Autodisplay of catalytically active human hyaluronidase hPH-20 and testing of enzyme inhibitors

European Journal of Pharmaceutical Sciences

Volumn 42, Issue 1-2, 2011, Pages 138-147

  Kaeßler, Andre ^a   Olgen, Sureyya ^b   Jose, Joachim ^a  

^a HEINRICH HEINE UNIVERSITY   (Germany)

^b ANKARA UNIVERSITY   (Turkey)

Author keywords

Autodisplay; Hyaluronic acid; Hyaluronidase; Inhibitor testing; Recombinant expression

Indexed keywords

6 PALMITOYL ASCORBIC ACID; AMIDE; ASCORBIC ACID DERIVATIVE; ENZYME INHIBITOR; HPH 2; HYALURONIC ACID; HYALURONIDASE; HYALURONIDASE ANTIBODY; HYBRID PROTEIN; LIPOPOLYSACCHARIDE; N (4 CHLOROBENZYL) 1 (4 FLUOROBENZYL) 1H INDOLE 3 CARBOXAMIDE; N (4 FLUOROBENZYL) 1 BENZYL 1H INDOLE 2 CARBOXAMIDE; POLYSACCHARIDE; UNCLASSIFIED DRUG;

ARTICLE; AUDIOVISUAL EQUIPMENT; AUTODISPLAY; BACTERIAL STRAIN; BREAST CANCER; CELL INCLUSION; CELL PROLIFERATION; CELL SURFACE; CELL TRANSFORMATION; COMPETITIVE INHIBITION; CONTROLLED STUDY; COW; ENZYME ACTIVE SITE; ENZYME ACTIVITY; ENZYME INHIBITION; ENZYME MECHANISM; ENZYME STRUCTURE; ESCHERICHIA COLI; EXTRACELLULAR MATRIX; HUMAN; HUMAN CELL; LARYNX CANCER; NONHUMAN; PH; PRIORITY JOURNAL; PROTEIN EXPRESSION; TESTIS;

BACTERIAL OUTER MEMBRANE PROTEINS; BASE SEQUENCE; BINDING, COMPETITIVE; BIOTECHNOLOGY; BLOTTING, WESTERN; CATALYTIC DOMAIN; CELL ADHESION MOLECULES; ELECTROPHORESIS, POLYACRYLAMIDE GEL; ENZYME INHIBITORS; ESCHERICHIA COLI; HUMANS; HYALURONIC ACID; HYALURONOGLUCOSAMINIDASE; LIPOPOLYSACCHARIDES; MOLECULAR SEQUENCE DATA; MOLECULAR STRUCTURE; PLASMIDS; RECOMBINANT FUSION PROTEINS;

EID: 78650677215     PISSN: 09280987     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ejps.2010.11.004     Document Type: Article

References (58)

