Hydrophobic and ionic factors in the binding of local anesthetics to the major variant of human α1-acid glycoprotein

Journal of Pharmacology and Experimental Therapeutics

Volumn 304, Issue 1, 2003, Pages 71-80

  Taheri, Saeed ^a   Cogswell III, Lawrence P ^b   Gent, Alison ^a   Strichartz, Gary R ^a,c  

^a BRIGHAM AND WOMEN S HOSPITAL   (United States)

^b HARVARD UNIVERSITY   (United States)

^c HARVARD MEDICAL SCHOOL   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 (N ETHYL N METHYLAMINO) 2',6' ACETOXYLIDIDE; 2 (N METHYL N PENTYLAMINO) 2',6' ACETOXYLIDIDE; 2 (N METHYL N PROPYLAMINO) 2',6' ACETOXYLIDIDE; 4 DIETHYLAMINO N (2,6 DIMETHYLPHENYL)BUTYRAMIDE; BUPIVACAINE; LEA 104; LIDOCAINE; LIDOCAINE ETHOBROMIDE; LOCAL ANESTHETIC AGENT; MEPIVACAINE; N (2,6 DIMETHYLPHENYLCARBAMOYLETHYL)DIETHYLAMINE; N (2,6 DIMETHYLPHENYLCARBAMOYLMETHYL)ETHYLMETHYLAMINE; N (2,6 DIMETHYLPHENYLCARBAMOYLMETHYL)ETHYLPENTYLAMINE; N (2,6 DIMETHYLPHENYLCARBAMOYLMETHYL)ETHYLPROPYLAMINE; N (2,6 DIMETHYLPHENYLCARBAMOYLPROPYL)DIETHYLAMINE; OROSOMUCOID; ROPIVACAINE; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; CORRELATION ANALYSIS; DISSOCIATION CONSTANT; DRUG BINDING SITE; DRUG PROTEIN BINDING; DRUG STRUCTURE; HUMAN; HYDROPHOBICITY; IONIZATION; LOCAL ANESTHESIA; PRIORITY JOURNAL; PROTEIN TERTIARY STRUCTURE; PROTEIN VARIANT; SPECTROFLUOROMETRY; STRUCTURE ACTIVITY RELATION;

ALGORITHMS; ANESTHETICS, LOCAL; CHEMISTRY, PHYSICAL; FLUORESCENT DYES; HUMANS; HYDROGEN-ION CONCENTRATION; KINETICS; OROSOMUCOID; PROTEIN BINDING; SOLUTIONS; SPECTROMETRY, FLUORESCENCE; STRUCTURE-ACTIVITY RELATIONSHIP; SURFACE PROPERTIES;

EID: 0037215586     PISSN: 00223565     EISSN: None     Source Type: Journal    
DOI: 10.1124/jpet.102.042028     Document Type: Article

References (34)

