Evaluation of 3-O-methylfluorescein as a selective fluorometric substrate for CYP2C19 in human liver microsomes

Drug Metabolism and Disposition

Volumn 35, Issue 6, 2007, Pages 841-847

  Sudsakorn, Sirimas ^a   Skell, Jeffrey ^a   Williams, David A ^b   O'Shea, Thomas J ^a   Liu, Hanlan ^a  

^a GENZYME CORPORATION   (United States)

^b MASSACHUSETTS COLLEGE OF PHARMACY AND HEALTH SCIENCES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3 O METHYLFLUORESCEIN; CYTOCHROME P450 1A2; CYTOCHROME P450 2C19; CYTOCHROME P450 2C9; FLUORESCEIN DERIVATIVE; FURAFYLLINE; SULFAPHENAZOLE; TICLOPIDINE; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; DEMETHYLATION; ENZYME KINETICS; ENZYME SUBSTRATE; FLUOROMETRY; HUMAN; HUMAN CELL; IC 50; LIQUID CHROMATOGRAPHY; LIVER MICROSOME; MASS SPECTROMETRY; PRIORITY JOURNAL;

ARYL HYDROCARBON HYDROXYLASES; FLUORESCEINS; FLUOROMETRY; HUMANS; MEPHENYTOIN; MICROSOMES, LIVER; MIXED FUNCTION OXYGENASES;

EID: 34249013833     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.106.014472     Document Type: Article

References (42)

