| Name | UGT1A6 |
|---|---|
| Synonyms | GNT1; UGT 1; UGT1; GNT1; UDPGT; HLUGP; HLUGP 1; HLUGP1… |
| Name | 1-naphthol |
|---|---|
| CAS | 1-naphthalenol |
| PubMed | Abstract | RScore(About this table) | |
|---|---|---|---|
| 10415114 | Senay C, Battaglia E, Chen G, Breton R, Fournel-Gigleux S, Magdalou J, Radominska-Pandya A: Photoaffinity labeling of the aglycon binding site of the recombinant human liver UDP-glucuronosyltransferase UGT1A6 with 7-azido-4-methylcoumarin. Arch Biochem Biophys. 1999 Aug 1;368(1):75-84. Moreover, inhibition was partially prevented by 1-naphthol, a surrogate substrate for the enzyme, or by preincubation with an active-site directed inhibitor, 5'-O-[[(2-decanoylamino-3-phenyl-propyloxycarbonyl) amino]-su lfonyl]-2 ',3'-O-isopropylideneuridine. |
5(0,0,0,5) | Details |
| 10049505 | Iwano H, Yokota H, Ohgiya S, Yuasa A: The significance of amino acid residue Asp446 for enzymatic stability of rat UDP-glucuronosyltransferase UGT1A6. Arch Biochem Biophys. 1999 Mar 1;363(1):116-20. These mutants, except D446K, had catalytic activities toward 1-naphthol and 4-methylumbelliferone. |
4(0,0,0,4) | Details |
| 9750165 | Suleman FG, Abid A, Gradinaru D, Daval JL, Magdalou J, Minn A: Identification of the glucuronosyltransferase isoform UGT1A6 in rat brain and in primary cultures of neurons and astrocytes. Arch Biochem Biophys. 1998 Oct 1;358(1):63-7. The expression of a glucuronosyltransferase (UGT) was investigated in rat brain homogenate and in primary cultures of astrocytes and neurons, by means of model substrates (1-naphthol and 4-methylumbelliferone) assays, Western blot analysis and reverse transcription-polymerase chain reaction (RT-PCR) experiments. |
4(0,0,0,4) | Details |
| 10901286 | Sabolovic N, Magdalou J, Netter P, Abid A: Nonsteroidal anti-inflammatory drugs and phenols glucuronidation in Caco-2 cells: identification of the UDP-glucuronosyltransferases UGT1A6, 1A3 and 2B7. Life Sci. 2000;67(2):185-96. Glucuronidation of phenols (1-naphthol, 4-methylumbelliferone) and nonsteroidal anti-inflammatory drugs (NSAIDs) such as ketoprofen, and carprofen was investigated in human colon carcinoma Caco-2 cell clones. |
3(0,0,0,3) | Details |
| 19023562 | Gradinaru D, Minn AL, Artur Y, Minn A, Heydel JM: Drug metabolizing enzyme expression in rat choroid plexus: effects of in vivo xenobiotics treatment. Arch Toxicol. 2009 Jun;83(6):581-6. Epub 2008 Nov 21. We present the changes in mRNA expression and enzymatic activities of UDP-glucuronosyltransferase, UGT1A6 isoform and NADPH-cytochrome P450 reductase, after in vitro treatment with xenobiotic molecules known to act in the liver as inducers or inhibitors of these drug metabolizing enzymes. Choroidal 1-naphthol glucuronidation activities were significantly induced by 3-MC and PQ administration (354 +/- 85 and 257 +/- 49 vs. 115 +/- 24 nmol/h per mg protein, in control group), whereas the other molecules were without effect. |
3(0,0,0,3) | Details |
| 7827113 | Battaglia E, Elass A, Drake RR, Paul P, Treat S, Magdalou J, Fournel-Gigleux S, Siest G, Vergoten G, Lester R, et al.: Characterization of a new class of inhibitors of the recombinant human liver UDP-glucuronosyltransferase, UGT1*6. Biochim Biophys Acta. 1995 Jan 18;1243(1):9-14. |
3(0,0,0,3) | Details |
