Accumulation and metabolism of drugs and CYP probe substrates in zebrafish larvae

Xenobiotica

Volumn 40, Issue 8, 2010, Pages 547-557

  Alderton, W ^a   Berghmans, S ^a   Butler, P ^b   Chassaing, H ^b   Fleming, A ^a,c   Golder, Z ^a   Richards, F ^a,d   Gardner, I ^b  

^a SUMMIT PLC   (United Kingdom)

^b PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United Kingdom)

^c UNIVERSITY OF CAMBRIDGE   (United Kingdom)

^d ANGLIA RUSKIN UNIVERSITY   (United Kingdom)

Author keywords

Chlorpromazine; Cisapride; Dextromethorphan; Verapamil

Indexed keywords

AMFEBUTAMONE; AMODIAQUINE; CHLORPROMAZINE; CISAPRIDE; CYTOCHROME P450; DEXTROMETHORPHAN; DEXTRORPHAN; DICLOFENAC; DRUG METABOLITE; FELODIPINE; MEPHENYTOIN; MIDAZOLAM; PARACETAMOL; PHENACETIN; TACRINE; TESTOSTERONE; VERAPAMIL; DRUG;

ARTICLE; CONTROLLED STUDY; DEALKYLATION; DEMETHYLATION; DRUG ACCUMULATION; DRUG GLUCURONIDATION; DRUG METABOLISM; DRUG OXIDATION; DRUG SAFETY; DRUG STRUCTURE; DRUG SULFATION; ENZYME SUBSTRATE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOTOPE LABELING; LARVA; NONHUMAN; QUANTITATIVE ANALYSIS; ZEBRA FISH; ANIMAL; ENZYME SPECIFICITY; GROWTH, DEVELOPMENT AND AGING; METABOLISM; PHARMACOKINETICS;

DANIO RERIO; MAMMALIA;

ANIMALS; CHLORPROMAZINE; CISAPRIDE; CYTOCHROME P-450 ENZYME SYSTEM; LARVA; PHARMACEUTICAL PREPARATIONS; PHARMACOKINETICS; SUBSTRATE SPECIFICITY; VERAPAMIL; ZEBRAFISH;

EID: 77954642090     PISSN: 00498254     EISSN: 13665928     Source Type: Journal    
DOI: 10.3109/00498254.2010.493960     Document Type: Article

References (43)

