Synthesis and biological evaluation of an orally active glycosylated endomorphin-1

Journal of Medicinal Chemistry

Volumn 55, Issue 12, 2012, Pages 5859-5867

  Varamini, Pegah ^a   Mansfeld, Friederike M ^a   Blanchfield, Joanne T ^a   Wyse, Bruce D ^a   Smith, Maree T ^a   Toth, Istvan ^a  

^a UNIVERSITY OF QUEENSLAND   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

ENDOMORPHIN 1; MORPHINE; NALOXONE; PROPRANOLOL;

ANALGESIA; ANALGESIC ACTIVITY; ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTINOCICEPTION; AREA UNDER THE CURVE; ARTICLE; CONTROLLED STUDY; DOSE RESPONSE; DRUG ABSORPTION; DRUG POTENCY; DRUG SCREENING; DRUG STABILITY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IN VIVO STUDY; MALE; NEUROPATHIC PAIN; NONHUMAN; RAT; SINGLE DRUG DOSE; STRUCTURE ACTIVITY RELATION;

ABSORPTION; ADMINISTRATION, ORAL; ANALGESICS, OPIOID; ANIMALS; CHEMISTRY TECHNIQUES, SYNTHETIC; CHO CELLS; CONSTIPATION; CRICETINAE; CRICETULUS; GLYCOSYLATION; MALE; NALOXONE; NEURALGIA; OLIGOPEPTIDES; RATS; RATS, SPRAGUE-DAWLEY; RECEPTORS, OPIOID;

EID: 84863092840     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm300418d     Document Type: Article

References (52)

