Impaired intrinsic chiral inversion activity of ibuprofen in rats with adjuvant-induced arthritis

References

• Belpaire FM, De Smet F, Chindavijak B, Fraeyman N, Bogaert MG. Effect of turpentine-induced inflammation on the disposition kinetics of propranolol, metoprolol, and antipyrine in the rat. Fundamentals in Clinical Pharmacology 1989; 3: 79–88
   PubMed Web of Science ®Google Scholar
• Bogacka I, Xie H, Bray GA, Smith SR. The effect of pioglitazone on peroxisome proliferator-activated receptor-gamma target genes related to lipid storage in vivo. Diabetes Care 2004; 27: 1660–1667
   PubMed Web of Science ®Google Scholar
• Brugger R, Garcia Alia B, Reichel C, Waibel R, Menzel S, Brune K, Geisslinger G. Isolation and characterization of rat liver microsomal R-ibuprofenoyl-CoA synthetase. Biochemistry and Pharmacology 1996; 52: 1007–1013
   PubMed Web of Science ®Google Scholar
• Chen CS, Chen T, Shieh WR. Metabolic stereoisomeric inversion of 2-arylpropionic acids. On the mechanism of ibuprofen epimerization in rats. Biochimica et Biophysica Acta 1990; 1033: 1–6
   PubMed Web of Science ®Google Scholar
• Dipasquale G, Welaj P, Rassaert CL. Prolonged pentobarbital sleeping time in adjuvant-induced polyarthritic rats. Research Communications in Chemical Pathology and Pharmacology 1974; 9: 253–264
   PubMedGoogle Scholar
• Fujino T, Kang MJ, Suzuki H, Iijima H, Yamamoto T. Molecular characterization and expression of rat acyl-CoA synthetase 3. Journal of Biology and Chemistry 1996; 271: 16748–16752
   PubMed Web of Science ®Google Scholar
• Fujino T, Yamamoto T. Cloning and functional expression of a novel long-chain acyl-CoA synthetase expressed in brain. Journal of Biochemistry (Tokyo) 1992; 111: 197–203
   PubMed Web of Science ®Google Scholar
• Kang MJ, Fujino T, Sasano H, Minekura H, Yabuki N, Nagura H, Iijima H, Yamamoto TT. A novel arachidonate-preferring acyl-CoA synthetase is present in steroidogenic cells of the rat adrenal, ovary, and testis. Proceedings of the National Academy of Sciences, USA 1997; 94: 2880–2884
   PubMed Web of Science ®Google Scholar
• Kim JH, Lewin TM, Coleman RA. Expression and characterization of recombinant rat acyl-CoA synthetases 1, 4, and 5. Selective inhibition by triacsin C and thiazolidinediones. Journal of Biology and Chemistry 2001; 276: 24667–24673
   PubMed Web of Science ®Google Scholar
• Kim MS, Sweeney TR, Shigenaga JK, Chui LG, Moser A, Grunfeld C, Feingold KR. Tumor necrosis factor and interleukin 1 decrease RXRalpha, PPARalpha, PPARgamma, LXRalpha, and the coactivators SRC-1, PGC-1alpha, and PGC-1beta in liver cells. Metabolism 2007; 56: 267–279
   PubMedGoogle Scholar
• Komura H, Iwaki M. Nonlinear pharmacokinetics of propafenone in rats and humans: Application of a substrate depletion assay using hepatocytes for assessment of nonlinearity. Drug Metabolism and Disposition 2005a; 33: 726–732
   PubMed Web of Science ®Google Scholar
• Komura H, Iwaki M. Usefulness of hepatocytes for evaluating the genetic polymorphism of CYP2D6 substrates. Xenobiotica 2005b; 35: 575–587
   PubMed Web of Science ®Google Scholar
• Laethem ME, Belpaire FM, Wijnant P, Rosseel MT, Bogaert MG. Influence of endotoxin on the stereoselective pharmacokinetics of oxprenolol, propranolol, and verapamil in the rat. Chirality 1994; 6: 405–410
   PubMed Web of Science ®Google Scholar
• Martin G, Schoonjans K, Lefebvre AM, Staels B, Auwerx J. Coordinate regulation of the expression of the fatty acid transport protein and acyl-CoA synthetase genes by PPARalpha and PPARgamma activators. Journal of Biology and Chemistry 1997; 272: 28210–28217
   PubMed Web of Science ®Google Scholar
• Menzel S, Waibel R, Brune K, Geisslinger G. Is the formation of R-ibuprofenyl-adenylate the first stereoselective step of chiral inversion?. Biochemistry and Pharmacology 1994; 48: 1056–1058
   PubMed Web of Science ®Google Scholar
• Meunier CJ, Verbeeck RK. Glucuronidation kinetics of R,S-ketoprofen in adjuvant-induced arthritic rats. Pharmaceutical Research 1999a; 16: 1081–1086
   PubMed Web of Science ®Google Scholar
• Meunier CJ, Verbeeck RK. Glucuronidation of R- and S-ketoprofen, acetaminophen, and diflunisal by liver microsomes of adjuvant-induced arthritic rats. Drug Metabolism and Disposition 1999b; 27: 26–31
   PubMed Web of Science ®Google Scholar
• Muller S, Mayer JM, Etter JC, Testa B. Metabolic chiral inversion of ibuprofen in isolated rat hepatocytes. Chirality 1990; 2: 74–78
   PubMed Web of Science ®Google Scholar
