Variation of the net charge, lipophilicity, and side chain flexibility in Dmt1-DALDA: Effect on opioid activity and biodistribution

Journal of Medicinal Chemistry

Volumn 55, Issue 22, 2012, Pages 9549-9561

  Novoa, Alexandre ^a   Van Dorpe, Sylvia ^b   Wynendaele, Evelien ^b   Spetea, Mariana ^c   Bracke, Nathalie ^b   Stalmans, Sofie ^b   Betti, Cecilia ^a   Chung, Nga N ^d   Lemieux, Carole ^d   Zuegg, Johannes ^e   Cooper, Matthew A ^e   Tourwé, Dirk ^a   De Spiegeleer, Bart ^b   Schiller, Peter W ^d   Ballet, Steven ^a  

^a VRIJE UNIVERSITEIT BRUSSEL   (Belgium)

^b GHENT UNIVERSITY   (Belgium)

^c UNIVERSITY OF INNSBRUCK   (Austria)

^d CLIN RESEARCH INSTITUTE OF MONTREAL   (Canada)

^e UNIVERSITY OF QUEENSLAND   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

2',6' DIMETHYL TYROSYL DEXTRO ARGINYLPHENYLALANYL N METHYL LYSINAMIDE; 2',6' DIMETHYL TYROSYL DEXTRO ARGINYLPHENYLALANYLLYSINAMIDE; 2',6' DIMETHYL TYROSYL DEXTRO CITRULLINYL PHENYLALANYL N METHYL LYSINAMIDE; [2',6' DIMETHYL TYROSYL N METHYL 4 LYSINE] TYROSYL DEXTRO ARGINYLPHENYLALANYLLYSINAMIDE; AMIDE; AMINO ACID; BENZAZEPINE DERIVATIVE; DELTA OPIATE RECEPTOR; DERMORPHIN; MORPHINE; MU OPIATE RECEPTOR; MU OPIATE RECEPTOR AGONIST; PHENYLALANINE; TYROSYL DEXTRO ARGINYLPHENYLALANYLLYSINAMIDE; UNCLASSIFIED DRUG;

ANALGESIC ACTIVITY; ANIMAL EXPERIMENT; ANIMAL TISSUE; ANTINOCICEPTION; ARTICLE; BRAIN BLOOD FLOW; CHEMICAL BOND; CHEMICAL MODIFICATION; CONTROLLED STUDY; DOSE TIME EFFECT RELATION; DRUG DISTRIBUTION; DRUG POTENCY; DRUG RECEPTOR BINDING; DRUG TRANSPORT; IN VITRO STUDY; IN VIVO STUDY; LIPOPHILICITY; MALE; MOUSE; NONHUMAN; RECEPTOR AFFINITY; STRUCTURE ACTIVITY RELATION; TAIL FLICK TEST; TISSUE DISTRIBUTION;

ANALGESICS, OPIOID; ANIMALS; BLOOD-BRAIN BARRIER; BRAIN; MICE; MOLECULAR STRUCTURE; NOCICEPTION; OLIGOPEPTIDES; OPIOID PEPTIDES; PAIN MEASUREMENT; RECEPTORS, OPIOID; STRUCTURE-ACTIVITY RELATIONSHIP; TISSUE DISTRIBUTION;

EID: 84870002158     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm3008079     Document Type: Article

References (50)

