Chiral distinction between the enantiomers of bicyclic alcohols by UDP-glucuronosyltransferases 2B7 and 2B17

References

Agranat, I. and Sarel, S. (1996). Reflections on chiral discrimination. Discrimination is between equals, distinction is between unequals. Enantiomer1, 249–250.Search in Google Scholar

Agranat, I., Caner, H., and Caldwell, A. (2002). Putting chirality to work: the strategy of chiral switches. Nat. Rev. Drug Discov.1, 753–768.10.1038/nrd915Search in Google Scholar

Ariëns, E.J. (1984). Stereochemistry, a basis for sophisticated nonsense in pharmacokinetics and clinical pharmacology. Eur. J. Clin. Pharmacol.26, 663–668.10.1007/BF00541922Search in Google Scholar

Barlow, R.B., Franks, F.M., and Pearson, J.D.M. (1972). Relation between biological activity and degree of resolution of optical isomers. J. Pharm. Pharmacol.24, 753–761.Search in Google Scholar

Caldwell, J. (2001). Do single enantiomers have something special to offer? Hum. Psychopharmacol.16,S67–S71.10.1002/hup.339Search in Google Scholar

Copeland, R.A. (2005) Evaluation of Enzyme Inhibitors in Drug Discovery: A Guide for Medicinal Chemists and Pharmacologists (Hoboken, NJ, USA: John Wiley & Sons).Search in Google Scholar

Corey, E.J. and Helal, C.J. (1998). Reduction of carbonyl compounds with chiral oxazaborolidine catalysts: a new paradigm for enantioselective catalysis and a powerful new synthetic method. Angew. Chem. Int. Ed.37, 1986–2012.10.1002/(SICI)1521-3773(19980817)37:15<1986::AID-ANIE1986>3.0.CO;2-ZSearch in Google Scholar

Corey, E.J., Bakshi, R.K., and Shibata, S. (1987). Highly enantioselective borane reduction of ketones catalyzed by chiral oxazaborolidines – mechanism and synthetic implications. J. Am. Chem. Soc.109, 5551–5553.10.1021/ja00252a056Search in Google Scholar

Court, M.H., Duan, S.X., Guillemette, C., Journault, K., Krishnaswamy, S., von Moltke, L.L., and Greenblatt, D.J. (2002). Stereoselective conjugation of oxazepam by human UDP-glucuronosyltransferases (UGTs): S-oxazepam is glucuronidated by UGT2B15, while R-oxazepam is glucuronidated by UGT2B7 and UGT1A9. Drug Metab. Dispos.30, 1257–1265.10.1124/dmd.30.11.1257Search in Google Scholar

Crossley, R. (1995). Chirality and the Biological Activity of Drugs (Boca Raton, FL, USA: CRC Press), pp. 1–46 (and references therein).Search in Google Scholar

Dieter, R.K. and Li, S.J. (1997). Copper cyanide-catalyzed palladium coupling of N-tert-butoxycarbonyl-protected α-lithio amines with aryl iodides or vinyl iodides. J. Org. Chem.62, 7726–7735.10.1021/jo970985bSearch in Google Scholar

Eichelbaum, M., Testa, B., and Somogyi, A. (2003). Stereochemical Aspects of Drug Action and Disposition (Heidelberg, Berlin: Springer-Verlag).10.1007/978-3-642-55842-9Search in Google Scholar

Garrett, C.E., Prasad, K., Repic, O., and Blacklock, T.J. (2002). The enantioselective reduction of 2′-fluoroacetophenone utilizing a simplified CBS-reduction procedure. Tetrahedron Asymmetry13, 1347–1349.10.1016/S0957-4166(02)00373-7Search in Google Scholar

Green, M.D., Belanger, G., Hum, D.W., Belanger, A., and Tephly, T.R. (1997). Glucuronidation of opioids, carboxylic acid-containing drugs, and hydroxylated xenobiotics catalyzed by expressed monkey UDP-glucuronosyltransferase 2B9 protein. Drug Metab. Dispos.25, 1389–1394.Search in Google Scholar

