Addition of antimicrobial properties to hyaluronic acid by grafting of antimicrobial peptide

European Polymer Journal

Volumn 51, Issue 1, 2014, Pages 182-190

  Lequeux, Isabelle ^c   Ducasse, Emmanuel ^c   Jouenne, Thierry ^c   Thebault, Pascal ^a,b  

^a UNIVERSITÉ DE ROUEN   (France)

^b CNRS   (France)

^c NORMANDIE UNIVERSITÉ   (France)

Author keywords

Antimicrobial peptide; Grafting; Hyaluronic acid; Hydrogel; Nisin

Indexed keywords

ANTIBIOTICS; BACTERIA; BIOMATERIALS; GRAFTING (CHEMICAL); HYDROGELS; MICROORGANISMS; ORGANIC ACIDS; PEPTIDES; POLYETHYLENES;

ANTI-MICROBIAL ACTIVITY; ANTI-MICROBIAL PROPERTIES; ANTIMICROBIAL PEPTIDE; BACTERIAL CONTAMINATION; MODIFIED POLYSACCHARIDES; NISIN; PSEUDOMONAS AERUGINOSA BACTERIA; STAPHYLOCOCCUS EPIDERMIDIS;

HYALURONIC ACID;

EID: 84893655160     PISSN: 00143057     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.eurpolymj.2013.11.012     Document Type: Article

References (47)

