Effects of amino acid chirality and the chemical linker on the cell permeation characteristics of cyclic prodrugs of opioid peptides

Journal of Medicinal Chemistry

Volumn 49, Issue 4, 2006, Pages 1261-1270

  Liederer, Bianca M ^a   Fuchs, Tarra ^a   Velde, David Vander ^a   Siahaan, Teruna J ^a   Borchardt, Ronald T ^a  

^a UNIVERSITY OF KANSAS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ENKEPHALIN[2 ALANINE 5 DEXTRO LEUCINE]; ENKEPHALIN[2 ALANINE 5 LEUCINE]; ENKEPHALIN[2 DEXTRO ALANINE 5 DEXTRO LEUCINE]; LEUCINE ENKEPHALIN[2 DEXTRO ALANINE]; OPIATE PEPTIDE; PRODRUG; UNCLASSIFIED DRUG;

AMINO TERMINAL SEQUENCE; ANIMAL CELL; ARTICLE; BLOOD BRAIN BARRIER; CARBOXY TERMINAL SEQUENCE; CELL MEMBRANE PERMEABILITY; CELL STRAIN CACO 2; CHIRALITY; CONTROLLED STUDY; DRUG ACTIVITY; DRUG CONFORMATION; DRUG STRUCTURE; INTESTINE MUCOSA PERMEABILITY; MOLECULAR DYNAMICS; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHYSICAL CHEMISTRY;

ALANINE; CACO-2 CELLS; CELL MEMBRANE PERMEABILITY; CYCLIZATION; HUMANS; LEUCINE; MAGNETIC RESONANCE SPECTROSCOPY; MEMBRANE TRANSPORT PROTEINS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; OPIOID PEPTIDES; PEPTIDES, CYCLIC; PRODRUGS; SOLUTIONS; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 33144469997     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm050277f     Document Type: Article

References (40)