1. Horan, P.; Tallarida, R. J.; Haaseth, R. C.; Matsunaga, T. O.; Hruby, V. J.; Porreca, F. Antinociceptive interactions of opioid delta receptor agonists with morphine in mice: supra- and sub-additivity Life Sci. 1992, 50, 1535-1541
2. He, L.; Lee, N. M. Delta Opioid Receptor Enhancement of Mu Opioid Receptor-Induced Antinociception in Spinal Cord J. Pharmacol. Exp. Ther. 1998, 285, 1181-1186
3. Coop, A.; Rice, K. C. Role of delta-opioid receptors in biological processes Drug News Perspect. 2000, 13, 481-487
4. Schiller, P. W.; Weltrowska, G.; Schmidt, R.; Nguyen, T. M. D.; Berezowska, I.; Lemieux, C.; Chung, N. N.; Carpenter, K. A.; Wilkes, B. C. Four different types of opioid peptides with mixed μ agonist/δ antagonist properties Analgesia 1995, 1, 703-706
5. Purington, L. C.; Pogozheva, I. D.; Traynor, J. R.; Mosberg, H. I. Pentapeptides displaying mu opioid receptor agonist and delta opioid receptor partial agonist/antagonist properties J. Med. Chem. 2009, 52, 7724-7731
6. Purington, L. C.; Sobczyk-Kojiro, K.; Pogozheva, I. D.; Traynor, J. R.; Mosberg, H. I. Development and in vitro characterization of a novel bifunctional mu-agonist/delta-antagonist opioid tetrapeptide ACS Chem. Biol. 2011, 6, 1375-1381
7. For discussion and literature overview of MOR agonists/DOR antagonists: Schiller, P. W. Bi- or multi-functional opioid peptide drugs Life Sci. 2010, 86, 598-603 and references therein.
8. Schiller, P. W.; Nguyen, T. M. D.; Berezowska, I.; Dupuis, S.; Weltrowska, G.; Chung, N. N.; Lemieux, C. Synthesis and in vitro opioid activity profiles of DALDA analogues Eur. J. Med. Chem. 2000, 35, 895-901
9. Szeto, H. H.; Lovelace, J. L.; Fridland, G.; Soong, Y.; Fasolo, J.; Wu, D.; Desiderio, D. M.; Schiller, P. W. In vivo pharmacokinetics of selective mu-opioid peptide agonists J. Pharmacol. Exp. Ther. 2001, 298, 57-61
10. 1]-DALDA J. Pharmacol. Exp. Ther. 2001, 297, 364-371
11. 1]DALDA, a highly potent and selective mu-opioid peptide Eur. J. Pharmacol. 2001, 419, 15-23
12. Zhao, G. M.; Wu, D. L.; Soong, Y.; Shimoyama, M.; Berezowska, I.; Schiller, P. W.; Szeto, H. H. Profound spinal tolerance after repeated exposure to a highly selective mu-opioid peptide agonist: role of delta-opioid receptors J. Pharmacol. Exp. Ther. 2002, 302, 188-196
13. Sagan, S.; Karoyan, P.; Lequin, O.; Chassaing, G.; Lavielle, S. N- and C-alfa methylation in biologically active peptides: synthesis, structural and functional aspects Curr. Med. Chem. 2004, 11, 2799-2822
14. Toniolo, C.; Goodman, M. Introduction to the Synthesis of Peptidomimetic. In Methods of Organic Chemistry: Synthesis of Peptides and Peptidomimetics Goodman, M., Ed.; Thieme: Stuttgart, New York, 2003, Vol. E22c
15. Hruby, V. J.; Li, G.; Haskell-Luevano, C.; Shenderovich, M. Design of peptides, proteins and peptidomimetics in Chi space Biopolymers 1996, 43, 219-266
16. Grauer, A.; König, B. Peptidomimetics - A versatile Route to Biologically Active Compounds Eur. J. Org. Chem. 2009, 5099-5111
17. Ballet, S.; Feytens, D.; Buysse, K.; Chung, N. N.; Tumati, S.; Keresztes, A.; Van Duppen, J.; Lai, J.; Varga, F.; Porreca, F.; Schiller, P. W.; Vanden Broeck, J.; Tourwé, D. Design of Novel Neurokinin 1 Receptor Antagonists Besed on Conformationally Constrained Aromatic Amino Acids and Discovery of a Potent Chimeric Opioid Agonist-Neurokinin 1 Receptor Antagonist J. Med. Chem. 2011, 54, 2467-2476
18. Ballet, S.; Feytens, D.; De Wachter, R.; De Vlaeminck, M.; Marczak, E. D.; Salvadori, S.; de Graaf, C.; Rognan, D.; Negri, L.; Lattanzi, R.; Lazarus, L. H.; Tourwé, D.; Balboni, G. Conformationally Constrained Opioid Ligands: The Dmt-Aba and Dmt-Aia versus Dmt-Tic Scaffold Bioorg. Med. Chem. Lett. 2009, 19, 433-437
