Binding a heparin derived disaccharide to defensin inspired peptides: Insights to antimicrobial inhibition from gas-phase measurements

Physical Chemistry Chemical Physics

Volumn 12, Issue 14, 2010, Pages 3589-3596

  McCullough, Bryan J ^a,d   Kalapothakis, Jason M ^a   Chin, Wutharath ^a,e   Taylor, Karen ^b   Clarke, David J ^a   Eastwood, Hayden ^a   Campopiano, Dominic ^a   MacMillan, Derek ^c   Dorin, Julia ^b   Barran, Perdita E ^a  

^a UNIVERSITY OF EDINBURGH   (United Kingdom)

^b UNIVERSITY OF EDINBURGH   (United Kingdom)

^c UNIVERSITY COLLEGE LONDON   (United Kingdom)

^d LGC   (United Kingdom)

^e CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIINFECTIVE AGENT; DEFENSIN; DISACCHARIDE; HEPARIN; PEPTIDE;

ARTICLE; BINDING SITE; CHEMICAL STRUCTURE; CHEMISTRY; GAS; MASS SPECTROMETRY;

ANTI-INFECTIVE AGENTS; BINDING SITES; DEFENSINS; DISACCHARIDES; GASES; HEPARIN; MASS SPECTROMETRY; MODELS, MOLECULAR; PEPTIDES;

EID: 77950249584     PISSN: 14639076     EISSN: None     Source Type: Journal    
DOI: 10.1039/b923784d     Document Type: Article

References (41)

