Pharmacology of a new tritiated endomorphin-2 analog containing the proline mimetic cis-2-aminocyclohexanecarboxylic acid

Peptides

Volumn 32, Issue 4, 2011, Pages 722-728

  Keresztes, Attila ^a   Birkás, Erika ^a   Páhi, Annamária ^a   Tóth, Géza ^a   Bakota, Lidia ^b   Gulya, Károly ^b   Szücs, Mária ^a  

^a INSTITUTE OF EXPERIMENTAL MEDICINE   (Hungary)

^b UNIVERSITY OF SZEGED   (Hungary)

Author keywords

2 Aminocylcohexanecarboxylic acid (ACHC); Autoradiography; Endomorphin; Peptide synthesis; Proteolytic stability; Radiolabeling; Receptor binding

Indexed keywords

(2 AMINOCYCLOHEXANECARBOXYLIC ACID) 2 ENDOMORPHIN 2; 3,4 DICHLORO N METHYL N [2 (1 PYRROLIDINYL)CYCLOHEXYL]BENZENEACETAMIDE; CYCLOHEXANECARBOXYLIC ACID DERIVATIVE; ENDOMORPHIN 2; ENKEPHALIN[2 DEXTRO ALANINE 4 METHYLPHENYLALANINE 5 GLYCINE]; MU OPIATE RECEPTOR; NALOXONE; PROLINE; RADIOLIGAND; SODIUM ION; TRITIUM; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; AUTORADIOGRAPHY; BINDING AFFINITY; BINDING KINETICS; BINDING SITE; BRAIN MEMBRANE; DRUG SYNTHESIS; ISOTOPE LABELING; MALE; NONHUMAN; PRIORITY JOURNAL; RAT; RECEPTOR DENSITY;

ANIMALS; AUTORADIOGRAPHY; CARBOXYLIC ACIDS; CYCLOBUTANES; KINETICS; MOLECULAR MIMICRY; OLIGOPEPTIDES; PROLINE; RADIOLIGAND ASSAY; RATS;

RATTUS;

EID: 79952817629     PISSN: 01969781     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.peptides.2011.01.017     Document Type: Article

References (39)

