Enantioselective covalent binding of 2-phenylpropionic acid to protein in vitro in rat hepatocytest

Chemical Research in Toxicology

Volumn 15, Issue 11, 2002, Pages 1480-1487

  Li, Chunze ^a   Benet, Leslie Z ^a   Grillo, Mark P ^a,b  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYL COENZYME A; BORNEOL; GLUCURONIDE; HYDRATROPIC ACID; PIVALIC ACID; PROTEIN; THIOESTER; ACYL COENZYME A; GLUCURONIC ACID; PHENYLPROPIONIC ACID DERIVATIVE;

ANIMAL CELL; ARTICLE; CELL ISOLATION; CHEMICAL BINDING; CONTROLLED STUDY; COVALENT BOND; DOSE TIME EFFECT RELATION; DRUG PROTEIN BINDING; ENANTIOSELECTIVITY; GLUCURONIDATION; INCUBATION TIME; INHIBITION KINETICS; ISOMERISM; LIVER CELL; MALE; METABOLIC REGULATION; NONHUMAN; PROTEIN BINDING; RAT; SPECIES IDENTIFICATION; ANIMAL; CONFORMATION; IN VITRO STUDY; METABOLISM; SPRAGUE DAWLEY RAT; STEREOISOMERISM;

ANIMALIA;

ACYL COENZYME A; ANIMALS; GLUCURONIC ACIDS; HEPATOCYTES; MALE; MOLECULAR CONFORMATION; PHENYLPROPIONATES; PROTEINS; RATS; RATS, SPRAGUE-DAWLEY; STEREOISOMERISM;

EID: 0036851821     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx025600l     Document Type: Article

References (31)