1. C. Dalvit E. Ardini M. Flocco G. P. Fogliatto N. Mongelli M. Veronesi A general NMR method for rapid, efficient, and reliable biochemical screening J. Am. Chem. Soc. 2003 125 47 14620 14625
2. J. Kaddis C. Zurita J. Moran M. Borra N. Polder C. R. Meyer F. A. Gomez Estimation of binding constants for the substrate and activator of Rhodobacter sphaeroides adenosine 5′-diphosphate-glucose pyrophosphorylase using affinity capillary electrophoresis Anal. Biochem. 2004 327 2 252 260
3. T. N. Doman S. L. McGovern B. J. Witherbee T. P. Kasten R. Kurumbail W. C. Stallings D. T. Connolly B. K. Shoichet Molecular docking and high-throughput screening for novel inhibitors of protein tyrosine phosphatase-1B J. Med. Chem. 2002 45 11 2213 2221
4. M. M. Zhu D. L. Rempel M. L. Gross Modeling data from titration, amide H/D exchange, and mass spectrometry to obtain protein-ligand binding constants J. Am. Soc. Mass Spectrom. 2004 15 3 388 97
5. H. Xiao I. A. Kaltashov S. J. Eyles Indirect assessment of small hydrophobic ligand binding to a model protein using a combination of ESI MS and HDX/ESI MS J. Am. Soc. Mass Spectrom. 2003 14 5 506 515
6. K. D. Powell M. C. Fitzgerald High-throughput screening assay for the tunable selection of protein ligands J. Comb. Chem. 2004 6 2 262 269
7. C. J. Petzold M. D. Leavell J. A. Leary Screening and identification of acidic carbohydrates in bovine colostrum by using ion/molecule reactions and Fourier transform ion cyclotron resonance mass spectrometry: Specificity toward phosphorylated complexes Anal. Chem. 2004 76 1 203 210
8. S. Kramer, T. O. Joos and M. F. Templin, Protein microarrays, Curr. Protoc. Protein. Sci., 2005, ch. 23, Unit 23 5
9. H.-J. Bohm and G. Schneider, Protein-Ligand Interactions: From Molecular Recognition to Drug Design, Wiley-VCH, Berlin, 2003
10. R. Lehrer Primate defensins Nat. Rev. Microbiol. 2004 2 9 727 738
11. M. Ouellet F. Otis N. Voyer M. Auger Biophysical studies of the interactions between 14-mer and 21-mer model amphipathic peptides and membranes: Insights on their modes of action Biochim. Biophys. Acta, Biomembr. 2006 1758 9 1235 1244
12. Y. Shai Mechanism of the binding, insertion and destabilization of phospholipid bilayer membranes by α-helical antimicrobial and cell non-selective membrane-lytic peptides Biochim. Biophys. Acta, Biomembr. 1999 1462 1-2 55
13. 2+ Biophys. J. 2003 85 4 2363 2373
14. H. Leontiadou A. E. Mark S. J. Marrink Antimicrobial peptides in action J. Am. Chem. Soc. 2006 128 37 12156 12161
15. T. J. Falla D. N. Karunaratne R. E. W. Hancock Mode of action of the antimicrobial peptide indolicidin J. Biol. Chem. 1996 271 32 19298 19303
16. A. Peschel How do bacteria resist human antimicrobial peptides? Trends Microbiol. 2002 10 4 179 86
17. H. Sahly S. Schubert J. Harder P. Rautenberg U. Ullmann J. Schroder R. Podschun Burkholderia is highly resistant to human β-defensin 3 Antimicrob. Agents Chemother. 2003 47 5 1739 1741
18. F. D. Menozzi K. Pethe P. Bifani F. Soncin M. J. Brennan C. Locht Enhanced bacterial virulence through exploitation of host glycosaminoglycans Mol. Microbiol. 2002 43 6 1379 1386
19. E. Andersson V. Rydengard A. Sonesson M. Morgelin L. Bjorck A. Schmidtchen Antimicrobial activities of heparin-binding peptides Eur. J. Biochem. 2004 271 6 1219 26
20. A. Schmidtchen I. M. Frick L. Bjorck Dermatan sulfate is released by proteinases of common pathogenic bacteria and inactivates antibacterial α-defensin Mol. Microbiol. 2001 39 3 708 713
21. A. D. Cardin D. A. Demeter H. J. R. Weintraub R. L. Jackson Molecular Design and Modeling of Protein Heparin Interactions Methods Enzymol. 1991 203 556 583
22. M. Sobel D. F. Soler J. C. Kermode R. B. Harris Localization and Characterization of a Heparin Binding Domain Peptide of Human Vonwillebrand-Factor J. Biol. Chem. 1992 267 13 8857 8862
23. F. Bauer K. Schweimer E. Kluver J. R. Conejo-Garcia W. G. Forssmann P. Rosch K. Adermann H. Sticht Structure determination of human and murine beta-defensins reveals structural conservation in the absence of significant sequence similarity Protein Sci. 2001 10 12 2470 9
