Analogues of trypsin inhibitor SFTI-1 modified in the conserved P1' position by synthetic or non-proteinogenic amino acids retain their inhibitory activity

Journal of Peptide Science

Volumn 17, Issue 4, 2011, Pages 281-287

  Rafał, Łukajtis ^a   Anna, Łȩgowska ^a   Magdalena, Wysocka ^a   Dawid, Dȩbowski ^a   Adam, Lesner ^a   Krzysztof, Rolka ^a  

^a UNIVERSITY OF GDA SK   (Poland)

Author keywords

Chemical synthesis; Peptides; Peptomers; Proteinase inhibitors; SFTI 1

Indexed keywords

ALANINE; CHYMOTRYPSIN A; GLYCINE DERIVATIVE; HOMOSERINE; PHENYLALANINE; SERINE; SFTI 1 PEPTIDE; SFTI 1 PEPTIDE DERIVATIVE; TRYPSIN INHIBITOR; UNCLASSIFIED DRUG;

AMINO ACID SUBSTITUTION; ARTICLE; CONTROLLED STUDY; DRUG PROTEIN BINDING; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; ENZYME SPECIFICITY; EQUILIBRIUM CONSTANT; PRIORITY JOURNAL; PROTEIN DEGRADATION; SOLID PHASE SYNTHESIS;

AMINO ACID SEQUENCE; AMINO ACIDS; ANIMALS; CATTLE; MASS SPECTROMETRY; MOLECULAR SEQUENCE DATA; PEPTIDES, CYCLIC; TRYPSIN; TRYPSIN INHIBITORS;

BOVINAE;

EID: 79952481833     PISSN: 10752617     EISSN: 10991387     Source Type: Journal    
DOI: 10.1002/psc.1330     Document Type: Article

References (27)

