Elucidation of the contribution of active site and exosite interactions to affinity and specificity of peptidylic serine protease inhibitors using non-natural arginine analogs

Molecular Pharmacology

Volumn 80, Issue 4, 2011, Pages 585-597

  Hosseini, Masood ^a,b   Jiang, Longguang ^c   Sørensen, Hans Peter ^b   Jensen, Jan K ^b   Christensen, Anni ^b   Fogh, Sarah ^b   Yuan, Cai ^c   Andersen, Lisbeth M ^b   Huang, Mingdong ^c   Andreasen, Peter A ^b   Jensen, Knud J ^a  

^a UNIVERSITY OF COPENHAGEN   (Denmark)

^b AARHUS UNIVERSITY   (Denmark)

^c FUJIAN INSTITUTE OF RESEARCH ON THE STRUCTURE OF MATTER   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ARGININE DERIVATIVE; PROTEINASE INHIBITOR;

ARTICLE; CHIMERA; CONTROLLED STUDY; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TARGETING; ENZYME ACTIVE SITE; MOLECULAR INTERACTION; PRIORITY JOURNAL; SUBSTITUTION REACTION; X RAY CRYSTALLOGRAPHY;

AMINO ACID SEQUENCE; ANIMALS; ARGININE; CATALYTIC DOMAIN; CRYSTALLOGRAPHY, X-RAY; HEK293 CELLS; HUMANS; MICE; MOLECULAR SEQUENCE DATA; PEPTIDES; PEPTIDES, CYCLIC; PROTEIN BINDING; PROTEIN STRUCTURE, TERTIARY; RECOMBINANT PROTEINS; SERINE PROTEINASE INHIBITORS;

EID: 80053200008     PISSN: 0026895X     EISSN: 15210111     Source Type: Journal    
DOI: 10.1124/mol.111.072280     Document Type: Article

References (36)

