development of an in vitro screening model for the biosynthesis of ...

development of an in vitro screening model for the biosynthesis of ... development of an in vitro screening model for the biosynthesis of ...

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of the glucuronide of ketoprofen enantiomers to human serum albumin. Biochem Pharmacol 48:1693–1699. Dubois N, Lapicque F, Maurice MH, Pritchard M, Fournel-Gigleux S, Magdalou J, Abiteboul M, Siest G, and Netter P (1993) In vitro irreversible binding of ketoprofen glucuronide to plasma proteins. Drug Metab Dispos 21:617–623. Ebner T, Heinzel G, Prox A, Beschke K, and Wachsmuth H (1999) Disposition and chemical stability of telmisartan 1-O-acyl glucuronide. Drug Metab Dispos 27:1143–1149. Faed EM (1984) Properties of acyl glucuronides: implications for studies of the pharmacokinetics and metabolism of acidic drugs. Drug Metab Dispos 15:1213–1249. Hasegawa J, Smith PC, and Benet LZ (1982) Apparent intramolecular acyl migration of zomepirac glucuronide. Drug Metab Dispos 10:469–473. Hayball JP, Nation LR, and Bochner F (1992) Stereoselective interactions of ketoprofen glucuronides with human plasma protein and serum albumin. Biochem Pharmacol 44:291–299. Hyneck ML, Smith PC, Munafo A, McDonagh FA, and Benet LZ (1988a) Disposition and irreversible plasma protein binding of Tolmetin in humans. Clin Pharmacol Ther 44:107– 114. Hyneck ML, Munafo A, and Benet LZ (1988b) Effect of pH on acyl migration and hydrolysis of tolmetin glucuronide. Drug Metab Dispos 16:322–324. Kretz-Rommel A and Boelsterli URSA (1994) Mechanism of covalent adduct formation of Diclofenac to rat hepatic microsomal proteins. Retention of the glucuronic acid moiety in the adduct. Drug Metab Dispos 22:956–961. Mizuma T, Benet LZ, and Lin ET (1999) Interaction of human serum albumin with Furosemide glucuronide: a role of albumin in isomerization, hydrolysis, reversible binding and irreversible binding of a 1-O-acyl glucuronide metabolite. Biopharm Drug Dispos 20:131–136. Munafo A, McDonagh AF, Smith PC, and Benet LZ (1989) Irreversible binding of Tolmetin glucuronic acid esters to albumin in vitro. Pharm Res 7:21–27. Ojingwa JC, Spahn-Langguth H, and Benet LZ (1988) Studies of Tolmetin reversible and irreversible binding to proteins via its glucuronide conjugates. Pharm Res 5 (Suppl):S214. Ojingwa JC, Spahn-Langguth H, and Benet LZ (1994) Irreversible binding of tolmetin to macromolecules via its glucuronide: binding to blood constituents, tissue homogenates and subcellular fractions in vitro. Xenobiotica 24:495–506. IN VITRO ASSESSMENT OF ACYL GLUCURONIDE REACTIVITY 413 Park BK, Coleman JW, and Kitteringham NR (1987) Drug disposition and drug hypersensitivity. Biochem Pharmacol 36:581–590. Presle N, Lapicque F, Fournel-Gigleux S, Magdalou J, and Netter P (1996) Stereoselective irreversible binding of ketoprofen glucuronides to albumin. Characterization of the site and the mechanism. Drug Metab Dispos 24:1050–1057. Riley RJ and Leeder JS (1995) In vitro analysis of metabolic predisposition to drug hypersensitivity reactions. Clin Exp Immunol 99:1–6. Smith PC, Benet LZ, and McDonagh AF (1990) Covalent binding of zomepirac glucuronide to proteins: evidence for a Shiff base mechanism. Drug Metab Dispos 18:639–644. Smith PC and Liu JH (1993) Covalent binding of suprofen acyl glucuronide to albumin. In Vitro Xenobiotica 23:337–348. Smith PC, McDonagh AF, and Benet LZ (1986) Irreversible binding of zomepirac to plasma protein in vitro and in vivo. J Clin Invest 77:934–939. Smith PC, Song WQ, and Rodriguez RJ (1992) Covalent binding of etodolac acyl glucuronide to albumin in vitro. Drug Metab Dispos 20:962–965. Spahn-Langguth H and Benet LZ (1992) Acyl glucuronides revisited: is the glucuronidation process a toxification as well as a detoxification mechanism? Drug Metab Rev 24:5–48. Spahn-Langguth H, Dahms M, and Hermening A (1996) Acyl glucuronides. Covalent binding and its potential relevance. Adv Exp Med Biol 387:313–328. Sidelmann U, Hansen SH, Gvaghan C, Nicholls AW, Carless HAJ, Lindon JC, Wilson ID, and Nicholson JK (1996) Development of a simple liquid chromatographic method for the separation of mixtures of positional isomers and anomers of synthetic 2-, 3- and 4-fluorobenzoic acid glucuronides formed via acyl migration reactions. J chromatogr 685: 113–122. Volland C, Sun H, Dammeyer J, and Benet LZ (1991) Stereoselective degradation of the Fenoprofen acyl glucuronide enantiomers and irreversible binding to plasma protein. Drug Metab Dispos 19:1080–1086. Williams AM and Dickinson RG (1994) Studies on the reactivity of acyl glucuronides-IV. Modulations of reversible and covalent interaction of diflunisal acyl glucuronide and its isomers with human plasma protein in vitro. Biochem Pharmacol 47:457–467. Downloaded from dmd.aspetjournals.org by guest on May 29, 2013

