Enhanced transepithelial transport of peptides by conjugation to cholic acid

Bioconjugate Chemistry

Volumn 8, Issue 4, 1997, Pages 520-525

  Swaan, Peter W ^a,b   Hillgren, Kathleen M ^a,c   Szoka Jr , Francis C ^a   Øie, Svein ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b OHIO STATE UNIVERSITY   (United States)

^c SANOFI   (France)

Author keywords

[No Author keywords available]

Indexed keywords

BODY FLUIDS; CELL CULTURE; METABOLISM; MOLECULES; PHYSIOLOGY;

ACID CHAINS; AMIDE BOND; BILE ACID; CELL LINES; CHAINS LENGTH; INTESTINAL CELLS; NATURAL SUBSTRATES; PASSIVE DIFFUSIONS; TAUROCHOLIC ACIDS; TRANSEPITHELIAL TRANSPORT;

PEPTIDES;

EID: 0031193858     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc970076t     Document Type: Article

References (20)

1. Swaan, P. W., Øie, S., and Szoka, F. C., Jr. (1996) Carrier-mediated oral drug delivery - preface. Adv. Drug Delivery Rev. 20, 1-3.
2. Ho, N. (1987) Utilizing bile acid carrier mechanisms to enhance liver and small intestine absorption. Ann. N.Y. Acad. Sci. 507, 315-329.
3. Swaan, P. W., Øie, S., and Szoka, F. C., Jr. (1996) Use of the bile acid transporter for drug delivery. Adv. Drug Delivery Rev. 20, 59-82.
4. Kim, D. C., Harrison, A. W., Ruwart, M. J., Wilkinson, K. F., Fisher, J. F., Hidalgo, I. J., and Borchardt, R. T. (1993) Evaluation of the bile acid transporter in enhancing intestinal permeability to renin-inhibitory peptides. J. Drug Targeting 1, 347-359.
5. Kramer, W., Wess, G., Schubert, G., Bickel, M., Girbig, F., Gutjahr, U., Kowalewski, S., Baringhaus, K.-H., Enhsen, A., Glombik, H., Müllner, S., Neckermann, G., Schulz, S., and Petzinger, E. (1992) Liver-specific drug targeting by coupling to bile acids. J. Biol. Chem. 267, 18598-18604.
6. Kramer, W., Wess, G., Enhsen, A., Bock, K., Falk, E., Hoffmann, A., Neckermann, G., Gantz, D., Schulz, S., Nickau, L., Petzinger, E., Turley, S., and Dietschy, J. M. (1994) Bile acid derived HMG-CoA reductase inhibitors. Biochim. Biophys. Acta 1227, 137-154.
7. Kramer, W., Wess, G., Neckermann, G., Schubert, G., Fink, J., Girbig, F., Gutjahr, U., Kowalewski, S., Baringhaus, K. H., Böger, G., Enhsen, A., Falk, E., Friedrich, M., Glombik, H., Hoffmann, A., Pittius, C., and Urmann, M. (1994) Intestinal absorption of peptides by coupling to bile acids. J. Biol. Chem. 269, 10621-10627.
8. 3 by liver targeting with cholic acid. Biochem. Pharmacol. 43, 1969-1974.
9. Mills, C. O., and Elias, E. (1992) Biliary excretion of chenodeoxycholyllysylrhodamine in Wistar rats: a possible role of a bile acid as a carrier for drugs. Biochim. Biophys. Acta 1126, 35-40.
10. Kågedahl, M., Swaan, P. W., Redemann, C. T., Tang, M., Craik, C. S., Szoka, F. C., Jr., and Øie, S. (1997) Use of the intestinal bile acid carrier for the transport of HIV-1 protease inhibitors. Pharm. Res. 14, 176-180.
11. Knorr, R., Trzeciak, A., Bannwarth, W., and Gillessen, D. (1989) New coupling reagents in peptide chemistry. Tetrahedron Lett. 30, 1927-1930.
12. Lack, L., and Weiner, I. M. (1966) Intestinal bile salt transport: structure-activity relationships and other properties. Am. J. Physiol. 210, 1142-1152.
13. Hidalgo, I. J., and Borchardt, R. T. (1990) Transport of bile acids in a human intestinal epithelial cell line, CaCo-2. Biochim. Biophys. Acta 1035, 97-103.
14. Chandler, C. E., Zaccaro, L. M., and Moberly, J. B. (1993) Transepithelial transport of cholyltaurine by CaCo-2 cell monolayers is sodium dependent. Am. J. Physiol. 264, G1118-G1125.
15. Biaselle, C. J., and Millar, D. B. (1975) Studies on Triton X-100 detergent micelles. Biophys. Chem. 3, 355-361.
16. Mills, C. O., Martin, G. H., and Elias, E. (1986) The effect of tyrosine conjugation on the critical micellar concentration of free and glycine-conjugated bile salts. Biochim. Biophys. Acta 876, 677-683.
17. M. D. Taylor and G. L. Amidon, Eds. (1995) Peptide-based Drug Design: Controlling Transport and Metabolism, pp 1-567, American Chemical Society, Washington, DC.
18. Jumarie, C., and Malo, C. (1994) Alkaline phosphatase and peptidase activities in CaCo-2 cells: differential response to triiodothyronine. In Vitro Cell. Dev. Biol. 30A, 753-760.
19. Howell, S., Kenny, A. J., and Turner, A. J. (1992) A survey of membrane peptidases in two human colonic cell lines, CaCo-2 and HT-29. Biochem. J. 284, 595-601.
20. Augustijns, P. F., and Borchardt, R. T. (1995) Transport and metabolism of delta sleep-inducing peptide in cultured human intestinal epithelial cell monolayers. Drug Metab. Dispos. 23, 1372-1378.