1. Anichtchik O, Sallinen V, Peitsaro N, Panula P. (2006). Distinct structure and activity of monoamine oxidase in the brain of zebrafish (Danio rerio). J Comp Neurol 498:593-610.
2. Barros TP, Reynolds HR, Clarke S, Roach AG, Alderton W, Berghmans S. (2008). Zebrafish: An automated high content screening platform for safety pharmacology. J Pharmacol Toxicol Methods 58:150.
3. Berghmans S, Butler P, Goldsmith P, Waldron G, Gardner I, Golder Z, Richards FM, Kimber G, Roach A, Alderton W, Fleming A. (2008). Zebrafish based assays for the assessment of cardiac, visual and gut function-potential safety screens for early drug discovery. J Pharmacol Toxicol Methods 58:59-68.
4. Brookes LG, Forrest IS. (1973). Intra-species variation in chlorpromazine metabolism. Res Commun Chem Pathol Pharmacol 5:741-758
5. Choudhary D, Jansson I, Sarfarazi M, Schenkman JB. (2004). Xenobiotic-metabolizing cytochromes P450 in ontogeny: evolving perspective. Drug Metab Rev 36:549-568
6. Corley-Smith GE, Su HT, Wang-Buhler JL, Tseng HP, Hu CH, Hoang T, Chung WG, Buhler DR. (2006). CYP3C1, the first member of a new cytochrome P450 subfamily found in zebrafish (Danio rerio). Biochem Biophys Res Commun 340:1039-1046
7. Dasmahapatra AK, Doucet HL, Bhattacharyya C, Carvan MJ 3rd. (2001). Developmental expression of alcohol dehydrogenase (ADH3) in zebrafish (Danio rerio). Biochem Biophys Res Commun 286:1082-1086
8. Doshna C, Benbow J, Depasquale M, Okerberg C, Turnquist S, Stedman D, Chapin B, Sivaraman L, Waldron G, Navetta K, Brady J, Banker M, Casimiro-Garcia A, Hill A, Jones M, Ball J, Aleo M. (2009). Multi-phase analysis of uptake and toxicity in Zebrafish: relationship to compound physical-chemical properties. Toxicol Sci 108(S-1):78.
9. Eichelbaum M, Ende M, Remberg G, Schomerus M, Dengler HJ. (1979). The metabolism of DL-[14C]verapamil in man. Drug Metab Dispos 7:145-148
10. Eimon PM, Rubinstein AL. (2009). The use of in vivo zebrafish assays in drug toxicity screening. Expert Opin Drug Metab Toxicol 5:393-401.
11. Goldstone JV, Jonsson ME, Behrendt L, Woodin BR, Jenny MJ, Nelson DR, Stegeman JJ. (2009). Cytochrome P450 1D1: a novel CYP1A-related gene that is not transcriptionally activated by PCB126 or TCDD. Arch Biochem Biophys 482: 7-16.
12. Green DE, Forrest IS. (1966). In vivo metabolism of chlorpromazine. Can Psychiatr Assoc J 11:299-302.
13. Gu X, Xu F, Song W, Wang X, Hu P, Yang Y, Gao X, Zhao Q. (2006). A novel cytochrome P450, zebrafish Cyp26D1, is involved in metabolism of all-trans retinoic acid. Mol Endocrinol 20:1661-1672
14. Hollosi L, Kettrup A, Schramm KW. (2004). MMSPE-RP-HPLC method for the simultaneous determination of methimazole and selected metabolites in fish homogenates. J Pharm Biomed Anal 36:921-924
15. Iannelli MA, Marcucci I, Vittozzi L. (1994). Xenobiotic-metabolizing enzyme systems in test fish. V. Comparative studies of liver microsomal glucuronyltransferases. Ecotoxicol Environ Saf 28:172-180
16. Joensson M, Orrego R, Woodbin B, Goldstone J, Stegeman J. (2007). Basal and 3,3′,4,4′,5-pentachlorobiphenyl-induced expression of cytochrome P450 1A, 1B and 1C genes in zebrafish. Toxicol Appl Pharmacol 221:29-41.
17. Jones H, Panter G, Hutchinson T, Chipman J. (2008). Cytochromes P450 and glucuronyl transferases in zebrafish larvae. Toxicology 253:12.
18. Jones H, Trollope H, Hutchinson T, Panter G, Chipman J. (2009). Assessment of an ibuprofen metabolism by zebrafish larvae, using liquid chromatography-mass spectrometry (LC-MS). Toxicology 262:14-15.
19. Kantharaj E, Tuytelaars A, Proost PE, Ongel Z, van Assouw HP, Gilissen RA. (2003). Simultaneous measurement of drug metabolic stability and identification of metabolites using iontrap mass spectrometry. Rapid Commun Mass Spectrom 17: 661-668
20. Kimmel CB, Ballard WW, Kimmel SR, Ullmann B, Schilling TF. (1995). Stages of embryonic development of the zebrafish. Dev Dyn 203:253-310.
21. Lassen N, Estey T, Tanguay RL, Pappa A, Reimers MJ, Vasiliou V. (2005). Molecular cloning, baculovirus expression, and tissue distribution of the zebrafish aldehyde dehydrogenase 2. Drug Metab Dispos 33:649-656
22. Lieschke GJ, Currie PD. (2007). Animal models of human disease: zebrafish swim into view. Nat Rev Genet 8:353-367.