<strong>of</strong> <strong>the</strong> glucuronide <strong>of</strong> ketopr<strong>of</strong>en en<strong>an</strong>tiomers to hum<strong>an</strong> serum album<strong>in</strong>. Biochem Pharmacol<br />

48:1693–1699.<br />

Dubois N, Lapicque F, Maurice MH, Pritchard M, Fournel-Gigleux S, Magdalou J, Abiteboul M,<br />

Siest G, <strong>an</strong>d Netter P (1993) In <strong>vitro</strong> irreversible b<strong>in</strong>d<strong>in</strong>g <strong>of</strong> ketopr<strong>of</strong>en glucuronide to plasma<br />

prote<strong>in</strong>s. Drug Metab Dispos 21:617–623.<br />

Ebner T, He<strong>in</strong>zel G, Prox A, Beschke K, <strong>an</strong>d Wachsmuth H (1999) Disposition <strong>an</strong>d chemical<br />

stability <strong>of</strong> telmisart<strong>an</strong> 1-O-acyl glucuronide. Drug Metab Dispos 27:1143–1149.<br />

Faed EM (1984) Properties <strong>of</strong> acyl glucuronides: implications <strong>for</strong> studies <strong>of</strong> <strong>the</strong> pharmacok<strong>in</strong>etics<br />

<strong>an</strong>d metabolism <strong>of</strong> acidic drugs. Drug Metab Dispos 15:1213–1249.<br />

Hasegawa J, Smith PC, <strong>an</strong>d Benet LZ (1982) Apparent <strong>in</strong>tramolecular acyl migration <strong>of</strong><br />

zomepirac glucuronide. Drug Metab Dispos 10:469–473.<br />

Hayball JP, Nation LR, <strong>an</strong>d Bochner F (1992) Stereoselective <strong>in</strong>teractions <strong>of</strong> ketopr<strong>of</strong>en glucuronides<br />

with hum<strong>an</strong> plasma prote<strong>in</strong> <strong>an</strong>d serum album<strong>in</strong>. Biochem Pharmacol 44:291–299.<br />

Hyneck ML, Smith PC, Munafo A, McDonagh FA, <strong>an</strong>d Benet LZ (1988a) Disposition <strong>an</strong>d<br />

irreversible plasma prote<strong>in</strong> b<strong>in</strong>d<strong>in</strong>g <strong>of</strong> Tolmet<strong>in</strong> <strong>in</strong> hum<strong>an</strong>s. Cl<strong>in</strong> Pharmacol Ther 44:107–<br />

