Biological active analogues of the opioid peptide biphalin: Mixed α/β3-peptides

Journal of Medicinal Chemistry

Volumn 56, Issue 8, 2013, Pages 3419-3423

  Mollica, Adriano ^a   Pinnen, Francesco ^a   Costante, Roberto ^a   Locatelli, Marcello ^a   Stefanucci, Azzurra ^a   Pieretti, Stefano ^b   Davis, Peg ^c   Lai, Josephine ^c   Rankin, David ^c   Porreca, Frank ^c   Hruby, Victor J ^d  

^a UNIVERSITY OF CHIETI   (Italy)

^b ISTITUTO SUPERIORE DI SANITÀ   (Italy)

^c UNIVERSITY OF ARIZONA COLLEGE OF MEDICINE   (United States)

^d University of Arizona   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA BETA3 PEPTIDE; ANTINOCICEPTIVE AGENT; BIPHALIN; BIPHALIN DERIVATIVE; OPIATE PEPTIDE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTINOCICEPTION; ARTICLE; BINDING AFFINITY; CONTROLLED STUDY; DRUG SYNTHESIS; ENZYME STABILITY; HUMAN; HUMAN TISSUE; IN VITRO STUDY; IN VIVO STUDY; MOUSE; NONHUMAN;

ANALGESICS, OPIOID; ANIMALS; BIOLOGICAL ASSAY; DRUG STABILITY; ENKEPHALINS; HUMANS; RATS; RECEPTORS, OPIOID, DELTA; RECEPTORS, OPIOID, MU; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84876884182     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm301456c     Document Type: Article

References (33)

