Synthesis of enzymatically resistant nociceptin-related peptides containing a carbamic acid residue

Journal of Peptide Science

Volumn 12, Issue 7, 2006, Pages 481-490

  Ligeti, Melinda ^a   Bösze, Szilvia ^a   Csámpai, Antal ^d   Gündüz, Özge ^b   Al Khrasani, Mahmud ^c   Rónai, András Z ^c   Medzihradszky Schweiger, Hedvig ^a   Benyhe, Sándor ^b   Borsodi, Anna ^b   Hudecz, Ferenc ^a,d   Magyar, Anna ^a  

^a EÖTVÖS LORÁND UNIVERSITY   (Hungary)

^b INSTITUTE OF EXPERIMENTAL MEDICINE   (Hungary)

^c SEMMELWEIS UNIVERSITY   (Hungary)

^d EÖTVÖS LORÁND UNIVERSITY   (Hungary)

Author keywords

Aminopeptidase M; Carbamic acid residue; Enzymatic stability; GTP S assay; Mouse vas deferens bioassay; Nociceptin; NOP receptor; Radioligand binding; Rat brain membrane homogenate

Indexed keywords

AMINOPEPTIDASE; CARBAMIC ACID DERIVATIVE; HISTIDYLPHENYL BETA ALANYL AMINOCARBAMOYLPHENYLTHREONYLGLYCYLALANYLARGINYLLYSYLSERYLALANYLARGINYLLYSYLAMIDE; HISTIDYLPHENYL BETA ALANYLPHENYLTHREONYLGLYCYLALANYLARGINYLLYSYLSERYLALANYLARGINYLLYSYLAMIDE; HISTIDYLPHENYLAMINOCARBAMOYL BETA ALANYLPHENYLTHREONYLGLYCYLALANYLARGINYLLYSYLSERYLALANYLARGINYLLYSYLAMIDE; HISTIDYLPHENYLGLYCYLGLYCYLPHENYLTHREONYLGLYCYLALANYLLYSYLSERYLALANYLARGINYLLYSYLAMIDE; NOCICEPTIN DERIVATIVE; RADIOLIGAND; SYNTHETIC PEPTIDE; UNCLASSIFIED DRUG;

AMINO ACID SEQUENCE; AMINO TERMINAL SEQUENCE; ANIMAL TISSUE; ARTICLE; BINDING AFFINITY; BINDING ASSAY; BINDING COMPETITION; BRAIN HOMOGENATE; CHEMICAL MODIFICATION; CONFORMATIONAL TRANSITION; CONTROLLED STUDY; DRUG HALF LIFE; DRUG RECEPTOR BINDING; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVITY; ENZYME DEGRADATION; ENZYME METABOLISM; ENZYME STABILITY; NONHUMAN; PEPTIDE SYNTHESIS; PRIORITY JOURNAL; PROTEIN STRUCTURE; RAT; RESIDUE ANALYSIS; STRUCTURE ACTIVITY RELATION; VAS DEFERENS;

ANIMALS; ANTIGENS, CD13; BRAIN; CARBAMATES; MALE; MICE; OPIOID PEPTIDES; PEPTIDES; PROTEIN BINDING; RATS; RECEPTORS, OPIOID; VAS DEFERENS;

EID: 33745954515     PISSN: 10752617     EISSN: 10991387     Source Type: Journal    
DOI: 10.1002/psc.753     Document Type: Article

References (46)