1. Truini, A.; Cruccu, G. Pathophysiological mechanisms of neuropathic pain Neurol. Sci. 2006, 27, S179-S182
2. Dworkin, R. H.; O'Connor, A. B.; Backonja, M.; Farrar, J. T.; Finnerup, N. B.; Jensen, T. S.; Kalso, E. A.; Loeser, J. D.; Miaskowski, C.; Nurmikko, T. J.; Portenoy, R. K.; Rice, A. S. C.; Stacey, B. R.; Treede, R.-D.; Turk, D. C.; Wallace, M. S. Pharmacologic management of neuropathic pain: evidence-based recommendations Pain 2007, 132, 237-251
3. Gentilucci, L. New trends in the development of opioid peptide analogues as advanced remedies for pain relief Curr. Top. Med. Chem. 2004, 4, 19-38
4. Zadina, J. E.; Hackler, L.; Ge, L.-J.; Kastin, A. J. A potent and selective endogenous agonist for the μ-opiate receptor Nature 1997, 386, 499-502
5. Horvath, G. Endomorphin-1 and endomorphin-2: pharmacology of the selective endogenous μ-opioid receptor agonists Pharmacol. Ther. 2000, 88, 437-463
6. Przewlocki, R.; Przewlocka, B. Opioids in chronic pain Eur. J. Pharmacol. 2001, 429, 79-91
7. Czapla, M. A.; Gozal, D.; Alea, O. A.; Beckerman, R. C.; Zadina, J. E. Differential cardiorespiratory effects of endomorphin 1, endomorphin 2, DAMGO, and morphine Am. J. Respir. Crit. Care Med. 2000, 162, 994-999
8. Sugimoto-Watanabe, A.; Kubota, K.; Fujibayashi, K.; Saito, K. Antinociceptive effect and enzymatic degradation of endomorphin-1 in newborn rat spinal cord Jpn. J. Pharmacol. 1999, 81, 264-270
9. Tomboly, C.; Peter, A.; Toth, G. In vitro quantitative study of the degradation of endomorphins Peptides 2002, 23, 1573-1580
10. Allt, G.; Lawrenson, J. G. The blood-nerve barrier: enzymes, transporters and receptors - a comparison with the blood-brain barrier Brain Res. Bull. 2000, 52, 1-12
11. Egleton, R. D.; Abbruscato, T. J.; Thomas, S. A.; Davis, T. P. Transport of opioid peptides into the central nervous system J. Pharm. Sci. 1998, 87, 1433-1439
12. 1] endomorphin analogs with six-membered proline surrogates in position 2 Bioorg. Med. Chem. 2009, 17, 3789-3794
13. Soignier, R. D.; Vaccarino, A. L.; Brennan, A. M.; Kastin, A. J.; Zadina, J. E. Analgesic effects of endomorphin-1 and endomorphin-2 in the formalin test in mice Life Sci. 2000, 67, 907-912
14. Goldberg, I. E.; Rossi, G. C.; Letchworth, S. R.; Mathis, J. P.; Ryan-Moro, J.; Leventhal, L.; Su, W.; Emmel, D.; Bolan, E. A.; Pasternak, G. W. Pharmacological characterization of endomorphin-1 and endomorphin-2 in mouse brain J. Pharmacol. Exp. Ther. 1998, 286, 1007-1013
15. Soltero, R., Oral Protein and Peptide Drug Delivery; John Wiley & Sons, Inc.: New York, 2005; pp 189-200.
16. Ogawa, T.; Araki, M.; Miyamae, T.; Okayama, T.; Hagiwara, M.; Sakurada, S.; Morikawa, T. Synthesis and antinociceptive activity of orally active opioid peptides: improvement of oral bioavailability by esterification Chem. Pharm. Bull. (Tokyo) 2003, 51, 759-771
17. 2]dermorphin(1-4) analogues, N (alpha)-amidino-Tyr- d -Arg-Phe-X Chem. Pharm. Bull. (Tokyo) 2002, 50, 771-780
18. Clark, R. J.; Jensen, J.; Nevin, S. T.; Callaghan, B. P.; Adams, D. J.; Craik, D. J. The engineering of an orally active conotoxin for the treatment of neuropathic pain Angew. Chem., Int. Ed. Engl. 2010, 49, 6545-6548
19. Muthu, D.; Polt, R. New Prospects for Glycopeptide Based Analgesia: Glycoside-Induced Penetration of the Blood-Brain Barrier Curr. Drug Delivery 2005, 2, 59-73
20. Polt, R.; Palian, M. M. Glycopeptide analgesics Drugs Future 2001, 26, 561-576
21. Simerska, P.; Moyle, P. M.; Toth, I. Modern lipid-, carbohydrate-, and peptide-based delivery systems for peptide, vaccine, and gene products Med. Res. Rev. 2009, 31, 520-547
22. Toth, I.; Malkinson, J. P.; Flinn, N. S.; Drouillat, B.; Horvath, A.; Erchegyi, J.; Idei, M.; Venetianer, A.; Artursson, P.; Lazorova, L.; Szende, B.; Keri, G. Novel lipoamino acid- and liposaccharide-based system for peptide delivery: application for oral administration of tumor-selective somatostatin analogues J. Med. Chem. 1999, 42, 4010-4013
23. Koda, Y.; Del Borgo, M.; Wessling, S. T.; Lazarus, L. H.; Okada, Y.; Toth, I.; Blanchfield, J. T. Synthesis and in vitro evaluation of a library of modified endomorphin 1 peptides Bioorg. Med. Chem. 2008, 16, 6286-6296
24. Elmagbari, N. O.; Egleton, R. D.; Palian, M. M.; Lowery, J. J.; Schmid, W. R.; Davis, P.; Navratilova, E.; Dhanasekaran, M.; Keyari, C. M.; Yamamura, H. I.; Porreca, F.; Hruby, V. J.; Polt, R.; Bilsky, E. J. Antinociceptive structure-activity studies with enkephalin-based opioid glycopeptides J. Pharmacol. Exp. Ther. 2004, 311, 290-297
25. Do Carmo, G. P.; Polt, R.; Bilsky, E. J.; Rice, K. C.; Negus, S. S. Behavioral pharmacology of the mu/delta opioid glycopeptide MMP2200 in rhesus monkeys J. Pharmacol. Exp. Ther. 2008, 326, 939-948
26. Alewood, P.; Alewood, D.; Miranda, L.; Love, S.; Meutermans, W.; Wilson, D., Rapid in situ neutralization protocols for Boc and Fmoc solid-phase chemistries. In Methods in Enzymology; Gregg, B. F., Ed.; Academic Press: New York, 1997; Vol. 289, pp 14-29.