Hamdoune, M., Mounie, J., Magdalou, J., Masmoudi, T., Goudonnet, H., and Escousse, A. (1995). Characterization of the in vitro glucuronidation of flurbiprofen enantiomers. Drug Metab. Dispos.23, 343–348.Search in Google Scholar

Jin, C., Miners, J.O., Lillywhite, K.J., and Mackenzie, P.I. (1993). Complementary deoxyribonucleic acid cloning and expression of a human liver uridine diphosphate-glucuronosyltransferase glucuronidating carboxylic acid-containing drugs. J. Pharmacol. Exp. Ther.264, 475–479.Search in Google Scholar

Kaivosaari, S., Salonen, J.S., Mortensen, J., and Taskinen, J. (2001). High-performance liquid chromatographic method combining radiochemical and ultraviolet detection for determination of low activities of uridine 5′-diphosphate-glucuronosyltransferase. Anal. Biochem.292, 178–187.10.1006/abio.2001.5092Search in Google Scholar

Kakkar, T., Boxenbaum, H., and Mayersohn, M. (1999). Estimation of K_i in a competitive enzyme-inhibition model: comparisons among three methods of data analysis. Drug Metab. Dispos.27, 756–762.Search in Google Scholar

Kuehl, G.E., Lampe, J.W., Potter, J.D., and Bigler, J. (2005). Glucuronidation of nonsteroidal anti-inflammatory drugs: identifying the enzymes responsible in human liver microsomes. Drug Metab. Dispos.33, 1027–1035.10.1124/dmd.104.002527Search in Google Scholar

Kurkela, M., Garcia-Horsman, J.A., Luukkanen, L., Mörsky, S., Taskinen, J., Baumann, M., Kostiainen, R., Hirvonen, J., and Finel, M. (2003). Expression and characterization of recombinant human UDP-glucuronosyltransferases (UGTs). UGT1A9 is more resistant to detergent inhibition than other UGTs and was purified as an active dimeric enzyme. J. Biol. Chem.278, 3536–3544.10.1074/jbc.M206136200Search in Google Scholar

Luukkanen, L., Taskinen, J., Kurkela, M., Kostiainen, R., Hirvonen, J., and Finel, M. (2005). Kinetic characterization of the 1A subfamily of recombinant human UDP-glucuronosyltransferases. Drug Metab. Dispos.33, 1017–1026.10.1124/dmd.105.004093Search in Google Scholar

Mackenzie, P.I., Owens, I.S., Burchell, B., Bock, K.W., Bairoch, A., Belanger, A., Fournel-Gigleux, S., Green, M., Hum, D.W., Iyanagi, T., et al. (1997). The UDP glycosyltransferase gene superfamily: recommended nomenclature update based on evolutionary divergence. Pharmacogenetics7, 255–269.10.1097/00008571-199708000-00001Search in Google Scholar

Maire-Gauthier, R., Buronfosse, T., Magdalou, J., Herber, R., Besse, S., Delatour, P., and Benoit, E. (1998). Species-dependent enantioselective glucuronidation of carprofen. Xenobiotica28, 595–604.10.1080/004982598239344Search in Google Scholar

Meech, R. and Mackenzie, P.I. (1997). Structure and function of uridine diphosphate glucuronosyltransferases. Clin. Exp. Pharmacol. Physiol.24, 907–915.10.1111/j.1440-1681.1997.tb02718.xSearch in Google Scholar

Motulsky, H.J. and Christopoulos, A. (2003). Fitting Models to Biological Data using Linear and Nonlinear Regression. A Practical Guide to Curve Fitting (San Diego, CA, USA: GraphPad Software Inc.), pp. 143–148.Search in Google Scholar

Parascandola, J. (1975). The evolution of stereochemical concepts in pharmacology. In: van't Hoff-LeBell Centennial, O.B. Ramsay, ed. (Washington, DC, USA: American Chemical Society), pp. 143–158.10.1021/bk-1975-0012.ch011Search in Google Scholar

