Decreased secretory transport of a quarternary ammonium, TBuMA, across LLC-PK1 cells by the anionic kidney extract

Archives of Pharmacal Research

Volumn 31, Issue 5, 2008, Pages 671-677

  Shim, Won Sik ^a   Choi, Min Koo ^a   Kim, In Wha ^a   Kwon, Tae Sik ^a   Song, Im Sook ^b   Han, Liwei ^c   Kim, Dae Duk ^a   Chung, Suk Jae ^a   Shim, Chang Koo ^a  

^a Seoul National University   (South Korea)

^b Inje University College of Medicine   (South Korea)

^c BEIJING UNIVERSITY OF CHINESE MEDICINE   (China)

Author keywords

Apparent partition coefficient (APC); Endogenous organic anion (OA); Ion pair complex; LLC PK1; Mw threshold; Quarternary ammonium (QA); Secretory transport

Indexed keywords

ANION; BILE ACID; BUFFER; CATION; OCTANOL; PHOSPHATE; QUATERNARY AMMONIUM DERIVATIVE; TISSUE EXTRACT; TRI-N-BUTYLMETHYLAMMONIUM; TRIBUTYLMETHYLAMMONIUM;

ANIMAL; ARTICLE; CELL STRAIN; CHEMISTRY; ION TRANSPORT; KIDNEY; LIVER; MALE; METABOLISM; MOLECULAR WEIGHT; RAT; SPRAGUE DAWLEY RAT; SWINE;

1-OCTANOL; ANIMALS; ANIONS; BILE ACIDS AND SALTS; BUFFERS; CATIONS; ION TRANSPORT; KIDNEY; LIVER; LLC-PK1 CELLS; MALE; MOLECULAR WEIGHT; PHOSPHATES; QUATERNARY AMMONIUM COMPOUNDS; RATS; RATS, SPRAGUE-DAWLEY; SWINE; TISSUE EXTRACTS;

EID: 43749092563     PISSN: 02536269     EISSN: 19763786     Source Type: Journal    
DOI: 10.1007/s12272-001-1211-8     Document Type: Article

References (26)