| 18004206 | Udomuksorn W, Elliot DJ, Lewis BC, Mackenzie PI, Yoovathaworn K, Miners JO: Influence of mutations associated with Gilbert and Crigler-Najjar type II syndromes on the glucuronidation kinetics of and other UDP-glucuronosyltransferase 1A substrates. Pharmacogenet Genomics. 2007 Dec;17(12):1017-29. This work compared the effects of (a) the individual UGT1A1 mutations on the glucuronidation kinetics 4-methylumbelliferone (4MU) and 1-naphthol (1NP), and (b) the Y486 mutation, which occurs in the conserved carboxyl terminal domain of UGT1A enzymes, on 4MU, 1NP and glucuronidation by UGT1A3, UGT1A6 and UGT1A10. |
2(0,0,0,2) | Details |
| 19487247 | Kerdpin O, Mackenzie PI, Bowalgaha K, Finel M, Miners JO: Influence of N-terminal domain and residues on the substrate selectivities of human UDP-glucuronosyltransferase 1A1, 1A6, 1A9, 2B7, and 2B10. Drug Metab Dispos. 2009 Sep;37(9):1948-55. Epub 2009 Jun 1. The conserved N-terminal domain of UGT1A1, UGT1A6, UGT1A9, and UGT2B7 was mutated to and 34 of UGT2B10 was substituted with and the capacity of the wild-type and mutant proteins to glucuronidate 4MU, 1NP, LTG, TFP, and was characterized. |
2(0,0,0,2) | Details |
| 9990312 | Kobayashi T, Yokota H, Ohgiya S, Iwano H, Yuasa A: UDP-glucuronosyltransferase UGT1A7 induced in rat small intestinal mucosa by oral administration of 2-naphthoflavone. Eur J Biochem. 1998 Dec 15;258(3):948-55. In the rat intestine, UDP-glucuronosyltransferase (UGT) isoforms were highly induced by oral administration of 2-naphthoflavone, as shown by intestinal UGT activity toward 1-naphthol (1-NA). Using UGT1A6 cDNA as a probe, we obtained three types of clones corresponding to UGT1A2, UGT1A6 and UGT1A7, in a ratio of 1:1:8, from a cDNA library constructed from the 2-naphthoflavone-treated rat intestine. |
2(0,0,0,2) | Details |
| 18694909 | Siissalo S, Zhang H, Stilgenbauer E, Kaukonen AM, Hirvonen J, Finel M: The expression of most UDP-glucuronosyltransferases (UGTs) is increased significantly during Caco-2 cell differentiation, whereas UGT1A6 is highly expressed also in undifferentiated cells. Drug Metab Dispos. 2008 Nov;36(11):2331-6. Epub 2008 Aug 11. The mRNA findings were confirmed at the enzyme activity level by measuring the glucuronidation of 1-naphthol, a very good substrate for UGT1A6, as well as that is not glucuronidated by this enzyme. |
2(0,0,0,2) | Details |
| 15802387 | Luukkanen L, Taskinen J, Kurkela M, Kostiainen R, Hirvonen J, Finel M: Kinetic characterization of the 1A subfamily of recombinant human UDP-glucuronosyltransferases. Drug Metab Dispos. 2005 Jul;33(7):1017-26. Epub 2005 Mar 31. The glucuronidation of entacapone by UGT1A9 was inhibited by 1-naphthol in a competitive fashion, with respect to entacapone, and an uncompetitive fashion, with respect to UDP- (UDPGA). Despite the identical primary structure of the C-terminal halves of the UGT1A isoforms, there were marked differences in the respective K (m) values for UDPGA, ranging from 52 microM for UGT1A6 to 1256 microM for UGT1A8. |
2(0,0,0,2) | Details |
| 9464459 | Ullrich D, Munzel PA, Beck-Gschaidmeier S, Schroder M, Bock KW: Drug-metabolizing enzymes in pharyngeal mucosa and in oropharyngeal cancer tissue. Biochem Pharmacol. 1997 Nov 15;54(10):1159-62. Cytochrome P4501A1 (CYP1A1) and the UDP-glucuronosyltransferase isoform UGT1A6 were studied in pharyngeal mucosa and squamous cancer tissue obtained from 27 male subjects (10 healthy nonsmoking volunteers, 10 smokers, and 7 smokers with pharyngeal cancer). |
2(0,0,0,2) | Details |
