Analogues of AVP modified in the N-terminal part of the molecule with Pip isomers: TFA-catalysed peptide bond hydrolysis

Journal of Peptide Science

Volumn 15, Issue 3, 2009, Pages 161-165

  Sobolewski, Dariusz ^a   Prahl, Adam ^a   Kwiatkowska, Anna ^a   Slaninová, Jiřina ^b   Lammek, Bernard ^a  

^a UNIVERSITY OF GDA SK   (Poland)

^b INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

Author keywords

Amide bond hydrolysis; AVP; Biological activity; Pip

Indexed keywords

ARGININE; ARGIPRESSIN DERIVATIVE; IMINO ACID; NONAPEPTIDE; PEPTIDE; PHENYLALANINE; PIPECOLIC ACID; RESIN; VALINE; FLUORENE DERIVATIVE; TRIFLUORENYLAMINE; VASOPRESSIN DERIVATIVE;

AMINO TERMINAL SEQUENCE; ANIMAL EXPERIMENT; ANTIDIURESIS; BIOASSAY; CATALYSIS; CHEMICAL BOND; CONFERENCE PAPER; CONTROLLED STUDY; DEPROTECTION REACTION; FRAGMENTATION REACTION; HYDROLYSIS; IN VITRO STUDY; ISOMER; NONHUMAN; PEPTIDE SYNTHESIS; PRIORITY JOURNAL; RAT; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STRUCTURE ACTIVITY RELATION;

RATTUS;

FLUORENES; HYDROLYSIS; MOLECULAR STRUCTURE; PHENYLALANINE; STRUCTURE-ACTIVITY RELATIONSHIP; VASOPRESSINS;

EID: 63449111690     PISSN: 10752617     EISSN: 10991387     Source Type: Journal    
DOI: 10.1002/psc.1094     Document Type: Conference Paper

References (36)

