A catenary model to study transport and conjugation of baicalein, a bioactive flavonoid, in the caco-2 cell monolayer: Demonstration of substrate inhibition

Journal of Pharmacology and Experimental Therapeutics

Volumn 326, Issue 1, 2008, Pages 117-126

  Sun, Huadong ^a   Zhang, Li ^b   Chow, Edwin Chiu Yuen ^a   Lin, Ge ^b   Zuo, Zhong ^b   Pang, K Sandy ^a  

^a UNIVERSITY OF TORONTO   (Canada)

^b and Hong Kong Branch of CAS Center for Excellence in Animal Evolution and Genetics   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

BAICALEIN; BARIUM SULFATE; GLUCURONIDE; MULTIDRUG RESISTANCE PROTEIN 2;

ABSORPTION; APICAL MEMBRANE; ARTICLE; CELL LYSATE; CELL MEMBRANE PERMEABILITY; CELL STRAIN CACO 2; CONTROLLED STUDY; DRUG CONJUGATION; DRUG METABOLISM; DRUG PENETRATION; DRUG TRANSPORT; ENZYME INHIBITION; GLUCURONIDATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; INHIBITION KINETICS; INTRACELLULAR SPACE; LIQUID CHROMATOGRAPHY; MICHAELIS CONSTANT; PRIORITY JOURNAL; PROTEIN BINDING; PROTEIN SECRETION; SULFATION; TANDEM MASS SPECTROMETRY;

BIOLOGICAL TRANSPORT; CACO-2 CELLS; FLAVANONES; FLAVONOIDS; HUMANS; MODELS, BIOLOGICAL; PROTEIN BINDING; SUBSTRATE SPECIFICITY;

EID: 44349185775     PISSN: 00223565     EISSN: 15210103     Source Type: Journal    
DOI: 10.1124/jpet.108.137463     Document Type: Article

References (40)