| 16819192 | Naganuma M, Saruwatari A, Okamura S, Tamura H: and modulate the conjugation of 1-naphthol in Caco-2 cells. Biol Pharm Bull. 2006 Jul;29(7):1476-9. Moreover, and in contrast to the moderate inhibition of UGT activity by and both induce the expression of the UGT1A1 and UGT1A6 genes, revealed by real-time PCR analysis. |
1(0,0,0,1) | Details |
| 7646562 | Abid A, Bouchon I, Siest G, Sabolovic N: Glucuronidation in the Caco-2 human intestinal cell line: induction of UDP-glucuronosyltransferase 1*6. Biochem Pharmacol. 1995 Aug 8;50(4):557-61. Glucuronidation of hydroxylated or carboxylic acid compounds such as 1-naphthol, chloramphenicol, and morphine could be determined in microsomal fractions of Caco-2 cells. The results suggest that several isoforms, including UGT1*6, are expressed in Caco-2 cells. |
1(0,0,0,1) | Details |
| 15499179 | Mizuma T, Momota R, Haga M, Hayashi M: Factors affecting glucuronidation activity in Caco-2 cells. Drug Metab Pharmacokinet. 2004 Apr;19(2):130-4. The factors affecting glucuronidation activity in Caco-2 cells seeded in Transwell (4.7 cm (2)) require clarification to establish an in-vitro system to assess intestinal glucuronidation metabolism for novel drug development. alpha-Naphthol (alpha-NA), a substrate for UGT1A6 in Caco-2 cells, has often been used as a model substrate for gluruonidation. alpha-Naphthol glucuronidation activity increased from 7 to 21 culture days after seeding in Transwell and stabilized after 21 days. |
1(0,0,0,1) | Details |
| 16906435 | Elovaara E, Mikkola J, Stockmann-Juvala H, Luukkanen L, Keski-Hynnila H, Kostiainen R, Pasanen M, Pelkonen O, Vainio H: Polycyclic aromatic hydrocarbon (PAH) metabolizing enzyme activities in human lung, and their inducibility by exposure to naphthalene, phenanthrene, pyrene, chrysene, and benzo (a) pyrene as shown in the rat lung and liver. Arch Toxicol. 2007 Mar;81(3):169-82. Epub 2006 Aug 12. PAH treatment increased the CYP1A-catalyzed activity of pyrene 1-hydroxylation and 7-ethoxyresorufin O-deethylation in rat liver by up to 28- and 279-fold, and in rat lung by up to 22- and 51-fold, respectively. 1-Naphthol (hUGT1A6), 1-hydroxypyrene (hUGT1A6/1A9), and entacapone (hUGT1A9) are markers of PAH-glucuronidating human uridine diphosphate-glucuronosyltransferases (UGT). In human lung (non-smokers), the marker activities of CYP1A1, UGT1A6/1A9, and NQO1 were lower than those in rat lung. |
1(0,0,0,1) | Details |
| 15684482 | Okamura S, Suzuki K, Yanase M, Koizumi M, Tamura HO: The effects of coffee on conjugation reactions in human colon carcinoma cells. Biol Pharm Bull. 2005 Feb;28(2):271-4. After supplementing Caco-2 cultures with both 1-naphthol (200 microM) and various concentrations of coffee, the accumulation of 1-naphthyl and in the growth medium was determined by analytical HPLC over a 24-h period. |
0(0,0,0,0) | Details |
| 9176741 | Le HT, Lamb JG, Franklin MR: Drug metabolizing enzyme induction by benzoquinolines, acridine, and quinacrine; tricyclic aromatic molecules containing a single heterocyclic J Biochem Toxicol. 1996;11(6):297-303. Acridine treatment increased UDP-glucuronosyltransferase activity toward morphine (47%), 1-naphthol (28%), (19%), and (19%). |
0(0,0,0,0) | Details |