19. Tourwé, D.; Verschueren, K.; Frycia, A.; Davis, P.; Porreca, F.; Hruby, V. J.; Toth, G.; Jaspers, H.; Verheyden, P.; Van Binst, G. Conformational restriction of Tyr and Phe side chains in opioid peptides: Information about preferred and bioactive side-chain topology Biopolymers 1996, 38, 1-12
20. 2 using the 4-amino-2-benzazepin-3-one scaffold J. Pept. Res. 2005, 66, 222-230
21. Guillemyn, K.; Kleczkowska, P.; Novoa, A.; Vandormael, B.; Van den Eynde, I.; Kosson, P.; Asim, M. F.; Schiller, P. W.; Spetea, M.; Lipkowski, A. W.; Tourwé, D.; Ballet, S. In vivo antinociception of potent mu opioid agonist tetrapeptide analogues and comparison with a compact opioid agonist-NK1 receptor antagonist chimera Mol. Brain 2012, 5, 4
22. Weltrowska, G.; Berezowska, I.; Lemieux, C.; Chung, N. N.; Wilkes, B. C.; Schiler, P. W. N -Methylated cyclic analogues retain high opioid receptor binding affinity Chem. Biol. Drug. Des. 2010, 75, 182-188
23. Hansen, P. E.; Morgan, B. A. Structure-activity relationships in enkephalin peptides. In The Peptides: Analysis, Synthesis, Biology, Vol. 6: Opioid Peptides: Biology, Chemistry and Genetics; Udenfriend, S.; Meienhofer, J., Eds.; Academic Press: Orlando, FL, 1984; pp 269-321.
24. Ballet, S.; Misicka, A.; Kosson, P.; Lemieux, C.; Chung, N. N.; Schiller, P. W.; Lipkowski, A. W.; Tourwé, D. Dermorphin Tetrapeptide Analogues: Role of Lipophilicity vs Structural Flexibility J. Med. Chem. 2008, 51, 2571-2574
25. B. Vandormael, B.; Fourla, D.-D.; Gramowski-Vaz, A.; Kosson, P.; Weiss, D. G.; Schröder, O. H.-U.; Lipkowski, A. W.; Georgoussi, Z.; Tourwé, D. Superpotent [Dmt1]Dermorphin Tetrapeptides Containing the 4-Aminotetrahydro-2-benzazepin-3-one Scaffold with Mixed m/d Opioid Receptor Agonistic Properties J. Med. Chem. 2011, 54, 7848-7859
26. Van Rompaey, K.; Van den Eynde, I.; De Kimpe, N.; Tourwé, D. A versatile synthesis of 2-substituted 4-amino-1,2,4,5-tetrahydro-2-benzazepine-3- ones Tetrahedron 2003, 59, 4421-4432
27. Ballet, S.; Mayorov, A.; Cai, M.; Tymecka, D.; Chandler, K. B.; Palmer, E. S.; Van Rompaey, M.; Misicka, A.; Tourwé, D.; Hruby, V. J. Novel selective human melanocortin-3 receptor ligands: Use of the 4-amino-1,2,4,5- tetrahydro-benzazepin-3-one (Aba) scaffold Bioorg. Med. Chem. Lett. 2007, 17, 2492-2498
28. Casimir, J. R.; Guichard, G.; Briand, J. P. Methyl 2-((succinimidooxy) carbonyl)benzoate (MSB): a new, efficient reagent for N -phthaloylation of amino acid and peptide derivatives J. Org. Chem. 2002, 67, 3764-3768
29. Gjedde, A High-affinity and low-affinity transport of d -glucose from blood to brain J. Neurochem. 1981, 36, 1463-1471
30. Van Dorpe, S.; Adriaens, A.; Polis, I.; Peremans, K.; Van Bocxlaer, J.; De Spiegeleer, B. Analytical characterization and comparison of the blood-brain barrier permeability of eight opioid peptides Peptides 2010, 31, 1390-1399
31. Van Dorpe, S; Adriaens, A; Vermeire, S; Polis, I; Peremans, K; De Spiegeleer, B. Desirability function combining metabolic stability and functionality of peptides J. Pept. Sci. 2011, 17, 398-404
32. Van Dorpe, S; Bronselaer, A; Nielandt, J; Stalmans, S; Wynendaele, E; Audenaert, K; Van De Wiele, C; Burvenich, C; Peremans, K; Hsuchou, H; De Tré, G; De Spiegeleer, B. Brainpeps: the blood-brain barrier peptide database Brain Struct. Funct. 2012, 10.1007/s00429-011-0375-0
33. 1]DALDA is highly selective and potent at mu opioid receptors, but is not cross-tolerant with systemic morphine Curr. Med. Chem. 2002, 9, 31-39
