Conformational and biochemical analysis of the cyclic peptides which modulate serine protease activity

Journal of Peptide Science

Volumn 10, Issue 7, 2004, Pages 439-447

  Pakkala, Miikka ^a   Jylhäsalmi, Anu ^a   Wu, Ping ^b   Leinonen, Jari ^b   Stenman, Ulf Håkan ^b   Santa, Harri ^a   Vepsäläinen, Jouka ^a   Peräkylä, Mikael ^a   Närvänen, Ale ^a  

^a UNIVERSITY OF EASTERN FINLAND   (Finland)

^b HELSINKI UNIVERSITY CENTRAL HOSPITAL   (Finland)

Author keywords

Amino acid replacement; Cyclic peptide; NMR; Peptide conformation; Prostate specific antigen; PSA

Indexed keywords

ALANINE; AMINO ACID; ASPARAGINE; CYCLOPEPTIDE; CYSTEINE; GLUTAMINE; HISTIDINE; ISOLEUCINE; LEUCINE; PHENYLALANINE; PROSTATE SPECIFIC ANTIGEN; SERINE; SERINE PROTEINASE; THREONINE; TRYPTOPHAN; TYROSINE; VALINE;

AMINO ACID SUBSTITUTION; ARTICLE; BIOCHEMISTRY; CONTROLLED STUDY; CYCLIZATION; ENZYME ACTIVITY; MODULATION; PEPTIDE ANALYSIS; PEPTIDE SYNTHESIS; PRIORITY JOURNAL; PROTEIN BINDING; PROTEIN CONFORMATION; PROTEIN PROTEIN INTERACTION; PROTEIN STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS;

AMINO ACID SEQUENCE; KALLIKREINS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR SEQUENCE DATA; PEPTIDES, CYCLIC; PROSTATE-SPECIFIC ANTIGEN; PROTEIN BINDING; PROTEIN CONFORMATION; TEMPERATURE;

EID: 4143128805     PISSN: 10752617     EISSN: None     Source Type: Journal    
DOI: 10.1002/psc.557     Document Type: Article

References (32)

