UGT3A: novel UDP-glycosyltransferases of the UGT superfamily

References

• Abe, T., Kakyo, M., Tokui, T., Nakagomi, R., Nishio, T., Nakai, D., et al. (1999). Identification of a novel gene family encoding human liver-specific organic anion transporter LST-1. J Biolog Chem 274:17159–17163.
   PubMed Web of Science ®Google Scholar
• Arcos, M., and Lieberman, S. (1967). 5-pregnene-3-beta,20-alpha-diol-3-sulfate-20-(2’-acetamido-2’-deoxy-alpha-D-glucoside) and 5-pregnene-3-beta,20-alpha-diol-3,20-disulfate. Two novel urinary conjugates. Biochemistry 6:2032–2039.
   PubMed Web of Science ®Google Scholar
• Collins, D. C., Jirku, H., Layne, D. S. (1968). Steroid N-acetylglucosaminyl transferase. Localization and some properties of the enzyme in rabbit tissues. J Biol Chem 243:2928–2933.
   PubMed Web of Science ®Google Scholar
• Dykens, J. A., Moos, W. H., Howell, N. (2005). Development of 17alpha-estradiol as a neuroprotective therapeutic agent: rationale and results from a phase I clinical study. Ann N Y Acad Sci 1052:116–135.
   PubMed Web of Science ®Google Scholar
• Finkelstein, M., Weidenfeld, J., Ne’eman, Y., Samuni, A., Mizrachi, Y., Ben-Uzilio, R. (1981). Comparative studies of the aromatization of testosterone and epitestosterone by human placental aromatase. Endocrinology 108:943–947.
   PubMed Web of Science ®Google Scholar
• Gall, W. E., Zawada, G., Mojarrabi, B., Tephly, T. R., Green, M. D., Coffman, B. L., et al. (1999). Differential glucuronidation of bile acids, androgens, and estrogens by human UGT1A3 and 2B7. J Steroid Biochem Mol Biol 70:101–108.
   PubMed Web of Science ®Google Scholar
• Han, M. V., Hahn, M. W. (2009). Identifying parent-daughter relationships among duplicated genes. Pac Symp Biocomput 14:114–125.
   Google Scholar
• Jirku, H., Levitz, M. (1969). Biliary and urinary metabolites of estrone-6,7-3H-sulfate-35S in a woman. J Clin Endocrinol Metab 29:615–637.
   PubMed Web of Science ®Google Scholar
• Kubota, T., Lewis, B. C., Elliot, D. J., Mackenzie, P. I., Miners, J. O. (2007). Critical roles of residues 36 and 40 in the phenol and tertiary amine aglycone substrate selectivities of UDP-glucuronosyltransferases 1A3 and 1A4. Mol Pharmacol 72:1054–1062.
   PubMed Web of Science ®Google Scholar
• Layne, D. S., Sheth, N. A., Kirdani, R.Y. (1964). The isolation from rabbit urine of a conjugate of 17agr-estradiol with N-acetylglucosamine. J Biol Chem 239:3221–3225.
   PubMed Web of Science ®Google Scholar
• Levesque, E., Girard, H., Journault, K., Lepine, J., Guillemette, C. (2007). Regulation of the UGT1A1 bilirubin-conjugating pathway: role of a new splicing event at the UGT1A locus. Hepatology 45:128–138.
   PubMed Web of Science ®Google Scholar
• Levin-Allerhand, J. A., Lominska, C. E., Wang, J., Smith, J. D. (2002). 17alpha-estradiol and 17beta-estradiol treatments are effective in lowering cerebral amyloid-beta levels in AbetaPPSWE transgenic mice. J Alzheimers Dis 4:449–457.
   PubMed Web of Science ®Google Scholar
• Li, D., Fournel-Gigleux, S., Barre, L., Mulliert, G., Netter, P., Magdalou, J., et al. (2007). Identification of aspartic acid and histidine residues mediating the reaction mechanism and the substrate specificity of the human UDP-glucuronosyltransferases 1A. J Biolog Chem 282:36514–36524.
   PubMed Web of Science ®Google Scholar
• Li, W. H., Gu, Z, Wang, H., Nekrutenko, A. (2001). Evolutionary analyses of the human genome. Nature 409:847–849.