1. Abu-Zahra, T. N., Wolkoff, A. W., Kim, R. B., and Pang, K. S., Uptake of enalapril and expression of organic anion transporting polypeptide 1 in zonal, isolated rat hepatocytes. Drug. Metab. Dispos., 28, 801-806 (2000).
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, 880-885 (1991).
3. Fauth, C., Rossier, B., and Roch-Ramel, F., Transport of tetraethylammonium by a kidney epithelial cell line (LLC-PK1). Am. J. Physiol., 254, F351-F357 (1988).
4. Fouda, A. K., Fauth, C., and Roch-Ramel, F., Transport of organic cations by kidney epithelial cell line LLC-PK1. J. Pharmacol. Exp. Ther, 252, 286-292 (1990).
5. Han, Y. H., Chung, S. J., and Shim, C. K., Canalicular membrane transport is primarily responsible for the difference in hepatobiliary excretion of triethylmethylammonium and tributylmethylammonium in rats. Drug. Metab. Dispos., 27, 872-879 (1999).
6. Hughes, R. D., Millburn, P., and Williams, R. T., Molecular weight as a factor in the excretion of monoquaternary ammonium cations in the bile of the rat, rabbit and guinea pig. Biochem. J., 136, 967-978 (1973).
7. Kanai, N., Lu, R., Bao, Y., Wolkoff, A. W., Vore, M., and Schuster, V. L., Estradiol 17 beta-D-glucuronide is a high-affinity substrate for oatp organic anion transporter. Am. J. Physiol., 270, F326-F331 (1996).
8. Kim, M. K., Han, L., Choi, M. K., Han, Y. H., Kim, D. D., Chung, S. J., and Shim, C. K., Dose dependency in the oral bioavailability of an organic cation model, tributylmethyl ammonium (TBuMA), in rats: association with the saturation of efflux by the P-gp system on the apical membrane of the intestinal epithelium. J. Pharm. Sci., 94, 2644-2655 (2005).
9. Launay-Vacher, V., Izzedine, H., Karie, S., Hulot, J. S., Baumelou, A., and Deray, G., Renal tubular drug transporters. Nephron, 103, 97-106 (2006).
10. Lee, H. K., Chien, Y. W., and Lin, T. K., Functional group contribution of bile salt molecules to partitioning of a quaternary ammonium N,N-dimethyl derivative of propranolol. J. Pharm. Sci., 67, 847-849 (1978).
11. Li, H., Chung, S. J., Kim, D. C., Kim, H. S., Lee, J. W., and Shim, C. K., The transport of a reversible proton pump antagonist, 5, 6-dimethyl-2-(4-Fluorophenylamino)-4-(1-methyl-1,2,3, 4-tetrahydroisoquinoline- 2-yl) pyrimidine hydrochloride (YH1885), across caco-2 cell monolayers. Drug. Metab. Dispos., 29, 54-59 (2001).
12. Maeng, H. J., Yoo, H. J., Kim, I. W., Song, I. S., Chung, S. J., and Shim, C. K., P-glycoprotein-mediated transport of berberine across Caco-2 cell monolayers. J. Pharm. Sci., 91, 2614-2621 (2002).
13. Neubert, R., Ion pair transport across membranes. Pharm. Res., 6, 743-747 (1989).
14. Saito, H., Yamamoto, M., Inui, K., and Hori, R., Transcellular transport of organic cation across monolayers of kidney epithelial cell line LLC-PK. Am. J. Physiol., 262, C59-C66 (1992).
15. Sakakura, H., Kimura, N., Takeda, H., Komatsu, H., Ishizaki, K., and Nagata, S., Simultaneous determination of bile acids in rat liver tissue by high-performance liquid chromatography. J. Chromatogr. B Biomed. Sci. Appl., 718, 33-40 (1998).
16. Seelig, A., A general pattern for substrate recognition by P-glycoprotein. European Journal of Biochemistry I FEBS, 251, 252-261 (1998).
17. Sekine, T., Cha, S. H., and Endou, H., The multispecific organic anion transporter (OAT) family. Pflugers Arch., 440, 337-350 (2000).
18. Shim, C. K., Chung, S. J., Lee, J. U., Lee, M. H., and Kim, S. K., Effect of bile salt on the pharmacokinetics of bretylium in the rat (I): increased lipophilicity of bretylium by ion-pair complexation with taurodeoxycholate. Arch. Pharm. Res., 9, 111-114 (1986).
19. Shim, C. K., Nashigaki, R., Iga, T., and Hanano, M., Determination of extraction coefficient, true partition coefficient and formation constant of ion-paring complexes of quaternary ammonium salts, tetrabutylammonium bromide and isopropamide iodide with some organic anions by a solvent extraction technique. Int. J. Pharm., 8, 143-151 (1981).
20. Siskos, P. A., Cahill, P. T., and Javitt, N. B., Serum bile acid analysis: a rapid, direct enzymatic method using dual-beam spectrophotofluorimetry. J. Lipid. Res., 18, 666-671 (1977).
21. Song, I. S., Chung, S. J., and Shim, C. K., Contribution of ion pair complexation with bile salts to biliary excretion of organic cations in rats. Am. J. Physiol Gastrointest Liver Physiol., 281, G515-G525 (2001).
22. Song, I. S., Han, Y. H., Chung, S. J., and Shim, C. K., Contribution of ion-pair complexation with bile salts to the transport of organic cations across LLC-PK1 cell monolayers. Pharm. Res., 20, 597-604 (2003).
23. Takayama, A., Okazaki, Y., Fukuda, K., Takano, M., Inui, K., and Hori, R., Transport of cyclosporin A in kidney epithelial cell line (LLC-PK1). J. Pharmacol. Exp. Ther, 257, 200-204 (1991).
24. Van Gelder, J., Witvrouw, M., Pannecouque, C., Henson, G., Bridger, G., Naesens, L., De Clercq, E., Annaert, P., Shafiee, M., Van Den Mooter, G., Kinget, R., and Augustijns, P., Evaluation of the potential of ion pair formation to improve the oral absorption of two potent antiviral compounds, AMD3100 and PMPA. Int. J. Pharm., 186, 127-136 (1999).
25. Zhang, L., Brett, C. M., and Giacomini, K. M., Role of organic cation transporters in drug absorption and elimination. Annu. Rev. Pharmacol. Toxicol., 38, 431-460 (1998).
26. Zhang, L., Gorset, W., Dresser, M. J., and Giacomini, K. M., The interaction of n-tetraalkylammonium compounds with a human organic cation transporter, hOCT1. J. Pharmacol. Exp. Ther, 288, 1192-1198 (1999).