Caco-2 cell monolayers as a tool to study simultaneous phase II metabolism and metabolite efflux of indomethacin, paracetamol and 1-naphthol

International Journal of Pharmaceutics

Volumn 383, Issue 1-2, 2010, Pages 24-29

  Siissalo, Sanna ^a   Laine, Laura ^a   Tolonen, Ari ^b   Kaukonen, Ann M ^a   Finel, Moshe ^a   Hirvonen, Jouni ^a  

^a UNIVERSITY OF HELSINKI   (Finland)

^b Novamass Ltd   (Finland)

Author keywords

Caco 2 cells; Efflux; Glucuronidation; In vitro method; Phase II metabolism; Sulfation

Indexed keywords

1 NAPHTHOL; 1 NAPHTHOL GLUCURONIDE; DRUG METABOLITE; INDOMETACIN; PARACETAMOL; PARACETAMOL GLUCURONIDE; PARACETAMOL SULFATE; UNCLASSIFIED DRUG;

ARTICLE; CELL STRAIN CACO 2; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG DETERMINATION; DRUG METABOLISM; DRUG PENETRATION; DRUG TRANSPORT; HUMAN; HUMAN CELL; IN VITRO STUDY; INHIBITION KINETICS; LIQUID CHROMATOGRAPHY; MONOLAYER CULTURE; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; TANDEM MASS SPECTROMETRY;

ACETAMINOPHEN; BIOLOGICAL TRANSPORT; CACO-2 CELLS; HUMANS; INDOMETHACIN; INTESTINAL ABSORPTION; NAPHTHOLS;

EID: 70449535545     PISSN: 03785173     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ijpharm.2009.08.044     Document Type: Article

References (43)