   PubMed Web of Science ®Google Scholar
• Lynch, M., Conery, J. S. (2000). The evolutionary fate and consequences of duplicate genes. Science 290:1151–1155.
   PubMed Web of Science ®Google Scholar
• Mackenzie, P., Little, J.M., Radominska-Pandya, A. (2003). Glucosidation of hyodeoxycholic acid by UDP-glucuronosyltransferase 2B7. Biochem Pharmacol 65:417–421.
   PubMed Web of Science ®Google Scholar
• Mackenzie, P. I. (1995). The UDP glucuronosyltransferase multigene family. In: Hodgson, E., Bend, J. R., Philpot, R. M. (Eds.), Reviews in biochemical toxicology (pp 29–72 ). Raleigh, North Carolina, USA: Toxicology Communications Inc.
   Google Scholar
• Mackenzie, P. I., Rogers, A., Treloar, J., Jorgensen, B. R., Miners, J. O., Meech, R. (2008). Identification of UDP glycosyltransferase 3A1 as a UDP N-acetylglucosaminyltransferase. J Biol Chem 283:36205–36210.
   PubMed Web of Science ®Google Scholar
• MacLusky, N. J., Luine, V. N., Hajszan, T., Leranth, C. (2005). The 17alpha and 17beta isomers of estradiol both induce rapid spine synapse formation in the CA1 hippocampal subfield of ovariectomized female rats. Endocrinology 146:287–293.
   PubMed Web of Science ®Google Scholar
• Marschall, H. U., Green, G., Egestad, B., Sjovall, J. (1988). Isolation of bile acid glucosides and N-acetylglucosaminides from human urine by ion-exchange chromatography and reversed-phase high-performance liquid chromatography. J Chromatogr 452:459–468.
   PubMed Web of Science ®Google Scholar
• Marschall, H. U., Griffiths, W. J., Gotze, U., Zhang, J., Wietholtz, H., Busch, N., et al. (1994). The major metabolites of ursodeoxycholic acid in human urine are conjugated with N-acetylglucosamine. Hepatology 20:845–853.
   PubMed Web of Science ®Google Scholar
• Matern, H., Fiebig, H. H., Matern, S. (1987). Glycoside conjugation in microsomes from hepatic and renal carcinoma of man. Hepatology 7:931–936.
   PubMed Web of Science ®Google Scholar
• Matern, H., Matern, S., Gerok, W. (1984). Formation of bile acid glucosides by a sugar nucleotide-independent glucosyltransferase isolated from human liver microsomes. Proc Natl Acad Sci U S A 81:7036–7040.
   PubMed Web of Science ®Google Scholar
• McClean, J., Nunez, J.L. (2008). 17alpha-estradiol is neuroprotective in male and female rats in a model of early brain injury. Exp Neurol 210:41–50.
   PubMed Web of Science ®Google Scholar
• Miley, M. J., Zielinska, A. K., Keenan, J. E., Bratton, S. M., Radominska-Pandya, A., Redinbo, M. R. (2007). Crystal structure of the cofactor-binding domain of the human phase II drug-metabolism enzyme UDP-glucuronosyltransferase 2B7. J Mol Biol 369:498–511.
   PubMed Web of Science ®Google Scholar
• Niwa, T., Fujita, K., Goto, J., Nambara, T. (1993). Separation and characterization of ursodeoxycholate 7-N-acetylglucosaminides in human urine by high-performance liquid chromatography with fluorescence detection. J Liquid Chromatog Relat Technol 16:2531–2544.
   Web of Science ®Google Scholar
• Patana, A-S., Kurkela, M., Goldman, A., Finel, M. (2007). The human UDP-glucuronosyltransferase: identification of key residues within the nucleotide-sugar binding site. Mol Pharmacol 72:604–611.
   PubMed Web of Science ®Google Scholar
• Paumgartner, G., Beuers, U. (2002). Ursodeoxycholic acid in cholestatic liver disease: mechanisms of action and therapeutic use revisited. Hepatology 36:525–531.
   PubMed Web of Science ®Google Scholar
• Paumgartner, G., Beuers, U. (2004). Mechanisms of action and therapeutic efficacy of ursodeoxycholic acid in cholestatic liver disease. Clin Liver Dis 8:67–81, vi.