1. Mollereau C, Parmentier M, Mailleux P, Butour JL, Moisand C, Chalon P, Caput D, Vassart G, Meunier JC. ORL1, a novel member of the opioid receptor family. Cloning, functional expression and localization. FEBS Lett. 1994; 341(1): 33-38.
2. Bunzow JR, Saez C, Mortrud M, Bouvier C, Williams JT, Low M, Grandy DK. Molecular cloning and tissue distribution of a putative member of the rat opioid receptor gene family that is not a mu, delta or kappa opioid receptor type. FEBS Lett. 1994; 347(2-3): 284-288.
3. Reinscheid RK, Nothacker HP, Bourson A, Ardati A, Henningsen RA, Bunzow JR, Grandy DK, Langen H, Monsma FJ Jr, Civelli O. Orphanin FQ: a neuropeptide that activates an opioidlike G protein-coupled receptor. Science 1995; 270(5237): 792-794.
4. Meunier JC, Mollereau C, Toll L, Suaudeau C, Moisand C, Alvinerie P, Butour JL, Guillemot JC, Ferrara P, Monsarrat B. Isolation and structure of the endogenous agonist of opioid receptor-like ORL1 receptor. Nature 1995; 377(6549): 532-535.
5. Mollereau C, Simons MJ, Soularue P, Liners F, Vassart G, Meunier JC, Parmentier M. Structure, tissue distribution, and chromosomal localization of the prepronociceptin gene. Proc. Natl. Acad. Sci. U.S.A. 1996; 93(16): 8666-8670.
6. Nothacker HP, Reinscheid RK, Mansour A, Henningsen RA, Ardati A, Monsma FJ Jr, Watson SJ, Civelli O. Primary structure and tissue distribution of the orphanin FQ precursor. Proc. Natl. Acad. Sci. U.S.A. 1996; 93(16): 8677-8682.
7. Calo G, Rizzi A, Bigoni R, Guerrini R, Salvadori S, Regoli D. Pharmacological profile of nociceptin/orphanin FQ receptors. Clin. Exp. Pharmacol. Physiol. 2002; 29(3): 223-228.
8. Mogil JS, Pasternak GW. The molecular and behavioral pharmacology of the orphanin FQ/nociceptin peptide and receptor family. Pharmacol. Rev. 2001; 53(3): 381-415.
9. Heinricher MM. Orphanin FQ/nociceptin: from neural circuitry to behavior. Life Sci. 2003; 73(6): 813-822.
10. Yu J, Chait BT, Toll L, Kreek MJ. Nociceptin in vitro biotransformation in human blood. Peptides 1996; 17(5): 873-876.
11. Terenius L, Sandin J, Sakurada T. Nociceptin/orphanin FQ metabolism and bioactive metabolites. Peptides 2000; 21(7): 919-922.
12. Dooley CT, Houghten RA. Orphanin FQ: receptor binding and analog structure activity relationships in rat brain. Life Sci. 1996; 59(1): PL23-PL29.
13. Lagrille O, Taillades J, Boiteau L, Commeyras A. N-carbamoyl derivatives and the nitrosation by gaseous NOx: a new promising tool in peptide stepwise synthesis. Eur. J. Org. Chem. 2002; 1026-1032.
14. 2 N-terminal tetrapeptide and discovery of a nociceptin receptor antagonist. J. Med. Chem. 1998; 41(18): 3360-3366.
15. Guerrini R, Calo G, Bigoni R, Rizzi A, Varani K, Toth G, Gessi S, Hashiba E, Hashimoto Y, Lambert DG, Borea PA, Tomatis R, Salvadori S, Regoli D. Further studies on nociceptin-related peptides: discovery of a new chemical template with antagonist activity on the nociceptin receptor. J. Med. Chem. 2000; 43(15): 2805-2813.
16. Okada K, Sujaku T, Chuman Y, Nakashima R, Nose T, Costa T, Yamada Y, Yokoyama M, Nagahisa A, Shimohigashi Y. Highly potent nociceptin analog containing the Arg-Lys triple repeat. Biochem. Biophys. Res. Commun. 2000; 278(2): 493-498.
17. 2, a novel potent and selective antagonist of the nociceptin/orphanin FQ receptor. Br. J. Pharmacol. 2002; 136(2): 303-311.
18. Guerrini R, Calo G, Rizzi A, Bianchi C, Lazarus LH, Salvadori S, Temussi PA, Regoli D.Address and message sequences for the nociceptin receptor: a structure-activity study of nociceptin-(1-13)-peptide amide. J. Med. Chem. 1997: 40(12): 1789-1793.
19. Carpino LA, Cohen BJ, Stephens KE, Sadataalaee SY, Tien JH, Langridge DC. ((9-Fluorenylmethyl)oxy)carbonyl (fmoc) amino-acid chlorides - synthesis, characterization, and application to the rapid synthesis of short peptide segments. J. Org. Chem. 1986; 51(19): 3732-3734.
20. Müller A, Vogt C, Sewald N. Synthesis of Fmoc-β-homoamino acids by ultrasound-promoted Wolff-rearrangement. Synthesis 1998; 6: 837-841.
21. Corwin AH, Damerel CI. Carbamic acid peptides. A new type of peptide and a new possible source of Ammonia from proteins. J. Am. Chem. Soc. 1943; 65(10): 1974-1984.
22. Chung SJ, Kim DH. N-(Hydroxyaminocarbonyl)phenylalanine: a novel class of inhibitor for carboxypeptidase A. Bioorg. Med. Chem. 2001; 9(1): 185-189.