114.<br />

Hyneck ML, Munafo A, <strong>an</strong>d Benet LZ (1988b) Effect <strong>of</strong> pH on acyl migration <strong>an</strong>d hydrolysis<br />

<strong>of</strong> tolmet<strong>in</strong> glucuronide. Drug Metab Dispos 16:322–324.<br />

Kretz-Rommel A <strong>an</strong>d Boelsterli URSA (1994) Mech<strong>an</strong>ism <strong>of</strong> covalent adduct <strong>for</strong>mation <strong>of</strong><br />

Dicl<strong>of</strong>enac to rat hepatic microsomal prote<strong>in</strong>s. Retention <strong>of</strong> <strong>the</strong> glucuronic acid moiety <strong>in</strong> <strong>the</strong><br />

adduct. Drug Metab Dispos 22:956–961.<br />

Mizuma T, Benet LZ, <strong>an</strong>d L<strong>in</strong> ET (1999) Interaction <strong>of</strong> hum<strong>an</strong> serum album<strong>in</strong> with Furosemide<br />

glucuronide: a role <strong>of</strong> album<strong>in</strong> <strong>in</strong> isomerization, hydrolysis, reversible b<strong>in</strong>d<strong>in</strong>g <strong>an</strong>d irreversible<br />

b<strong>in</strong>d<strong>in</strong>g <strong>of</strong> a 1-O-acyl glucuronide metabolite. Biopharm Drug Dispos 20:131–136.<br />

Munafo A, McDonagh AF, Smith PC, <strong>an</strong>d Benet LZ (1989) Irreversible b<strong>in</strong>d<strong>in</strong>g <strong>of</strong> Tolmet<strong>in</strong><br />

glucuronic acid esters to album<strong>in</strong> <strong>in</strong> <strong>vitro</strong>. Pharm Res 7:21–27.<br />

Oj<strong>in</strong>gwa JC, Spahn-L<strong>an</strong>gguth H, <strong>an</strong>d Benet LZ (1988) Studies <strong>of</strong> Tolmet<strong>in</strong> reversible <strong>an</strong>d<br />

irreversible b<strong>in</strong>d<strong>in</strong>g to prote<strong>in</strong>s via its glucuronide conjugates. Pharm Res 5 (Suppl):S214.<br />

Oj<strong>in</strong>gwa JC, Spahn-L<strong>an</strong>gguth H, <strong>an</strong>d Benet LZ (1994) Irreversible b<strong>in</strong>d<strong>in</strong>g <strong>of</strong> tolmet<strong>in</strong> to<br />

macromolecules via its glucuronide: b<strong>in</strong>d<strong>in</strong>g to blood constituents, tissue homogenates <strong>an</strong>d<br />

subcellular fractions <strong>in</strong> <strong>vitro</strong>. Xenobiotica 24:495–506.<br />

IN VITRO ASSESSMENT OF ACYL GLUCURONIDE REACTIVITY<br />

413<br />

Park BK, Colem<strong>an</strong> JW, <strong>an</strong>d Kitter<strong>in</strong>gham NR (1987) Drug disposition <strong>an</strong>d drug hypersensitivity.<br />

Biochem Pharmacol 36:581–590.<br />

Presle N, Lapicque F, Fournel-Gigleux S, Magdalou J, <strong>an</strong>d Netter P (1996) Stereoselective<br />

irreversible b<strong>in</strong>d<strong>in</strong>g <strong>of</strong> ketopr<strong>of</strong>en glucuronides to album<strong>in</strong>. Characterization <strong>of</strong> <strong>the</strong> site <strong>an</strong>d <strong>the</strong><br />

mech<strong>an</strong>ism. Drug Metab Dispos 24:1050–1057.<br />

Riley RJ <strong>an</strong>d Leeder JS (1995) In <strong>vitro</strong> <strong>an</strong>alysis <strong>of</strong> metabolic predisposition to drug hypersensitivity<br />

reactions. Cl<strong>in</strong> Exp Immunol 99:1–6.<br />

Smith PC, Benet LZ, <strong>an</strong>d McDonagh AF (1990) Covalent b<strong>in</strong>d<strong>in</strong>g <strong>of</strong> zomepirac glucuronide to<br />

prote<strong>in</strong>s: evidence <strong>for</strong> a Shiff base mech<strong>an</strong>ism. Drug Metab Dispos 18:639–644.<br />