1. Barberis C, Tribollet E. Vasopressin and oxytocin receptors in the central nervous system. Crit. Rev. Neurobiol. 1996; 10: 119-154.
2. Jard S. Vasopressin receptors. A historical survey. Adv. Exp. Med. Biol. 1998; 449: 1-13.
3. 1a receptor. Evidence for a major localization within transmembrane regions. J. Biol. Chem. 1995; 270: 25771-25777.
4. Jastrzȩbska B, Derdowska I, Kowalczyk W, Machova A, Slaninová J, Lammek B. Influence of 1-aminocyclohexane-1-carboxylic acid in position 2 or 3 of AVP and its analogues on their pharmacological properties. J. Pept. Res. 2003; 62: 70-77.
5. 2 agonists of arginine vasopressin. J. Med. Chem. 2004; 47: 6020-6024.
6. Kowalczyk W, Prahl A, Dawidowska O, Derdowska I, Sobolewski D, Hartrodt B, Neubert K, Slaninová J, Lammek B. The influence of 1-aminocyclopentane-1-carboxylic acid at position 2 or 3 of AVP and its analogues on their pharmacological properties. J. Pept. Sci. 2005; 11: 584-588.
7. Tanaka H, Kuroda A, Marusawa H, Hatanaka H, Kino T, Goto T, Hashimoto M, Taga T. Structure of FK506, a novel immunosuppressant isolated from Streptomyces. J. Am. Chem. Soc. 1987; 109: 5031-5033.
8. Rosen MK, Standaert RF, Galat A, Nakatsuka M, Schreiber SL. Inhibition of FKBP rotamase activity by immunosuppressant FK506: twisted amide surrogate. Science 1990; 248: 863-866.
9. Emmer G, Grassberger MA, Meingassner JG, Schulz G, Schaude M. Derivatives of a novel cyclopeptolide. Synthesis, antifungal activity, and structure-activity relationships. J. Med. Chem. 1994; 37: 1908-1917.
10. Gante J. Peptidomimetics - tailored enzyme inhibitors. Angew. Chem., Int. Ed. Engl. 1994; 33: 1699-1720.
11. Giannis A, Kolter T. Peptidomimetics for receptor ligands- discovery, development and medical perspectives. Angew. Chem., Int. Ed. Engl. 1993; 32: 1244-1267.
12. Morgan BA, Gainor JA. Approach to the discovery of non-peptide ligands for peptide receptors and peptidases. Annu. Rep.Med. Chem. 1989; 24: 243-252.
13. Fields CG, Fields GB. Minimization of tryptophan alkylation following 9-fluorenylmethoxycarbonyl solid-phase peptide synthesis. Tetrahedron Lett. 1993; 34: 6661-6664.
14. Hill RL. In Advances in Protein Chemistry, Anfinsen CB, Anson ML, Edsall JT, Richards FM (eds). Academic Press: New York, 1965; 37.
15. Burgeson IE, Kostić NM. Selective hydrolysis of unactivated peptide bonds, promoted by platinum(II) complexes anchored to amino acid side chains. Inorg. Chem. 1991; 30: 4299-4305.
16. Vandeputte-Rutten L, Gros P.Novel proteases: common themes and surprising features. Curr. Opin. Struct. Biol. 2002; 12: 704-708.
17. Milović NM, Kostić NM. Palladium(II) complex as a sequence-specific peptidase: hydrolytic cleavage under mild conditions of X-Pro peptide bonds in X-Pro-Met and X-Pro-His segments. J. Am. Chem. Soc. 2003; 125: 781-788.
18. Urban J, Vaisar T, Shen R, Lee MS. Lability of N-alkylated peptides towards TFA cleavage. Int. J. Pept. Protein Res. 1996; 47: 182-189.
19. Creighton CJ, Romoff TT, Bu JH, Goodman M. Mechanistic studies of an unusual amide bond scission. J. Am. Chem. Soc. 1999; 121: 6786-6791.
20. Rubini C, Osler A,Calderan A,Guiotto A, Ruzza P. Mechanistic studies of amide bond scission during acidolytic deprotection of Pip containing peptide. J. Pept. Sci. 2008; 14: 989-997.
21. Williams A. Dilute acid-catalyzed amid hydrolysis: efficiency of the N-protonation mechanism. J. Am. Chem. Soc. 1976; 98: 5645-5651.
22. Antonczak S, Ruiz-Lopez MF, Rivail JL. Ab initio analysis of water-assisted reaction mechanisms in amide hydrolysis. J. Am. Chem. Soc. 1994; 116: 3912-3921.
23. - - promoted amide hydrolysis. Acc. Chem. Res. 1992; 25: 481-488.
24. 2 agonist. J. Med. Chem. 2007; 50: 2926-2929.
25. Kowalczyk W, Prahl A, Derdowska I, Sobolewski D, Olejnik J, Zabrocki J, Borovičková L, Slaninováa J, Lammek B. Analogues of neurohypophyseal hormones, oxytocin and arginine vasopressin, conformationally restricted in the N-terminal part of the molecule. J. Med. Chem. 2006; 59: 2016-2021.
26. Bodanszky M, Bodanszky A. The Practice of Peptide Synthesis. Springer-Verlag: Berlin, 1984; 83.
27. Kaiser E, Colescott RI, Bossinger CD, Cook P. Color test for detection of free terminal amino groups in the solid-phase synthesis of peptides. Anal. Biochem. 1970; 34: 595-598.
28. Christensen TC. A chloranil color test for monitoring coupling completeness in solid-phase peptide synthesis. In Peptides-Structure and Biological Function, Gross E, Meienhofer J (eds). Pierce Chem. Corp.: Rockford, IL, 1979; 385.
29. Flouret G, Terada S, Kato T, Gualtieri R, Lipkowski A. Synthesis of oxytocin using iodine for oxidative cyclization and silica gel adsorption chromatography for purification. Int. J. Pept. Protein Res. 1979; 13: 137-141.
30. Holton P. A modification of the method of Dale and Laidlaw for standardization of posterior pituitary extract. Br. J. Pharmacol. 1948; 3: 328-334.
31. Rudinger J, Krejçi I. Dose-response relations for some synthetic analogues of oxytocin, and the mode of action of oxytocin on the isolated uterus. Experientia 1962; 18: 585-588.
32. Munsick RA. Effect of magnesium ion on the response of the rat uterus to neurohypophyseal hormones and analogues. Endocrinology 1960; 66: 451-457.
33. Dekanski J. The quantitative assay of vasopressin. Br. J. Pharmacol. 1952; 7: 567-572.
34. Burn HJ, Finney DJ, Goodwin LG. Biological Standardization, 2nd edn. Oxford University Press: London, 1950; 187.
35. Vávra I, Machová A, Krejči I. Antidiuretic action of 1-deamino-8-D-arginine vasopressin in unanesthetized rats. J. Pharmacol. Exp. Ther. 1974; 188: 241-247.
36. Slaninová J. Fundamental biological evaluation. In Handbook of Neurohypophyseal Hormone Analogs, Vol. I, Jošt K, Lebl M, Brtník F (eds). CRC Press Inc.: Boca Raton, FL, 1987; 83-107, Part 2.