1. Mah TFC, OToole GA Mechanisms of biofilm resistance to antimicrobial agents. Trends Microbiol 2001; 9:34-9.
2. Blin T, Purohit V, Leprince J., Jouenne T, Glinel K. Bactericidal microparticles decorated by an antimicrobial peptide for the easy disinfection of sensitive aqueous solutions. Biomacromolecules 2011; 12:1259-64.
3. Glinel K, Thebault P, Humblot V., Pradier CM, Jouenne T. Antibacterial surfaces developed from bio-inspired approaches. Acta Biomater 2012; 8:1670-84.
4. Guyomard A, De E, Jouenne T., Malandain JJ, Muller G, Glinel K. Incorporation of a hydrophobic antibacterial peptide into amphiphilic polyelectrolyte multilayers: a bioinspired approach to prepare biocidal thin coatings. Adv Funct Mater 2008; 18:758-65. (Pubitemid 351430217)
5. Haynie SL, Crum GA Doele BA. Antimicrobial activities of amphiphilic peptides covalently bonded to a water-insoluble resin. Antimicrob Agents Chemother 1995; 39:301-7.
6. Humblot V, Yala JF, Thebault P, Boukerma K., Hequet A, Berjeaud JM, et al The antibacterial activity of magainin I immobilized onto mixed thiols self-assembled monolayers. Biomaterials 2009; 30:3503-12.
7. Hequet A, Humblot V, Berjeaud J.M., Pradier CM Optimized grafting of antimicrobial peptides on stainless steel surface and biofilm resistance tests. Colloid Surf B-Biointerfaces 2011; 84:301-9.
8. Qi XB, Poernomo G, Wang K.A., Chen YA, Chan-Park MB, Xu R, et al Covalent immobilization of nisin on multi-walled carbon nanotubes: superior antimicrobial and anti-biofilm properties. Nanoscale 2011; 3:1874-80.
9. Zhao HX, Kinnunen PKJ. Binding of the antimicrobial peptide temporin L to liposomes assessed by Trp fluorescence. J Biol Chem 2002; 277:25170-7. (Pubitemid 34951823)
10. Malheiros PD, Micheletto YMS, da Silveira NP, Brandelli A Development and characterization of phosphatidylcholine nanovesicles containing the antimicrobial peptide nisin. Food Res Int 2010; 43:1198-203.
11. Cheigh CI, Pyun YR Nisin biosynthesis and its properties. Biotechnol Lett 2005; 27:1641-8.
12. Ryder MP, Schilke KF, Auxier J.A., McGuire J., Neff JA Nisin adsorption to polyethylene oxide layers and its resistance to elution in the presence of fibrinogen. J Colloid Interface Sci 2010; 350:194-9.
13. Carroll J, Draper LA, O'Connor PM, Coffey A, Hill C., Ross RP, et al Comparison of the activities of the lantibiotics nisin and lacticin 3147 against clinically significant mycobacteria. Int J Antimicrob Agents 2010; 36:132-6.
14. Schante CE, Zuber G, Herlin C., Vandamme TF Chemical modifications of hyaluronic acid for the synthesis of derivatives for a broad range of biomedical applications. Carbohydr Polym 2011; 85:469-89.
15. Uppal R, Ramaswamy GN, Arnold C, Goodband R Wang Y. Hyaluronic acid nanofiber wound dressing-production, characterization, and in vivo behavior. J Biomed Mater Res Part B 2011; 97B:20-9.
16. Yeom J, Bhang SH, Kim B.S., Seo MS, Hwang EJ, Cho IH, et al Effect of cross-linking reagents for hyaluronic acid hydrogel dermal fillers on tissue augmentation and regeneration. Bioconjugate Chem 2010; 21:240-7.
17. Balazs EA. Hyaluronan as an ophthalmic viscoelastic device. Curr Pharm Biotechnol 2008; 9:236-8.
18. Burdick JA Prestwich GD. Hyaluronic acid hydrogels for biomedical applications. Adv Mater 2011; 23:H41-56.
19. Scheuer CA, Fridman KM, Barniak V.L., Burke SE, Venkatesh S. Retention of conditioning agent hyaluronan on hydrogel contact lenses. Contact Lens Anterior Eye 2010; 33:S2-6.
20. Luensmann D, Jones L. Protein deposition on contact lenses: the past, the present, and the future. Contact Lens Anterior Eye 2012; 35:53-64.
21. Rah MJ. A review of hyaluronan and its ophthalmic applications. Optometry 2011; 82:38-43.
22. Teh BM, Shen Y, Friedland P.L., Atlas MD, Marano RJ A review on the use of hyaluronic acid in tympanic membrane wound healing. Expert Opin Biol Ther 2012; 12:23-36.
23. Galeano M, Polito F, Bitto A., Irrera N, Campo GM, Avenoso A, et al Systemic administration of high-molecular weight hyaluronan stimulates wound healing in genetically diabetic mice. Biochim Biophys Acta-Mol Basis Dis 2011; 1812:752-9.
24. Ardizzoni A, Neglia RG, Baschieri M.C., Cermelli C., Caratozzolo M, Righi E, et al Influence of hyaluronic acid on bacterial and fungal species, including clinically relevant opportunistic pathogens. J Mater Sci-Mater Med 2011; 22:2329-38.