24. S. E. Crown Y. H. Yu M. D. Sweeney J. A. Leary T. M. Handel Heterodimerization of CCR2 chemokines and regulation by glycosaminoglycan binding J. Biol. Chem. 2006 281 35 25438 25446
25. J. Zaia On-line separations combined with MS for analysis of glycosaminoglycans Mass Spectrom. Rev. 2009 28 2 254 72
26. B. Xia J. A. Royall G. Damera G. P. Sachdev R. D. Cummings Altered O-glycosylation and sulfation of airway mucins associated with cystic fibrosis Glycobiology 2005 15 8 747 75
27. T. Wyttenbach and M. T. Bowers, Gas-phase conformations: The ion mobility/ion chromatography method, in Modern Mass Spectrometry Topics In Current Chemistry, Springer-Verlag, Berlin, 2003, vol. 225, pp. 207-232
28. A. E. Ashcroft Recent developments in electrospray ionisation mass spectrometry: noncovalently bound protein complexes Nat. Prod. Rep. 2005 22 4 452 464
29. J. L. P. Benesch B. T. Ruotolo D. A. Simmons C. V. Robinson Protein Complexes in the Gas Phase: Technology for Structural Genomics and Proteomics Chem. Rev. 2007 107 8 3544 3567
30. S. L. Bernstein T. Wyttenbach A. Baumketner J. E. Shea G. Bitan D. B. Teplow M. T. Bowers Amyloid beta-protein: Monomer structure and early aggregation states of A beta 42 and its Pro(19) alloform J. Am. Chem. Soc. 2005 127 7 2075 2084
31. B. J. McCullough H. Eastwood D. J. Clark N. C. Polfer D. J. Campopiano J. A. Dorin A. Maxwell R. J. Langley J. R. W. Govan S. L. Bernstein M. T. Bowers P. E. Barran Characterisation of DEFB107 by mass spectrometry: Lessons from an anti-antimicrobial defensin Int. J. Mass Spectrom. 2006 252 2 180 188
32. B. J. McCullough J. Kalapothakis H. Eastwood P. Kemper D. MacMillan K. Taylor J. Dorin P. E. Barran Development of an ion mobility quadrupole time of flight mass spectrometer Anal. Chem. 2008 80 16 6336 6344
33. L. Jin P. E. Barran J. A. Deakin M. Lyon A. Uhrin Conformation of glycosaminoglycans by ion mobility mass spectrometry and molecular modelling Phys. Chem. Chem. Phys. 2005 7 19 3464 3471
34. S. Zhang C. K. VanPelt D. B. Wilson Quantitative Determination of Noncovalent Binding Interactions Using Automated Nanoelectrospray Mass Spectrometry Anal. Chem. 2003 75 13 3010 3018
35. P. R. Kemper M. T. Bowers A Hybrid Double-Focusing Mass-Spectrometer- High-Pressure Drift Reaction Cell to Study Thermal-Energy Reactions of Mass-Selected Ions J. Am. Soc. Mass Spectrom. 1990 1 3 197 207
36. D. A. Case, T. A. Darden, T. E. Cheatham, C. L. Simmerling, J. Wang, R. E. Duke, R. Luo, K. M. Merz, D. A. Wang, D. A. Pearlman, M. Crowley, S. Brozell, T. V., G. H., J. Mongan, V. Hornak, G. Cui, P. Beroza, S. C., J. W. Caldwell, W. S. Ross and P. Kollman, AMBER 8, University of California, San Francisco, 2004
37. A. A. Shvartsburg G. C. Schatz M. F. Jarrold Mobilities of carbon cluster ions: Critical importance of the molecular attractive potential J. Chem. Phys. 1998 108 6 2416 2423
38. K. Taylor B. McCullough D. J. Clarke R. J. Langley T. Pechenick A. Hill D. J. Campopiano P. E. Barran J. R. Dorin J. R. Govan Covalent dimer species of β-defensin Defr1 display potent antimicrobial activity against multidrug-resistant bacterial pathogens Antimicrob. Agents Chemother. 2007 51 5 1719 24
39. K. Taylor D. J. Clarke B. McCullough W. Chin E. Seo D. Yang J. Oppenheim D. Uhrin J. R. Govan D. J. Campopiano D. Macmillan P. Barran J. R. Dorin Analysis and Separation of Residues Important for the Chemoattractant and Antimicrobial Activities of β-Defensin 3 J. Biol. Chem. 2008 283 11 6631 9
40. D. J. Campopiano D. J. Clarke N. C. Polfer P. E. Barran R. J. Langley J. R. W. Govan A. Maxwell J. R. Dorin Structure-activity relationships in defensin dimers-A novel link between β-defensin tertiary structure and antimicrobial activity J. Biol. Chem. 2004 279 47 48671 48679
41. D. J. Schibli H. N. Hunter V. Aseyev T. D. Starner J. M. Wiencek P. B. McCray, Jr. B. F. Tack H. J. Vogel The solution structures of the human β-defensins lead to a better understanding of the potent bactericidal activity of HBD3 against Staphylococcus aureus J. Biol. Chem. 2002 277 10 8279 89