Synthesis of phospholipid-conjugated bile salts and interaction of bile salt-coated liposomes with cultured hepatocytes

Journal of Lipid Research

Volumn 46, Issue 11, 2005, Pages 2325-2338

  Putz G ^a   Schmider, W ^b   Nitschke, R ^c   Kurz, G ^a   Blum, H E ^a  

^a UNIVERSITY OF FREIBURG   (Germany)

^b SANOFI AVENTIS DEUTSCHLAND GMBH   (Germany)

^c UNIVERSITY OF FREIBURG   (Germany)

Author keywords

Bile salt carrier; Hepatic drug delivery; Hepatocyte specific drug targeting; Modified liposomes

Indexed keywords

BILE SALT; DISODIUM 3ALPHA [2 (1,2 O DISTEAROYLGLYCERO 3 PHOSPHO 2' ETHANOLAMIDOSUCCINYLOXY)ETHOXY] 5BETA CHOLAN 24 OYL 2' AMINOETHANSULFONATE; DISODIUM 3BETA (1,2 O DISTEAROYLGLYCERO 3 PHOSPHO 2' ETHANOLAMIDOSUCCINYLOYXY)ETHOXY 5BETA CHOLAN 24 OYL 2' AMINOETHANSULFONATE; DRUG CARRIER; LIGAND; LIPOSOME; ORGANIC COMPOUND; PHOSPHATIDYLCHOLINE; PHOSPHOLIPID; TAUROLITHOCHOLIC ACID; TRITIUM; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; BINDING AFFINITY; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; CONFOCAL LASER MICROSCOPY; CONTROLLED STUDY; DRUG DELIVERY SYSTEM; DRUG TARGETING; ENCAPSULATION; LIVER CELL; LIVER CELL CULTURE; MALE; MICELLE; NONHUMAN; PRIORITY JOURNAL; PROTEIN CONTENT; PROTON NUCLEAR MAGNETIC RESONANCE; RADIOACTIVITY; RAT; STEREOCHEMISTRY; SYNTHESIS;

ANIMALS; BILE ACIDS AND SALTS; CELLS, CULTURED; DRUG DELIVERY SYSTEMS; ENDOCYTOSIS; ESTERS; HEPATOCYTES; LIGANDS; LIPOSOMES; MALE; MICROSCOPY, CONFOCAL; MODELS, CHEMICAL; MODELS, THEORETICAL; PHOSPHATIDYLCHOLINES; PHOSPHOLIPIDS; PROTEIN BINDING; RATS; RATS, WISTAR; SALTS; STEREOISOMERISM; TAUROCHOLIC ACID; TIME FACTORS;

EID: 27444444137     PISSN: 00222275     EISSN: None     Source Type: Journal    
DOI: 10.1194/jlr.M500144-JLR200     Document Type: Article

References (42)