1. Pauletti, G. M.; Gangwar, S.; Siahaan, T. J.; Aubé, J.; Borchardt, R. T. Improvement of oral peptide bioavailability: Peptidomimetics and prodrug strategies. Adv. Drug Delivery Rev. 1997, 27, 235-256.
2. Pardridge, W. M. Blood-brain barrier drug targeting: the future of brain drug development. Mol. Interventions 2003, 3, 90-105, 151.
3. Veber, D. F.; Johnson, S. R.; Cheng, H. Y.; Smith, B. R.; Ward, K. W.; Kopple, K. D. Molecular properties that influence the oral bioavailability of drug candidates. J. Med. Chem. 2002, 45, 2615-2623.
4. Atkinson, F.; Cole, S.; Green, C.; van de Waterbeemd, H. Lipophilicity and other parameters affecting brain penetration. Curr. Med. Chem.: Cent. Nerv. Syst. Agents 2002, 2, 229-240.
5. Pauletti, G. M.; Gangwar, S.; Knipp, G. T.; Nerkurkar, M. M.; Okumu, F. W.; Tamura, K.; Siahaan, T. J.; Borchardt, R. T. Structural requirements for intestinal absorption of peptide drugs. J. Controlled Release 1996, 41, 3-17.
6. Wacher, V. J.; Silverman, J. A.; Zhang, Y.; Benet, L. Z. Role of P-glycoprotein and cytochrome P450 3A in limiting oral absorption of peptides and peptidomimetics. J. Pharm. Sci. 1998, 87, 1322-1330.
7. Borchardt, R. T. Optimizing oral absorption of peptides using prodrug strategies. J. Controlled Release 1999, 62, 231-238.
8. Ouyang, H.; Vander Velde, D. G.; Borchardt, R. T.; Siahaan, T. J. Synthesis and conformational analysis of a coumarinic acid-based cyclic prodrug of an opioid peptide with modified sensitivity to esterase-catalyzed bioconversion. J. Pept. Res. 2002, 59, 183-195.
9. Yang, J. Z.; Chen, W.; Borchardt, R. T. In vitro stability and in vivo pharmacokinetic studies of a model opioid peptide, H-Tyr-D-Ala-Gly-Phe-D-Leu-OH (DADLE), and its cyclic prodrugs. J. Pharmacol. Exp. Ther. 2002, 303, 840-848.
10. Ouyang, H.; Tang, F.; Siahaan, T. J.; Borchardt, R. T. A modified coumarinic acid-based cyclic prodrug of an opioid peptide: its enzymatic and chemical stability and cell permeation characteristics. Pharm. Res. 2002, 19, 794-801.
11. Tang, F.; Borchardt, R. T. Characterization of the efflux transporter(s) responsible for restricting intestinal mucosa permeation of the coumarinic acid-based cyclic prodrug of the opioid peptide DADLE. Pharm. Res. 2002, 19, 787-793.
12. Tang, F.; Borchardt, R. T. Characterization of the efflux transporter(s) responsible for restricting intestinal mucosa permeation of an acyloxyalkoxy-based cyclic prodrug of the opioid peptide DADLE. Pharm. Res. 2002, 19, 780-786.
13. Chen, W.; Yang, J. Z.; Andersen, R.; Nielsen, L. H.; Borchardt, R. T. Evaluation of the permeation characteristics of a model opioid peptide, H-Tyr-D-Ala-Gly-Phe-D-Leu-OH (DADLE), and its cyclic prodrugs across the blood-brain barrier using an in situ perfused rat brain model. J. Pharmacol. Exp. Ther. 2002, 303, 849-857.
14. Morley, J. S. Structure-activity relationships of enkephalin-like peptides. Annu. Rev. Pharmacol. Toxicol. 1980, 20, 81-110.
15. Ling, N. M. S.; Lazarus, L.; Rivier, J.; Guillemin, R. Structure-activity relationships of enkephalin and endorphin analogs. Pept., Proc. Am. Pept. Symp., 5th 1977, 96-99.
16. Eriksson, L.; Jonsson, J.; Hellberg, S.; Lindgren, F.; Skagerberg, B.; Sjostrom M.; Wold, S. Peptide QSAR on substance P analogues, enkephalins and bradykinins containing L- and D-amino acids. Acta Chem. Scand. 1990, 44, 50-55.
17. Bergstrom, C. A.; Strafford, M.; Lazorova, L.; Avdeef, A.; Luthman, K.; Artursson, P. Absorption classification of oral drugs based on molecular surface properties. J. Med. Chem. 2003, 46, 558-570.
18. Seelig, A. A general pattern for substrate recognition by P-glycoprotein. Eur. J. Biochem. 1998, 251, 252-261.
19. Seelig, A.; Blatter, X. L.; Wohnsland, F. Substrate recognition by P-glycoprotein and the multidrug resistance-associated protein MRP1: a comparison. Int. J. Clin. Pharmacol. Ther. 2000, 38, 111-121.
20. Schwab, D.; Fischer, H.; Tabatabaei, A.; Poli, S.; Huwyler, J. Comparison of in vitro P-glycoprotein screening assays: recommendations for their use in drug discovery. J. Med. Chem. 2003, 46, 1716-1725.
