Prodrugs of peptides and peptidomimetics for improved formulation and delivery

Advanced Drug Delivery Reviews

Volumn 19, Issue 2, 1996, Pages 275-286

  Oliyai, Reza ^a  

^a GILEAD SCIENCES   (United States)

Author keywords

Delivery; Formulation; Peptide; Peptidomimetic; Prodrug; Transport

Indexed keywords

AMINO ACIDS; DRUG THERAPY; MEMBRANES; PHYSICAL PROPERTIES; POLYPEPTIDES;

CYCLIZATION; ORAL BIOAVAILABILITY; PEPTIDES; PEPTIDOMIMETICS; PHARMACOLOGY;

DRUG PRODUCTS;

CARBOXYPEPTIDASE A; CHYMOTRYPSIN A; METENKEPHALIN; PEPTIDE; PRODRUG; PROTEINASE INHIBITOR;

CYCLIZATION; DRUG DELIVERY SYSTEM; DRUG DESIGN; DRUG FORMULATION; DRUG HYDROLYSIS; PHARMACEUTICS; PHARMACOKINETICS; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; PROTEIN DEGRADATION; PROTEIN METABOLISM; PROTEIN TRANSPORT; REVIEW;

EID: 0343026460     PISSN: 0169409X     EISSN: None     Source Type: Journal    
DOI: 10.1016/0169-409X(95)00110-S     Document Type: Review

References (93)