| 8161205 | Ouzzine M, Pillot T, Fournel-Gigleux S, Magdalou J, Burchell B, Siest G: Expression and role of the human liver UDP-glucuronosyltransferase UGT1*6 analyzed by specific antibodies raised against a hybrid protein produced in Escherichia coli. Arch Biochem Biophys. 1994 Apr;310(1):196-204. Interestingly, in human kidney microsomes, antibodies revealed a high level of UGT1*6 expression on immunoblot and inhibited 1-naphthol glucuronidation up to 55%, indicating that this isoform is also expressed in kidney and extensively contributes to glucuronidation in this tissue. |
115(1,2,2,5) | Details |
| 11317477 | Ito M, Yamamoto K, Sato H, Fujiyama Y, Bamba T: Inhibitory effect of troglitazone on glucuronidation catalyzed by human -glucuronosyltransferase 1A6. Eur J Clin Pharmacol. 2001 Mar;56(12):893-5. METHODS: Human cDNA-expressed UGT1A6 was coincubated with troglitazone (inhibitor) and 1-naphthol (substrate). |
114(1,2,2,4) | Details |
| 17998297 | Fujiwara R, Nakajima M, Yamanaka H, Katoh M, Yokoi T: Product inhibition of UDP-glucuronosyltransferase (UGT) enzymes by UDP obfuscates the inhibitory effects of UGT substrates. Drug Metab Dispos. 2008 Feb;36(2):361-7. Epub 2007 Nov 12. Substrates that are specific for certain UDP-glucuronosyltransferase (UGT) isoforms are usually used as specific inhibitors to identify UGT isoforms responsible for the glucuronidation of drugs. 1-Naphthol and are probe substrates for human UGT1A6. |
87(1,1,2,2) | Details |
| 17301691 | Kurkela M, Patana AS, Mackenzie PI, Court MH, Tate CG, Hirvonen J, Goldman A, Finel M: Interactions with other human UDP-glucuronosyltransferases attenuate the consequences of the Y485D mutation on the activity and substrate affinity of UGT1A6. Pharmacogenet Genomics. 2007 Feb;17(2):115-26. Using 1-naphthol as the aglycone substrate, the Km of 6YD for the cosubstrate UDP- was about 50 times higher than in UGT1A6. |
85(1,1,1,5) | Details |
| 11437353 | Soars MG, Smith DJ, Riley RJ, Burchell B: Cloning and characterization of a canine UDP-glucuronosyltransferase. Arch Biochem Biophys. 2001 Jul 15;391(2):218-24. The enzyme expressed stably in V79 cells predominantly catalyzed the glucuronidation of simple, planar phenols (e.g., for 1-naphthol, K (m) = 41 microM, V (max) = 0.07 nmol/min/mg protein), a class of compounds extensively glucuronidated by human UGT1A6. |
84(1,1,1,4) | Details |
| 8738480 | Abid A, Sabolovic N, Magdalou J: Inducibility of ethoxyresorufin deethylase and UDP-glucuronosyltransferase activities in two human hepatocarcinoma cell lines KYN-2 and Mz-Hep-1. Cell Biol Toxicol. 1996 Apr;12(2):115-23. Both 1-naphthol glucuronidation and the level of UGT1*6 protein detected by immunoblot and supporting this activity were lowered by DMSO treatment and increased by beta-naphthoflavone treatment in KYN-2 cells. |
81(1,1,1,1) | Details |
| 9180348 | Abid A, Sabolovic N, Magdalou J: Expression and inducibility of UDP-glucuronosyltransferases 1-naphthol in human cultured hepatocytes and hepatocarcinoma cell lines. Life Sci. 1997;60(22):1943-51. Their properties were compared to those of UGT1*6 stably expressed in the V79 cell line (V79UGT1*6), which glucuronidates 1-naphthol preferentially. |
33(0,1,1,3) | Details |
| 10478938 | Gradinaru D, Suleman FG, Leclerc S, Heydel JM, Grillasca JP, Magdalou J, Minn A: UDP-glucuronosyltransferase in the rat olfactory bulb: identification of the UGT1A6 isoform and age-related changes in 1-naphthol glucuronidation. Neurochem Res. 1999 Aug;24(8):995-1000. |
31(0,1,1,1) | Details |