1. Bachmann B, Biscoping J, Sinning E, and Hempelmann G (1990) Protein binding of prilocaine in human plasma: Influence of concentration, pH and temperature. Acta Anaesthesiol Scand 34:311-314.
2. Belaiba R, Riant P, Urien S, Brée F, Albengres E, Barre J, and Tillement JP (1989) Blood binding and tissue transfer of drugs: The influence of alpha 1-acid glycoprotein binding. Prog Clin Biol Res 300:287-305.
3. Belpaire FM and Bogaert MG (1989) Pharmacokinetic and pharmacodynamic consequences of altered binding of drugs to alpha 1-acid glycoprotein. Prog Clin Biol Res 300:337-350.
4. Benet LZ and Hoener B (2002) Changes in plasma protein binding have little clinical relevance. Clin Pharmacol Ther 71:115-121.
5. Bokesch PM, Post C, and Strichartz G (1986) Structure-activity relationship of lidocaine homologs producing tonic frequency-dependent impulse blockade in nerve. J Pharmacol Exp Ther 237:773-781.
6. Cogswell LP, Raines DE, Parekh S, Jonas O, Maggio JE, and Strichartz GR (2001) Development of a novel probe for measuring drug binding to the F1*S variant of human alpha 1-acid glycoprotein. J Pharm Sci 90:1407-1423.
7. Denson D, Coyle D, Thompson G, and Myers J (1984) Alpha 1-acid glycoprotein and albumin in human serum bupivacaine binding. Clin Pharmacol Ther 35:409-415.
8. Essassi D, Zini R, and Tillement JP (1989) ANS-drug interactions to AAG and HSA: Fluorescence and equilibrium dialysis studies. Prog Clin Biol Res 300:423-426.
9. Hartrick CT, Dirkes WE, Coyle DE, Raj PP, and Denson DD (1984) Influence of bupivacaine on mepivacaine protein binding. Clin Pharmacol Ther 36:546-550.
10. Hervé F, Caron G, Duché JC, Gaillard P, Abd Rahman N, Tsantili-Kakoulidou A, Carrupt PA, d'Athis P, Tillement JP, and Testa B (1998) Ligand specificity of the genetic variants of human alpha 1-acid glycoprotein: Generation of a three-dimensional quantitative structure-activity relationship model for drug binding to the A variant. Mol Pharmacol 54:129-138.
11. Hervé F, Duché JC, d'Athis P, Marche C, Barre J, and Tillement JP (1996) Binding of disopyramide, methadone, dipyridamole, chlorpromazine, lignocaine and progesterone to the two main genetic variants of human alpha 1-acid glycoprotein: Evidence for drug-binding differences between the variants and for the presence of two separate drug-binding sites on alpha 1-acid glycoprotein. Pharmacogenetics 6:403-415.
12. Hervé F, Fouache F, Marche C, and Tillement JP (1997) Abnormal microheterogeneity detected in one commercial alpha 1-acid glycoprotein preparation using chromatography on immobilized metal affinity adsorbent and on hydroxyapatite. J Chromatogr B Biomed Appl 688:35-46.
13. Jolliet-Riant P, BoukefMF, Duche JC, Simon N, and Tillement JP (1998) The genetic variant A of human alpha 1-acid glycoprotein limits the blood to brain transfer of drugs it binds. Pharmacol Lett 62:219-226.
14. Kaliszan R, Nasal A, and Turowski M (1996) Binding site for basic drugs on alpha 1-acid glycoprotein as revealed by chemometric analysis of biochromatographic data. Biomed Chromatogr 9:211-215.
15. Kaliszan R, Nasal A, and Turowski M (1996) Quantitative structure-retention relationships in the examination of the topography of the binding site of antihistamine drugs on alpha 1-acid glycoprotein. J Chromatogr A 722:25-32.
16. Kremer JM, Wilting J, and Janssen LH (1988) Drug binding to human alpha-l-acid glycoprotein in health and disease. Pharmacol Rev 40:1-47.
17. Lakowicz JR (1999) Principles of Fluorescence Spectroscopy, 2nd ed, Kluwer Academic/Plenum Publishers, New York.
18. Lunde PKM, Pike E, and Bredsen JE (1986) Inflammation and alpha 1-acid glycoprotein: Effect on drug binding, in Drug-Protein Binding (Reidenbery MM and Erill S eds) pp 201-219, Praeger Publishers, New York.
19. 1-acid glycoprotein. J Pharm Sci 81:16-20.
20. Maruyama T, Otagiri M, and Schulman SG (1990) Binding characteristics of coumarin anticoagulants to human α1-acid glycoprotein and human serum albumin. Int J Pharm 59:137-143.
21. Mazoit JX, Cao LS, and Samii K (1996) Binding of bupivacaine to human serum proteins, isolated albumin and isolated alpha-1-acid glycoprotein. Differences between the two enantiomers are partly due to cooperativity. J Pharmacol Exp Ther 276:109-115.
22. McNamara PJ, Slaughter RL, Pieper JA, Wyman MG, and Lalka D (1981) Factors influencing serum protein binding of lidocaine in humans. Anesth Analg 60:395-400.
23. Miyoshi T, Sukimoto K, and Otagiri M (1992) Investigation of the interaction mode of phenothiazine neuroleptics with alpha 1-acid glycoprotein. JPharm Pharmacol 44:28-33.
24. Morin D, Zini R, Ledewyn S, and Tillement JP (1986) Inhibition of binedaline binding to human alpha 1-acid glycoprotein and other serum proteins by chlorpromazine, imipramine and propranolol. J Pharm Sci 75:883-885.
25. Porter JM, Kellerher N, Flynn R, and Shorten GD (2001) Epidural ropivacaine hydrochloride during labour: Protein binding, placental transfer and neonatal outcome. Anaesthesia 56:418-423.
26. Porter JM, Markos F, Snow HM, and Shorten GD (2000) Effects of respiratory and metabolic pH changes and hypoxia on ropivacaine-induced cardiotoxicity in dogs. Br J Anaesth 84:92-94.
27. Ravis WR, Parsons DL, and Wang SJ (1988) Buffer and pH effects on propranolol binding to human albumin and alpha 1-acid glycoprotein. J Pharm Pharmacol 40:459-463.
28. Routledge PA (1986) The plasma protein binding of basic drugs. Br J Clin Pharmacol 22:499-506.
29. Sanchez V, Arthur GR, and Strichartz GR (1987) Fundamental properties of local anesthetics. I. The dependence of lidocaine's ionization and octanol:buffer partitioning on solvent and temperature. Anesth Analg 66:159-165.
30. Stanski D and Watkins WD (1986) Pharmacokinetic principles, in Drug Disposition in Anesthesia (Kitz RJ and Laver M, eds) pp 31-38, Grune & Stratton, New York.
31. a values of clinically used drugs. Anesth Analg 71:158-170.
32. Urien S, Brée F, Testa B, and Tillement J-P (1991) pH-dependency of basic ligand binding to alpha 1-acid glycoprotein(orosomucoid). Biochem J 280:277-280.
33. Wood M (1986) Plasma drug binding: Implications for anesthesiologists. Anesth Analg 65:786-804.
34. Wulf H, Munstedt P, and Maier C (1991) Plasma protein binding of bupivacaine in pregnant women at term. Acta Anaesthesiol Scand 35:129-133.