1. Amiche M, Sagan S, Mor A, Delfour A, Nicolas P. Characterization of the receptor binding profile of (3H)-dermorphin in the rat brain. Int J Pept Protein Res 1988;32:506-11. (Pubitemid 19042056)
2. 3H]Tyr-Tic-(2S,3R)-β-MePhe-Phe- OH. Neuropeptides 2008;42:57-67.
3. Borics A, Tóth G. Structural comparison of μ-opioid receptor selective peptides confirmed four parameters of bioactivity. J Mol Graph Model 2010;28:495-505.
4. Bozó B, Fülöp F, Tóth G, Szucombining double acute accentcs M. Synthesis and opioid binding activity of dermorphin analogues containing cyclic β-amino acids. Neuropeptides 1997;31:367-72.
5. Chang KJ. Structure-activity relationship and pharmacology of the highly selective mu-opioid agonist morphiceptin. NIDA Res Monogr 1986;69:101-11.
6. Chavkin C, James IF, Goldstein A. Dynorphin is a specific endogenous ligand of the κ opioid receptor. Science 1982;215:413-5. (Pubitemid 12132127)
7. 50) of an enzymatic reaction. Biochem Pharmacol 1973;22:3099-108.
8. Fülöp F. The chemistry of 2-aminocycloalkanecarboxylic acids. Chem Rev 2001;101:2181-204. (Pubitemid 35377795)
9. Forro E, Fülöp F. Advanced procedure for the enzymatic ring opening of unsaturated alicyclic β-lactams. Tetrahedron Asymmetry 2004;15:2875-80. (Pubitemid 39278022)
10. Gentilucci L, Tolomelli A. Recent advances in the investigation of the bioactive conformation of peptides active at the μ-opioid receptor. Conformational analysis of endomorphins. Curr Top Med Chem 2004;4:105-21. (Pubitemid 38842562)
11. Goldberg IE, Rossi GC, Letchworth SR, Mathis JP, Ryan-Moro J, Leventhal L, et al. Pharmacological characterization of Endomorphin-1 and Endomorphin-2 in mouse brain. J Pharm Exp Ther 1998;286:1007-13. (Pubitemid 29003497)
12. Goldstein A. Endorphins: physiology and clinical implications. Ann N Y Acad Sci 1978;311:49-58.
13. Gulya K, Gehlert DR, Wamsley JK, Mosberg H, Hruby VJ, Yamamura HI. Light microscopic autoradiographic localization of delta opioid receptors in the rat brain using a highly selective bis-penicillamine cyclic enkephalin analog. J Pharmacol Exp Ther 1986;238:720-6. (Pubitemid 16039620)
14. 61-64 posessing selective agonist activity at μ-opiate receptors. Eur J Pharmacol 1981;70:531-40.
15. Hughes J, Smith TW, Kosterlitz HW, Fothergill LA, Morgan GA, Morris HR. Identification of two related pentapeptides from the brain with potent opiate agonist activity. Nature 1975;258:577-80.
16. Janecka A, Staniszewska R, Fichna J. Endomorphin analogs. Curr Med Chem 2007;14:3201-8.
17. Kaiser E, Colescott RL, Bossinger CD, Cook PI. Color test for detection of free terminal amino groups in the solid phase peptide synthesis of peptides. Anal Biochem 1970;34:595-8.
18. 2]endomorphin-2. Peptides 2006;27: 3315-21.
19. Keresztes A, Szucombining double acute accentcs M, Borics A, Kövér EK, Forró E, Fülöp F, et al. New endomorphin analogues containing alicyclic β-amino acids: influence on conformation and pharmacological profile. J Med Chem 2008;51:4270-9. (Pubitemid 352032451)
20. Keresztes A, Borics A, Tóth G. Recent advances in endomorphin engineering. Chem Med Chem 2010;5:1176-96.
21. Kieffer BL, Befort K, Gaveriaux-Ruff C, Hirth CG. The delta-opioid receptor: isolation of a cDNA by expression cloning and pharmcological characterization. Proc Natl Acad Sci USA 1992;89:12048-52. (Pubitemid 23004782)
22. Lahti A, Von Voigtlander PF, Barsuhn C. Properties of a selective kappa agonist, U50,488H. Life Sci 1982;31:2257-60.
23. Leitgeb B. Structural investigation of endomorphins by experimental and theoretical methods. Hunting for the bioactive conformation. Chem Biodiv 2007;4:2703-24.
24. Li CH, Chung D. Isolation and structure of an untriakontapeptide with opiate activity from camel pituitary glands. Proc Natl Acad Sci 1976;73: 1145-8.
25. Mansour A, Fox CA, Akil H, Watson SJ. Opioid-receptor mRNA expression in the rat CNS: anatomical and functional implications. Trends Neurosci 1995;18:22-9.
26. Mansour A, Khachaturian H, Lewis ME, Akil H, Watson SJ. Autoradiographic differentiation of Mu, delta and kappa opioid receptors in the rat forebrain and midbrain. J Neurosci 1987;7:2445-64.
27. Meisel H. Chemical characterization and opioid activity of an exorphin isolated from in vivo digest of casein. FEBS Lett 1986;196:223-7. (Pubitemid 16047465)
28. Mierke DF, Nöbner G, Schiller PW, Goodman M. Morphiceptin analogs containing 2-aminocyclopentane carboxylic acid as a peptidomimetic for proline. Int J Peptide Protein Res 1990;35:35-45. (Pubitemid 20090565)
29. Nyberg F, Sanderson K, Glamsta EL. The hemorphins: a new class of opioid peptides derived from the blood protein hemoglobin. Biopolymers 1997;43:147-56. (Pubitemid 27291394)
30. Paxinos G, Watson G. The rat brain in stereotaxic coordinates. San Diego, CA: Academic Press; 1997.
31. Péter A, Fülöp F. High performance liquid chromatographic methods for the separation of isomers of cis- and trans-2-aminocyclopentane carboxylic acid. J Chromatogr A 1995;715:219-26.
32. Pradhan AAA, Clarke PBS. Comparision between δ-Opioid receptor functional response and autoradiographic labeling in rat brain and spinal cord. J Comp Neurol 2005;481:416-26.
33. 2]deltorphin II analogs with high affinity and selectivity for delta-opioid recetor. Biochem Biophys Res Commun 1991;180:822-7.
34. Schiller PW, Nguyen TM, Berezowska I, Dupuis S, Weltrowska G, Chung NN, et al. Synthesis and in vitro opioid activity profiles of DALDA analogues. Eur J Med Chem 2000;35:895-901.
35. Tóth G, Keresztes A, Tömböly Cs, Péter A, Fülöp F, Tourwé D, et al. New endomorphin analogs with μ-agonist and δ-antagonist properties. Pure Appl Chem 2004;76:951-7.
36. Tóth G, Lovas S, Ötvös F. Tritium labeling of neuropeptides in Methods in Molecular Biology. Neuropept Protoc 1997;73:219-30.
37. 4] morphiceptin analogs incorporating cis-2-aminocyclopentane carboxylic acid as a peptidomimetic for proline. Int J Peptide Protein Res 1991;37:364-81.
38. Zadina JE, Hackler L, Ge LJ, Kastin AJ. A potent and selective endogenous agonist for the mu-opiate receptor. Nature 1997;386:499-502. (Pubitemid 27164076)
39. Zadina JE, Kastin AJ, Hackler L, Chang SL. Cyclic analogues of Tyr-W-MIF with prolonged analgesic activity and potency comparable to DAMGO and morphine. Peptides 1994;15:1567-9. (Pubitemid 24381535)