Predicting phenolic acid absorption in Caco-2 cells: A theoretical permeability model and mechanistic study

Drug Metabolism and Disposition

Volumn 40, Issue 2, 2012, Pages 397-406

  Farrell, Tracy L ^a   Poquet, Laure ^b   Dew, Tristan P ^a   Barber, Stuart ^a   Williamson, Gary ^a,b  

^a UNIVERSITY OF LEEDS   (United Kingdom)

^b NESTLÉ RESEARCH CENTER   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

3,4 DIMETHOXYCINNAMIC ACID; 3,5 DI O CAFFEOYLQUINIC ACID; 5 FERULOYLQUINIC ACID; 5 O CAFFEOYLQUINIC ACID; ALPRENOLOL; CAFFEIC ACID; CEFTRIAXONE; CORTICOSTERONE; COUMARIN; DEXAMETHASONE; DIAZEPAM; FELODIPINE; FERULIC ACID; HYDROCORTISONE; HYDROXYACID; IMIPRAMINE; KETOPROFEN; LIDOCAINE; METOPROLOL; MIBEFRADIL; MORPHINE; NITRENDIPINE; PHENAZONE; PHENYTOIN; PIROXICAM; PRACTOLOL; PROPRANOLOL; REMIKIREN; SULPIRIDE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ARTICLE; CELL MEMBRANE PERMEABILITY; CELL STRAIN CACO 2; CELL TRANSPORT; DRUG ABSORPTION; DRUG PENETRATION; DRUG TRANSPORT; HUMAN; HUMAN CELL; IN VITRO STUDY; MOLECULAR WEIGHT; NONLINEAR REGRESSION ANALYSIS; PRIORITY JOURNAL;

ARTIFICIAL INTELLIGENCE; CACO-2 CELLS; CELL MEMBRANE PERMEABILITY; CINNAMATES; ENTEROCYTES; HUMANS; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; INTESTINAL ABSORPTION; KINETICS; MODELS, BIOLOGICAL; MOLECULAR CONFORMATION; OSMOLAR CONCENTRATION; PHENOLS;

EID: 84856016533     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.111.041665     Document Type: Article

References (40)