1. Horan, P. J.; Mattia, A.; Bilsky, E. J.; Weber, S.; Davis, T. P.; Yamamura, H. I.; Malatynska, E.; Appleyard, S. M.; Slaninova, J.; Misicka, A. Antinociceptive profile of Biphalin, a dimeric enkephalin analog J. Pharmacol. Exp Ther. 1993, 265, 1446-1454
2. Lipkowski, A. W.; Misicka, A.; Davis, P.; Stropova, D.; Janders, J.; Lachwa, M.; Porreca, F.; Yamamura, H. I.; Hruby, V. Biological activity of fragments and analogues of the potent dimeric opioid peptide, Biphalin Bioorg. Med. Chem. Lett. 1999, 9, 2763-2766
3. Silbert, B. S.; Lipkowski, A. W.; Cepeda, M. S.; Szyfelbein, S. K.; Osgood, P. F.; Carr, D. B. Analgesic activity of a novel bivalent opioid peptide compared to morphine via different routes of administration Agents Actions 1991, 3, 382-387
4. Flippen-Anderson, J. L.; Deschamps, J. R.; George, C.; Hruby, V. J.; Misicka, A.; Lipkowski, A. W. Crystal structure of Biphalin sulfate: a multireceptor opioid peptide J. Pept. Res. 2002, 59, 123-133
5. Abbruscato, T. J.; Thomas, S. A.; Hruby, V. J.; Davis, T. P. Brain and spinal cord distribution of Biphalin: correlation with opioid receptor density and mechanism of CNS entry J. Neurochem. 1997, 69, 1236-1245
6. Yamazaki, M.; Suzuki, T.; Narita, M.; Lipkowski, A. W. The opioid peptide analogue Biphalin induces less physical dependence than morphine Life Sci. 2001, 69, 1023-1028
7. Koda, Y.; Del Borgo, M.; Wessling, S. T.; Lazarus, L. H.; Okada, Y.; Toth, I.; Blanchfieldm, J. T. Synthesis and in vitro evaluation of a library of modified endomorphin 1 peptides Bioorg. Med. Chem. 2008, 16, 6286-6296
8. Tömböly, C.; Péter, A.; Tóth, G. In vitro quantitative study of the degradation of endomorphins Peptides 2002, 23, 1573-1580
9. Mollica, A.; Davis, P.; Ma, S. W.; Porreca, F.; Lai, J.; Hruby, V. J. Synthesis and biological activity of the first cyclic Biphalin analogues Bioorg. Med. Chem. Lett. 2006, 16, 367-372
10. Mollica, A.; Guardiani, G.; Davis, P.; Ma, S. W.; Porreca, F.; Lai, J.; Mannina, L.; Sobolev, A. P.; Hruby, V. J. Synthesis of stable and potent δ/μ opioid peptides: analogues of H-Tyr-c[ d -Cys-Gly-Phe- d -Cys]-OH by ring-closing metathesis J. Med. Chem. 2007, 50, 3138-3142
11. Zieleniak, A.; Rodziewicz-Motowidło, S.; Rusak, L.; Chung, N. N.; Czaplewski, C.; Witkowska, E.; Schiller, P. W.; Ciarkowski, J.; Izdebski, J. Deltorphin analogs restricted via a urea bridge: structure and opioid activity J. Pept. Sci. 2008, 14, 830-837
12. Weltrowska, G.; Berezowska, I.; Lemieux, C.; Chung, N. N.; Wilkes, B. C.; Schiller, P. W. N -Methylated cyclic enkephalin analogues retain high opioid receptor binding affinity Chem. Biol. Drug. Des. 2010, 75, 82-88
13. Hruby, V. J. Designing peptide receptor agonists and antagonists Nature Rev. Drug Discovery 2002, 1, 847-858
14. Seebach, D.; Beck, A. K.; Bierbaum, D. J. The world of β- and γ-peptides comprised of homologated proteinogenic amino acids and other components Chem. Biodiversity 2004, 1, 1111-1239
15. Steer, D. L.; Lew, R. A.; Perlmutter, P.; Smith, A. I.; Aguilar, M. I. Design and Synthesis of Inhibitors Incorporating β-Amino Acids of Metalloendopeptidase EC 3.4.24.15 J. Pept. Sci. 2000, 6, 470-477
16. 3-Peptides with Proteinaceous Side Chains: Synthesis and Solution Structures of Constitutional Isomers, a Novel Helical Secondary Structure and the Influence of Solvation and Hydrophobic Interactions on Folding Helv. Chim. Acta 2003, 86, 2098-2103
17. Seebach, D.; Matthews, J. L. β-Peptides: a surprise at every turn Chem. Commun. 1997, 21, 2015-2126
18. 3-Peptides with Proteinaceous Side Chains: Synthesis and Solution Structures of Constitutional Isomers, a Novel Helical Secondary Structure and the Influence of Solvation and Hydrophobic Interactions on Folding Helv. Chim. Acta 1998, 81, 932-982
19. Stachowiak, K.; Khosla, M. C.; Plucinska, K.; Khairallah, P. A.; Bumpus, F. M. Synthesis of angiotensin II analogues by incorporating β-homotyrosine or β-homoisoleucine residues J. Med. Chem. 1979, 9, 1128-1130
20. Zablocki, J. A.; Tjoeng, F. S.; Bovy, P. R.; Miyano, M.; Garland, R. B.; Williams, K.; Schretzman, L.; Zupec, M. E.; Rico, J. G.; Lindmark, R. J.; Toth, M. V.; McMakins, D. E.; Adams, S. P.; Panzer-Knodle, S. G.; Nicholson, N. S.; Taite, B. B.; Salyers, A. K.; King, L. W.; Campion, J. G.; Feigen, L. P. A novel series of orally active antiplatelet agents Bioorg. Med. Chem. 1995, 5, 539-551
21. 3-peptides with proteinogenic side chains. Monosubstituted analogues of the chemotactic tripeptide For-Met-Leu-Phe-OMe J. Pept. Sci. 2004, 10, 510-523
22. 3-homo-amino acids J. Pept. Sci. 2009, 15, 777-782
23. Bozü, B.; Fülöp, F.; Tóth, G. K.; Tóth, G.; Szücs, M. Synthesis and opioid binding activity of dermorphin analogues containing cyclic β-amino acids Neuropeptides 1997, 31, 367-372
24. Cardillo, G.; Gentilucci, L.; Qasem, A. R.; Sgarzi, F.; Spampinato, S. Endomorphin-1 analogues containing β-proline are μ-opioid receptor agonists and display enhanced enzymatic hydrolysis resistance J. Med. Chem. 2002, 45, 2571-2578
25. Misicka, A.; Lipkowski, A. W.; Horvath, R.; Davis, P.; Kramer, T. H.; Yamamura, H. I.; Hruby, V. J. Topographical requirements for delta opioid ligands: common structural features of dermenkephalin and deltorphin Life Sci. 1992, 51, 1025-1032
26. 35S]thio)triphosphate to NG108-15 cell membranes: characterization of agonist and inverse agonist effects J. Pharmacol. Exp. Ther. 1997, 283, 1276-1284
27. Yamamoto, T.; Nair, P.; Largent-Milnes, T. M.; Jacobsen, N. E.; Davis, P.; Ma, S. W.; Yamamura, H. I.; Vanderah, T. W; Porreca, F.; Lai, J.; Hruby, V. J. Discovery of a potent and efficacious peptide derivative for δ/μ opioid agonist/neurokinin 1 antagonist activity with a 2′,6′- dimethyl- l -tyrosine: in vitro, in vivo, and NMR-based structural studies J. Med. Chem. 2011, 54, 2029-2038
28. Pieretti, S.; Di Giannuario, A.; De Felice, M.; Perretti, M.; Cirino, G. Stimulus-dependent specificity for annexin 1 inhibition of the inflammatory nociceptive response: the involvement of the receptor for formylated peptides Pain 2004, 109, 52-63
29. Al-Fayoumi, S. I.; Brugos, B.; Arya, V.; Mulder, E.; Eppler, B.; Mauderli, A. P.; Hochhaus, G. Identification of stabilized dynorphin derivatives for suppressing tolerance in morphine-dependent rats Pharm. Res. 2004, 21, 1450-1456
30. Shimohigashi, Y.; Costa, T.; Chen, H. C.; Rodbard, D. Dimeric tetrapeptide enkephalins display extraordinary selectivity for the δ opiate receptor Nature 1982, 297, 333-335
31. Mollica, A.; Davis, P.; Ma, S. W.; Lai, J.; Porreca, F.; Hruby, V. J. Synthesis and biological evaluation of new Biphalin analogues with non-hydrazine linkers Bioorg. Med. Chem. Lett. 2005, 15, 2471-2475
32. Mollica, A.; Pinnen, F.; Feliciani, F.; Stefanucci, A.; Lucente, G.; Davis, P.; Porreca, F.; Ma, S. W.; Lai, J.; Hruby, V. J. New potent Biphalin analogues containing p -fluoro- l -phenylalanine at the 4,4′ positions and non-hydrazine linkers Amino Acids 2011, 40, 1503-1511
33. Leone, S.; Chiavaroli, A.; Orlando, G.; Mollica, A.; Di Nisio, C.; Brunetti, L.; Vacca, M. The analgesic activity of Biphalin and its analog AM 94 in rats Eur. J. Pharmacol. 2012, 685, 70-73