21. Pajeva, I. K.; Wiese, M. Pharmacophore model of drugs involved in P-glycoprotein multidrug resistance: explanation of structural variety (hypothesis). J. Med. Chem. 2002, 45, 5671-5686.
22. Penzotti, J. E.; Lamb, M. L.; Evensen, E.; Grootenhuis, P. D. A computational ensemble pharmacophore model for identifying substrates of P-glycoprotein. J. Med. Chem. 2002, 45, 1737-1740.
23. Ekins, S.; Kim, R. B.; Leake, B. F.; Dantzig, A. H.; Schuetz, E. G.; Lan, L. B.; Yasuda, K.; Shepard, R. L.; Winter, M. A.; Schuetz, J. D.; Wikel, J. H.; Wrighton, S. A. Application of three-dimensional quantitative structure-activity relationships of P-glycoprotein inhibitors and substrates. Mol. Pharmacol. 2002, 61, 974-981.
24. Österberg, T.; Norinder, U. Theoretical calculation and prediction of P-glycoprotein-interacting drugs using MolSurf parametrization and PLS statistics. Eur. J. Pharm. Sci. 2000, 10, 295-303.
25. Reid, R. C.; Kelso, M. J.; Scanlon, M. J.; Fairlie, D. P. Conformationally constrained macrocycles that mimic tripeptide beta-strands in water and aprotic solvents. J. Am. Chem. Soc. 2002, 124, 5673-5683.
26. Gudmundsson, O. S.; Jois, S. D.; Vander Velde, D. G.; Siahaan, T. J.; Wang, B.; Borchardt, R. T. The effect of conformation on the membrane permeation of coumarinic acid- and phenylpropionic acid-based cyclic prodrugs of opioid peptides. J. Pept. Res. 1999, 53, 383-392.
27. Gudmundsson, O. S.; Vander Velde, D. G.; Jois, S. D.; Bak, A.; Siahaan, T. J.; Borchardt R. T. The effect of conformation of the acyloxyalkoxy-based cyclic prodrugs of opioid peptides on their membrane permeability. J. Pept. Res. 1999, 53, 403-413.
28. Conradi, R. A.; Hilgers, A. R.; Ho, N. F.; Burton, P. S. The influence of peptide structure on transport across Caco-2 cells. II. Peptide bond modification which results in improved permeability. Pharm. Res. 1992, 9, 435-439.
29. Conradi, R. A.; Hilgers, A. R.; Ho, N. F.; Burton, P. S. The influence of peptide structure on transport across Caco-2 cells. Pharm. Res. 1991, 8, 1453-1460.
30. Wüthrich, K. NMR of Protein and Nucleic Acids; John Wiley & Sons, Inc.: New York, 1986.
31. Rose, G. D.; Gierasch, L. M.; Smith, J. A. Turns in peptides and proteins. Adv. Protein Chem. 1985, 37, 1-109.
32. Clark, D. E. Rapid calculation of polar molecular surface area and its application to the prediction of transport phenomena. 2. Prediction of blood-brain barrier penetration. J. Pharm. Sci. 1999, 88, 815-821.
33. Kelder, J.; Grootenhuis, P. D.; Bayada, D. M.; Delbressine, L. P.; Ploemen, J. P. Polar molecular surface as a dominating determinant for oral absorption and brain penetration of drugs. Pharm. Res. 1999, 16, 1514-1519.
34. He, Y. L.; Murby, S.; Gifford, L.; Collett, A.; Warhurst, G. et al. Oral absorption of D-oligopeptides in rats via the paracellular route. Pharm. Res. 1996, 13, 1673-1678.
35. Wils, P.; Warnery, A.; Phung-Ba, V.; Legrain, S.; Scherman, D. High lipophilicity decreases drug transport across intestinal epithelial cells. J. Pharmacol. Exp. Ther. 1994, 269, 654-658.
36. Lipinski, C. A. Drug-like properties and the causes of poor solubility and poor permeability. J. Pharmacol. Toxicol. Methods 2000, 44, 235-249.
37. Seelig, A. How does P-glycoprotein recognize its substrates? Int. J. Clin. Pharmacol. Ther. 1998, 36, 50-54.
38. Buchi, G.; Weinreb, S. M. Total syntheses of aflatoxins M1 and G1 and an improved synthesis of aflatoxin B1. J. Am. Chem. Soc. 1971, 93, 746-752.
39. Gao, J.; Hugger, E. D.; Beck-Westermeyer, M. S.; Borchardt, R. T. Protocols in the application of Caco-2 cells in measuring permeability coefficient of drugs. Current Protocols in Pharmacology, John Wiley and Sons: New York, 2000; pp 1-23.
40. Yang, J. Z.; Bastian, K. C.; Moore, R. D.; Stobaugh, J. F.; Borchardt, R. T. Quantitative analysis of a model opioid peptide and its cyclic prodrugs in rat plasma using high-performance liquid chromatography with fluorescence and tandem mass spectrometric detection. J. Chromatogr. B Anal. Technol. Biomed. Life Sci. 2002, 780, 269-281.