1. Andersson TB, Bredberg E, Ericsson H, and Sjöberg H (2004) An evaluation of the in vitro metabolism data for predicting the clearance and drug-drug interaction potential of CYP2C9 substrates. Drug Metab Dispos 32:715-721.
2. Atkinson A, Kenny JR, and Grime K (2005) Automated assessment of time-dependent inhibition of human cytochrome P450 enzymes using liquid chromatography-tandem mass spectrometry analysis. Drug Metab Dispos 33:1637-1647.
3. Bapiro TE, Egnell A, Hasler JA, and Masimirembwa CM (2001) Application of higher throughput screening (HTS) inhibition assays to evaluate the interaction of antiparasitic drugs with cytochrome P450S. Drug Metab Dispos 29:30-35.
4. Chauret N, Dobbs B, Lackman RL, Bateman K, Nicoll-Griffith DA, Stresser DM, Ackermann JM, Turner SD, Miller VP, and Crespi CL (2001) The use of 3-[2-(N,N-diethyl-N-methylammonium)ethyl]-7-methoxy-4- methylcoumarin (AMMC) as a specific CYP2D6 probe in human liver microsomes. Drug Metab Dispos 29:1196-1200.
5. Chauret N, Tremblay N, Lackman RL, Gauthier JY, Silva JM, Marois J, Yergey JA, and Nicoll-Griffith DA (1999) Description of a 96-well plate assay to measure cytochrome P4503A inhibition in human liver microsomes using a selective fluorescent probe. Anal Biochem 276:215-226.
6. Cohen LH, Remley MJ, Raunig D, and Vaz AND (2003) In vitro drug interaction of cytochrome P450: an evaluation of fluorogenic to conventional substrates. Drug Metab Dispos 31:1005-1015.
7. Crespi CL, Miller VP, and Penman BW (1997) Microtiter plate assays for inhibition of human drug metabolizing cytochromes P450. Anal Biochem 248:188-190.
8. Dierks EA, Stams KR, Lim H, Cornelius G, Zhang H, and Ball SE (2001) A method for the simultaneous evaluation of the activities of seven major human drug-metabolizing cytochrome P450s using an in vitro cocktail of probe substrates and fast gradient liquid chromatography tandem mass spectrometry. Drug Metab Dispos 29:23-29.
9. Donahue SR, Flockhart DA, Abernethy DR, and Ko JW (1997) Ticlopidine inhibition of phenytoin metabolism mediated by potent inhibition of CYP2C19. Clin Pharmacol Ther 62:572-577.
10. Donato MT, Jiménez N, Castell JV, and Gómez-Lechón J (2004) Fluorescence-based assays for screening nine cytochrome P450 (P450) activities in intact cells expressing individual human P450 enzymes. Drug Metab Dispos 32:699-706.
11. Ghosal A, Hapangama N, Yuan Y, Lu X, Horne D, Patrick JE, and Zbaida S (2003) Rapid determination of enzyme activities of recombinant human cytochromes P450, human liver microsomes and hepatocytes. Biopharm Drug Dispos 24:375-384.
12. Glue P, Banfield CR, Perhach JL, Mather GG, Racha JK, and Levy RH (1997) Pharmacokinetic interaction with felbamate. Clin Pharmacokinet 33:214-224.
13. Ha-Duong N, Dijols S, Macherey A, Goldstein JA, Dansette PM, and Mansuy D (2001) Ticlopidine as a selective mechanism-based inhibitor of human cytochrome P450 2C19. Biochemistry 40:12112-12122.
14. Ito K, Iwatsubo T, Kanamitsu S, Ueda K, Suzuki H, and Sugiyama Y (1998) Prediction of pharmacokinetic alterations caused by drug-drug interaction: metabolic interaction in the liver. Pharmacol Rev 50:387-411.
15. Jurima-Romet M, Crawford K, Cyr T, and Inaba T (1994) In vitro inhibition by macrolide antibiotics and azole antifungals. Drug Metab Dispos 22:849-857.
16. Ko JW, Desta Z, and Flockhart DA (1998) Evaluation of omeprazole and lansoprazole as inhibitors of cytochrome P450 isoforms. Drug Metab Dispos 26:775-778.
17. Ko JW, Desta Z, Soukhova NV, Tracy T, and Flockhart DA (2000) In vitro inhibition of the cytochrome P450 (CYP) system by the antiplatelet drug ticlopidine: potent effect on CYP2C19 and CYP2D6. Br J Clin Pharmacol 49:343-351.
18. Ko JW, Sukhova N, Thacker D, Chen P, and Flockhart DA (1997) Evaluation of omeprazole and lansoprazole as inhibitors of cytochrome P450 isoforms. Drug Metab Dispos 25:853-862.
19. Kobayashi K, Yamamoto T, Chiba K, Tani M, Ishizaki T, and Kuroiwa Y (1995) The effects of selective serotonin reuptake inhibitors and their metabolites on S-mephenytoin 4′-hydroxylase activity in human liver microsomes. Br J Clin Pharmacol 40:481-485.
20. Li X, Andersson T, Ahlstrom M, and Weidolf L (2004) Comparison of inhibitory effects of the proton pump-inhibiting drugs omeprazole, esomeprazole, lansoprazole, pantoprazole, and rabeprazole on human cytochrome P450 activities. Drug Metab Dispos 32:821-827.