23. Lloyd-Williams P, Albericio F, Giralt E. Solid Phase Peptide Synthesis. In Chemical Approaches to the Synthesis of Peptides and Proteins, Rees CW (ed.). CRC-Press: Boca Raton, 1997; 19-93.
24. Matsueda GR, Stewart JM. A p-methylbenzhydrylamine resin for improved solid-phase synthesis of peptide amides. Peptides 1981; 2(1): 45-50.
25. Knorr R, Trzeciak A, Bannwarth W, Gillessen D. New coupling reagents in peptide chemistry. Tetrahedron Lett. 1989; 30: 1927-1930.
26. Kaiser E, Colescott RL, Bossinger CD, Cook PI. Color test for detection of free terminal amino groups in the solid-phase synthesis of peptides. Anal. Biochem. 1970; 34(2): 595-598.
27. Chan WC, White PD. Basic procedures. In Fmoc Solid Phase Peptide Synthesis: A Practical Approach, White PD (ed.). Oxford University Press: Oxford, 2000; 41-76.
28. Sakakibara S, Shimonishi Y, Kishida Y, Okada M, Sugihara H. Use of anhydrous hydrogen fluoride in peptide synthesis. I. Behavior of various protective groups in anhydrous hydrogen fluoride. Bull. Chem. Soc. Jpn. 1967; 40(9): 2164-2167.
29. Lenard J, Robinson AB. Use of hydrogen fluoride in merrifield solid-phase peptide synthesis. J. Am. Chem. Soc. 1967; 89(1): 181-182.
30. Pfleiderer G, Celliers PG, Stanulovic M, Wachsmuth ED, Determann H, Braunitzer G. Properties and analytical uses of aminopeptidase from kidney particles. Biochem. Z. 1964; 340: 552-564.
31. Pfleiderer G, Celliers PG. Isolation of an aminopeptidase from kidney particles. Biochem. Z. 1963; 339: 186-189.
32. Wachsmuth ED, Fritze I, Pfleiderer G. An aminopeptidase occurring in pig kidney. II. A study on the mechanism of the hydrolysis. Biochemistry 1966; 5(1): 175-182.
33. Wachsmuth ED, Fritze I, Pfleiderer G. An aminopeptidase occurring in pig kidney. I. An improved method of preparation. Physical and enzymic properties. Biochemistry 1966; 5(1): 169-174.
34. Pfleiderer G. Particle-bound aminopeptidase from pig kidney. Methods Enzymol. 1970; 19: 514-521.
35. Simon J, Benyhe S, Abutidze K, Borsodi A, Szucs M, Toth G, Wollemann M. Kinetics and physical parameters of rat brain opioid receptors solubilized by digitonin and CHAPS. J. Neurochem. 1986; 46(3): 695-701.
36. Bradford MM. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal. Biochem. 1976; 72: 248-254.
37. Ligeti M, Gunduz O, Magyar A, Kato E, Ronai AZ, Vita C, Varga I, Hudecz F, Toth G, Borsodi A, Benyhe S. Synthesis and biological studies of nociceptin derivatives containing the DTPA chelating group for further labeling with therapeutic radionuclides. Peptides 2005; 26(7): 1159-1166.
38. Cheng Y, Prusoff WH. Relationship between the inhibition constant (K1) and the concentration of inhibitor which causes 50 per cent inhibition (I50) of an enzymatic reaction. Biochem. Pharmacol. 1973; 22(23): 3099-3108.
39. Kocsis L, Orosz G, Magyar A, Al-Khrasani M, Kato E, Ronai AZ, Bes B, Meunier JC, Gunduz O, Toth G, Borsodi A, Benyhe S. Nociceptin antagonism: probing the receptor by N-acetyl oligopeptides. Regul. Pept. 2004; 122(3): 199-207.
40. Dooley CT, Spaeth CG, Berzetei-Gurske IP, Craymer K, Adapa ID, Brandt SR, Houghten RA, Toll L. Binding and in vitro activities of peptides with high affinity for the nociceptin/orphanin FQ receptor, ORL1. J. Pharmacol. Exp. Ther. 1997; 283(2): 735-741.
41. Hwang SY, Kingsbury WD, Hall NM, Jakas DR, Dunn GL, Gilvarg C.Determination of leucine aminopeptidase using phenylalanyl-3-thia-phenylalanine as substrate. Anal. Biochem. 1986; 154(2): 552-558.
42. Malfroy B, Kado-Fong H, Gros C, Giros B, Schwartz JC, Hellmiss R. Molecular cloning and amino acid sequence of rat kidney aminopeptidase M: a member of a super family of zinc-metallohydrolases. Biochem. Biophys. Res. Commun. 1989; 161(1): 236-241.
43. Wachsmuth ED. Essential tyrosine of aminopeptidase from particles of pig kidneys. Biochem. Z. 1967; 346(5): 446-457.
44. Tomboly C, Peter A, Toth G. In vitro quantitative study of the degradation of endomorphins. Peptides 2002; 23(9): 1573-1580.
45. Carra G, Calo G, Spagnolo B, Guerrini R, Arduin M, Marzola E, Trapella C, Regoli D, Salvadori S. Tryptophan replacement in the nociceptin/ orphanin FQ receptor ligand Ac-RYYRWK-NH2. J. Pept. Res. 2005; 66: 39-47.
46. Arunlakshana O, Schild HO. Some quantitative uses of drug antagonists. Br. J. Pharmacol. 1959; 14(1): 48-58.