1. Sliedregt, L. A., P. C. Rensen, E. T. Rump, P. J. van Santbrink, M. K. Bijsterbosch, A. R. Valentijn, G. A. van der Marel, J. H. van Boom, T. J. van Berkel, and E. A. Biessen. 1999. Design and synthesis of novel amphiphilic dendritic galactosides for selective targeting of liposomes to the hepatic asialoglycoprotein receptor. J. Med. Chem. 42: 609-618.
2. Mitrahashi, N., U. Ishihara, A. Sasaki, M. Sakagami, and H. Hamana. 1997. Hepatic accumulation of glutamic acid branched neogalactosyllipid modified liposomes. Biol. Pharm. Bull. 20: 259-266.
3. Wu, J., P. Liu, J. L. Zhii, S. Maddukuri, and M. A. Zern. 1998. Increased liver uptake of liposomes and improved targeting efficacy by labeling with asialofetuin in rodents. Hepatology. 27: 772-778.
4. Osaka, S., H. Tsuji, and H. Kiwada. 1994. Uptake of liposomes surface-modified with glycyrrhizin by primary cultured rat hepatocytes. Biol. Pharm. Bull. 17: 940-943.
5. Shimizu, K., X. R. Qi, Y. Maitani, M. Yoshii, K. Kawano, K. Takayama, and T. Nagai. 1998. Targeting of soybean-derived sterylglucoside liposomes to liver tumors in rat and mouse models. Biol. Pharm. Bull. 21: 741-746.
6. Koning, G. A., J. A. A. M. Kamps, and G. L. Scherphof. 2002. Efficient intracellular delivery of 5-fluorodeoxyuridine into colon cancer cells by targeted immunoliposomes. Cancer Detect. Prev. 26: 299-307.
7. Trauner, M., and J. L. Boyer. 2003. Bile salt transporters: molecular characterization, function, and regulation. Physiol. Rev. 83: 633-671.
8. Meier, P. J., and B. Stieger. 2002. Bile salt transporters. Annu. Rev. Physiol. 64: 635-661.
9. St. Pierre, M. V., G. A. Kullak-Ublick, B. Hagenbuch, and P. J. Meier. 2001. Transport of bile acids in hepatic and non-hepatic tissues (Review). J. Exp. Biol. 204: 10-86.
10. Schramm, U., C. Flicker, H-P. Buscher, W. Gerok, and G. Kurz. 1993. Fluorescent derivatives of bile salts. III. Uptake of 7β-NBD-NCT into isolated hepatocytes by the transport system for cholyltaurine. J. Lipid Res. 34: 741-757.
11. Schwab, D., B. Stieger, B. Hagenbuch, P. J. Meier, W. Gerok, and G. Kurz. 1997. Uptake of 3alpha,7alpha,12alpha-trihydroxy-24-nor-5beta-cholan-23- sulfonate into isolated rat hepatocytes by three transport systems. J. Lipid Res. 38: 935-948.
12. Kramer, W., and G. Wess. 1996. Bile acid transport systems as pharmaceutical targets. Eur. J. Clin. Invest. 26: 715-732.
13. Kramer, W., G. Wess, A. Enhsen, E. Falk, A. Hoffmann, G. Neckermann, G. Schubert, and M. Urmann. 1997. Modified bile acids as carriers for peptides and drugs. J. Control. Release. 46: 17-30.
14. Lowry, O. H., N. J. Rosebrough, A. L. Farr, and R. J. Randall. 1951. Protein measurement with the Folin phenol reagent. J. Biol. Chem. 193: 265-275.
15. Hope, M. J., M. B. Bally, G. Webb, and P. R. Gullis. 1985. Production of large unilamellar vesicles by a rapid extrusion procedure. Characterization of size distribution, trapped volume and ability to maintain a membrane potential. Biochim. Biophys. Acta. 812: 55-65.
16. MacDonald, R. G., R. I. MacDonald, B. P. M. Menco, K. Takeshita, N. K. Subbarao, and L-R. Hu. 1991. Small-volume extrusion apparatus for preparation of large, unilamellar vesicles. Biochim. Biophys. Acta. 1061: 297-303.
17. Stewart, J. G. M. 1980. Colorimetric determination of phospholipids with ammonium ferrothiocyanate. Anal. Biochem. 104: 10-14.
18. Allain, C. C., L. S. Poon, C. S. G. Chan, W. Richmond, and P. C. Fu. 1974. Enzymatic determination of total serum cholesterol. Clin. Chem. 20: 470-475.
19. Roeschlau, P., E. Bernt, and W. Gruber. 1974. Enzymatic determination of total cholesterol in serum. Z. Klin. Chem. Klin. Biochem. 12: 226.
20. McIntyte, J., and R. G. Sleight. 1991. Fluorescence assay for phospholipid membrane asymmetry. Biochemistry. 30: 11819-11827.
21. Schubert, R., and K. H. Schmidt. 1988. Structural changes in vesicle membranes and mixed micelles of various lipid compositions after binding of different bile salts. Biochemistry. 27: 8787-8794.
