The effect of conformation of the acyloxyalkoxy-based cyclic prodrugs of opioid peptides on their membrane permeability

Journal of Peptide Research

Volumn 53, Issue 4, 1999, Pages 403-413

  Gudmundsson, O S ^a,b   Vander Velde, D G ^a   Jois, S D S ^a   Bak, A ^c   Siahaan, T J ^a   Borchardt, Ronald T ^a  

^a UNIVERSITY OF KANSAS   (United States)

^b BRISTOL MYERS SQUIBB   (United States)

^c UNIVERSITY OF COPENHAGEN   (Denmark)

Author keywords

Apically polarized efflux systems; Membrane permeability; Nuclear magnetic resonance spectroscopy; Opioid peptide delivery; Solution conformation

Indexed keywords

COUMARIN DERIVATIVE; ENKEPHALIN[2 DEXTRO ALANINE 5 DEXTRO LEUCINE]; GLYCOPROTEIN P; LEUCINE ENKEPHALIN; OPIATE PEPTIDE; PHENYLPROPIONIC ACID DERIVATIVE; PRODRUG; TYROSINE;

ARTICLE; BETA CHAIN; CELL MEMBRANE PERMEABILITY; CHEMICAL BINDING; CIRCULAR DICHROISM; CIS TRANS ISOMERISM; MATHEMATICAL COMPUTING; MOLECULAR DYNAMICS; MOLECULAR MODEL; MOLECULAR RECOGNITION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; PROTEIN CONFORMATION; PROTEIN STRUCTURE; SPATIAL ORIENTATION; STRUCTURE ANALYSIS;

BIOLOGICAL TRANSPORT; CELL MEMBRANE PERMEABILITY; CELLS, CULTURED; CIRCULAR DICHROISM; ENKEPHALIN, LEUCINE; ENKEPHALIN, LEUCINE-2-ALANINE; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; OPIOID PEPTIDES; PEPTIDES, CYCLIC; PRODRUGS; PROTEIN CONFORMATION; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0033002915     PISSN: 1397002X     EISSN: None     Source Type: Journal    
DOI: 10.1034/j.1399-3011.1999.00077.x     Document Type: Article

References (32)