1. Alsenz J and Haenel E (2003) Development of a 7-day, 96-well Caco-2 permeability assay with high-throughput direct UV compound analysis. Pharm Res 20:1961-1969. (Pubitemid 38005527)
2. Artursson P and Karlsson J (1991) Correlation between oral drug absorption in humans and apparent drug permeability coefficients in human intestinal epithelial (Caco-2) cells. Biochem Biophys Res Commun 175:880-885.
3. Artursson P, Palm K, and Luthman K (2001) Caco-2 monolayers in experimental and theoretical predictions of drug transport. Adv Drug Deliv Rev 46:27-43.
4. Avdeef A and Tam KY (2010) How well can the Caco-2/Madin-Darby canine kidney models predict effective human jejunal permeability? J Med Chem 53:3566-3584.
5. Bernards CM and Hill HF (1992) Physical and chemical properties of drug molecules governing their diffusion through the spinal meninges. Anesthesiology 77:750-756.
6. Camenisch G, Alsenz J, van de Waterbeemd H, and Folkers G (1998) Estimation of permeability by passive diffusion through Caco-2 cell monolayers using the drugs' lipophilicity and molecular weight. Eur J Pharm Sci 6:313-319. (Pubitemid 28468539)
7. 2: enhancing chromatographic quantification and application in Caco-2 cell metabolism. J Pharm Biomed Anal 55:1245-1254.
8. Fraga S and Soares-da-Silva P (2006) P-glycoprotein and multidrug resistance-associated protein (MRP) reverse the intestinal transport of L-DOPA, a LAT2 substrate. FASEB J 20:A841.
9. Garberg P, Ball M, Borg N, Cecchelli R, Fenart L, Hurst RD, Lindmark T, Mabondzo A, Nilsson JE, Raub TJ, et al. (2005) In vitro models for the blood-brain barrier. Toxicol In Vitro 19:299-334. (Pubitemid 40248750)
10. Gramatté T, Oertel R, Terhaag B, and Kirch W (1996) Direct demonstration of small intestinal secretion and site-dependent absorption of the β-blocker talinolol in humans. Clin Pharmacol Ther 59:541-549. (Pubitemid 26191376)
11. Guy PA, Renouf M, Barron D, Cavin C, Dionisi F, Kochhar S, Rezzi S, Williamson G, and Steiling H (2009) Quantitative analysis of plasma caffeic and ferulic acid equivalents by liquid chromatography tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci 877:3965-3974.
12. Henry-Vitrac C, Ibarra A, Roller M, Mérillon JM, and Vitrac X (2010) Contribution of chlorogenic acids to the inhibition of human hepatic glucose-6-phosphatase activity in vitro by Svetol, a standardized decaffeinated green coffee extract. J Agric Food Chem 58:4141-4144.
13. Hilgendorf C, Spahn-Langguth H, Regårdh CG, Lipka E, Amidon GL, and Langguth P (2000) Caco-2 versus Caco-2/HT29-MTX co-cultured cell lines: permeabilities via diffusion, insideand outside-directed carrier-mediated transport. J Pharm Sci 89:63-75. (Pubitemid 30080155)
14. Hosoya K, Yamamoto A, Akanuma S, and Tachikawa M (2010) Lipophilicity and transporter influence on blood-retinal barrier permeability: a comparison with blood-brain barrier permeability. Pharm Res 27:2715-2724.
15. Hubatsch I, Ragnarsson EG, and Artursson P (2007) Determination of drug permeability and prediction of drug absorption in Caco-2 monolayers. Nat Protoc 2:2111-2119. (Pubitemid 351565848)
16. Kern C and Bernards CM (1997) Ascorbic acid inhibits spinal meningeal catechol-O-methyl transferase in vitro, markedly increasing epinephrine bioavailability. Anesthesiology 86:405-409. (Pubitemid 27093384)
17. Konishi Y and Kobayashi S (2004) Transepithelial transport of chlorogenic acid, caffeic acid, and their colonic metabolites in intestinal caco-2 cell monolayers. J Agric Food Chem 52:2518-2526.
18. Lennernas H, Palm K, Fagerholm U, and Artursson P (1996) Comparison between active and passive drug transport in human intestinal epithelial (Caco-2) cells in vitro and human jejunum in vivo. Int J Pharm 127:103-107. (Pubitemid 26069155)
19. Liu X, Testa B, and Fahr A (2011) Lipophilicity and its relationship with passive drug permeation. Pharm Res 28:962-977.
20. Matsson P, Pedersen JM, Norinder U, Bergström CA, and Artursson P (2009) Identification of novel specific and general inhibitors of the three major human ATP-binding cassette transporters P-gp, BCRP and MRP2 among registered drugs. Pharm Res 26:1816-1831.
21. Mazzobre MF, Román MV, Mourelle AF, and Corti HR (2005) Octanol-water partition coefficient of glucose, sucrose, and trehalose. Carbohydr Res 340:1207-1211. (Pubitemid 40431800)
22. Obata K, Sugano K, Saitoh R, Higashida A, Nabuchi Y, Machida M, and Aso Y (2005) Prediction of oral drug absorption in humans by theoretical passive absorption model. Int J Pharm 293:183-192. (Pubitemid 40385116)
23. Palm K, Stenberg P, Luthman K, and Artursson P (1997) Polar molecular surface properties predict the intestinal absorption of drugs in humans. Pharm Res 14:568-571. (Pubitemid 27220272)
24. Poquet L, Clifford MN, and Williamson G (2008) Transport and metabolism of ferulic acid through the colonic epithelium. Drug Metab Dispos 36:190-197.
25. Press B and Di Grandi D (2008) Permeability for intestinal absorption: Caco-2 assay and related issues. Curr Drug Metab 9:893-900.
26. Shen Q, Lin Y, Handa T, Doi M, Sugie M, Wakayama K, Okada N, Fujita T, and Yamamoto A (2006) Modulation of intestinal P-glycoprotein function by polyethylene glycols and their derivatives by in vitro transport and in situ absorption studies. Int J Pharm 313:49-56.
27. 1-adrenoceptor antagonist talinolol mediated by P-glycoprotein and organic anion transporting polypeptide (OATP). Pharm Res 26:560-567.
28. Stehle RG and Higuchi WI (1972) In vitro model for transport of solutes in three-phase system. I. Theoretical principles. J Pharm Sci 61:1922-1930.
29. Stein PC, di Cagno M, and Bauer-Brandl A (2011) A novel method for the investigation of liquid/liquid distribution coefficients and interface permeabilities applied to the water-octanol-drug system. Pharm Res 28:2140-2146.
30. Sugano K, Kansy M, Artursson P, Avdeef A, Bendels S, Di L, Ecker GF, Faller B, Fischer H, Gerebtzoff G, et al. (2010) Coexistence of passive and carrier-mediated processes in drug transport. Nat Rev Drug Discov 9:597-614.
31. Sun D, Lennernas H, Welage LS, Barnett JL, Landowski CP, Foster D, Fleisher D, Lee KD, and Amidon GL (2002) Comparison of human duodenum and Caco-2 gene expression profiles for 12,000 gene sequences tags and correlation with permeability of 26 drugs. Pharm Res 19:1400-1416. (Pubitemid 35266543)
32. Troutman MD and Thakker DR (2003) Rhodamine 123 requires carrier-mediated influx for its activity as a P-glycoprotein substrate in Caco-2 cells. Pharm Res 20:1192-1199. (Pubitemid 36951844)
33. van Dam RM and Hu FB (2005) Coffee consumption and risk of type 2 diabetes: a systematic review. JAMA 294:97-104.
34. van de Waterbeemd H (1998) The fundamental variables of the biopharmaceutics classification system (BCS): a commentary. Eur J Pharm Sci 7:1-3.
35. van de Waterbeemd H (2009) Improving compound quality through in vitro and in silico physicochemical profiling. Chem Biodivers 6:1760-1766.
36. van de Waterbeemd H and Gifford E (2003) ADMET in silico modelling: towards prediction paradise? Nat Rev Drug Discov 2:192-204. (Pubitemid 37361664)
37. Wang Z, Clifford MN, and Sharp P (2008) Analysis of chlorogenic acids in beverages prepared from Chinese health foods and investigation, in vitro, of effects on glucose absorption in cultured Caco-2 cells. Food Chem 108:369-373.
38. Xiang TX and Anderson BD (1994) The relationship between permeant size and permeability in lipid bilayer membranes. J Membr Biol 140:111-122.
39. Yamashita S, Furubayashi T, Kataoka M, Sakane T, Sezaki H, and Tokuda H (2000) Optimized conditions for prediction of intestinal drug permeability using Caco-2 cells. Eur J Pharm Sci 10:195-204. (Pubitemid 30190095)
40. Yazdanian M, Glynn SL, Wright JL, and Hawi A (1998) Correlating partitioning and Caco-2 cell permeability of structurally diverse small molecular weight compounds. Pharm Res 15:1490-1494. (Pubitemid 28427942)