22. Berry, M. N., and D. S. Friend. 1969. High-yield preparation of isolated rat liver parenchymal cells. J. Biol. Chem. 43: 506-520.
23. Berry, M. N., A. M. Edwards, G. J. Barritt, M. B. Grivell, H. J. Halls, B. J. Gannon, and D. S. Friend. 1991. Isolated hepatocytes. Preparation, properties and applications. In Laboratory Techniques in Biochemistry and Molecular Biology. Vol. 21. R. H. Burdon and P. H. van Knippenberg, editors. Elsevier, Amsterdam. 15-58.
24. Galivan, J. 1982. Stabilisation of cholic acid uptake in primary cultures of hepatocytes by dexamethasone and tocopherole. Arch. Biochem. Biophys. 214: 113-121.
25. Albrecht, O., H. Gruler, and S. Sackmann. 1982. Pressure-composition phase diagrams of cholesterol/lecithin, choleslerol/phosphatidic acid, and lecithin/phosphatidic acid mixed monolayers: a Langmuir film balance study. J. Colloid Interface Sci. 79: 319-338.
26. Lisboa, B. P. 1969. Thin-layer chromatography of steroids, sterols and related compounds. Methods Enzymol. XV: 3-158.
27. Dittmer, J. C., and R. L. Lester. 1964. A simple, specific spray for the detection of phospholipids on thin-layer chromatograms. J. Lipid Res. 5: 126-127.
28. Wess, G., W. Kramer, A. Bartmann, A. Enhsen, H. Glombik, S. Müllner, K. Bock, A. Dries, H. Kleine, and W. Schmitt. 1992. Modified bile acids: preparation of 7α,12α-dihydroxy-3β- and 7α,12α- dihydroxy-3α-(hydroxyethoxy)-5β-cholanic acid and their biological activity. Tetrahedron Lett. 33: 195-198.
29. Kramer, W., and G. Kurz. 1983. Photolabile derivatives of bile salts. Synthesis and suitability for photoaffinity labeling. J. Lipid Res. 24: 910-923.
30. Lee, R. J., and P. S. Low. 1994. Delivery of liposomes into cultured KB cells via folate receptor-mediated endocytosis. J. Biol. Chem. 269: 3198-3204.
31. Schubert, R., K. Beyer, H. Wolburg, and K. H. Schmidt. 1986. Structural changes in membranes of large unilamellar vesicles after binding of sodium cholate. Biochemistry. 25: 5263-5269.
32. Schramm, U., A. Dietrich, S. Schneider, H-P. Buscher, W. Gerok, and G. Kurz. 1991. Fluorescent derivatives of bile salts. II. Suitability of NBD-amino-derivatives of bile salts for the study of biological transport. J. Lipid Res. 32: 1769-1779.
33. Blume, G., G. Cevc, M. D. J. A. Crommelin, J. A. J. M. Bakker-Woudenberg, C. Kluft, and G. Strom. 1993. Specific targeting with poly(ethylene glycol)-modified liposomes: coupling of homing devices to the ends of the polymeric chains combines effective target binding with long circulating times. Biochim. Biophys. Acta. 1149: 180-184.
34. Rigotti, A., S. L. Acton, and M. Krieger. 1995. The class B scavenger receptors SR-BI and CD36 are receptors for anionic phospholipids. J. Biol. Chem. 270: 16221-16224.
35. Fukasawa, M., H. Adachi, K. Hirota, M. Tsujimoto, H. Arai, and K. Inoue. 1996. SRB1, a class B scavenger receptor, recognizes both negatively charged liposomes and apoptotic cells. Exp. Cell Res. 222: 246-250.
36. +/taurocholate cotransport by cyclic AMP. J. Biol. Chem. 268: 17734-17741.
37. Schliess, F., A. K. Kurz, S. V. Dahl, and D. Häussinger. 1997. Mitogen-activated protein kinases mediate the stimulation of bile acid secretion by tauroursodeoxycholate in rat liver. Gastroenterology. 113: 1306-1314.
38. Dranoff, J. A., M. McClure, A. D. Burgstrahler, L. A. Denson, A. R. Crawford, J. M. Crawford, S. J. Karpen, and M. H. Nathason. 1999. Short-term regulation of bile acid uptake by microfilament-dependent translocation of rat ntep to the plasma membrane. Hepatology. 30: 223-229.
39. +-taurocholate cotransport by translocating transporter to plasma membranes. Am. J. Physiol. 273: G842-G848.
40. Von Dippe, P., and D. Levy. 1990. Expression of the bile acid transport protein during liver development and in hepatoma cells. J. Biol. Chem. 265: 5942-5945.
41. Kurz, A. K., D. Graf, M. Schmitt, D. S. Vom, and D. Häussinger. 2001. Tauroursodeoxycholate-induced choleresis involves p38(MAPK) activation and translocation of the bile salt export pump in rats. Gastroenterology. 121: 407-419.
42. +/taurocholate cotransport. J. Biol. Chem. 273: 30039-30045.