23. Meuldermans W, Hendrickx J, Lauwers W, Hurkmans R, Mostmans E, Swysen E, Bracke J, Knaeps A, Heykants J. (1988a). Excretion and biotransformation of cisapride in rats after oral administration. Drug Metab Dispos 16:410-419
24. Meuldermans W, van Peer A, Hendrickx J, LauwersW, Swysen E, Bockx M, Woestenborghs R, Heykants J. (1988b) Excretion and biotransformation of cisapride in dogs and humans after oral administration. Drug Metab Dispos 16:403-409
25. Miranda CL, Chung WG, Wang-Buhler JL, Musafia-Jeknic T, Baird WM, Buhler DR. (2006). Comparative in vitro metabolism of benzo[a] pyrene by recombinant zebrafish CYP1A and liver microsomes from beta-naphthoflavone-treated rainbow trout. Aquat Toxicol 80:101-108
26. Noury P, Geffard O, Tutundjian R, Garric J. (2006). Non-destructive in vivo measurement of ethoxyresorufin biotransformation by zebrafish prolarva: development and application. Environ Toxicol 21:324-331
27. Pflugmacher S, Wiegand C. (2001). Metabolism of microcystin-LR in aquatic organisms. Cyanotoxins 257-260:276-280
28. Rawls JF, Samuel BS, Gordon JI. (2004). Gnotobiotic zebrafish reveal evolutionarily conserved responses to the gut microbiota. Proc Natl Acad Sci USA 101:4596-4601
29. Reder-Hilz B, Ullrich M, Ringel M, Hewitt N, Utesch D, Oesch F, Hengstler JG. (2004). Metabolism of propafenone and verapamil by cryopreserved human, rat, mouse and dog hepatocytes: comparison with metabolism in vivo. Naunyn Schmiedebergs Arch Pharmacol 369:408-417
30. Reimers MJ, Hahn ME, Tanguay RL. (2004). Two zebrafish alcohol dehydrogenases share common ancestry with mammalian class I, II, IV, and V alcohol dehydrogenase genes but have distinct functional characteristics. J Biol Chem 279:38303-38312
31. Reschly EJ, Bainy AC, Mattos JJ, Hagey LR, Bahary N, Mada SR, Ou J, Venkataramanan R, Krasowski MD. (2007). Functional evolution of the vitamin D and pregnane X receptors. BMC Evol Biol 7:222.
32. Rubinstein AL. (2006). Zebrafish assays for drug toxicity screening. Expert Opin Drug Metab Toxicol 2:231-240
33. Stegeman JJ, Goldstone JV, Jonsson M, Woodin B. (2007). Oxidative xenobiotic metabolism in zebrafish: The cytochrome P450 gene complement, regulation and function. 234th ACS National meeting. Boston, MA, American Chemical Society.
34. Tseng HP, Hseu TH, Buhler DR, Wang WD, Hu CH. (2005). Constitutive and xenobiotics-induced expression of a novel CYP3A gene from zebrafish larva. Toxicol Appl Pharmacol 205:247-258
35. van den Hurk R, Schoonen WG, van Zoelen GA, Lambert JG. (1987). The biosynthesis of steroid glucuronides in the testis of the zebrafish, Brachydanio rerio, and their pheromonal function as ovulation inducers. Gen Comp Endocrinol 68:179-188
36. Wang-Buhler JL, Lee SJ, Chung WG, Stevens JF, Tseng HP, Hseu TH, Hu CH, Westerfield M, Yang YH, Miranda CL, Buhler DR. (2005). CYP2K6 from zebrafish (Danio rerio): cloning, mapping, developmental/ tissue expression, and aflatoxin B1 activation by baculovirus expressed enzyme. Comp Biochem Physiol C Toxicol Pharmacol 140:207-219
37. Wang L, Yao J, Chen L, Chen J, Xue J, Jia W. (2007). Expression and possible functional roles of cytochromes P450 2J1 (zfCyp 2J1) in zebrafish. Biochem Biophys Res Commun 352:850-855
38. Westerfield M. (1995). The zebrafish book: a guide for the laboratory use of zebrafish (danio rerio). Eugene, OR: University of Oregon Press. p. 385.
39. Wiegand C, Krause E, Steinberg C, Pflugmacher S. (2001). Toxicokinetics of atrazine in embryos of the zebrafish (Danio rerio). Ecotoxicol Environ Saf 49:199-205.
40. Wiegand C, Pflugmacher S, Giese M, Frank H, Steinberg C. (2000). Uptake, toxicity, and effects on detoxication enzymes of atrazine and trifluoroacetate in embryos of zebrafish. Ecotoxicol Environ Saf 45:122-131
41. Yasuda S, Kumar AP, Liu MY, Sakakibara Y, Suiko M, Chen L, Liu MC. (2005). Identification of a novel thyroid hormone-sulfating cytosolic sulfotransferase, SULT1 ST5, from zebrafish. Febs J 272:3828-3837
42. Yasuda S, Liu MY, Yang YS, Snow R, Takahashi S, Liu MC. (2006). Identification of novel hydroxysteroid-sulfating cytosolic SULTs, SULT2 ST2 and SULT2 ST3, from zebrafish: cloning, expression, characterization, and developmental expression. Arch Biochem Biophys 455:1-9.
43. Zok S, Gorge G, Kalsch W, Nagel R. (1991). Bioconcentration, metabolism and toxicity of substituted anilines in the zebrafish (Brachydanio rerio). Sci Total Environ 109- 110: 411-421