Smith PC <strong>an</strong>d Liu JH (1993) Covalent b<strong>in</strong>d<strong>in</strong>g <strong>of</strong> supr<strong>of</strong>en acyl glucuronide to album<strong>in</strong>. In Vitro<br />

Xenobiotica 23:337–348.<br />

Smith PC, McDonagh AF, <strong>an</strong>d Benet LZ (1986) Irreversible b<strong>in</strong>d<strong>in</strong>g <strong>of</strong> zomepirac to plasma<br />

prote<strong>in</strong> <strong>in</strong> <strong>vitro</strong> <strong>an</strong>d <strong>in</strong> vivo. J Cl<strong>in</strong> Invest 77:934–939.<br />

Smith PC, Song WQ, <strong>an</strong>d Rodriguez RJ (1992) Covalent b<strong>in</strong>d<strong>in</strong>g <strong>of</strong> etodolac acyl glucuronide<br />

to album<strong>in</strong> <strong>in</strong> <strong>vitro</strong>. Drug Metab Dispos 20:962–965.<br />

Spahn-L<strong>an</strong>gguth H <strong>an</strong>d Benet LZ (1992) Acyl glucuronides revisited: is <strong>the</strong> glucuronidation<br />

process a toxification as well as a detoxification mech<strong>an</strong>ism? Drug Metab Rev 24:5–48.<br />

Spahn-L<strong>an</strong>gguth H, Dahms M, <strong>an</strong>d Hermen<strong>in</strong>g A (1996) Acyl glucuronides. Covalent b<strong>in</strong>d<strong>in</strong>g<br />

<strong>an</strong>d its potential relev<strong>an</strong>ce. Adv Exp Med Biol 387:313–328.<br />

Sidelm<strong>an</strong>n U, H<strong>an</strong>sen SH, Gvagh<strong>an</strong> C, Nicholls AW, Carless HAJ, L<strong>in</strong>don JC, Wilson ID,<br />

<strong>an</strong>d Nicholson JK (1996) Development <strong>of</strong> a simple liquid chromatographic method <strong>for</strong> <strong>the</strong><br />

separation <strong>of</strong> mixtures <strong>of</strong> positional isomers <strong>an</strong>d <strong>an</strong>omers <strong>of</strong> syn<strong>the</strong>tic 2-, 3- <strong>an</strong>d 4-fluorobenzoic<br />

acid glucuronides <strong>for</strong>med via acyl migration reactions. J chromatogr 685:<br />

113–122.<br />

Voll<strong>an</strong>d C, Sun H, Dammeyer J, <strong>an</strong>d Benet LZ (1991) Stereoselective degradation <strong>of</strong> <strong>the</strong><br />

Fenopr<strong>of</strong>en acyl glucuronide en<strong>an</strong>tiomers <strong>an</strong>d irreversible b<strong>in</strong>d<strong>in</strong>g to plasma prote<strong>in</strong>. Drug<br />

Metab Dispos 19:1080–1086.<br />

Williams AM <strong>an</strong>d Dick<strong>in</strong>son RG (1994) Studies on <strong>the</strong> reactivity <strong>of</strong> acyl glucuronides-IV.<br />

Modulations <strong>of</strong> reversible <strong>an</strong>d covalent <strong>in</strong>teraction <strong>of</strong> diflunisal acyl glucuronide <strong>an</strong>d its<br />

isomers with hum<strong>an</strong> plasma prote<strong>in</strong> <strong>in</strong> <strong>vitro</strong>. Biochem Pharmacol 47:457–467.<br />

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