1. Sanders, L.M. (1990) Drug delivery system and routes of administration of peptide and protein drugs. Eur. J. Drug Metab. Pharmacokinet. 15, 95-102.
2. Davis, S.S. (1986) Advanced delivery systems for peptides and proteins-pharmaceutical considerations. In: S.S. Davis, L. Ilium and E. Tomlinson (Eds), Delivery Systems for Peptide Drugs. Plenum Press, New York, pp. 1-21.
3. Humphrey, M.J. and Ringrose, P.S. (1986) Peptides and related drugs: A review of their absorption, metabolism and excretion. Drug Metab. Rev. 17, 283-310.
4. Lee, V.H.L. and Yamamoto, A. (1990) Penetration and enzymatic barriers to peptide and protein absorption. Adv. Drug Del. Rev. 4, 171-207.
5. Wiedhaup, K. (1981) The stability of small peptides in the gastrointestinal tract. In: D.D. Breimer and P. Speiser (Eds), Topics in Pharmaceutical Sciences, Elsevier, Amsterdam, pp. 307-324.
6. Higuchi, T. and Stella, V.J. (1975) Prodrugs: an overview and definition. Prodrugs as Novel Drug Delivery Systems, American Chemical Society, Washington, DC.
7. Bundgaard, H. (1985) Design of Prodrugs, Elsevier, New York.
8. Oliyai, R. and Stella, V.J. (1993) Prodrugs of peptides and proteins for improved formulation and delivery. Annu. Rev. Pharmacol. Toxicol, 32, 521-544.
9. Young, S.D., Payne, L.S., Thompson, W.J., Gaffin, N. Lyle, T.A. et al. (1992) HIV-1 protease inhibitor based on hydroxyethylene dipeptide isosteres: An investigation into the role of the P1′ side chain on structure-activity. J. Med. Chem. 35, 1702-1709.
10. Tucker. T.J., Lumma, W.C., Payne, L.S., Wai, J.M., De Solms, S.J. et al. (1992) Series of potent HIV-1 protease inhibitors containing a hydroxyethyl secondary amine transition state isostere: Synthesis, enzyme inhibition, and antiviral activity. J. Med. Chem. 35, 2525-2533.
11. Ismailos, G., Reppas, C., Dressman, J.B. and Macheras, P. (1991) Unusual solubility behavior of cyclosporin A in aqueous media. J. Pharm. Pharmacol. 43, 287-289.
12. Balkovec, J.M., Black, R.M., Hammond, M.L., Heck, J.V., Zambias, R.A., et al. (1992) Synthesis, stability, and biological evaluation of water-soluble prodrugs of a new echinocandin lipopeptide. Discovery of a potential clinical agent for the treatment of systemic candidiasis and Pneumocystis carinii pneumonia (PCP). J. Med. Chem. 35, 194-198.
13. Hajdu, R., Sundelof, J.G., Bartizal, K., Abruzzo, G., Trainor, C., et. al. (1991) Comparative pharmacokinetics in four animal species of L-688,786 and its water-soluble prodrug L-693,989. Proc. 31st ICAAC, Chicago, IL, Sept. 29-Oct. 2, Abstr. 209.
14. Chong, K.-T., Ruwart, M., Hinshaw, R.R., Wilkinson, K.F., Rush, D.B., Yancey, M.F., Strohbach, J.W. and Thaisrivongs, S. (1993) Peptidomimetics HIV protease inhibitors: Phosphate prodrugs with improved biological activities. J. Med. Chem. 36, 2575-2577.
15. Williams, A. and Naylor, R.A. (1971) Evidence for SN2(P) mechanism in the phosphorylation of alkaline phosphatase by substrate. J. Chem. Soc. B, 1973-1979.
16. Kearney, A.S. and Stella, V.J. (1992) The in vitro enzymatic labilities of chemically distinct phosphomonoester prodrugs. Pharm. Res. 9, 497-503.
17. Oliyai, R. and Stella, V.J. (1992) Kinetics and mechanism of isomerization of cyclosporin A. Pharm. Res. 9, 617-622.
18. Oliyai, R., Safadi, M., Meier, P.G., Hu, M.-K., Rich, D.H. and Stella, V.J. (1994) Kinetics of acid catalyzed degradation of cyclosporin A and tis analogs in aqueous solution. Int. J. Peptide Protein Res. 43, 239-247.
19. Oliyai, R., Siahaan, T. and Stella, V.J. (1995) The importance of structural factors on the rate and the extent of N,O-acyl migration in cyclic and linear peptides. Pharm. Res. 12, 1-7.
20. Bundgaard, H. and Friis, G.J. (1992) Prodrugs of peptides. 16. Isocyclosporin A as a potential prodrug of cyclosporin A. Int. J. Pharm. 82, 85-90.
21. Hurley, T.R., Colson, C.E., Hicks G. and Ryan, M.J. (1993) Orally active water-soluble N,O-acyl transfer products of a β,γ-bishydroxyl amide containing renin inhibitor. J. Med, Chem. 36, 1496-1498.
22. Oliyai, R. and Stella, V.J. (1995) Structural factors affecting O,N-acyl transfer in O-peptide prodrugs of polypeptides. Bioorg. Med. Chem. Lett. 5, 2735-2740.