| 20145913 | Donato MT, Montero S, Castell JV, Gomez-Lechon MJ, Lahoz A: Validated assay for studying activity profiles of human liver UGTs after drug exposure: inhibition and induction studies. Anal Bioanal Chem. 2010 Mar;396(6):2251-63. Epub 2010 Feb 10. The assays are based on analysis and quantification by high-performance liquid chromatography-tandem mass spectrometry of glucuronides formed from selective probe substrates, namely, (UGT1A1, 3- 1-naphthol (UGT1A6), propofol (UGT1A9), and naloxone (UGT2B7). |
31(0,1,1,1) | Details |
| 12153725 | Yokota H, Kunimasa Y, Shimoyama Y, Kobayashi T, Matsumoto J, Yuasa A: Effects on extrahepatic UDP-glucuronosyltransferases in hypophysectomized rat. J Biochem. 2002 Aug;132(2):265-70. The mRNA of UGT1A6, which is an isoform contributing to the glucuronidation of various phenolic xenobiotics such as 1-naphthol, were decreased drastically in the liver, kidney, and testis by hypophysectomy. |
31(0,1,1,1) | Details |
| 7786300 | Gschaidmeier H, Seidel A, Burchell B, Bock KW: Formation of mono- and diglucuronides and other glycosides of benzo (a) pyrene-3,6- by V79 cell-expressed human UDP-glucuronosyltransferases of the UGT1 gene complex. Biochem Pharmacol. 1995 May 26;49(11):1601-6. Therefore, mono- and diglucuronide formation of benzo (a) pyrene-3,6- was investigated and compared to that of structurally related 3,6-dihydroxychrysene and simple phenols (1-naphthol and 4-methylumbelliferone) using V79 cell-expressed human UGT1.6 (= P1) and human UGT1.7 (= P4). |
9(0,0,1,4) | Details |
| 8068691 | Lamb JG, Straub P, Tukey RH: Cloning and characterization of cDNAs encoding mouse Ugt1.6 and rabbit UGT1.6: differential induction by 2,3,7,8-tetrachlorodibenzo-p-dioxin. Biochemistry. 1994 Aug 30;33(34):10513-20. The expressed UGTs conjugated small planar phenolic molecules such as 1-naphthol, and 4-methylumbelliferone. |
7(0,0,0,7) | Details |
| 1847492 | Fournel-Gigleux S, Sutherland L, Sabolovic N, Burchell B, Siest G: Stable expression of two human UDP-glucuronosyltransferase cDNAs in V79 cell cultures. Mol Pharmacol. 1991 Feb;39(2):177-83. The established recombinant V79 cell lines stably expressed the UDP-glucuronosyltransferase activities towards 1-naphthol (HLUGP1) and (HLUG25) at levels 10-20-fold higher than with transient expression, and in the range found in human liver. |
7(0,0,1,2) | Details |
| 15788539 | Di Marco A, D'Antoni M, Attaccalite S, Carotenuto P, Laufer R: Determination of drug glucuronidation and UDP-glucuronosyltransferase selectivity using a 96-well radiometric assay. Drug Metab Dispos. 2005 Jun;33(6):812-9. Epub 2005 Mar 23. The major UGT isoforms identified were UGT1A6, UGT1A7, and UGT1A9 for 4-methylumbelliferone; UGT1A6 and UGT1A8 for 1-naphthol; UGT2B7 for naloxone; UGT1A3 and UGT2B7 for ketoprofen; and UGT1A4 for trifluoperazine. |
6(0,0,1,1) | Details |
| 9429234 | Ciotti M, Marrone A, Potter C, Owens IS: Genetic polymorphism in the human UGT1A6 (planar UDP-glucuronosyltransferase: pharmacological implications. Pharmacogenetics. 1997 Dec;7(6):485-95. UGT1A6*2 (181 A+ and 184S+) metabolized 4-tert-butylphenol, 3-ethylphenol/4-ethylphenol, butylated anisole and butylated toluene, with the pH 6.4 preference, at only 27-75% of the rate of the wild-type isozyme whereas 1-naphthol, 3-iodophenol, 7-hydroxycoumarin, and 7--4-methylcoumarin were metabolized at essentially the normal level. |
6(0,0,0,6) | Details |