   PubMedGoogle Scholar
• Paumgartner, G., Pauletzki, J., Sackmann, M. (1994). Ursodeoxycholic acid treatment of cholesterol gallstone disease. Scand J Gastroenterol Suppl 204:27–31.
   PubMedGoogle Scholar
• Schuetz, E. G., Strom, S., Yasuda, K., Lecureur, V., Assem, M., Brimer, C., et al. (2001). Disrupted bile acid homeostasis reveals an unexpected interaction among nuclear hormone receptors, transporters, and cytochrome P450. Jf Biol Chem 276:39411–39418.
   Google Scholar
• Senafi, S. B., Clarke, D. J., Burchell, B. (1994). Investigation of the substrate specificity of a cloned expressed human bilirubin UDP-glucuronosyltransferase: UDP-sugar specificity and involvement in steroid and xenobiotic glucuronidation. Biochem J 303:233–240.
   PubMed Web of Science ®Google Scholar
• Singh, M., Setalo, G., Jr, Guan, X., Frail, D. E., Toran-Allerand, C. D. (2000). Estrogen-induced activation of the mitogen-activated protein kinase cascade in the cerebral cortex of estrogen receptor-alpha knock-out mice. J Neurosci 20:1694–1700.
   PubMedGoogle Scholar
• Stahl, N., Jurevics, H., Morell, P., Suzuki, K., Popko, B. (1994). Isolation, characterization, and expression of cDNA clones that encode rat UDP-galactose: ceramide galactosyltransferase. J Neurosci Res 38:234–242.
   PubMed Web of Science ®Google Scholar
• Tang, C., Hochman, J. H., Ma, B., Subramanian, R., Vyas, K. P. (2003). Acyl glucuronidation and glucosidation of a new and selective endothelin ET(A) receptor antagonist in human liver microsomes. Drug Metab Dispos 31:37–45.
   PubMed Web of Science ®Google Scholar
• Tang, C., Ma, B. (2005). Glycosidation of an endothelin ET(A) receptor antagonist and diclofenac in human liver microsomes: aglycone-dependent UDP-sugar selectivity. Drug Metab Dispos 33:1796–1802.
   PubMed Web of Science ®Google Scholar
• Toide, K., Terauchi, Y., Fujii, T., Yamazaki, H., Kamataki, T. (2004). Uridine diphosphate sugar-selective conjugation of an aldose reductase inhibitor (AS-3201) by UDP-glucuronosyltransferase 2B subfamily in human liver microsomes. Biochem Pharmacol 67:1269–1278.
   PubMed Web of Science ®Google Scholar
• Toran-Allerand, C. D. (2005). Estrogen and the brain: beyond ER-alpha, ER-beta, and 17beta-estradiol. Ann N Y Acad Sci 1052:136–144.
   PubMed Web of Science ®Google Scholar
• Toran-Allerand, C. D., Tinnikov, A. A., Singh, R. J., Nethrapalli, I. S. (2005). 17{alpha}-estradiol: a brain-active estrogen? Endocrinology 146:3843–3850.
   PubMed Web of Science ®Google Scholar
• Trottier, J., Verreault, M., Grepper, S., Monte, D., Belanger, J., Kaeding, J., et al. (2006). Human UDP-glucuronosyltransferase (UGT)1A3 enzyme conjugates chenodeoxycholic acid in the liver. Hepatology 44:1158–1170.
   PubMed Web of Science ®Google Scholar
• Wells, P. G., Mackenzie, P. I., Chowdhury, J. R., Guillemette, C., Gregory, P. A., Ishii, Y., et al. (2004). Glucuronidation and the UDP-glucuronosyltransferases in health and disease. Drug Metab Dispos 32:281–290.
   PubMed Web of Science ®Google Scholar
• Wolfe, K. (2000). Robustness—it’s not where you think it is. Nat Genet 25:3–4.
   PubMed Web of Science ®Google Scholar
• Xiong, Y., Patana, A-S., Miley, M. J., Zielinska, A. K., Bratton, S. M., Miller, G. P., et al. (2008). The first aspartic acid of the DQxD motif for human UDP-glucuronosyltransferase 1A10 interacts with UDP-glucuronic acid during catalysis. Drug Metab Dispos 36:517–522.
   PubMed Web of Science ®Google Scholar