Pfeiffer, C.C. (1956). Optical isomerism and pharmacological action, a generalization. Science124, 29–31.10.1126/science.124.3210.29Search in Google Scholar

Price, M.D., Kurth, M.J., and Schore, N.E. (2002). Comparison of solid-phase and solution-phase chiral auxiliaries in the alkylation/iodolactonization sequence to γ-butyrolactones. J. Org. Chem.67, 7769–7773.10.1021/jo0260692Search in Google Scholar

Ritter, J.K., Chen, F., Sheen, Y.Y., Tran, H.M., Kimura, S., Yeatman, M.T., and Owens, I.S. (1992). A novel complex locus UGT1 encodes human bilirubin, phenol, and other UDP-glucuronosyltransferases isozymes with identical carboxyl termini. J. Biol. Chem.267, 3257–3261.10.1016/S0021-9258(19)50724-4Search in Google Scholar

Salunkhe, A.M. and Burkhardt, E.R. (1997). Highly enantioselective reduction of prochiral ketones with N,N-diethylaniline borane (DEANB) in oxazaborolidine-catalyzed reductions. Tetrahedron Lett.38, 1523–1526.10.1016/S0040-4039(97)00128-7Search in Google Scholar

Sorich, M.J., Miners, J.O., McKinnon, R.A., and Smith, P.A. (2004a). Multiple pharmacophores for the investigation of human UDP-glucuronosyltransferase isoform substrate selectivity. Mol. Pharmacol.65, 301–308.10.1124/mol.65.2.301Search in Google Scholar

Sorich, M.J., McKinnon, R.A., Miners, J.O., Winkler, D.A., and Smith, P.A. (2004b). Rapid prediction of chemical metabolism by human UDP-glucuronosyltransferase isoforms using quantum chemical descriptors derived with electronegativity equalization method. J. Med. Chem.47, 5311–5317.10.1021/jm0495529Search in Google Scholar

Stone, A.N., Mackenzie, P.I., Galetin, A., Houston, J.B., and Miners, J.O. (2003). Isoform selectivity and kinetics of morphine 3- and 6-glucuronidation by human UDP-glucuronosyltransferases: evidence for atypical glucuronidation kinetics by UGT2B7. Drug Metab. Dispos.31, 1086–1089.10.1124/dmd.31.9.1086Search in Google Scholar

Sweeny, D.J. and Nellans, H.N. (1995). Stereoselective glucuronidation of zileuton isomers by human hepatic microsomes. Drug Metab. Dispos.23, 149–153.Search in Google Scholar

Tucker, G.T. (2000). Chiral switches. Lancet355, 1085–1087.10.1016/S0140-6736(00)02047-XSearch in Google Scholar

Turgeon, D., Carrier, J.S., Levesque, E., Hum, D.W., and Belanger, A. (2001). Relative enzymatic activity, protein stability, and tissue distribution of human steroid-metabolizing UGT2B subfamily members. Endocrinology142, 778–787.10.1210/endo.142.2.7958Search in Google Scholar PubMed

Turgeon, D., Carrier, J.S., Chouinard, S., and Belanger, A. (2003). Glucuronidation activity of the UGT2B17 enzyme toward xenobiotics. Drug Metab. Dispos.31, 670–676.10.1124/dmd.31.5.670Search in Google Scholar PubMed

Wells, P.G., Mackenzie, P.I., Chowdhury, J.R., Guillemette, C., Gregory, P.A., Ishii, Y., Hansen, A.J., Kessler, F.K., Kim, P.M., Chowdhury, N.R., and Ritter, J.K. (2004). Glucuronidation and the UDP-glucuronosyltransferases in health and disease. Drug Metab. Dispos.32, 281–290.10.1124/dmd.32.3.281Search in Google Scholar PubMed

Xu, J., Wei, T., and Zhang, Q. (2004). Influences of electronic effects and anions on the enantioselectivity in the oxazaborolidine-catalyzed asymmetric borane reduction of ketones. J. Org. Chem.69, 6860–6866.10.1021/jo048959iSearch in Google Scholar PubMed