1. Lilja H, Abrahamsson PA, Lundwall A. Semenogelin, the predominant protein in human semen. Primary structure and identification of closely related proteins in the male accessory sex glands and on the spermatozoa. J. Biol. Chem. 1989; 264: 1894-1900.
2. Stenman U-H, Leinonen J, Alfthan H, Rannikko S, Tuhkanen K, Alfthan O. A complex between prostate-specific antigen and alpha 1-antichymotrypsin is the major form of prostate-specific antigen in serum of patients with prostatic cancer: assay of the complex improves clinical sensitivity for cancer. Cancer Res. 1991; 51: 222-226.
3. Lilja H, Christensson A, Dahlen U, Matikainen MT, Nilsson O, Pettersson K, Lovgren T. Prostate-specific antigen in serum occurs predominantly in complex with alpha 1-antichymotrypsin. Clin. Chem. 1991; 37: 1618-1625.
4. Killian CS, Corral DA, Kawinski E, Constantine RI. Mitogenic response of osteoblast cells to prostate-specific antigen suggests an activation of latent TGF-beta and a proteolytic modulation of cell adhesion receptors. Biochem. Biophys. Res. Commun. 1993; 192: 940-947.
5. Yoshida E, Ohmura S, Sugiki M, Maruyama M, Mihara H. Prostate- specific antigen activates single-chain urokinase-type plasminogen activator. Int. J. Cancer 1995; 63: 863-865.
6. Cohen P, Graves HC, Peehl DM, Kamarei M, Giudice LC, Rosenfeld RG. Prostate-specific antigen (PSA) is an insulin-like growth factor binding protein-3 protease found in seminal plasma. J. Clin. Endocrinol. Metab. 1992; 75: 1046-1053.
7. Heidtmann HH, Nettelbeck DM, Mingels A, Jager R, Welker HG, Kontermann RE. Generation of angiostatin-like fragments from plasminogen by prostate-specific antigen. Br. J. Cancer 1999; 81: 1269-1273.
8. Fortier AH, Nelson BJ, Grella DK, Holaday JW. Antiangiogenetic activity of prostate-specific antigen. J. Natl Cancer Inst. 1999; 91: 1635-1640.
9. Carvalho AL, Sanz L, Barettino D, Romero A, Calvete JJ, Romão MJ. Crystal structure of a prostate kallikrein isolated from stallion seminal plasma: A homologue of human PSA. J. Mol. Biol. 2002; 322: 325-337.
10. Stamey TA, Yang N, Hay AR, McNeal JE, Freiha FS, Redwine E. Prostate-specific antigen as a serum marker for adenocarcinoma of the prostate. N. Engl. J. Med. 1987; 317: 909-916.
11. Chen Z, Chen H, Stamey TA. Prostate specific antigen in benign prostatic hyperplasia: purification and characterization. J. Urol. 1997; 157: 2166-2170.
12. Stenman U-H, Leinonen J, Zhang WM, Finne P. Prostate-specific antigen. Semin. Cancer. Biol. 1999; 9: 83-93.
13. Leinonen J, Wu P, Koivunen E, Närvänen A, Stenman U-H. Development of novel peptide ligands modulating the enzyme activity of prostate-specific antigen. Scand. J. Clin. Lab. Invest. Suppl. 2000; 233: 59-64.
14. Wu P, Leinonen J, Koivunen E, Lankinen H, Stenman U-H. Identification of novel prostate-specific antigen-binding peptides modulating its enzyme activity. Eur. J. Biochem. 2000; 267: 6212-6220.
15. Wu P, Leinonen J, Pakkala M, Närvänen A, Stenman U-H. Separation of enzymatically active and inactive prostate-specific antigen (PSA) by peptide affinity chromatography. Prostate (in press)
16. Bax A, Davis DG. MLEV-17-based two-dimensional homonuclear magnetization transfer spectroscopy. J. Magn. Reson. 1985; 65: 355-360.
17. Jeener J, Meier BH, Bachmann P, Ernst RR. Investigation of exchange processes by two-dimensional NMR spectroscopy. J. Chem. Phys. 1979; 71: 4546-4553.
18. Güntert P, Mumenthaler C, Wüthrich K. Torsion angle dynamics for NMR structure calculation with the new program DYANA. J. Mol. Biol. 1997; 273: 283-298.
19. Wüthrich K. NMR of Proteins and Nucleic Acids. Wiley-Interscience: New York, 1996.
20. Brooks BR, Bruccoleri RE, Olafson BD, States DJ, Swaminathan S, Karplus M. CHARMM: A program for macromolecular energy, minimization, and dynamics calculations. J. Comput. Chem. 1983; 4: 187-217.
21. Wishart DS, Sykes BD, Richards FM. Relationship between nuclear magnetic resonance chemical shift and protein secondary structure. J. Mol. Biol. 1991; 222: 311-333.
22. Raghothama S, Chaddha M, Balaram P. NMR analysis of a conformational transition in an acyclic peptide. Model system for studying helix unfolding. J. Phys. Chem. 1996; 100: 19666-19671.
23. Maynard AJ, Sharman GJ, Searle MS. Origin of β-hairpin stability in solution: Structural and thermodynamic analysis of folding of a model peptide supports hydrophobic stabilization in water. J. Am. Chem. Soc. 1998; 120: 1996-2007.
24. Hutchinson G, Thornton JM. A revised set of potentials for β-turn formation in proteins. Protein Sci. 1994; 3: 2207-2216.
25. Wilmot CM, Thornton JM. Analysis and prediction of the different types of β-turn in proteins. J. Mol. Biol. 1998; 203: 221-232.
26. Gunasekaran K, Gomathi L, Ramakrishnan C, Chandrasekhar J, Balaram P. Conformational interconversions in peptide β-turns: Analysis of turns in proteins and computational estimates of barriers. J. Mol. Biol. 1998; 284: 1505-1516.
27. Scott JK, Smith GP. Searching for peptide ligands with an epitope library. Science 1990; 249: 386-390.
28. Devlin JJ, Panganiban LC, Devlin PE. Random peptide libraries: a source of specific protein binding molecules. Science 1990; 249: 404-406.
29. Cwirla SE, Peters EA, Barrett RW, Dower WJ. Peptides on phage: a vast library of peptides for identifying ligands. Proc. Natl Acad. Sci. 1990; 87: 6378-6382.
30. Beck-Sickinger AG, Jung G. From multiple peptide synthesis to peptide libraries. In Combinatorial Peptide and Nonpeptide Libraries. A Handbook, Jung G (ed.). VCH Verlagsgesellschaft mbH: Winheim, Germany, 1996.
31. Dyson HJ, Wright PE. Defining solution conformations of small linear peptides. Annu. Rev. Biophys. Chem. 1991; 20: 519-538.
32. Dyson HJ, Rance M, Houghten RA, Lerner RA, Wright PE. Folding of immunogenic peptide fragments of protein in water solution. I. Sequence requirements for the formation of a reverse turn. J. Mol. Biol. 1988; 201: 161-200.