1. Abid A., Bouchon I., Siest G., and Sabolovic N. Glucuronidation in the Caco-2 human intestinal cell line: induction of UDP-glucuronosyltransferase 1*6. Biochem. Pharmacol. 50 (1995) 557-561
2. Artursson P., and Karlsson J. Correlation between oral drug absorption in humans and apparent drug permeability coefficients in human intestinal epithelial (Caco-2) cells. Biochem. Biophys. Res. Commun. 175 (1991) 880-885
3. Blanchard R.L., Freimuth R.R., Buck J., Weinshilboum R.M., and Coughtrie M.W.H. A proposed nomenclature system for the cytosolic sulfotransferase (SULT) superfamily. Pharmacogenetics 14 (2004) 199-211
4. Cerveny L., Svecova L., Anzenbacherova E., Vrzal R., Staud F., Dvorak Z., Ulrichova J., Anzenbacher P., and Pavek P. Valproic acid induces CYP3A4 and MDR1 gene expression by activation of constitutive androstane receptor and pregnane X receptor pathways. Drug Metab. Dispos. 35 (2007) 1032-1041
5. Chikhale P.J., and Borchardt R.T. Metabolism of l-α-methyldopa in cultured human intestinal epithelial (Caco-2) cell monolayers. Comparison with metabolism in vivo. Drug Metab. Dispos. 22 (1994) 592-600
6. Christians U. Transport proteins and intestinal metabolism, P-glycoprotein and cytochrome P4503A. Ther. Drug Monit. 26 (2004) 104-106
7. El-Sheikh A.A.K., van den Heuvel J.J.M.W., Koenderink J.B., and Russel F.G.M. Interaction of nonsteroidal anti-inflammatory drugs with multidrug resistance protein (MRP)2/ABCC2- and MRP4/ABCC4-mediated methotrexate transport. J. Pharmacol. Exp. Ther. 320 (2007) 229-235
8. EMEA. Committee for Proprietary Medicinal Products (CPMP): Replacement of Animal Studies with In Vitro Models (1997). http://www.emea.europa.eu/pdfs/human/swp/072895en.pdf Retrieved December 28, 2008, from http://www.emea.europa.eu/pdfs/human/swp/072895en.pdf
9. Falany C.N. Enzymology of human cytosolic sulfotransferases. FASEB J. 11 (1997) 206-216
10. Gamage N., Barnett A., Hempel N., Duggleby R.G., Windmill K.F., Martin J.L., et al. Human sulfotransferases and their role in chemical metabolism. Toxicol. Sci. 90 (2006) 5-22
11. Haimeur A., Conceil G., Deeley R.G., and Cole S.P.C. The MRP-related and BCRP/ABCG2 multidrug resistance proteins: biology, substrate specificity and regulation. Curr. Drug Metab. 5 (2004) 21-53
12. Hayeshi R., Hilgendorf C., Artursson P., Augustijns P., Brodin B., Dehertogh P., Fisher K., Fossati L., Hovenkamp E., Korjamo T., Masungi C., Maubon N., Mols R., Müllertz A., Mönkkönen J., O'Driscoll C., Oppers-Tiemissen H.M., Ragnarsson E.G., Rooseboom M., and Ungell A.-L. Comparison of drug transporter gene expression and functionality in Caco-2 cells from 10 different laboratories. Eur. J. Pharm. Sci. 35 (2008) 383-396
13. Hilgers A.R., Conradi R.A., and Burton P.S. Caco-2 cell monolayers as a model for drug transport across the intestinal mucosa. Pharm. Res. 7 (1990) 902-910
14. Hubatsch I., Ragnarsson E.G.E., and Artursson P. Determination of drug permeability and prediction of drug absorption in Caco-2 monolayers. Nat. Protoc. 2 (2007) 2111-2119
15. Jeong E.J., Lin H., and Hu M. Disposition mechanisms of raloxifene in the human intestinal Caco-2 cell model. J. Pharmacol. Exp. Ther. 310 (2004) 376-385
16. Jeong E.J., Liu X., Jia X., Chen J., and Hu M. Coupling of conjugating enzymes and efflux transporters: impact on bioavailability and drug interactions. Curr. Drug Metab. 6 (2005) 455-468
17. Komura H., and Iwaki M. Species differences in in vitro and in vivo small intestinal metabolism of CYP3A substrates. J. Pharm. Sci. 97 (2007) 1775-1800
18. Kouzuki H., Suzuki H., and Sugiyama Y. Pharmacokinetic study of the hepatobiliary transport of indomethacin. Pharm. Res. 17 (2000) 432-438
19. Kuehl G.E., Lampe J.W., Potter J.D., and Bigler J. Glucuronidation of nonsteroidal anti-inflammatory drugs: identifying the enzymes responsible in human liver microsomes. Drug Metab. Dispos. 33 (2005) 1027-1035
20. Laitinen L.A., Tammela P.S.M., Galkin A., Vuorela H.J., Marvola M.L.A., and Vuorela P.M. Effects of extracts of commonly consumed food supplements and food fractions on the permeability of drugs across Caco-2 cell monolayers. Pharm. Res. 21 (2004) 1904-1916
21. Mano Y., Usui T., and Kamimura H. In vitro drug interaction between diflunisal and indomethacin via glucuronidation in humans. Biopharm. Drug Dispos. 27 (2006) 267-273
22. Mano Y., Usui T., and Kamimura H. Contribution of UDP-glucuronosyltransferases 1A9 and 2B7 to the glucuronidation of indomethacin in the human liver. Eur. J. Clin. Pharmacol. 63 (2007) 289-296
