In vitro study of fenoprofen chiral inversion in rat: comparison of brain versus liver

References

• BANNWARTH, B., LAPICQUE, F., PEHOURCQ, F., GILLET, P., SCHEVERBEKE, T., LABORDE, C., DEHAES, J., GAUCHER, A. and NETTER, P., 1995, Stereoselective disposition of ibuprofen enantiomers in human cerebrospinal fluid. British Journal of Clinical Pharmacology, 40, 266–269.
   PubMedGoogle Scholar
• BEN01 T, E., DELATOUR, P., OLIVIER, L. and CALDWELL, J., 1995, (— )-R-fenoprofen: formation of fenoprofenyl-co-enzyme A by rat liver microsomes. Biochemical Pharmacology, 49, 1717–1720.
   Google Scholar
• BHAGWAT, S. V., Bow, M. R. and RAVINDRANATH, V., 1995, Rat brain cytochrome P450. Reassessment of monooxygenase activities and cytochrome P450 levels. Drug Metabolism and Disposition, 23, 651–654.
   PubMed Web of Science ®Google Scholar
• BHUSHAN, A. and SINGH, I., 1987, Purification and characterization of palmitoyl-CoA ligase from rat brain microsomes. Preparative Biochemistry, 17, 173–193.
   PubMed Web of Science ®Google Scholar
• BRADFORD, M., 1976, A rapid sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein—dye binding. Analytical Biochemistry, 72, 248–254.
   PubMed Web of Science ®Google Scholar
• BROUSTAS C. G. and HAJRA, A. K., 1995, Purification, properties and specificity of rat brain cytosolic fatty acyl co-enzyme A hydrolase. Journal of Neurochemistry, 64, 2345–2353.
   PubMedGoogle Scholar
• BROUSTAS C. G., LARKINS, L. K., UHLER, M. D. and HMRA, A. K., 1996, Molecular cloning and expression of cDNA encoding rat brain cytosolic acyl-co-enzyme A thioester hydrolase. Journal of Biological Chemistry, 271, 10470–10476.
   PubMed Web of Science ®Google Scholar
• BRUGGER, R., GARCIA ALIA, B., REICH EL C., WAIBEL, R., MENZEL, S., BRUNE, K. and GEISSLINGER, G., 1996, Isolation and characterization of rat liver microsomal R-ibuprofenyl-CoA synthetase. Biochemical Pharmacology, 52, 1007–1013.
   Google Scholar
• CALDWELL, J., HUTT, A. J. and FOURNEL -GIGLEUX, S., 1988, The metabolic chiral inversion and dispositional enantioselectivity of the 2-arylpropionic acids and their biological consequences. Biochemical Pharmacology, 37, 105–114.
   Google Scholar
• CAMP, L. A., VERKRUYSE, L. A., AFENDIS, S. J., SLAUGHTER, C. A. and HOFFMANN, S. L., 1994, Molecular cloning and expression of palmitoyl-protein thioesterase. Journal of Biological Chemistry, 269, 23212–23219.
   PubMedGoogle Scholar
• CHEN, C. S., SHIEH, W. R., Lu, P. H., HARREVIAN, S. and CHEN, S. Y., 1991, Metabolic stereoisomeric inversion of IPF in mammals. Biochimica et Biophysica Acta, 1078, 411–417.
   PubMed Web of Science ®Google Scholar
• DODDS, P. F., 1991, Incorporation of xenobiotic carboxylic acids into lipids. Life Sciences, 49, 629–649.
   PubMedGoogle Scholar
• FunNo, T., KANG, M. J., Suzum, H., IuEviA, H. and YAMAMOTO, T., 1996, Molecular characterization and expression of rat acyl-CoA synthetase 3. Journal of Biological Chemistry, 271, 16748–16752.
   PubMedGoogle Scholar
• FunNo, T. and YAMAMOTO, T., 1992, Cloning and functional expression of a novel long-chain acyl-CoA synthetase expressed in brain. Journal of Biochemistry, 111, 197–203.
   PubMedGoogle Scholar
• GILL, P. E. and MURRAY, W., 1978, Algorithms for the solution of the nonlinear least-squares problems. SIAM Journal of Numerical Analysis, 15, 977–992.
   Web of Science ®Google Scholar
• HALL, S. D., HASSANZADEH -KHAYYAT M., KNADLER, M. P. and MA, P. R., 1992, Pulmonary inversion of 2-arylpropionic acids: influence of protein binding. Chirality, 4, 349–352.
   Google Scholar
• IuEvIA, H., Fun-No, T., MINEKURA, H., Suzum, H., KG, M. J. and YAMAMOTO, T., 1996, Biochemical studies of two rat acyl-CoA synthetases,ACS1 and ACS2. European Journal of Biochemistry, 242, 186–190.
