Bull 2002;25:695-704.
12. Petitpas I, Bhattacharya AA, Twine S, East M, Curry S. Crystal structure analysis of warfarin binding to human serum albumin: anatomy of drug site I. J Biol Chem 2001;276:22804-22809.
13. He J, Shibukawa A, Tokunaga S, Nakagawa T. Protein-binding high-performance frontal analysis of (R)- and (S)-warfarin on HSA with and without phenylbutazone. J Pharm Sci 1997;86:120-125.
14. Vorum H, Honore B. Influence of fatty acids on the binding of warfarin and phenprocoumon to human serum albumin with relation to anti-coagulant therapy. J Pharm Pharmacol 1996;48:870-875.
15. Birkett DJ, Myers SP, Sudlow G. Effects of fatty acids on two specific drug binding sites on human serum albumin. Mol Pharmacol 1997; 13:987-992.
16. Watanabe H, Tanase S, Nakajou K, Maruyama T, Kragh-Hansen U, Otagiri M. Role of arg-410 and tyr-411 in human serum albumin for ligand binding and esterase-like activity. Biochem J 2000;349:813-819.
17. Sueyasu M, Fujito K, Shuto H, Mizokoshi T, Kataoka Y, Oishi R. Protein binding and the metabolism of thiamylal enantiomers in vitro. Anesth Analg 2000;91:736-740.
18. Chuang VTG, Otagiri M. Flunitrazepam, a 7-nitro-1,4-benzodiazepine that is unable to bind to the indole-benzodiazepine site of human serum albumin. Biochim Biophys Acta 2001;1546:337-345.
19. Davies NM. Clinical pharmacokinetics of ibuprofen. The first 30 years. Clin Pharmacokinet 1998;34:101-154.
20. Itoh T, Saura Y, Tsuda Y, Yamada H. Stereoselectivity and enantiomer-enantiomer interactions in the binding of ibuprofen to human serum albumin. Chirality 1997;9:643-649.
21. Rahman MH, Maruyama T, Okada T, Yamasaki K, 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 1993;46:1721-1731.
22. Jamali F, Brocks DR. Clinical pharmacokinetics of ketoprofen and its enantiomers. Clin Pharmacokinet 1990;19:197-217.
23. Barbanoj MJ, Antonijoan RM, Gich I. Clinical pharmacokinetics of dexketoprofen. Clin Pharmacokinet 2001;40:245-262.
24. Lagrange F, Penhourcq F, Matoga M, Bannwarth B. Binding of ketoprofen enantiomers in various human albumin preparations. J Pharm Biomed Anal 2000;23:793-802.
25. Chuang VT, Kuniyasu A, Nakayama H, Matsushita Y, Hirono S, 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 1999;1434:18-30.
26. Curry S, Brick P, Franks NP. Fatty acid binding to human serum albumin: new insights from crystallographic studies. Biochim Biophys Acta 1999;1441:131-140.
27. Thumser AE, Buckland AG, Wilton DC. Monoacylglycerol binding to human serum albumin: evidence that monooleoylglycerol binds at the dansylsarcosine site. J Lipid Res 1998;39:1033-1038.
28. Petersen CE, Ha CE, Harohalli K, Feix JB, Bhagaven NV. A dynamic model for bilirubin binding to human serum albumin. J Biol Chem 2000;275:20985-20995.
29. Zunszain PA, Ghuman J, Komatsu T, Tsuchida E, Curry S. Crystal structural analysis of human serum albumin complexed with hemin and fatty acid. BMC Struct Biol 2003;3:6.
30. Sakai T, Takadate A, Otagiri M. Characterization of binding site of uremic toxins on human serum albumin. Biol Pharm Bull 1995;18:1755-1761.
31. Fitos I, Visy J, Simonyi M, Hermansson J. Stereoselective allosteric binding interaction on human serum albumin between ibuprofen and lorazepam acetate. Chirality 1999;11:115-120.
32. Rahman MH, Maruyama T, Okada T, Imai T, Otagiri M. Study of interaction of carprofen and its enantiomers with human serum albumin-II. Stereoselective site-to-site displacement of carprofen by ibuprofen. Biochem Pharmacol 1993;46:1733-1740.
33. Yamasaki K, Rahman MH, Tsutsumi Y, Maruyama T, Ahmed S, Kragh-Hansen U, Otagiri M. Circular dichroism simulation shows a site-II-to-site-I displacement of human serum albumin-bound diclofenac by ibuprofen. AAPS PharmSciTech 2000;1(2):E12.
34. Tsutsumi Y, Maruyama T, Takadate A, Goto M, Matsunaga H, Otagiri M. Interaction between two dicarboxylate endogenous substances, bilirubin and an uremic toxin, 3-carboxy-4-methyl-5-propyl-2-furanpropanoic acid, on human serum albumin. Pharm Res 1999;16:916-923.
35. Sakai T, Maruyama T, Imamura H, Shimada H, Otagiri M. Mechanism of stereoselective serum binding of ketoprofen after hemodialysis. J Pharmacol Exp Ther 1996;278:786-792.
36. Bhattacharya AA, Grune T, Curry S. Crystallographic analysis reveals common modes of binding of medium and long-chain fatty acids to human serum albumin. J Mol Biol 2000;303:721-732.
37. Fitos I, Visy J, Magyar A, Kajtar J, Simonyi M. Stereoselective effect of warfarin and bilirubin on the binding of 5-(o-chlorophenyl)-1,3-dihydro-3- methyl-7-nitro-2H-1,4-benzodiazepin-2-one enantiomers to human serum albumin. Chirality 1990;2:161-166.
38. Sakai T, Maruyama T, Sako T, Ahmed S, Zuidema X, Fujiyama S, Otagiri M. Stereoselective serum protein binding of ketoprofen in liver diseases. Enantiomer 1999;4:477-482.
39. Bertucci C. Enantioselective inhibition of the binding of rac-profens to human serum albumin induced by lithocholate. Chirality 2001;13:372-378.
40. Bhattacharya AA, Curry S, Franks NP. Binding of the general anesthetics propofol and halothane to human serum albumin. High-resolution crystal structures. J Biol Chem 2000;275:38731-38738.
41. Eckenhoff RG, Petersen CE, Ha CE, Bhagavan NV. Inhaled anesthetic binding sites in human serum albumin. J Biol Chem 2000;275:30439-30444.
42. Chuang VT, Otagiri M. How do fatty acids cause allosteric binding of drugs to human serum albumin? Pharm Res 2002;19:14558-14564.