25. Kemp MM, Kumar A, Clement D., Ajayan P, Mousa S, Linhardt RJ Hyaluronan- and heparin-reduced silver nanoparticles with antimicrobial properties. Nanomedicine 2009; 4:421-9.
26. Baier G, Cavallaro A, Vasilev K., Mailander V, Musyanovych A, Landfester K. Enzyme responsive hyaluronic acid nanocapsules containing polyhexanide and their exposure to bacteria to prevent infection. Biomacromolecules 2013; 14:1103-12.
27. Pongtharangkul T, Demirci A. Evaluation of agar diffusion bioassay for nisin quantification. Appl Microbiol Biotechnol 2004; 65:268-72. (Pubitemid 39222470)
28. Joshi PR, McGuire J, Neff JA Synthesis and antibacterial activity of nisin-containing block copolymers. J Biomed Mater Res Part B 2009; 91B:128-34.
29. Jones S, Bowler PG, Walker M. Antimicrobial activity of silver-containing dressings is influenced by dressing conformability with a wound surface. Wounds-Compend Clin Res Pract 2005; 17:263-70. (Pubitemid 41483138)
30. Bowler PG, Welsby S, Towers V., Booth R, Hogarth A, Rowlands V., et al Multidrug-resistant organisms, wounds and topical antimicrobial protection. Int Wound J 2012; 9:387-96.
31. El-Faham A., Albericio F. Peptide coupling reagents, more than a letter soup. Chem Rev 2011; 111:6557-602.
32. Valeur E, Bradley M. Amide bond formation: beyond the myth of coupling reagents. Chem Soc Rev 2009; 38:606-31.
33. Montalbetti C, Falque V. Amide bond formation and peptide coupling. Tetrahedron 2005; 61:10827-52. (Pubitemid 41447509)
34. Mota-Meira M., LaPointe G, Lacroix C., Lavoie MC MICs of mutacin B-Ny266, nisin A, vancomycin, and oxacillin against bacterial pathogens. Antimicrob Agents Chemother 2000; 44:24-9. (Pubitemid 30010667)
35. Coimbra P, Alves P, Valente TAM, Santos R, Correia I.J., Ferreira P. Sodium hyaluronate/chitosan polyelectrolyte complex scaffolds for dental pulp regeneration: synthesis and characterization. Int J Biol Macromol 2011; 49:573-9.
36. Luppi B, Bigucci F, Mercolini L., Musenga A, Sorrenti M, Catenacci L., et al Novel mucoadhesive nasal inserts based on chitosan/hyaluronzite polyelectrolyte complexes for peptide and protein delivery. J Pharm Pharmacol 2009; 61:151-7.
37. Tai YC, Joshi P, McGuire J., Neff JA Nisin adsorption to hydrophobic surfaces coated with the PEO-PPO-PEO triblock surfactant pluronic (R) F108. J Colloid Interface Sci 2008; 322:112-8.
38. Pfeiler E, Toyoda H, Williams M.D., Nieman RA Identification, structural analysis and function of hyaluronan in developing fish larvae (leptocephali). Comp Biochem Physiol B-Biochem Mol Biol 2002; 132:443-51. (Pubitemid 34603153)
39. Slijper M, Hilbers CW, Konings RNH, Vandeven FJM. Nmr-studies of lantibiotics assignment of the H-l-NMR spectrum of nisin and identification of interresidual contacts. FEBS Lett 1989; 252:22-8. (Pubitemid 19201070)
40. Bradford MM. Rapid and sensitive method for quantitation of microgram quantities of protein utilizing principle of protein-dye binding. Anal Biochem 1976; 72:248-54.
41. Ku HK, Lim HM, Oh K.H., Yang HJ, Jeong JS, Kim SK Interpretation of protein quantitation using the Bradford assay: comparison with two calculation models. Anal Biochem 2013; 434:178-80.
42. Stevens KA, Sheldon BW, Klapes NA Klaenhammer TR Nisin treatment for inactivation of salmonella species and other gram-negative bacteria. Appl Environ Microbiol 1991; 57:3613-5.
43. Li T, Tao T, Hong F. Study of the inhibition effect of nisin. J Am Sci 2005; 1:33-7.
44. Prestwich GD, Marecak DM, Marecek J.F., Vercruysse KP, Ziebell MR Controlled chemical modification of hyaluronic acid: synthesis, applications, and biodégradation of hydrazide derivatives. J Control Release 1998; 53:93-103. (Pubitemid 28218693)
45. Pouyani T, Harbison GS, Prestwich GD Novel hydrogels of hyaluronic-acid - synthesis, surface-morphology, and solid-state NMR. J Am Chem Soc 1994; 116:7515-22. (Pubitemid 24291810)
46. Luo Y, Kirker KR, Prestwich GD Cross-linked hyaluronic acid hydrogel films: new biomaterials for drug delivery. J Control Release 2000; 69:169-84.
47. Necas J, Bartosikova L, Brauner P., Kolar J. Hyaluronic acid (hyaluronan): a review. Vet Med 2008; 53:397-411.