23. Meinl W., Ebert B., Glatt H., and Lampen A. Sulfotransferase forms expressed in human intestinal Caco-2 and TC7 cells at varying stages of differentiation and role in benzo[a]pyrene metabolism. Drug Metab. Dispos. 36 (2008) 276-283
24. Mizuma T., Momota R., Haga M., and Hayashi M. Factors affecting glucuronidation affinity in Caco-2 cells. Drug Metab. Pharmacokin. 19 (2004) 130-134
25. Mutlib A.E., Goosen T.C., Bauman J.N., Williams J.A., Kulkarni S., and Kostrubsky S. Kinetics of acetaminophen glucuronidation by UDP-glucuronosyltransferases 1A1, 1A6, 1A9 and 2B15. Potential implications in acetaminophen-induced hepatotoxicity. Chem. Res. Toxicol. 19 (2006) 701-709
26. Neuhoff S., Ungell A.-L., Zamora I., and Artursson P. pH-Dependent passive and active transport of acidic drugs across Caco-2 cell monolayers. Eur. J. Pharm. Sci. 25 (2005) 211-220
27. Pang K.S., Weiss M., and Macheras P. Advanced pharmacokinetic models based on organ clearance, circulatory, and fractal concepts. AAPS J. 9 (2007) E268-E283
28. Prescott L.F. Kinetics and metabolism of paracetamol and phenacetin. Br. J. Clin. Pharmacol. 10 (1980) 291S-298S
29. Prueksaritanont T., Gorham L.M., Hochman J., Tran L., and Vyas K.P. Comparative studies of drug metabolizing enzymes in dog, monkey and human small intestines, and in Caco-2 cells. Drug Metab. Dispos. 24 (1996) 634-642
30. Sacolovic N., Magdalou J., Netter P., and Abid A. Nonsteroidal anti-inflammatory drugs and phenols glucuronidation in Caco-2 cells: identification of the UDP-glucuronosyltransferases UGT1A6, 1A3 and 2B7. Life Sci. 67 (2000) 185-196
31. Sergent T., Ribonnet L., Kolosova A., Garsou S., Schaut A., De Saeger S., Van Peteghem C., Larondelle Y., Pussemier L., and Schneider Y.-J. Molecular and cellular effects of food contaminants and secondary plant components and their plausible interactions at the intestinal level. Food Chem. Toxicol. 46 (2008) 813-841
32. Siissalo S., Laitinen L., Koljonen M., Vellonen K.-S., Kortejärvi H., Urtti A., Hirvonen J., and Kaukonen A.M. Effect of cell differentiation and passage number on the expression of efflux proteins in wild type and vinblastine-induced Caco-2 cell lines. Eur. J. Pharm. Biopharm. 67 (2007) 548-554
33. Siissalo S., Zhang H., Stilgenbauer E., Kaukonen A.M., Hirvonen J., and Finel M. The expression of most UDP-glucuronosyltransferases (UGTs) is increased significantly during Caco-2 cell differentiation, while UGT1A6 is highly expressed also in undifferentiated cells. Drug Metab. Dispos. 36 (2008) 2331-2336
34. Siissalo S., Hannukainen J., Kolehmainen J., Hirvonen J., and Kaukonen A.M. A Caco-2 cell based screening method for compounds interacting with MRP2 efflux protein. Eur. J. Pharm. Biopharm. 71 (2009) 332-338
35. Sun H., and Pang K.S. Permeability, transport and metabolism of solutes in Caco-2 cell monolayers: a theoretical study. Drug Metab. Dispos. 36 (2008) 102-123
36. Sun H., Zhang L., Chow E.C.Y., Lin G., Zuo Z., and Pang K.S. A catenary model to study transport and conjugation of baicalein, a bioactive flavonoid, in the Caco-2 cell monolayer: demonstration of substrate inhibition. J. Pharmacol. Exp. Ther. 326 (2008) 117-126
37. Van de Kerkhof E.G., De Graaf I.A.M., and Groothuis G.M.M. In vitro methods to study intestinal drug metabolism. Curr. Drug Metab. 8 (2007) 658-675
38. Van den Hurk P., Kubiczak G.A., Lehmler H.-J., and James M.O. Hydroxylated polychlorinated biphenyls as inhibitors of the sulfation and glucuronidation of 3-hydroxy-benzo[a]pyrene. Environ. Health Perspect. 110 (2002) 343-348
39. Wacher V.J., Wu C.-Y., and Benet L.Z. Overlapping substrate specificities and tissue distribution of cytochrome P450 3A and P-glycoprotein: implications for drug delivery and activity in cancer chemotherapy. Mol. Carsinog. 13 (1995) 129-134
40. Xia C.Q., Xiao G., Liu N., Pimprale S., Fox L., Patten C.J., Crespi C.L., Miwa G., and Gan L.-S. Comparison of species differences of P-glycoproteins in beagle dog, rhesus monkey, and human using ATPase activity assays. Mol. Pharm. 3 (2006) 78-86
41. Xia C.Q., Milton M.N., and Gan L.-S. Evaluation of drug-transporter interactions using in vitro and in vivo models. Curr. Drug Metab. 8 (2007) 341-363
42. Zelcer N., Huisman M.T., Reid G., Wielinga P., Breedveld P., Kuil A., Knipscheer P., Schellens J.H.M., Schinkel A.H., and Borst P. Evidence for two interacting ligand binding sites in human multidrug resistance protein 2 (ATP binding cassette C2). J. Biol. Chem. 26 (2003) 23538-23544
43. Zhang L., Zuo Z., and Lin G. Intestinal and hepatic glucuronidation of flavonoids. Mol. Pharm. 4 (2007) 833-845