34. Aldrich, J. V.; McLaughlin, J. P. Peptide Kappa Opioid Receptor Ligands: Potential for Drug Development AAPS J. 2009, 11, 312-322
35. 50) of an Enzymatic Reaction Biochem. Pharmacol. 1973, 22, 3099-3108
36. Paton, W. D. M. The Action of Morphine and Related Substances on Contraction and on Acetylcholine Output of Coaxially Stimulated Guinea Pig Ileum Br. J. Pharmacol. Chemother. 1957, 12, 119-127
37. Henderson, G.; Hughes, J.; Kosterlitz, H. W. A New Example of a Morphine-Sensitive Neuro-Effector Junction: Adrenergic Transmission in the Mouse Vas Deferens Br. J. Pharmacol. 1972, 46, 764-766
38. Schiller, P. W.; Lipton, A.; Horrobin, D. F.; Bodansky, M. Unsulfated C-Terminal 7-Peptide of Cholecystokinin: A New Ligand of the Opiate Receptor Biochem. Biophys. Res. Commun. 1978, 85, 1332-1338
39. DiMaio, J.; Nguyen, T. M. D.; Lemieux, C.; Schiller, P. W. Synthesis and Pharmacological Characterization in Vitro of Cyclic Enkephalin Analogues: Effect of the Conformational Constraints on Opioid Receptor Selectivity J. Med. Chem. 1982, 25, 1432-1438
40. 5-Analogue. Comparison of the Binding Properties of Methionine- and Leucine-Enkephalin Eur. J. Pharmacol. 1979, 58, 11-18
41. Vergote, V.; Baert, B.; Vandermeulen, E.; Peremans, K.; Van Bree, H.; Slegers, G.; Burvenich, C.; De Spiegeleer, B. LC-UV/MS characterisation and DOE optimization of the iodinated peptide obestatin J. Pharm. Biomed. Anal. 2008, 46, 127-136
42. Vergote, V.; Bode, S.; Peremans, K.; Van Bree, H.; Baert, B.; Slegers, G.; Burvenich, C.; De Spiegeleer, B. Analysis of iodinated peptides by LC-DAD/ESI ion trap mass spectrometry J. Chromatogr., B: Anal. Technol. Biomed. Life Sci. 2007, 850, 213-220
43. Kastin, A. J.; Akerstrom, V. Entry of exendin-4 into brain is rapid but may be limited at high doses Int. J. Obes. 2003, 27, 313-318
44. Triguero, D.; Buciak, J.; Pardridge, W. M. Capillary depletion method for quantification of blood-brain barrier transport of circulating peptides and plasma proteins J. Neurochem. 1990, 54, 1882-1888
45. Gutierrez, E. G.; Banks, W. A.; Kastin, A. J. Murine tumor necrosis factor-alpha is transported from blood to brain in the mouse J. Neuroimmunol. 1993, 47, 169-176
46. Banks, W. A.; Kastin, A. J.; Conn, P. M. Quantifying carrier-mediated transport of peptides from the brain to the blood. In Methods in Enzymology; Academic Press: New York, 1989; Vol. 168, pp 652-660.
47. Czihal, P.; Knappe, D.; Fritsche, S.; Zahn, M.; Berthold, N.; Piantavigna, S.; Müller, U.; Van Dorpe, S.; Herth, N.; Binas, A.; Köhler, G.; De Spiegeleer, B.; Martin, L. L.; Nolte, O.; Sträter, N.; Alber, G.; Hoffman, R. Api88 Is a Novel Antibacterial Designer Peptide To Treat Systemic Infections with Multidrug-Resistant Gram-Negative Pathogens ACS Chem. Biol. 2012, 7, 1281-1291
48. Svenson, J.; Vergote, V.; Karstad, R.; Burvenich, C.; Svendsen, J. S.; De Spiegeleer, B. Metabolic Fate of Lactoferricin-Based Antimicrobial Peptides: Effect of Truncation and Incorporation of Amino Acid Analogs on the In Vitro Metabolic Stability J. Pharmacol. Exp. Ther. 2010, 332, 1032-1039
49. Spetea, M.; Bohotin, C. R.; Asim, M. F.; Stübegger, K.; Schmidhammer, H. In vitro and in vivo pharmacological profile of the 5-benzyl analogue of 14-methoxymetopon, a novel μ opioid analgesic with reduced propensity to alter motor function Eur. J. Pharm. Sci. 2010, 41, 125-135
50. Litchfield, J. T., Jr.; Wilcoxon, F. A simplified method of evaluating dose-effect experiments J. Pharmacol. Exp. Ther. 1949, 96, 99-113