   Google Scholar
• KNADLER, M. P. and HALL, S. D., 1990, Stereoselective arylpropionyl-CoA thioester formation in vitro. Chirality, 2, 67–73.
   PubMed Web of Science ®Google Scholar
• KNrormou, R. D., DAY, R. O. and WILLIAMS, K. M., 1991, Chiral inversion of 2-arylpropionic acid non-steroidal anti-inflammatory drugs - II. Racemization and hydrolysis of (R)- and (S)-ibuprofen-CoA thioesters. Biochemical Pharmacology, 42, 1905–1911.
   PubMedGoogle Scholar
• NAKAMURA, Y., YAMAGUCHI, T., TAKAHASHI, S., HASHIMOTO, S., IWATANI, K. and NAKAGAWA, Y., 1981, Optical isomerization mechanism of R(— )-hydratropic acid derivatives. Journal of Pharmacobio-Dynamks, 4, 5–1.
   Google Scholar
• REICHEL C., BRUGGER, R., BANG, H., GEISSLINGER, G. and BRUNE, K., 1997, Molecular cloning and expression of a 2-arylpropionyl-CoA epimerase: a key enzyme in the inversion metabolism of ibuprofen. Molecular Pharmacology, 51, 576–582.
   Google Scholar
• SALLUSTIO, B. C., KNIGHTS, K. M. and MEETIN, P. J., 1990, The stereospecific inhibition of endogenous triacylglycerol synthesis by fenoprofen in rat isolated adipocytes and hepatocytes. Biochemical Pharmacology, 40, 1414–1417.
   PubMedGoogle Scholar
• SHIEH, W. R. and CHEN, C. S., 1993, Purification and characterization of novel `2.-arylpropionyl-CoA epimerases' from rat liver cytosol and mitochondria. Journal of Biological Chemistry, 268, 3487–3493.
   PubMed Web of Science ®Google Scholar
• SINGH, I., BHUSHAN, A., RELAN, N. K. and HASHEVIOTO, T., 1988, Acyl-CoA ligases from rat brain microsomes : an immunochemical study. Biochimica et Biophyska Acta, 1170, 44–52.
   Google Scholar
• STEWART, W. F., KAWAS, C., CORRADA, M. and METTER, J., 1997, Risk of Alzheimer's disease and duration of NSAID use. Neurology, 48, 626–632.
   PubMed Web of Science ®Google Scholar
• Suzum, H., KAWARABAYASI, Y., KONDO, J., ABE, T., NISHIKAWA, K., KIMURA, S., HASHEVIOTO, T. and YAMAMOTO, T., 1990, Structure and regulation of rat long-chain acyl-CoA synthetase. Journal of Biological Chemistry, 265, 8681–8685.
   PubMedGoogle Scholar
• TRACY, T. S. and HALL, S. D., 1992, Metabolic inversion of R-ibuprofen. Epimerization and hydrolysis of ibuprofenyl-co-enzyme A. Drug Metabolism and Disposition, 20, 322–327.
   PubMed Web of Science ®Google Scholar
• YAMADA, J., FURIHATA, T., IrDA, N., WATANABE, T., HOSOKAWA, M., SATOH, T., SOMEYA, A., NAGAOKA, I. and SUGA, T., 1997, Molecular cloning and expression of cDNAs encoding rat brain and liver cytosolic long-chain acyl-CoA hydrolases. Biochemical and Biophysical Research Communications, 232, 198–203.
   PubMedGoogle Scholar
• YAMADA, J., FURIHATA, T., TAMURA, H., WATANABE, T. and SUGA, T., 1996, Long-chain acyl-CoA hydrolase from rat brain cytosol: purification, characterization and immunohistochemical localization. Archives of Biochemistry and Biophysics, 326, 106–114.
   PubMedGoogle Scholar
• YAMAGUCHI, T. and NAKAMURA, Y., 1987, Stereoselective metabolism of 2-phenylpropionic acid in rat. II Studies on the organs responsible for the optical isomerization of 2-phenylpropionic acid in rat in vivo. Drug Metabolism and Disposition, 15, 535–539.
   PubMedGoogle Scholar
• WECHIER, W. J., LOUGHEAD, D. G., REISCHER, R. J., VAN GIESSEN, G. J. and KmsER, D. G., 1974, Enzymatic inversion at saturated carbon: nature and mechanism of the inversion of R(—)-p-isobutylhydratropic acid. Biochemical and Biophysical Research Communications, 61, 833–837.
   PubMedGoogle Scholar