23. Ishikawa, K., Fukami, T., Nagase, T., Fujita, K., Hayama, T. et al, (1992) Cyclic pentapeptide endothelin antagonists with high ETA selectivity. Potency-and solubility-enhancing modifications. J. Med. Chem. 35, 2139-2142.
24. Gordee, R.S., Zeckner, D.J., Howard, L.C., Alborn, W.E. and Debono, M. (1988) Anti-candida activity and toxicology of LY121019, a novel semisynthetic polypeptide antifungal antibiotic. Ann. N.Y. Acad. Sci. 544, 294-301.
25. Blaakmeer, J., Tijsse-Klasen, T. and Tesser, G.I. (1991) Enhancement of solubility by temporary dimethoxybenzyl-substitution of peptide bonds. Int. J. Peptide Protein Res. 37, 556-564.
26. Fournié-Zaluski, M.C., Coric, P. Turcaud, S. Lucas, E., Nobel, F. et al. (1992) 'Mixed-inhibitor-prodrug' as a new approach toward systemically active inhibitors of enkephalin-degrading enzymes. J. Med. Chem. 35, 2473-2481.
27. Fournié-Zaluski, M.C., Coric, P., Turcaud, S., Bruetschy, L., Lucas, E. et. al. (1992) Potent and systemically active aminopeptidase N inhibitors designed from active site investigation. J. Med. Chem. 35, 1259-1266.
28. Swynnerton, N.F., McGovern, E.P., Mangold, D.J., Nino, J.A., Gouse, E.M. and Fleckenstein, L. (1983) HPLC assay for S-2-(3-aminopropylamino)ethylphophorothioate (WR-2721) in plasma. J. Liquid Chromatogr. 6, 1523-1534.
29. Manning, M.C., Patel, K. and Borchardt, R.T. (1989) Stability of protein pharmaceuticals. Pharm. Res. 6, 903 918.
30. Ahern, T.J. and Manning, M.C. (1992) Stability of protein pharmaceuticals: Chemical and physical pathways of protein degradation. Pharmaceutical Biotechnology, Vol 2, Plenum Press, New York.
31. Friedman, D.I. and Amidon, G.L. (1991) Oral absorption of peptides: Influence of pH and inhibitors on the intestinal hydrolysis of Leu-enkephalin and analogues. Pharm. Res. 8, 93-96.
32. Friedman, D.I. and Amidon, G.L. (1989) Intestinal absorption mechanism of dipeptide angiotensin converting enzyme inhibitors of the lysyl-proline type: lisinopril and SQ 29,852. J. Pharm. Sci. 78, 995-998.
33. Matthews, D.M. (1975) Intestinal absorption of peptides. Physiol. Rev. 55, 537-607.
34. Adibi, S.A. (1971) Intestinal transport of dipeptide in man: Relative importance of hydrolysis and intact absorption. J. Clin. Invest. 50, 2266-2275.
35. Adibi, S.A. and Morse, E.L. (1977) The number of glycine residues which limit intact absorption of glycine oligopeptides in human jejunum. J. Clin. Invest. 60, 1008-1016.
36. Kenny, A.J. and Maroux, S. (1982) Topology of microvillar membrane hydrolases of kidney and intestine. Physiol. Rev. 62, 91-128.
37. Ward, P.E. and Sheridan, M.A. (1983) Immunoelectrophoretic analysis of renal and intestinal brush border converting enzyme. Biochem. Pharmacol. 32, 265-274.
38. Tobey, N., Haizers, W., Yeh, R., Huang, T.-I. and Hoffner, C. (1985) Human intestinal brush border peptidases. Gastroenterology 88, 913-926.
39. Hussain, M.M. (1985) Reconstitution of purified dipeptidyl peptidase IV. A comparison with aminopeptidase N with respect to morphology and influence of anchoring peptide on function. Biochim. Biophys. Acta 815, 306-312.
40. Krieter, P.A., Olins, G.M., Verret, S.P. and Durley, R.C. (1989) In vivo metabolism of atrial natriuretic peptide: Identification of plasma metabolites and enzyme responsible for their generation. J. Pharmacol. Exp. Ther. 249, 411-417.
41. Edgington, S.M. (1991) The anatomy of access: peptide drug delivery. Bio/Technology 9, 1327-1331.
42. Plattner, J.J., Marcotte, P.A., Kleinert, H.D., Stein, H.H., Greer, J. et al. (1988) Renin inhibitors. Dipeptide analogues of angiotensinogen utilizing a structurally modified phenylalanine residue to impart proteolytic stability. J. Med. Chem. 31, 2277-2288.
43. Morley, J.S. (1980) Structure-activity relationships of enkephalin-like peptides. Annu. Rev. Pharmacol. Toxicol. 20, 81-110.
44. Dressman, J, B., Amidon, G.L. and Fleisher, D. (1985). Absorption potential: Estimating the fraction absorbed for orally administered compounds. J. Pharm. Sci. 74, 588-590.
45. Ho, N.F.H., Day, J.S., Barsuhn, C.L., Burton, P.S. and Raub, T.J. (1990) Biophysical model approaches to mechanistic transepithelial studies of peptides. J. Control. Release 11, 3-24.