1. Abramowitz N, Schechter I, and Berger A (1967) On the size of the active site in proteases. II. Carboxypeptidase-A. Biochem Biophys Res Commun 29:862-867.
2. Andersen LM, Wind T, Hansen HD, and Andreasen PA (2008) A cyclic peptidylic inhibitor of murine urokinase-type plasminogen activator: changing species specificity by substitution of a single residue. Biochem J 412:447-457. (Pubitemid 351846410)
3. Andreasen PA, Egelund R, and Petersen HH (2000) The plasminogen activation system in tumor growth, invasion, and metastasis. Cell Mol Life Sci 57:25-40. (Pubitemid 30105328)
4. Blouse GE, Dupont DM, Schar CR, Jensen JK, Minor KH, Anagli JY, Gårdsvoll H, Ploug M, Peterson CB, and Andreasen PA (2009) Interactions of plasminogen activator inhibitor-1 with vitronectin involve an extensive binding surface and induce mutual conformational rearrangements. Biochemistry 48:1723-1735.
5. Boyar A and Marsh RE (1982) L-Canavanine, a paradigm for the structures of substituted guanidines. J Am Chem Soc 104:1995-1998.
6. Branden C and Tooze J (1991) Introduction to Protein Structure. Garland Publishing, New York.
7. Collaborative Computational Project, Number 4 (1994) The CCP4 suite: programs for protein crystallography. Acta Crystallogr D Biol Crystallogr 50:760-763.
8. Danø K, Nielsen LS, Møller V, and Engelhart M (1980) Inhibition of a plasminogen activator from oncogenic virus-transformed mouse cells by rabbit antibodies against the enzyme. Biochim Biophys Acta 630:146-151. (Pubitemid 10019442)
9. DeLano (2002) The PyMOL Molecular Graphics System, San Carlos, CA.
10. Dennis MS, Eigenbrot C, Skelton NJ, Ultsch MH, Santell L, Dwyer MA, O'Connell MP, and Lazarus RA (2000) Peptide exosite inhibitors of factor VIIa as anticoagulants. Nature 404:465-470. (Pubitemid 30186881)
11. Emsley P and Cowtan K (2004) Coot: model-building tools for molecular graphics. Acta Crystallogr D Biol Crystallogr 60:2126-2132. (Pubitemid 41742764)
12. Hajdin K, D'Alessandro V, Niggli FK, Schäfer BW, and Bernasconi M (2010) Furin targeted drug delivery for treatment of rhabdomyosarcoma in a mouse model. PLoS One 5:e10445.
13. Hansen M, Wind T, Blouse GE, Christensen A, Petersen HH, Kjelgaard S, Mathiasen L, Holtet TL, and Andreasen PA (2005) A urokinase-type plasminogen activator-inhibiting cyclic peptide with an unusual P2 residue and an extended protease binding surface demonstrates new modalities for enzyme inhibition. J Biol Chem 280:38424-38437. (Pubitemid 43853740)
14. Hartung R, Hitzel-Zerrahn F, Müller T, and Pietsch J (2005) inventors; Degussa AG, assignee. Process for the hydrogenation of aromatic compounds. World patent WO/2005/014526. 2005 Feb 17.
15. Hedstrom L (2002) Serine protease mechanism and specificity. Chem Rev 102:4501-4524.
16. Heinis C, Rutherford T, Freund S, and Winter G (2009) Phage-encoded combinatorial chemical libraries based on bicyclic peptides. Nat Chem Biol 5:502-507.
17. Hekim C, Leinonen J, Närvänen A, Koistinen H, Zhu L, Koivunen E, Väisänen V, and Stenman UH (2006) Novel peptide inhibitors of human kallikrein 2. J Biol Chem 281:12555-12560. (Pubitemid 43855343)
18. Jorgensen L and NielsenHM(2009) Delivery Technologies for Biopharmaceuticals Peptides, Proteins, Nucleic Acids and Vaccines. John Wiley & Sons, Chichester, UK.
19. Kaltoft K, Nielsen LS, Zeuthen J, and Danø K (1982) Monoclonal antibody that specifically inhibits a human Mr 52,000 plasminogen-activating enzyme. Proc Natl Acad Sci USA 79:3720-3723. (Pubitemid 12013538)
20. Kayser KJ, Glenn MP, Sebti SM, Cheng JQ, and Hamilton AD (2007) Modifications of the GSK3β substrate sequence to produce substrate-mimetic inhibitors of Akt as potential anti-cancer therapeutics. Bioorg Med Chem Lett 17:2068-2073.
21. Klinghofer V, Stewart K, McGonigal T, Smith R, Sarthy A, Nienaber V, Butler C, Dorwin S, Richardson P, Weitzberg M, et al. (2001) Species specificity of amidinebased urokinase inhibitors. Biochemistry 40:9125-9131. (Pubitemid 32730033)
22. Kocsis A, Kékesi KA, Szász R, Végh BM, Balczer J, Dobó J, Závodszky P, Gál P, and Pá1 G (2010) Selective inhibition of the lectin pathway of complement with phage display selected peptides against mannose-binding lectin-associated serine protease (MASP)-1 and -2: significant contribution of MASP-1 to lectin pathway activation. J Immunol 185:4169-4178.
23. Krook M, Lindbladh C, Eriksen JA, and Mosbach K (1997-1998) Selection of a cyclic nonapeptide inhibitor to α-chymotrypsin using a phage display peptide library. Mol Divers 3:149-159.
24. Lin Z, Jiang L, Yuan C, Jensen JK, Zhang X, Luo Z, Furie BC, Furie B, Andreasen PA, and Huang M (2011) Structural basis for recognition of urokinase-type plasminogen activator by plasminogen activator inhibitor-1. J Biol Chem 286:7027-7032.
25. Lund IK, Jögi A, Rønø B, Rasch MG, Lund LR, Almholt K, Gårdsvoll H, Behrendt N, Rømer J, and Høyer-Hansen G (2008) Antibody-mediated targeting of the urokinase-type plasminogen activator proteolytic function neutralizes fibrinolysis in vivo. J Biol Chem 283:32506-32515.
26. Otwinowski Z and Minor W (1997) Processing of X-ray diffraction data collected in oscillation mode. Methods Enzymol 276:307-326. (Pubitemid 27085611)
27. Petersen HH, Hansen M, Schousboe SL, and Andreasen PA (2001) Localization of epitopes for monoclonal antibodies to urokinase-type plasminogen activator - relationship between epitope localization and effects of antibodies on molecular interactions of the enzyme. Eur J Biochem 268:4430-4439. (Pubitemid 32862852)
28. Puente XS, Ordóñez GR, and López-Òtin (2008) The Cancer Degradome: Proteases and Cancer Biology. Springer, New York.
29. Rao PN, Peterson DM, Acosta CK, Bahr ML, and Kim HK (1991) Synthesis of cis-4-aminocyclohexyl-D-alanine and trans-4-aminocyclohexyl-D-alanine derivatives and determination of their stereochemistry. Org Prep Proced Int 23:103-110.
30. Rockway TW, Nienaber V, and Giranda VL (2002) Inhibitors of the protease domain of urokinase-type plasminogen activator. Curr Pharm Des 8:2541-2558. (Pubitemid 35331529)
31. Sassatelli M, Debiton E, Aboab B, Prudhomme M, and Moreau P (2006) Synthesis and antiproliferative activities of indolin-2-one derivatives bearing amino acid moieties. Eur J Med Chem 41:709-716. (Pubitemid 43866307)
32. Spraggon G, Phillips C, Nowak UK, Ponting CP, Saunders D, Dobson CM, Stuart DI, and Jones EY (1995) The crystal structure of the catalytic domain of human urokinase-type plasminogen-activator. Structure 3:681-691.
33. Walker B and Lynas JF (2001) Strategies for the inhibition of serine proteases. Cell Mol Life Sci 58:596-624. (Pubitemid 32382260)
34. Wu P, Leinonen J, Koivunen E, Lankinen H, and Stenman UH (2000) Identification of novel prostate-specific antigen-binding peptides modulating its enzyme activity. Eur J Biochem 267:6212-6220.
35. Wu P, Weisell J, Pakkala M, Peräkylä M, Zhu L, Koistinen R, Koivunen E, Stenman UH, Närvänen A, and Koistinen H (2010) Identification of novel peptide inhibitors for human trypsins. Biol Chem 391:283-293.
36. Zhao G, Yuan C, Wind T, Huang Z, Andreasen PA, and HuangM(2007) Structural basis of specificity of a peptidyl urokinase inhibitor, upain-1. J Struct Biol 160:1-10. (Pubitemid 47405230)