1. M. Asada Inhibitory effect of alginic acids on hyaluronidase and on histamine release from mast cells Biosci. Biotechnol. Biochem. 61 1997 1030 1032
2. D. Beech, A. Madan, and N. Deng Expression of PH-20 in normal and neoplastic breast tissue J. Surg. Res. 103 2004 203 207
3. N. Blom, T. Sicheritz-Pontén, R. Gupta, S. Gammeltoft, and S Brunak Prediction of post-translational glycosylation and phosphorylation of proteins from the amino acid sequence Proteomics 4 2004 1633 1649
4. L.H. Bookbinder A recombinant human enzyme for enhanced interstitial transport of therapeutics J. Control. Rel. 114 2006 230 241
5. A. Botzki l-Ascorbic acid 6-hexadecanoate, a potent hyaluronidase inhibitor - X-ray structure and molecular modeling of enzyme-inhibitor complexes J. Biol. Chem. 279 2004 45990 45997
6. A. Botzki, S. Salmen, G. Bernhardt, A. Buschauer, and S. Dove Structure-based design of bacterial hyaluronan lyase inhibitors QSAR Comb. Sci. 24 2005 458 469
7. K.L. Chao, L. Muthukumar, and O. Herzberg Structure of human hyaluronidase-1, a hyaluronan hydrolyzing enzyme involved in tumor growth and angiogenesis Biochemistry 46 2007 6911 6920
8. A.B. Csoka, G.I. Frost, and R. Stern The six hyaluronidase-like genes in the human and mouse genomes Matrix Biol. 20 2001 499 508
9. O. Emanuelsson, S. Brunak, G. von Heijne, and H. Nielsen Locating proteins in the cell using TargetP, SignalP and related tools Nat. Prot. 2 2007 953 971
10. R.M. Facino, M. Carini, R. Stefani, G. Aldini, and L. Saibene Anti-elastase and anti-hyaluronidase activities of saponins and sapogenins from Hedera helix, Aesculus hippocastanum, and Ruscus aculeatus: factors contributing to their efficacy in the treatment of venous insufficiency Archiv der Pharmazie 328 1995 720 724
11. D.A. Godin PH-20: a novel tumor marker for laryngeal cancer Arch. Otolaryngol.-Head Neck Surg. 126 2000 402 404
12. K. Hantke Regulation of ferric iron transport in Escherichia coli K12: isolation of a constitutive mutant Mol. Gen. Genet. 182 1981 288 292
13. W. Hertel, G. Peschel, J.H. Ozegowski, and P.J. Müller Inhibitory effects of triterpenes and flavonoids on the enzymatic activity of hyaluronic acid-splitting enzymes Arch. Pharm. 339 2006 313 318
14. E.S. Hofinger, M. Spickenreither, J. Oschmann, G. Bernhardt, R. Rudolph, and A. Buschauer Recombinant human hyaluronidase Hyal-1: insect cells versus Escherichia coli as expression system and identification of low molecular weight inhibitors Glycobiology 17 2007 444 453
15. E.S. Hofinger, G. Bernhardt, and A. Buschauer Kinetics of Hyal-1 and PH-20 hyaluronidases: comparison of minimal substrates and analysis of the transglycosylation reaction Glycobiology 17 2007 963 971
16. E.S. Hofinger, J. Hoechstetter, M. Oettl, G. Bernhardt, and A. Buschauer Isoenzyme-specific differences in the degradation of hyaluronic acid by mammalian-type hyaluronidases Glycoconj. J. 25 2008 101 109
17. G.R. Hunnicutt, P. Primakoff, and D.G. Myles Sperm surface protein PH-20 is bifunctional: one activity is a hyaluronidase and a second, distinct activity is required in secondary Sperm-Zona binding Biol. Reprod. 55 1996 80 86
18. T. Isoyama, D. Thwaites, M.G. Selzer, R.I. Carey, R. Barbucci, and V.B. Lokeshwar Differential selectivity of hyaluronidase inhibitors toward acidic and basic hyaluronidases Glycobiology 16 2006 11 21
19. J. Jose Autodisplay: efficient bacterial surface display of recombinant proteins Appl. Microbiol. Biotechnol. 69 2006 607 614
20. J. Jose, J.W. Chung, B.J. Jeon, R.M. Maas, C.H. Nam, and J.C. Pyun Escherichia coli with autodisplayed Z-domain of protein A for signal amplification of SPR biosensor Biosens. Bioelectron. 24 2009 1324 1329
21. J. Jose, and S. Handel Monitoring the cellular surface display of recombinant proteins by cysteine labeling and flow cytometry Chembiochem 4 2003 396 405
22. J. Jose, and T.F. Meyer The Autodisplay story, from discovery to biotechnical and biomedical applications Microbiol. Mol. Biol. Rev. 71 2007 600 619
23. J. Jose, M. Park, and J.C Pyun E. coli outer membrane with autodisplayed Z-domain as a molecular recognition layer of SPR biosensor Biosens. Bioelectron. 25 2010 1225 1228
24. J. Jose, and S. von Schwichow Autodisplay of active sorbitol dehydrogenase (SDH) yields a whole cell biocatalyst for the synthesis of rare sugars Chembiochem 5 2004 491 499
25. A. Kaessler, O. Algul, and J. Jose A microplate based screening of benzimidazole derivatives on hyaluronidase inhibition at pH 7 and 3.5 Lett. Drug Des. Discov. 4 2007 562 569
26. A. Kaessler, M.R. Nourrisson, M. Duflos, and J. Jose Indole carboxamides inhibit bovine testes hyaluronidase at pH 7.0 and indole acetamides activate the enzyme at pH 3.5 by different mechanisms J. Enzyme Inhib. Med. Chem. 23 2008 719 727
27. R. Koebnik, K.P. Locher, and P. Van Gelder Structure and function of bacterial outer membrane proteins: barrels in a nutshell Mol. Microbiol. 37 2000 239 253
28. J.L. Kovar, M.A. Johnson, W.M. Volcheck, J. Chen, and M.A Simpson Hyaluronidase expression induces prostate tumor metastasis in an orthotopic mouse model Am. J. Pathol. 169 2006 1415 1426