46. Conradi, R.A., Hilgers, A.R., Ho, N.F.H. and Burton, P.S. (1991) The influence of peptide structure on the transport across Caco-2 cells. Pharm. Res. 8, 1453-1460.
47. Amsberry, K.L. and Borchardt, R.T. (1990) The lactonization of 2′-hydroxyhydrocinnamic acid amides: A potential prodrug for amines. J. Org. Chem. 55, 5867-5877.
48. Amsberry, K.L. and Borchardt, R.T. (1991) Amine prodrugs which utilize hydroxy amide lactonization. I. A potential redox-sensitive amide prodrug. Pharm. Res. 8, 323-330.
49. Amsberry, K.L., Gerstenberger, A.E. and Borchardt, R.T. (1991) Amine prodrugs which utilize hydroxy amide lactonization. II. A potential esterase-sensitive amide prodrug. Pharm. Res. 8, 455-461.
50. Chikhale, P.J., Kawamura, Y., Nerurkar, M., Shah, P.K., Amsberry, K.L. and Borchardt, R.T. (1995) Intestinal transport and metabolism of novel enkephalin prodrugs. 9th AAPS Annual Meeting November 6-9, 1995, Miami, FL.
51. Rasmussen, G.J. and Bundgaard, H. (1991) Prodrugs of peptides. 15. 4-Imidazolidinone prodrug derivatives of enkephalins to prevent aminopeptidase-catalyzed metabolism in plasma and absorptive mucosa. Int. J. Pharm. 76, 113-122.
52. Naringrekar, V.H. and Stella, V.J. (1990) Mechanism of hydrolysis and structure-stability relationship of enaminones as potential prodrugs of model primary amines. J. Pharm. Sci. 79, 138-146.
53. Nishihata, T. and Kunieda, S. (1994) Preparation of enamine derivative of peptides as prodrugs. Jpn Kokai Tokkyo Koho, 10 pp.
54. Hanson, H.T. and Smith, E.L. (1948) The application of peptides containing β-alanine to the study of the specificity of various peptidases. J. Biol. Chem. 175, 833-848.
55. Snoke, J.E. and Neurath, H. (1949) Structural requirements of specific substrate for carboxypeptidases. J. Biol. Chem. 181, 789-802.
56. Bundgaard, H. and Rasmussen, G.J. (1991) Prodrugs of peptides. 9. Bioreversible N-α-Hydroxyalkylation of the peptide bond to effect protection against carboxypeptidases or other proteolytic enzymes. Pharm. Res. 8, 313-322.
57. Bundgaard, H. and Rasmussen, G.J. (1991) Prodrugs of peptides. 11. Chemical and enzymatic hydrolysis kinetics of N-acyloxymethyl derivatives of a peptide-like bond. Pharm. Res. 8, 1238-1242.
58. Bundgaard, H. (1992) Means to enhance penetration. (1) Prodrugs as means to improve the delivery of peptide drugs. Adv. Drug Deliv. Rev. 8, 1-38.
59. Delie, F., Couvreur, P., Nisato, D., Michel. J.-B., Puisieux, F. and Letourneux, Y. (1994) Synthesis and in vitro study of a diglyceride prodrug of a peptide. Pharm. Res. 11, 1082-1087.
60. Steitz, T.A., Henderson, R. and Blow, D.M. (1969) Structure of crystalline α-chymotrypsin. III. Crystallographic studies of substrates and inhibitors bound to the active site of α-chymotrypsin. J. Mol. Biol. 46, 337-348.
61. Bender, M.L. and Killheffer, J.V. (1973) Chymotrypsins. Crit. Rev. Biochem. 1, 149-199.
62. Konno, S. and Stammer, C.H. (1978) The synthesis of N-benzyloxycarbonyl-L-prolyl-dehydrophenylalanyl-L-histidyl-L-leucine, International J. Peptide Protein Res. 12, 222-231.
63. Kahns, A.H. and Bundgaard, H. (1991) Prodrugs of peptides. 14. Bioreversible derivatization of the tyrosine phenol group to effect protection of tyrosyl peptides against a-chymotrypsin. Int. J. Pharm. 76, 99-112.
64. Kundu, N., Roy, S. and Maenza, F. (1972) Esterase activity of chymotrypsin on oxygen-substituted tyrosine substrate. Eur. J. Biochem. 28, 311-315.
65. Griffiths, E.C. (1987) Clinical application of thyrotropin-releasing hormone. Clin. Sci. 73, 449-457.
66. Hichens, M. (1983) A comparison of thyrotropin-releasing hormone with analogs: influence of disposition upon pharmacology. Drug Metab. Rev. 14, 77-98.
67. Møss, J., Buur, A., Bundgaard, H. (1990) Prodrugs of peptides. 8. In vitro study of intestinal metabolism and penetration of thyrotropin-releasing hormone (TRH) and its prodrugs. Int. J. Pharm. 66, 183-191.
68. Lundin, S., Møss, J., Bundgaard, H., Artursson, P. (1991) Absorption of thyrotropin-releasing hormone (TRH) and a TRH prodrug in human intestinal cell line (Caco-2). Int. J. Pharm. 76, R1-R4.
69. Norbeck, D.W. Personal Communication.
70. Allen, M. and Wade, R. (1988) Synthesis of somatostatin analogs resistant to the action of trypsin. Int. J. Peptide Protein Res. 32, 89-97.