1. Adson A, Burton PS, Raub TJ, Barsuhn CL, Audus KL, and Ho NF (1995) Passive diffusion of weak organic electrolytes across Caco-2 cell monolayers: uncoupling the contributions of hydrodynamic, transcellular, and paracellular barriers. J Pharm Sci 84:1197-1204.
2. +-dependent sugar transport in Caco-2 cells and human fetal colon. J Membr Biol 99:113-125.
3. Bourdet DL, Pollack GM, and Thakker DR (2006) Intestinal absorptive transport of the hydrophilic cation ranitidine: a kinetic modeling approach to elucidate the role of uptake and efflux transporters and paracellular vs. transcellular transport in Caco-2 cells. Pharm Res 23:1178-1187.
4. Chen J, Lin H, and Hu M (2005) Absorption and metabolism of genistein and its five isoflavone analogs in the human intestinal Caco-2 model. Cancer Chemother Pharmacol 55:159-169.
5. Chiba M and Pang KS (1993) Effect of protein binding on 4-methylumbelliferyl sulfate desulfation kinetics in perfused rat liver. J Pharmacol Exp Ther 266:492-499.
6. Court MH, Duan SX, Guillemette C, Journault K, Krishnaswamy S, Von Moltke LL, and Greenblatt DJ (2002) Stereoselective conjugation of oxazepam by human UDP-glucuronosyltransferases (UGTs): S-oxazepam is glucuronidated by UGT2B15, while R-oxazepam is glucuronidated by UGT2B7 and UGT1A9. Drug Metab Dispos 30:1257-1265.
7. Fisher MB, Campanale K, Ackermann BL, VandenBranden M, and Wrighton SA (2000) In vitro glucuronidation using human liver microsomes and the poreforming peptide alamethicin. Drug Metab Dispos 28:560-566.
8. Galijatovic A, Walle UK, and Walle T (2000) Induction of UDP-glucuronosyltransferase by the flavonoids chrysin and quercetin in Caco-2 cells. Pharm Res 17:21-26.
9. González-Alvarez I, Fernandez-Teruel C, Garrigues TM, Casabo VG, Ruiz-Garcia A, and Bermejo M (2005) Kinetic modelling of passive transport and active efflux of a fluoroquinolone across Caco-2 cells using a compartmental approach in NONMEM. Xenobiotica 35:1067-1088.
10. Gutmann H, Fricker G, Torok M, Michael S, Beglinger C, and Drewe J (1999) Evidence for different ABC-transporters in Caco-2 cells modulating drug uptake. Pharm Res 16:402-407.
11. Ho NFH, Raub TJ, Burton PS, Barsuhn CL, Adson A, Audus KL and Borchardt RT (2000) Quantitative approaches to delineate passive transport mechanisms in cell culture monolayers, in Transport Processes in Pharmaceutical Systems (Amidon GL, Lee PI, and Topp EM eds) pp 219-317, Marcel Dekker, New York.
12. Huang XP, Spino M, and Thiessen JJ (2006) Transport kinetics of iron chelators and their chelates in Caco-2 cells. Pharm Res 23:280-290.
13. Hunter J, Jepson MA, Tsuruo T, Simmons NL, and Hirst BH (1993) Functional expression of P-glycoprotein in apical membranes of human intestinal Caco-2 cells. Kinetics of vinblastine secretion and interaction with modulators. J Biol Chem 268:14991-14997.
14. Ito S, Woodland C, Sarkadi B, Hockmann G, Walker SE, and Koren G (1999) Modeling of P-glycoprotein-involved epithelial drug transport in MDCK cells. Am J Physiol Renal Physiol 277:F84-F96.
15. Kalvass JC and Pollack GM (2007) Kinetic considerations for the quantitative assessment of efflux activity and inhibition: implications for understanding and predicting the effects of efflux inhibition. Pharm Res 24:265-276.
16. Kroon PA, Clifford MN, Crozier A, Day AJ, Donovan JL, Manach C, and Williamson G (2004) How should we assess the effects of exposure to dietary polyphenols in vitro? Am J Clin Nutr 80:15-21.
17. Li BH and Tian WX (2004) Inhibitory effects of flavonoids on animal fatty acid synthase. J Biochem 135:85-91.
18. Liu Y and Hu M (2002) Absorption and metabolism of flavonoids in the caco-2 cell culture model and a perused rat intestinal model. Drug Metab Dispos 30:370-377.
19. Manach C and Donovan JL (2004) Pharmacokinetics and metabolism of dietary flavonoids in humans. Free Radic Res 38:771-785.
20. Nagar S, Walther S, and Blanchard RL (2006) Sulfotransferase (SULT) 1A1 polymorphic variants *1, *2, and *3 are associated with altered enzymatic activity, cellular phenotype, and protein degradation. Mol Pharmacol 69:2084-2092.
21. Pendyala L and Creaven PJ (1993) In vitro cytotoxicity, protein binding, red blood cell partitioning, and biotransformation of oxaliplatin. Cancer Res 53:5970-5976.
22. Raub TJ, Barsuhn CL, Williams LR, Decker DE, Sawada GA, and Ho NF (1993) Use of a biophysical-kinetic model to understand the roles of protein binding and membrane partitioning on passive diffusion of highly lipophilic molecules across cellular barriers. J Drug Target 1:269-286.
23. Rosenthal HE (1967) A graphic method for the determination and presentation of binding parameters in a complex system. Anal Biochem 20:525-532.
24. Rosenthal HE, Pietrzak E, Slaunwhite WR Jr, and Sandberg AA (1972) Binding of estrone sulfate in human plasma. J Clin Endocrinol Metab 34:805-813.
25. Sun H and Pang KS (2008) Permeability, transport, and metabolism of solutes in caco-2 cell monolayers: a theoretical study. Drug Metab Dispos 36:102-123.
26. Tracy TS and Hummel MA (2004) Modeling kinetic data from in vitro drug metabolism enzyme experiments. Drug Metab Rev 36:231-242.
27. Tran TT, Mittal A, Aldinger T, Polli JW, Ayrton A, Ellens H, and Bentz J (2005) The elementary mass action rate constants of P-gp transport for a confluent monolayer of MDCKII-hMDR1 cells. Biophys J 88:715-738.
28. Uchaipichat V, Mackenzie PI, Guo XH, Gardner-Stephen D, Galetin A, Houston JB, and Miners JO (2004) Human UDP-glucuronosyltransferases: isoform selectivity and kinetics of 4-methylumbelliferone and 1-naphthol glucuronidation, effects of organic solvents, and inhibition by diclofenac and probenecid. Drug Metab Dispos 32:413-423.
29. Vaidyanathan JB and Walle T (2001) Transport and metabolism of the tea flavonoid (-)-epicatechin by the human intestinal cell line Caco-2. Pharm Res 18:1420-1425.
30. Walgren RA, Walle UK, and Walle T (1998) Transport of quercetin and its glucosides across human intestinal epithelial Caco-2 cells. Biochem Pharmacol 55:1721-1727.
31. Walle UK, Galijatovic A, and Walle T (1999) Transport of the flavonoid chrysin and its conjugated metabolites by the human intestinal cell line Caco-2. Biochem Pharmacol 58:431-438.
32. Wang Y, Cao J, and Zeng S (2005) Involvement of P-glycoprotein in regulating cellular levels of Ginkgo flavonols: quercetin, kaempferol, and isorhamnetin. J Pharm Pharmacol 57:751-758.
33. Wilson FA and Dietschy JM (1974) The intestinal unstirred layer: its surface area and effect on active transport kinetics. Biochim Biophys Acta 363:112-126.
34. Yamaguchi H, Yano I, Hashimoto Y, and Inui KI (2000) Secretory mechanisms of grepafloxacin and levofloxacin in the human intestinal cell line caco-2. J Pharmacol Exp Ther 295:360-366.
35. Yang CS, Landau JM, Huang MT, and Newmark HL (2001) Inhibition of carcinogenesis by dietary polyphenolic compounds. Annu Rev Nutr 21:381-406.
36. Yoshizuka K, Ohta H, Inoue K, Kitazaki H, and Ishimaru M (1996) Selective separation of flavonoids with a polyvinyl alcohol membrane. J Membr Sci 118:41-48.
37. Zhang L, Lin G, Chang Q, and Zuo Z (2005) Role of intestinal first-pass metabolism of baicalein in its absorption process. Pharm Res 22:1050-1058.
38. Zhang L, Lin G, Kovacs B, Jani M, Krajcsi P, and Zuo Z (2007a) Mechanistic study on the intestinal absorption and disposition of baicalein. Eur J Pharm Sci 31:221-231.
39. Zhang L, Lin G, and Zuo Z (2007b) Involvement of UDP- glucuronosyltransferases in the extensive liver and intestinal first-pass metabolism of flavonoid baicalein. Pharm Res 24:81-89.
40. Zhang L, Zheng Y, Chow MS, and Zuo Z (2004) Investigation of intestinal absorption and disposition of green tea catechins by Caco-2 monolayer model. Int J Pharm 287:1-12.