• Nagao T, Tanino T, Iwaki M. Stereoselective pharmacokinetics of flurbiprofen and formation of covalent adducts with plasma protein in adjuvant-induced arthritic rats. Chirality 2003; 15: 423–428
   PubMed Web of Science ®Google Scholar
• Oikawa E, Iijima H, Suzuki T, Sasano H, Sato H, Kamataki A, Nagura H, Kang MJ, Fujino T, Suzuki H, et al. A novel acyl-CoA synthetase, ACS5, expressed in intestinal epithelial cells and proliferating preadipocytes. Journal of Biochemistry 1998; 124: 679–685
   PubMedGoogle Scholar
• Philippe L, Gegout-Pottie P, Guingamp C, Bordji K, Terlain B, Netter P, Gillet P. Relations between functional, inflammatory, and degenerative parameters during adjuvant arthritis in rats. American Journal of Physiology 1997; 273: 1550–1556
   Google Scholar
• Piquette-Miller M, Jamali F. Effect of adjuvant arthritis on the disposition of acebutolol enantiomers in rats. Agents. Actions 1992; 37: 290–296
   PubMedGoogle Scholar
• Piquette-Miller M, Jamali F. Selective effect of adjuvant arthritis on the disposition of propranolol enantiomers in rats detected using a stereospecific HPLC assay. Pharmaceutical Research 1993; 10: 294–299
   PubMed Web of Science ®Google Scholar
• Reichel C, Bang H, Brune K, Geisslinger G, Menzel S. 2-Arylpropionyl-CoA epimerase: Partial peptide sequences and tissue localization. Biochemistry and Pharmacology 1995; 50: 1803–1806
   PubMed Web of Science ®Google Scholar
• Reichel C, Brugger R, Bang H, Geisslinger G, Brune K. Molecular cloning and expression of a 2-arylpropionyl-coenzyme A epimerase: A key enzyme in the inversion metabolism of ibuprofen. Molecular Pharmacology 1997; 51: 576–582
   PubMed Web of Science ®Google Scholar
• Sanins SM, Adams WJ, Kaiser DG, Halstead GW, Baillie TA. Studies on the metabolism and chiral inversion of ibuprofen in isolated rat hepatocytes. Drug Metabolism and Disposition 1990; 18: 527–533
   PubMed Web of Science ®Google Scholar
• Seglen PO. Preparation of isolated rat liver cells. Methods in Cell Biology 1976; 13: 29–83
   PubMedGoogle Scholar
• Sevoz C, Benoit E, Buronfosse T. Thioesterification of 2-arylpropionic acids by recombinant acyl-coenzyme A synthetases (ACS1 and ACS2). Drug Metabolism and Disposition 2000; 28: 398–402
   PubMed Web of Science ®Google Scholar
• Shibata N, Shimakawa H, Minouchi T, Yamaji A. Pharmacokinetics of cyclosporin A after intravenous administration to rats in various disease states. Biology and Pharmacology Bulletin 1993; 16: 1130–1135
   PubMed Web of Science ®Google Scholar
• Shibata Y, Takahashi H, Chiba M, Ishii Y. Prediction of hepatic clearance and availability by cryopreserved human hepatocytes: An application of serum incubation method. Drug Metabolism and Disposition 2002; 30: 892–896
   PubMed Web of Science ®Google Scholar
• Shieh WR, Chen CS. Purification and characterization of novel ‘2-arylpropionyl-CoA epimerases’ from rat liver cytosol and mitochondria. Journal of Biology and Chemistry 1993; 268: 3487–3493
   PubMed Web of Science ®Google Scholar
• Suzuki H, Kawarabayasi Y, Kondo J, Abe T, Nishikawa K, Kimura S, Hashimoto T, Yamamoto T. Structure and regulation of rat long-chain acyl-CoA synthetase. Journal of Biology and Chemistry 1990; 265: 8681–8685
   PubMed Web of Science ®Google Scholar
• Suzuki H, Watanabe M, Fujino T, Yamamoto T. Multiple promoters in rat acyl-CoA synthetase gene mediate differential expression of multiple transcripts with 5′-end heterogeneity. Journal of Biology and Chemistry 1995; 270: 9676–9682
   PubMed Web of Science ®Google Scholar
• Tan SC, Patel BK, Jackson SH, Swift CG, Hutt AJ. Stereoselectivity of ibuprofen metabolism and pharmacokinetics following the administration of the racemate to healthy volunteers. Xenobiotica 2002; 32: 683–697
   PubMed Web of Science ®Google Scholar
• Toda A, Ishii N, Kihara T, Nagamatsu A, Shimeno H. Effect of adjuvant-induced arthritis on hepatic drug metabolism in rats. Xenobiotica 1994; 24: 603–611
   PubMed Web of Science ®Google Scholar
• Tracy TS, Wirthwein DP, Hall SD. Metabolic inversion of (R)-ibuprofen. Formation of ibuprofenyl-coenzyme A. Drug Metabolism and Disposition 1993; 21: 114–120
   PubMed Web of Science ®Google Scholar
• Williams RO, Feldmann M, Maini RN. Anti-tumor necrosis factor ameliorates joint disease in murine collagen-induced arthritis. Proceedings of the National Academy of Sciences, USA 1992; 89: 9784–9788
   PubMed Web of Science ®Google Scholar
• Xiaotao Q, Hall SD. Modulation of enantioselective metabolism and inversion of ibuprofen by xenobiotics in isolated rat hepatocytes. Journal of Pharmacology and Experimental Therapy 1993; 266: 845–851
   PubMedGoogle Scholar