71. Sham, H., Rempel, C., Stein, H. and Cohen, J. (1990) Potent human renin inhibitors containing novel small cylic peptides and stable to chymotrypsin degradation. J. Chem. Soc. Chem. Commun. 666-7.
72. Nutt, R.F., Colton, C., Veber, D.F., Slater, E.L. and Saperstein, R. (1986) Somatotatin analogs with improved oral bioavailability. Klin. Wochenschr. 64, 71-73.
73. Conradi, R.A., Allen, R.H., Ho, N.F.H. and Burton, P.S. (1992). The influence of peptide structure on transport across caco-2 cells. II. Peptide bond modification which results in improved permeability. Pharm. Res. 9, 435-439.
74. Stein, W.D. (1967) The molecular basis of diffusion across cell membranes. The Movement of Molecules Across Cell Membranes, Academic Press, New York, pp. 65-125.
75. Diamond, J.M. and Wright, E.M. (1969) Molecular forces governing non-electrolyte permeation through cell membranes. Proc. Roy. Soc. B 172, 173-316.
76. Gangwar, S., Pauletti, G.M., Siahaan, T.J., Vander Velde, D.G., Stella, V.J. and Borchardt, R.T. (1995) Synthesis of a novel, enzyme-sensitive cyclic prodrug of a model hexapeptide having enhanced membrane permeability and enzymatic stability. I. Acyloxyalkoxycarbamates promoiety. 210th ACS Annual Meeting, August 20-24, 1995, Chicago, IL.
77. Wang, B. Gangwar, S. Pauletti, G.M., Siahaan, T.J. and Borchardt, R.T. (1995) Synthesis of a novel, enzyme-sensitive cyclic prodrug of a model hexapeptide having enhanced membrane permeability and enzymatic stability. II. 3-(2′-Hydroxy-4′-6′-dimethylphenyl)-2,2-dimethyl propionic acid promoiety. 210th ACS Annual Meeting, August 20-24, 1995, Chicago, IL.
78. Blick, M., Sherwin, S.A., Rosenblum, M. and Gutterman, J. (1987) Phase I study of recombinant tumor necrosis factor in cancer patients. Cancer Res. 47, 2986-2989.
79. Hilaire, R.J.S., Hradek, G.T. and Jones, A.L. (1983) Hepatic sequestration and biliary secretion of epidermal growth factor: Evidence for a high capacity uptake system. Proc. Natl. Acad. Sci. USA 80, 3791-3801.
80. Sugiyama, Y. and Hanano, M. (1989) Receptor-mediated transport of peptide hormones and its importance in the overall hormone disposition in the body. Pharm. Res. 6, 192-202.
81. Baumann, G., Vance, M.L., Shaw, M.A. and Thorner, M.O. (1990) Plasma transport of human growth hormone in vivo. Endocrinology 71, 470-473.
82. Kim, D.C., Sugiyama, Y., Sawada, Y. and Hanano, M. (1992) Renal tubular handling of p-aminohippurate and epidermal growth factor (EGF) in filtering and non-filtering perfused rat kidney. Pharm. Res. 9, 271-275.
83. Ishii, Y., Aramaki, Y., Hara, T. and Fuwa, T. (1989) Preparation of EGF labeled liposomes and their uptake by hepatocytes. Biochem. Biophys. Res. Commun. 160, 732-736.
84. Singh, J., Conzentino, P., Cundy, K., Gainor, J., Gilliam, C.L. et al. (1995) Relationship between structure and bioavailability in a series of hydroxamate based metalloprotease inhibitors. Bioorg. Med. Chem. Lett. 5, 337-342.
85. Knadker, M.P., Ackermann, J.E., Coutant, J.E. and Hurst, G.H. (1992) Metabolism of the anticoagulant peptide, MDL 28,050, in rats. Drug Metab. Dispos. 20, 89-95.
86. Ho, D.H., Brown, N.S., Yen, A., Holmes, R., Keating, M. et al. (1986) Clinical pharmacology of polyethylene glycol-L-asparaginase. Drug Metab. Dispos. 14, 349-352.
87. Rademacher, T.W., Parekh, R.B. and Dwek, R.A. (1988) Glycobiology. Annu. Rev. Biochem. 57, 785-838.
88. Markwardt, F. (1989) Acyl-enzymes as prodrugs. Pharmazie 44, 521-526.
89. Duckert, F. (1979) Thrombolytic therapy in myocardial infarction. Prog. Cardiovasc. Dis. 21, 342-350.
90. Wiman, B. and Collen, D. (1978) On the kinetics of the reaction between antiplasmin and plasmin. Eur. J. Biochem. 84, 573-578.
91. Christensen, U. and Clemmensen, I. (1977) Kinetic properties of the primary inhibitor of plasmin from human plasma. Biochem. J. 163, 389-391.
92. Smith, R.A.G., Dupe, R.J., English, P.D. and Green J. (1981) Fibrinolysis with acyl-enzyme: a new approach to thrombolytic therapy. Nature 290, 505-507.
93. Kubiak, T.M., Cleary, D.L., Krabill, L.F. (1992) N-terminally extented GRF analogs as pro-drugs for the liberation of the core GRF by bovine plasma in vitro. Peptides (1992) 739-740.