21. Lin JH and Lu AYH (1998) Inhibition and induction of cytochrome P450 and the clinical implications. Clin Pharmacokinet 35:361-390.
22. Mayer RT, Dolence EK, and Mayer GE (2007) A real-time fluorescence assay for measuring N-dealkylation. Drug Metab Dispos 35:103-109.
23. Michalets EL (1998) Update: clinically significant cytochrome P-450 drug interactions. Pharmacotherapy 18:84-112.
24. Motulsky HJ and Ransnas LA (1987) Fitting curves to data using nonlinear regression: a practical and nonmathematical review. FASEB J 1:365-374.
25. Nicoll-Griffith DA, Chauret N, Houle R, Day SH, D'Antoni M, and Silva JM (2004) Use of a benzyloxy-substituted lactone cyclooxygenase-2 inhibitor as a selective fluorescent probe for CYP3A activity in primary cultured rat and human hepatocytes. Drug Metab Dispos 32:1509-1515.
26. Onderwater RCA, Venhorst J, Commandeur JNM, and Vermeulen NPE (1999) Design, synthesis, and characterization of 7-methoxy-4-(aminomethyl)-coumarin as a novel and selective cytochrome P450 2D6 substrate suitable for high-throughput screening. Chem Res Toxicol 12:555-559.
27. Somogyi A and Muirhead M (1987) Pharmacokinetic interactions of cimetidine 1987. Clin Pharmacokinet 12:321-366.
28. Stresser DM, Blanchard AP, Turner SD, Erve JCL, Dandeneau AA, Miller VP, and Crespi CL (2000) Substrate-dependent modulation of CYP3A4 catalytic activity: analysis of 27 test compounds with four fluorometric substrates. Drug Metab Dispos 28:1440-1448.
29. Stresser DM, Turner SD, Blanchard AP, Miller VP, and Crespi CL (2002) Cytochrome P450 fluorometric substrates: identification of isoform-selective probes for rat CYP2D2 and human CYP3A4. Drug Metab Dispos 30:845-852.
30. Suzuki H, Kneller MB, Haining RL, Trager WF, and Rettie AE (2002) (+)-N-3-benzyl-nirvanol and (-)-N-3-benzyl-phenobarbital: new potent and selective in vitro inhibitors of CYP2C19. Drug Metab Dispos 30:235-239.
31. Tracy TS and Hummel MA (2004) Modeling kinetic data from in vitro drug metabolism enzyme experiments. Drug Metab Rev 36:231-242.
32. Tucker GT, Houston JB, and Huang SM (2001) Optimizing drug development: strategies to assess drug metabolism/transporter interaction potential - toward a consensus. Pharm Res (NY) 18:1071-1080.
33. Venhorst J, Onderwater RCA, Meerman JHN, Commandeur JNM, and Vermeulen NPE (2000a) Influence of N-substitution of 7-methoxy-4-(aminomethyl)- coumarin on cytochrome P450 metabolism and selectivity. Drug Metab Dispos 28:1524-1532.
34. Venhorst J, Onderwater RCA, Meerman JHN, Vermeulen NPE, and Commandeur JNM (2000b) Evaluation of a novel high-throughput assay for cytochrome P450 2D6 using 7-methoxy-4-(aminomethyl)-coumarin. Eur J Pharm Sci 12:151-158.
35. Walsky RL and Obach RS (2004) Validated assays for human cytochrome P450 activities. Drug Metab Dispos 32:647-660.
36. Weaver R, Graham KS, Beattie IG, and Riley RJ (2003) Cytochrome P450 inhibition using recombinant proteins and mass spectrometry/multiple reaction monitoring technology in a cassette incubation. Drug Metab Dispos 31:955-966.
37. Wienkers LC (2002) Factors confounding the successful extrapolation of in vitro CYP3A inhibition information in the in vivo condition. Eur J Pharm Sci 15:239-242.
38. Williams DA (2002) Drug metabolism, in Foye's Principles of Medicinal Chemistry (Lemke TL, Williams DA eds) ed 5, pp 174-233, Philadelphia, Williams & Wilkins.
39. Yamamoto T, Suzuki A, and Kohno Y (2003) High-throughput screening to estimate single or multiple enzymes involved in drug metabolism: microtitre plate assay using a combination of recombinant CYP2D6 and human liver microsomes. Xenobiotica 33:823-839.
40. Yan Z and Caldwell GW (2001) Metabolic profiling, and cytochrome P450 inhibition & induction in drug discovery. Curr Topics Med Chem 1:403-425.
41. Yao C, Kunze KL, Trager WF, Kharasch ED, and Levy RH (2003) Comparison of in vitro and in vivo inhibition potencies of fluvoxamine toward CYP2C19. Drug Metab Dispos 31:565-571.
42. Yu K, Yim D, Cho J, Park S, Park J, Lee K, Jang I, Yi S, Bae K, and Shin S (2001) Effect of meprazole on the pharmacokinetics of moclobemide according to the genetic polymorphism of CYP2C19. Clin Pharmacol Ther 69:266-273.