1. 1. Bak, A., Siahaan, T.J., Gudmundsson, OS., Gangwar, S., Friis, G.J. & Borchardt, R.T. (1999) J. Peptide Res. 53, 393-402.
2. 2. Wang, B., Nimkar, K., Wang, W., Zhang, H., Shan, D., Gudmundsson, O., Gangwar, S., Siahaan, T.J. & Borchardt, R.T. (1999) J. Peptide Res. 53, 370-382.
3. 3. Gudmundsson, O.S., Pauletti, G.M., Wang, W., Shan, D., Zhang, H., Wang, B. & Borchardt, R.T. (1999) Pharm. Res. 16, 7-15.
4. 4. Gudmundsson, O.S., Nimkar, K., Gangwar, S. & Borchardt, R.T. (1999) Pharm. Res. 16, 16-23.
5. 5. Bak, A., Gudmundsson, O.S., Friis, G.J., Sihaan, T.J. & Borchardt, R.T, (1999) Pharm. Res. 16, 24-29.
6. 6. Burton, P.S., Goodwill, J.T., Conradi, R.A., Ho, N.F.H. & Hilgers, A.R. (1997) Adv. Drug. Deliv. Rev. 23, 143-156.
7. 7. Gudmundsson, O.S., Jois, S.D.S., Vander Velde, D.G., Siahaan, T.J., Wang, B. & Borchardt, R.T. (1999) J. Peptide Res. 53, 383-392.
8. 8. Bax, A. & Davis, D.G. (1985) J. Magn. Reson. 63, 207-213.
9. 9. Rance, M., Sorensen, O.W., Bodenhausen, G., Wagner, G., Ernst, R.R. & Wuthrich, K. (1983) Biochem. Biophys. Res. Commun. 117, 479-485.
10. 10. Wurthrich, K. (1986) NMR of Proteins and Nucleic Acids. John Wiley and Sons, New York.
11. 11. Nilges, M., Gronenborn, A.M., Brungen, A.T. & Clore, G.M. (1988) Protein Eng. 2, 27-38.
12. 12. Ramachandran, G.N. & Mitra, A.K. (1976) J. Mol Biol. 107, 85-92.
13. 13. Gangwar, S., Jois, S.D.S., Siahaan, T.J., Vander Velde, D.G., Stella, V.J. & Borchardt, R.T. (1996) Pharm. Res. 13, 1657-1662.
14. 14. Suteliffe, M.J. (1993) In NMR of Macromolecules. A Practical Approach (Roberts, G.C.K., ed.).Oxford University Press, New York, pp. 359-390.
15. 15. Perezel, A. & Hollosi, M. (1996) In Circular Dichroism and the Conformational Analysis of Biomolecules (Fasman, G.D., ed.). Plenum Press, New York, pp. 285-380.
16. 16. Bystrov, V.F. (1976) Prog. NMR Spectroscopy 10, 41-81.
17. 17. Okumu, F.W., Pauletti, G.M., Vander Velde, D.G., Siahaan, T.J. & Borchardt, R.T. (1997) Pharm. Res. 14, 169-175.
18. 18. Knipp, G.T., Vander Velde, D.G., Siahaan, T.J. & Borchardt, R.T. (1997) Pharm. Res. 14, 1332-1340.
19. 19. Sorensen, M., Steenberg, B., Knipp, G.T., Wang, W., Steffansen, B., Frokjaer, S. & Borchardt, R.T. (1997) Pharm. Res. 14, 1341-1348.
20. 20. Tamura, K., Agrios, K.A., Vander Velde, D.G., Aubé, J. & Borchardt, R.T. (1997) Bioorg. Med. Chem. 5, 1859-1866.
21. 21. Conradi, R.A., Burton, P.S. & Borchardt, R.T. (1997) In Lipophilicity in Drug Action and Toxicity (Pliska, V., Testa, B. & Van de Waterbeemd, H., eds). VCH Weinheim, Weinheim, pp. 233-252.
22. 22. Burton, P.S., Conradi, R.A., Ho, N.F.H., Hilgers, A.R. & Borchardt, R.T. (1996) J. Pharm. Sci. 85, 1336-1340.
23. 23. Pauletti, G.M., Gangwar, S., Knipp, G.T., Nerurkar, M.M., Okumu, F.W., Tamura, K., Siahaan, T.J. & Borchardt, R.T. (1996) J. Control. Rel. 41, 3-17.
24. 24. Pauletti, G.M., Gangwar, S., Siahaan, T.J., Aube, J. & Borchardt, R.T. (1997) Adv. Drug Deliv. Rev. 27, 235-256.
25. 25. Hunter, J. & Hirst, B.H. (1997) Adv. Drug Deliv. Rev. 15, 129-157.
26. 26. Wacher, V.J., Salphati, L. & Benet, L.Z. (1996) Adv. Drug. Deliv. Rev. 20, 99-112.
27. 17. Sudoh, M., Pauletti, G.M., Yao, W., Sprengler, P.A., Smith, A.B., III, Hirschmann, R. & Borchardt, R.T. (1998) Pharm. Res. 15, 719-725.
28. 28. Seelig, A. (1998) Eur. J. Biochem. 251, 252-261.
29. 29. Augustijns, P.F., Bradshaw, T.P., Gan, L.S., Hendren, R.W. & Thakker, D.R. (1993) Biochem. Biophys. Res. Comm. 197, 360-365.
30. 30. Tayar, N.E., Mark, A.E., Vallet, P., Brunne, R.M., Testa, B. & Gunsteren, W.F.V. (1993) J. Med. Chem. 36, 3757-3764.
31. 31. Loosli, H.-R., Kessler, H., Oschkinat, H., Weher, H.-P., Peteher, T.J. & Widmer, A. (1985) Helv. Chim. Acta 68, 682-704.
32. 32. Vander Velde, D.G., Burton, P.S. & Borchardt, R.T. (1995) Keystone Symposium on Prospects and Drug Design Based on Peptides and Proteins, Taos, New Mexico, March 8-14, Abstract L-331.