Physicochemical properties and transport of steroids across Caco-2 cells

Pharmaceutical Research

Volumn 20, Issue 2, 2003, Pages 177-186

  Faassen, Fried ^a   Kelder, Jan ^a   Lenders, Johan ^a   Onderwater, Rob ^b   Vromans, Herman ^a,c  

^a NV Organon ^*  (Netherlands)

^b TNO   (Netherlands)

^c UTRECHT UNIVERSITY   (Netherlands)

Author keywords

Absorption; Caco 2 permeability; Physicochemical properties; Steroids

Indexed keywords

17ALPHA HYDROXY 11 METHYLENE 19 NORPREGNA 4,15 DIEN 20 YN 3 ONE; ALDOSTERONE; CEFALEXIN; CORTISONE; DEXAMETHASONE; ESTRADIOL; ETHINYLESTRADIOL; ETONOGESTREL; GESTODENE; GLUCOSE; HYDROCORTISONE; MACROGOL 4000; MANNITOL; NANDROLONE; NORETHISTERONE; NORGESTREL; ORG 32540; ORG 34694; ORG 36410; ORG 4060; ORG 4325; ORG OM 08; PHENAZONE; PREDNISOLONE; PROGESTERONE; SPIRONOLACTONE; STEROID; TESTOSTERONE; VERAPAMIL;

ARTICLE; CALCULATION; CELL MEMBRANE PERMEABILITY; CELL STRAIN CACO 2; CONTROLLED STUDY; DRUG ABSORPTION; DRUG SURVEILLANCE PROGRAM; DRUG TRANSPORT; HUMAN; HUMAN CELL; MOLECULAR WEIGHT; PHYSICAL CHEMISTRY; PRIORITY JOURNAL;

BIOLOGICAL TRANSPORT; CACO-2 CELLS; CHEMISTRY, PHYSICAL; HUMANS; SOLUBILITY; STEROIDS;

EID: 0037331305     PISSN: 07248741     EISSN: None     Source Type: Journal    
DOI: 10.1023/A:1022210801734     Document Type: Article

References (36)