1. Luckett S, Santiago Garcia R, Barker JJ, Konarev AV, Shewry PR, Clarke AR, Brady RL. High-resolution structure of a potent, cyclic proteinase inhibitor from sunflower seeds. J. Mol. Biol. 1999; 290: 525-533.
2. 1H NMR of the novel cyclic trypsin inhibitor SFTI-1 from sunflower seeds and an acyclic permutant. J. Mol. Biol. 2001; 311: 579-591.
3. Zabłotna E, Kaźmierczak K, Jaśkiewicz A, Stawikowski M, Kupryszewski G, Rolka K. Chemical synthesis and kinetic study of the smallest naturally occurring trypsin inhibitor SFTI-1 isolated from sunflower seeds and its analogues. Biochem. Biophys. Res. Commun. 2002; 292: 855-859.
4. McBride JD, Watson EM, Brauer ABE, Jaulent AM, Leatherbarrow RJ. Peptide mimics of the Bowman-Birk inhibitor reactive site loop. Biopolymers 2002; 66: 79-92.
5. Lu W, Apostol IMA, Qasim N, Warne R, Wynn WL, Zhang S, Anderson W, Chiang E, Ogin I, Rotherg K, Ryan M, Laskowski M Jr, Binding of amino acid side-chains to S1 cavities of serine proteinases. J. Mol. Biol. 1997; 266: 441-461.
6. 1 variants of bovine pancreatic trypsin inhibitor to four serine proteases. J. Mol. Biol. 1999; 289: 175-186.
7. 1 of trypsin inhibitor CMTI-III and Asp189 in the substrate pocket of trypsin has an essential influence on the inhibitory activity. Biochem. Biophys. Res. Commun. 1997; 240: 869-871.
8. Zabłotna E, Kaźmierczak K, Jaśkiewicz A, Kupryszewski G, Rolka K. Inhibition of bovine α-chymotrypsin by cyclic trypsin inhibitor SFTI-1 isolated from sunflower seeds and its two acyclic analogues. Lett. Pept. Sci. 2002; 9: 131-134.
9. 1 position of trypsin inhibitor SFTI-1 yields potent chymotrypsin and cathepsin G inhibitors. Bioorg. Med. Chem. 2009; 17: 3302-3307.
10. 1' reactive site. ChemBioChem 2005; 6: 1057-1061.
11. Łȩgowska A, Bulak E, Wysocka M, Jaśkiewicz A, Lesner A, Dȩbowski D, Rolka K. Peptomeric analogues of trypsin inhibitor SFTI-1 isolated from sunflower seeds. Bioorg. Med. Chem. 2008; 16: 5644-5652.
12. Odani S, Ikenaka T. Studies on soybean trypsin inhibitors. IV. Change of the inhibitory activity of Bowman-Birk inhibitor upon replacements of the alpha-chymotrypsin reactive site serine residue by other amino acids. J. Biochem. 1978; 84: 1-9.
13. Brauer ABE, Leatherbarrow RJ. A conserved cis peptide bond is necessary for the activity of Bowman-Birk inhibitor protein. Biochim. Biophys. Acta 2003; 308: 300-305.
14. Descours A, Moehle K, Renard A, Robinson JA. A new family of beta-hairpin mimetics based on a trypsin inhibitor from sunflower seeds. ChemBioChem 2002; 3: 318-323.
15. 3'-position of Bowman-Birk protease inhibitors is surmounted in the minimized SFTI-1 scaffold. J. Biol. Chem. 2006; 281: 23668-23675.
16. Austin J, Kimura RH, Woo Y-H, Camarero J. In vivo biosynthesis of an Ala-scan library based on the cyclic peptide SFTI-1. Amino Acids 2010; 38: 1313-22.
17. Hilpert K, Hansen G, Wessner H, Volkmer-Engert R, Höhne W. Complete substitutional analysis of a sunflower trypsin inhibitor with different serine proteases. J. Biochem. 2005; 138: 383-390.
18. 8]-dynorphin. J. Org. Chem. 1992; 57: 5399-5403.
19. Zuckermann RN, Kerr JM, Kent SBH, Moos WH. Efficient method for the preparation of peptoids [oligo(N-substituted glycines)] by submonomer solid phase synthesis. J. Am. Chem. Soc. 1992; 114: 10646-10647.
20. Yang Y, Sweeney WV, Schneider K, Chait BT, Tam JP. Two-step selective formation of three disulfide bridges in the synthesis of the C-terminal epidermal growth factor-like domain in human blood coagulation factor IX. Protein Sci. 1994; 3: 1267-1275.
21. Wysocka M, Kwiatkowska B, Rzadkiewicz M, Lesner A, Rolka K. Selection of new chromogenic substrates of serine proteinases using combinatorial chemistry methods. Comb. Chem. High Throughput Screen. 2007; 10: 171-80.
22. Chase T Jr, Shaw E. p-Nitrophenyl-p'-guanidinobenzoate HCl: a new active site titrant for trypsin. Biochem. Biophys. Res. Commun. 1967; 29: 508-514.
23. Empie MW, Laskowski M Jr. Thermodynamics and kinetics of single residue replacements in avian ovomucoid third domains: effect on inhibitor interactions with serine proteinases. Biochemistry 1982; 21: 2274-2284.
24. Otlewski J, Zbyryt T. Single peptide bond hydrolysis/resynthesis in squash inhibitors of serine proteinases. 1. Kinetics and thermodynamics of the interaction between squash inhibitors and bovine beta-trypsin. Biochemistry 1994; 33: 200-207.
25. Leatherbarrow RJ. GraFit Version 5. Erithacus Software, Horley, 2005.
26. Zabłotna E, Jaśkiewicz A, Łgowska A, Miecznikowska H, Lesner A, Rolka K. Design of serine proteinase inhibitors by combinatorial chemistry using trypsin inhibitor SFTI-1 as a starting structure. J. Pept. Sci. 2007; 13: 749-755.
27. Jaulent JA, Leatherbarrow RJ. Design, synthesis and analysis of novel bicyclic and bifunctional protease inhibitors. Protein Eng. Des. Sel. 2004; 17: 681-687.