1. Shen, T. Y. (1981) Nonsteroidal anti-inflammatory agents. In Burger's Medicinal Chemistry (Wolf, M. E., Ed.) 4th ed., Part III, pp 1205-1271, Wiley-Interscience, New York.
2. Spahn-Langguth, H., Benet, L. Z., Zia-Amirhosseini, P., Iwakawa, S., and Langguth, P. (1997) Kinetics of reactive phase II metabolites: stereochemical aspects of formation of epimeric acyl glucuronides and their reactivity. In The Impact of Stereochemistry on Drug Deveolpment and Use (Aboul-Enein, H. Y., and Wainer, I. W., Eds.) pp 125-170, John Wiley & Sons, New York.
3. Spahn-Langguth, H., and Benet, L. Z. (1992) Acyl glucuronides revisited: Is the glucuronidation process a toxification as well as detoxification mechanism? Drug Metab. Rev. 24, 5-47.
4. Munafo, A., Hyneck, M. L., and Benet, L. Z. (1993) Pharmaco-kinetics and irreversible binding of tolmetin and its glucuronic acid esters in the elderly. Pharmacology 47, 309-317.
5. Zia-Amirhosseini, P., Ojingwa, J., Spahn-Langguth, H., McDonagh, A. F., and Benet, L. Z. (1994) Enhanced covalent binding of tolmetin to proteins in humans after multiple dosing. Clin. Pharmacol. Ther. 55, 21-27.
6. Smith, P. C., McDonagh, A. F., and Benet, L. Z. (1986) Irreversible binding of zomepirac to plasma in vitro and in vivo. J. Clin. Invest. 77, 934-939.
7. Iwakawa, S., Spahn, H., Benet, L. Z. and Lin, E. T. (1988) Carprofen glucuronide: stereoselective degradation and interaction with human serum albumin. Pharm. Res. 5 (suppl.), S-214.
8. McKinnon, G. E., and Dickinson, R. G. (1989) Covalent binding of diflunisal and probenecid to plasma protein in humans: persistence of the adducts in the circulation. Res. Commun. Chem. Pathol. Pharmacol. 3, 1033-1039.
9. Volland, C., Sun, H., Dammeyer, J., and Benet, L. Z. (1991) Stereoselective degradation of the fenoprofen acyl glucuronide enantiomers and irreversible binding to plasma protein. Drug Metab. Dispos. 19, 1080-1086.
10. Dubois, N., Lapicque, F., Maurice, M., Pritchard, M., Fournel-Gigleux, S., Magdalou, J., Abiteboul, M., Siest, G., and Netter, P. (1993) In vitro irreversible binding of ketoprofen glucuronide to plasma proteins. Drug Metab. Dispos. 21, 617-623.
11. Ojingwa, J. C., Spahn-Langguth, H., and Benet, L. Z. (1994) Irreversible binding of tolmetin to macromolecules via its glucuronide: Binding to blood constituents, tissue homogenates and subcellular fractions in vitro. Xenobiotica 24, 495-506.
12. Kretz-Rommel, A., and Boelsterli, U. A. (1994) Mechanism of covalent adduct formation of diclofenac to rat hepatic microsome proteins, retention of the glucuronic acid moiety in the adduct. Drug Metab. Dispos. 22, 956-961.
13. Mayer, J. M., Roy-De, V. M., Audergon, C., Testa, B., and Etter, J. C. (1994) Interaction of anti-inflammatory 2-arylpropionates (profens) with the metabolism of fatty acids: In vitro studies. Int. J. Tiss. React. XVI, 59-72.
14. Hall, S. D., and Qian, X. (1994) The role of coenzyme A in the biotransformation of 2-arylpropionic acids. Chem-Biol. Interact. 90, 235-251.
15. 0 glycoprotein and a synthetic peptide containing the palmitoylation site are both autoacylated. J. Neurochem. 65, 1805-1815.
16. Duncan, J. A., and Gilman, A. G. (1996) Autoacylation of G protein alpha subunits. J. Biol. Chem. 27, 23594-23600.
17. Sallustio, B. C., Nunthasomboon, S., Drogemuller, C. J., and Knights, K. M. (2000) In vitro covalent binding of nafenopin-CoA to human liver proteins. Toxicol. Appl. Pharmacol. 163, 176-182.
18. Li, C., Grillo, M. P., and Benet, L. Z. (2002) Studies on the chemical reactivity of 2-phenylpropionic acid 1-O-acyl glucuronide and S-acyl-CoA thioester metabolites. Chem. Res. Toxicol. 15, 1209-1217.
19. Moldeus, P., Hogberg, J., and Orrenius, S. (1978) The isolation and the use of liver cells. Methods Enzymol. 52, 69-71.
20. Zimmerman, H. J. (1994) Hepatic injury associated with nonsteroidal anti-inflammatory drugs. In Nonsteroidal Antiinflammatory Drugs. Mechanisms and Clinical Use (Lewis, A. J., and Furst, D. E., Eds.) pp 171-194, Marcel Dekker Inc., New York.
21. Bakke, O. M., Manocchia. M., de Abajo, F., Kaitin, K. I., and Lasagna, L. (1995) Drug safety discontinuations in the United Kingdom, the United States and Spain from 1974 to 1993, a regulatory perspective. Clin. Pharmacol. Ther. 58, 108-117.
22. 14C]hydratropic acid and its variation with species. Xenobiotica 7, 707-715.
23. Fournel, S., and Caldwell, J. (1986) The metabolic chiral inversion of 2-phenylpropionic acid in rat, mouse and rabbit. Biochem. Pharmacol. 35, 4153-4159.
24. Benet, L. Z., Spahn-Langguth, H., Iwakawa, S., Volland, C., Mizuma, T., Mayer, S., Mutschler, E., and Lin, E. T. (1993) Predictability of the covalent binding of acidic drugs in man. Life Sci. 53, L141-146.
25. Zia-Amirhosseini, P., Harris, R. Z., Brodsky, F. M., and Benet, L. Z. (1995) Hypersensitivity to nonsteroidal anti-inflammatory drugs. Nat. Med. 1, 2-4.
26. Hargus, S. J., Amouzedeh, H. R., Pumford, N. R., Myers, T. G., McCoy, S. C., and Pohl, L. R. (1994) Metabolic activation and immunochemical localization of liver protein adducts of the nonsteroidal anti-inflammatory drug diclofenac. Chem. Res. Toxicol. 7, 575-582.
27. Bailey, M. J., and Dickinson, R. G. (1996) Chemical and immunochemical comparison of protein adduct formation of four carboxylate drugs in rat liver and plasma. Chem. Res. Toxicol. 9, 659-666.
28. Wade, L. T., Kenna, J. G., and Caldwell, J. (1997) Immunochemical identification of mouse hepatic protein adducts derived from the nonsteroidal anti-inflammatory drugs diclofenac, sulindac, and ibuprofen. Chem. Res. Toxicol. 10, 546-555.
29. Hertz, R., and Bar-Tana, J. (1988) The acylation of proteins by xenobiotic amphipathic carboxylic acids in cultured rat hepatocytes. Biochem. J. 254, 39-44.
30. Akira, K., Hasegawa, H., Shinohara, Y., Imachi, M., and Hashimoto, T. (2000) Stereoselective internal acyl migration of 1-beta-O-acyl glucuronides of enantiomeric 2-phenylpropionic acids. Biol. Pharm. Bull. 4, 50-510.
31. Dahms, M., and Spahn-Langguth, H. (1996) Covalent binding of acidic drugs via reactive intermediates: Detection of benoxaprofen and flunoxaprofen protein adducts in biological material. Pharmazie 11, 874-881.