1. J. G. Harman and L. E. Limbird. Goodman & Gilman's The Pharmacological Basis of Therapeutics. McGraw Hill, New York, 1996.
2. U. Norinder, T. Osterberg, and P. Artursson. Theoretical calculation and prediction of Caco-2 cell permeability using MolSurf parameterization and PLS statistics. Pharm. Res. 14:1786-1791 (1997).
3. M. C. Gres, B. Julian, M. Bourrie, V. Meunier, C. Roques, M. Berger, X. Boulenc, and Y. Berger. Correlation between oral drug absorption in humans, and apparent drug permeability in TC-7 cells, a human epithelial intestinal cell line: comparison with the parenteral Caco-2 cell line. Pharm. Res. 15:726-733 (1998). M.
4. M. Yazdanian, S. L. Glyn, J. L. Wright, and A. Hawi. Correlating partitioning and Caco-2 cell permeability of structurally diverse small molecular weight compounds. Pharm. Res. 15:1490-1494 (1998).
5. S. Yee. In vitro permeability across Caco-2 cells (colonic) can predict in vivo (small intestinal) absorption in man - fact or myth. Pharm, Res. 14:763-766 (1997).
6. E. Duizer. Permeability and Modulation of the Tntestinal Epithelial Barrier in Vitro, Ph.D. Thesis, Wageningen Agricultural University, The Netherlands, 1999.
7. P. Schmiedlin-Ren, K. E. Thummel, J. M. Fischer, M. F. Paine, K. S. Lown, and P. B. Watkins. Expression of enzymatically active CYP3A4 by Caco-2 cells grown on extracellular matrix-coated permeable supports in the presence of lalpha,25-dihydroxyvitamin D3. Mol. Pharmacol. 51:741-754 (1997).
8. S. D. Raeissi, I. J. Hidalgo, J. Segura-Aguilar, and P. Artursson. Interplay between CYP3A-mediated metabolism and polarized efflux of terfenadine and its metabolites in intestinal epithelial Caco-2 (TC7) cell monolayers. Pharm. Res. 16:625-632 (1999).
9. F. Labrie, V. Luu-The, and S. X. Lin. The key role of 17beta-hydroxysteroid dehydrogenases in sex steroid biology. Steroids 62:148-158 (1997).
10. S. Andersson and N. Moghrabi. Physiology and molecular genetics of 17beta-hydroxysteroid dehydrogenases. Steroids 62:143-147 (1997).
11. J. Kelder, P. D. Grootenhuis, D. M. Bayada, L. P. Delbressine, and J. P. Ploemen. Polar molecular surface as a dominating determinant for oral absorption and brain penetration of drugs. Pharm. Res. 16:1514-1519 (1999).
12. F. J. Zeelen. Medicinal Chemistry of Steroids, Elsevier Science Publishers BV, Amsterdam, 1990.
13. U. Kragh-Hansen. Molecular aspects of ligand binding to serum albumin. Pharmacol. Rev. 33:17-53 (1981).
14. S. Watanabe and T. Sato. Effects of free fatty acids on the binding of bovine and human serum albumin with steroid hormones. Biochim. Biophys. Acta 1289:385-396 (1996).
15. M. E. Baker. Albumin's role in steroid hormone action and the origin of vertebrates: is albumin an essential protein? FEBS Lett. 439:9-12 (1998).
16. J. M. Fischer, S. A. Wrighton, J. C. Calamia, D. D. Shen, and K. L. Kunze. Midazolam metabolism by modified Caco-2 monolayers: effects of extracellular protein binding. J. Pharmacol. Exp. Ther. 289:1143-1150 (1999).
17. S. Yamashita, T. Furubayashi, M. Kataoka, T. Sakane, H. Sezaki, and H. Tokuda. Optimized conditions for prediction of intestinall drug permeability using Caco-2 cells. Eur. J. Pharm. Sci. 10:195-204 (2000).
18. C. A. Lipinski, F. Lombardo, B. W. Dominy, and P. J. Feeny. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv. Drug. Deliv. Rev. 23:3-25 (1997).
19. A. Lampen, A. Bader, T. Bestmann, M. Winkler, L. Witte, and J. T. Borlak. Catalytic activities, protein- and mRNA-expression of cytochrome P450 isoenzymes in intestinal cell lines. Xenobiotica 28:429-441 (1998).
20. T. Prueksaritanont, L. M. Gotham, J. H. Hochmann, L. O. Tran, and K. P. Vyas. Comparative studies of drug-metabolizing enzymes in dog, monkey, and human small intestines, and in Caco-2 cells. Drug Metab. Dispos. 24:634-642 (1996).
21. C. H. M. Versantvoort, R. C. A. Onderwater, E. Duizer, J. J. M. Van de Sandt, A. J. Gilde, and J. P. Groten. Monolayers of IEC-18 cells as an in vitro model for screening the passive transcellular and paracellular transport across the intestinal barrier: comparison of active and passive transport with the human colon carcinoma Caco-2 cell line. Environ. Toxicol. Pharmacol. 11:335-344 (2002).
22. R. Sandstrom, A. Karlsson, L. Knutson, and H. Lennernas. Jejunal absorption and metabolism of R/S verapamil in humans. Pharm. Res. 15:856-862 (1998).
23. G. Ecker, M. Huber, D. Schmid, and P. Chiba. The importance of a nitrogen atom in modulators of multidrug resistance. Mol. Pharmacol. 56:791-796 (1999).
24. S. Ernest and E. Bello-Reuss. P-glycoprotein functions and substrates: possible roles of MDR1 gene in the kidney. Kidney Int. 65(Suppl):S11-S17 (1998).
25. K. M. Barnes, B. Dickstein, G. B. Cutler Jr., T. Fojo, and S. E. Bates. Steroid transport, accumulation, and antagonism of Pglycoprotein in multidrug resistant cells. Biochemistry 35:4820-4827 (1996).
26. G. Deliconstantinos and S. Fotiou. Sex steroid and prostaglandin interactions upon the purified rat myometrial plasma membranes. Mol. Cell. Endocrinol. 45:149-156 (1986).
27. H. Saitoh, M. Hatakeyama, O. Eguchi, M. Oda, and M. Takada. Involvement of intestinal P-glycoprotein in the restricted absorption of methylprednisolone from rat small intestine. J. Pharm. Sci. 87:73-75 (1998).
28. K. A. Lentz, J. W. Polli, S. A. Wring, J. E. Humphreys, and J. E. Polli. Influence of passive permeability on apparent P-glycoprotein kinetics. Pharm. Res. 17:1456-1460 (2000).
29. S. Winiwarter, N. M. Bonham, F. Ax, A. Hallberg, H. Lennernas, and A. Karlen. Correlation of human jejunal permeability (in vivo) of drugs with experimentally and theoretically derived parameters. A multivariate data analysis approach. J. Med. Chem. 41:4939-4949 (1998).
30. T. I. Oprea and J. Gottfries. Toward minimalistic modeling of oral drug absorption. J. Mol. Graphics Mod. 17:261-274 (1999).
31. H. van de Waterbeemd, G. Camenisch, G. Folkers, and O. A. Raevsky. Estimation of Caco-2 cell permeability using calculated molecular descriptors. Quant. Struct. Act. Relat. 15:480-490 (1996).
32. L. Stryer. Biochemistry, W.H. Freeman and Company, New York, 1995.
33. H. R. Lamche, P. T. Silberstein, A. C. Knabe, D. D. Thomas, H. S. Jacob, and D. E. Hammerschmidt. Steroids decrease granulocyte membrane fluidity, while phorbol ester increases membrane fluidity. Studies using electron paramagnetic resonance. Inflammation 14:61-70 (1990).
34. V. B. Mahesh, D. W. Brann, and L. B. Hendry. Diverse modes of action of progesterone and its metabolites. J. Steroid Biochem. Mol. Biol. 56:209-219 (1996).
35. G. A. Golden, R. P. Mason, T. N. Tulenko, G. S. Zubenko, and R. T. Rubin. Rapid and opposite effects of cortisol and estradiol on the human erythrocyte Na+,K+-ATPase activity: relationship to steroid intercalation into the cell membrane. Life Sci. 65:1247-1255 (1999).
36. D. B. Goldstein. The effects of drugs on membrane fluidity. Annu. Rev. Pharmacol. Toxicol. 24:43-64 (1984).