29. U.R. Kuppusamy, H.E. Khoo, and N.P. Das Structure-activity studies of flavonoids as inhibitors of hyaluronidase Biochem. Pharmacol. 40 1990 397 401
30. C.T. Lattemann, J. Maurer, E. Gerland, and T.F. Meyer Autodisplay: functional display of active β-lactamase on the surface of Escherichia coli by the AIDA-I autotransporter J. Bacteriol. 182 2000 3726 3733
31. V.B. Lokeshwar HYAL1-v1, an alternatively spliced variant of HYAL1 hyaluronidase: a negative regulator of bladder cancer Cancer Res. 66 2006 11219 11227
32. C. Maingonnat, R. Victor, P. Bertrand, M-N. Courel, R. Maunoury, and B. Delpech Activation and inhibition of human cancer cell hyaluronidase by proteins Anal. Biochem. 268 1999 30 34
33. J. Maurer, J. Jose, and T.F. Meyer Autodisplay: one-component system for efficient surface display and release of soluble recombinant proteins from Escherichia coli J. Bacteriol. 179 1997 794 804
34. J. Maurer, J. Jose, and T.F Meyer Characterization of the essential transport function of the AIDA-I autotransporter and evidence supporting structural predictions J. Bacteriol. 181 1999 7014 7020
35. K. Meyer Hyaluronidases The Enzymes 1971 307 320
36. K. Meyer, and M.M. Rapport The inhibition of testicular hyaluronidase by heavy metals J. Biol. Chem. 188 1951 485 490
37. K. Mio, and R. Stern Inhibitors of the hyaluronidases Matrix Biol. 21 2002 31 37
38. R. Montesano, S. Kumar, L. Orci, and M.S. Pepper Synergistic effect of hyaluronan oligosaccharides and vascular endothelial growth factor on angiogenesis in vitro Lab. Invest. 75 1996 249 262
39. S. Olgen, A. Kaeßler, D. Nebioglu, and J. Jose New potent indole derivatives as hyaluronidase inhibitors Chem. Biol. Drug Des. 70 2007 547 551
40. M. Park, J. Jose, and J.C. Pyun Hypersensitive immunoassay by using Escherichia coli outer membrane with autodisplayed Z-domains Enzyme Microb. Technol. 46 2010 309 314
41. P. Primakoff, and D.G. Myles Penetration, adhesion, and fusion in mammalian sperm-egg interaction Science 296 2002 2183 2185
42. D.J. Rigden Design of new benzoxazole-2-thione-derived inhibitors of Streptococcus pneumoniae hyaluronan lyase, structure of a complex with a 2-phenylindole Glycobiology 16 2006 757 765
43. K. Sabeur, G.N. Cherr, A.I. Yudin, P. Primakoff, M-W. Li, and J.W. Overstreet The PH-20 protein in human spermatozoa J. Androl. 18 1997 151 158
44. S. Salmen, J. Hoechstetter, C. Käsbauer, D.H. Paper, G. Bernhardt, and A. Buschauer Sulphated oligosaccharides as inhibitors of hyaluronidases from bovine testis, bee venom and Streptococcus agalactiae Planta Med. 71 2005 727 732
45. G. Schmidt, B. Jann, and K. Jann Immunochemistry of R lipopolysaccharides of Escherichia coli Eur. J. Biochem. 10 1969 501 510
46. G. Schmidt, B. Jann, and K. Jann Immunochemistry of R lipopolysaccharides of Escherichia coli; studies on R mutants with an incomplete core, derived from E. coli 08: K27 Eur. J. Biochem. 16 1970 382 392
47. E. Schultheiss, C. Paar, H. Schwab, and J. Jose Functional esterase surface display by the autotransporter pathway in Escherichia coli J. Mol. Catal. B: Enzym. 18 2002 89 97
48. E. Schultheiss, S. Weiss, E. Winterer, R. Maas, E. Heinzle, and J. Jose Esterase Autodisplay: enzyme engineering and whole-cell activity determination in microplates with pH sensors Appl. Environ. Microbiol. 74 2008 4782 4791
49. L.N. Soldatova Superior biologic activity of the recombinant bee venom allergen hyaluronidase expressed in baculovirus-infected insect cells as compared with Escherichia coli J. Allergy Clin. Immunol. 101 1998 691 698
50. M. Spickenreither, S. Braun, G. Bernhardt, S. Dove, and A. Buschauer Novel 6-O-acylated vitamin C derivatives as hyaluronidase inhibitors with selectivity for bacterial lyases Bioorg. Med. Chem. Lett. 16 2006 5313 5316
51. R. Stern Hyaluronan metabolism: a major paradox in cancer biology Pathol. Biol. 53 2005 372 382
52. R. Stern, A.A. Asari, and K.N. Sugahara Hyaluronan fragments: an information-rich system Eur. J. Cell Biol. 85 2006 699 715
53. R. Stern, and M.J. Jedrzejas Hyaluronidases: their genomics, structures, and mechanisms of action Chem. Rev. 106 2006 818 839
54. A. Suzuki, H. Toyoda, T. Toida, and T. Imanari Preparation and inhibitory activity on hyaluronidase of fully O-sulfated hyaluro-oligosaccharides Glycobiology 11 2001 57 64
55. K. Terpe Overview of bacterial expression systems for heterologous protein production: from molecular and biochemical fundamentals to commercial systems Appl. Microbiol. Biotechnol. 72 2006 211 222
56. T. Toida, Y. Ogita, A. Suzuki, H. Toyoda, and T. Imanari Inhibition of hyaluronidase by fully O-sulfonated glycosaminoglycans Arch. Biochem. Biophys. 370 1999 176 182
57. L. Udabage, G.R. Brownlee, R. Stern, and T.J. Brown Inhibition of hyaluronan degradation by dextran sulphate facilitates characterisation of hyaluronan synthesis: an in vitro and in vivo study Glycoconjug. J. 20 2004 461 471
58. R.A. Wolf, D. Glogar, and L.Y Chaung Heparin inhibits bovine testicular hyaluronidase activity in myocardium of dogs with coronary artery occlusion Am. J. Cardiol. 53 1984 941 944