27. Johnsson, G.; Regardh, C. G. Clinical pharmacokinetics of beta-adrenoreceptor blocking drugs Clin. Pharmacokinet. 1976, 1, 233-263
28. Klink, D.; Yu, Q. C.; Glick, M. C.; Scanlin, T. Lactosylated poly- l -lysine targets a potential lactose receptor in cystic fibrosis and non-cystic fibrosis airway epithelial cells Mol. Ther. 2003, 7, 73-80
29. Kato, Y.; Onishi, H.; Machida, Y. Biological characteristics of lactosaminated N -succinyl-chitosan as a liver-specific drug carrier in mice J. Controlled Release 2001, 70, 295-307
30. Harrison, C.; McNulty, S.; Smart, D.; Rowbotham, D. J.; Grandy, D. K.; Devi, L. A.; Lambert, D. G. The effects of endomorphin-1 and endomorphin-2 in CHO cells expressing recombinant μ-opioid receptors and SH-SY5Y cells Br. J. Pharmacol. 1999, 128, 472-478
31. Liu, H. M.; Zhang, B. Z.; Liu, X. F.; Wang, C. L.; Ni, J. M.; Wang, R. Endomorphin-1 analogs with enhanced metabolic stability and systemic analgesic activity: Design, synthesis, and pharmacological characterization Bioorg. Med. Chem. 2007, 15, 1694-1702
32. Egleton, R. D.; Mitchell, S. A.; Huber, J. D.; Palian, M. M.; Polt, R.; Davis, T. P. Improved blood-brain barrier penetration and enhanced analgesia of an opioid peptide by glycosylation J. Pharmacol. Exp. Ther. 2001, 299, 967-972
33. Janecka, A.; Staniszewska, R.; Gach, K.; Fichna, J. Enzymatic degradation of endomorphins Peptides 2008, 29, 2066-2073
34. Harbeck, H. T.; Mentlein, R. Aminopeptidase P from rat brain. Purification and action on bioactive peptides Eur. J. Biochem. 1991, 198, 451-8
35. Peter, A.; Toth, G.; Tomboly, C.; Laus, G.; Tourwe, D. Liquid chromatographic study of the enzymatic degradation of endomorphins, with identification by electrospray ionization mass spectrometry J. Chromatogr., A 1999, 846, 39-48
36. Berne, P. F.; Blanquet, S.; Schmitter, J. M. Carboxypeptidase Y-catalyzed transpeptidation of esterified oligo- and polypeptides and its use for the specific carboxyl-terminal labeling of proteins J. Am. Chem. Soc. 1992, 114, 2603-2610
37. Mignat, C.; Wille, U.; Ziegler, A. Affinity profiles of morphine, codeine, dihydrocodeine and their glucuronides at opioid receptor subtypes Life Sci. 1995, 56, 793-799
38. Smetanova, L.; Stetinova, V.; Svoboda, Z.; Kvetina, J. Caco-2 cells, biopharmaceutics classification system (BCS) and biowaiver Acta Med. (Hradec Kralove, Czech Republic) 2011, 54, 3-8
39. Lundquist, S.; Renftel, M.; Brillault, J.; Fenart, L.; Cecchelli, R.; Dehouck, M. P. Prediction of drug transport through the blood-brain barrier in vivo: a comparison between two in vitro cell models Pharm. Res. 2002, 19, 976-981
40. Garberg, P.; Ball, M.; Borg, N.; Cecchelli, R.; Fenart, L.; Hurst, R. D.; Lindmark, T.; Mabondzo, A.; Nilsson, J. E.; Raub, T. J.; Stanimirovic, D.; Terasaki, T.; Oberg, J. O.; Osterberg, T. In vitro models for the blood-brain barrier Toxicol. In Vitro 2005, 19, 299-334
41. Albert, R.; Marbach, P.; Bauer, W.; Briner, U.; Fricker, G.; Bruns, C.; Pless, J. SDZ CO 611: a highly potent glycated analog of somatostatin with improved oral activity Life Sci. 1993, 53, 517-525
42. Egleton, R. D.; Mitchell, S. A.; Huber, J. D.; Janders, J.; Stropova, D.; Polt, R.; Yamamura, H. I.; Hruby, V. J.; Davis, T. P. Improved bioavailability to the brain of glycosylated Met-enkephalin analogs Brain Res. 2000, 881, 37-46
43. Negri, L.; Lattanzi, R.; Tabacco, F.; Orru, L.; Severini, C.; Scolaro, B.; Rocchi, R. Dermorphin and Deltorphin Glycosylated Analogues: Synthesis and Antinociceptive Activity after Systemic Administration J. Med. Chem. 1999, 42, 400-404
44. Polt, R.; Porreca, F.; Szabo, L. Z.; Bilsky, E. J.; Davis, P.; Abbruscato, T. J.; Davis, T. P.; Harvath, R.; Yamamura, H. I.; Hruby, V. J. Glycopeptide enkephalin analogues produce analgesia in mice: evidence for penetration of the blood-brain barrier Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 7114-7118
45. Broadwell, R. D.; Balin, B. J.; Salcman, M. Transcytotic pathway for blood-borne protein through the blood-brain barrier Proc. Natl. Acad. Sci. U.S.A. 1988, 85, 632-636
46. Polt, R.; Dhanasekaran, M.; Keyari, C. M. Glycosylated neuropeptides: A new vista for neuropsychopharmacology? Med. Res. Rev. 2005, 25, 557-585
47. 5] enkephalin after intraperitoneal, intravenous, oral and subcutaneous administration J. Pharmacol. Exp. Ther. 1992, 263, 1308-1316
48. 5]-enkephalin (DPDPE) J. Pharmacol. Exp. Ther. 2001, 298, 848-856
49. Emese, C.; Gabriella, J.; Geza, T.; Ildiko, D.; Gyorgy, B.; Gyongyi, H. Antinociceptive effect of continuous intrathecal administration of endomorphin-1 Pain 2001, 94, 31-38
50. Holzer, P. Opioid receptors in the gastrointestinal tract Regul. Pept. 2009, 155, 11-17
51. Alewood, P.; Alewood, D.; Miranda, L.; Love, S.; Meutermans, W.; Wilson, D. Rapid in situ neutralization protocols for Boc and Fmoc solid-phase chemistries. In Methods in Enzymology; Gregg, B. F., Ed.; Academic Press: New York, 1997; Vol. 289, 14-29
52. Bennett, G. J.; Chung, J. M.; Honore, M.; Seltzer, Z., Models of neuropathic pain in the rat. Curr. Protoc. Neurosci. 2003, Unit 9.14.