Abstract
The accumulation of reactive oxygen species (ROS) in microbial biofilms has been recently recognized to play a role in promoting antibiotic resistance in biofilm-growing bacteria. ROS are also over-produced when a medical device is implanted and they can promote device susceptibility to infection or aseptic loosening. High levels of ROS seem also to be responsible for the establishment of chronic wounds.
In this study, a novel antioxidant polyacrylate was synthesized and investigated in terms of antimicrobial and antibiofilm activity. The polymer possesses in side-chain hydroxytyrosol (HTy), that is a polyphenolic compound extracted from olive oil wastewaters.
The obtained 60 nm in size polymer nanoparticles showed good scavenging and antibacterial activity versus a strain of Staphylococcus epidermidis. Microbial adherence assays evidenced that the hydroxytyrosol-containing polymer was able to significantly reduce bacterial adhesion compared to the control. These findings open novel perspective for a successful use of this antioxidant polymer for the prevention or treatment of biofilm-based infections as those related to medical devices or chronic wounds.
This is a preview of subscription content, log in via an institution to check access.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
Al Mohajer M, Darouiche RO (2012) Sepsis syndrome, bloodstream infections, and device-related infections. Med Clin N Am 96:1203–1223
Anderson JM, Rodriguez A, Chang DT (2008) Foreign body reaction to biomaterials. Semin Immunol 20:86–100
Balasubramanian V, Grusin NK, Bucher RW et al (1999) Residence-time dependent changes in fibrinogen adsorbed to polymeric biomaterials. J Biomed Mater Res 44:253–260
Bernini R, Mincione E, Barontini M et al (2008) Convenient synthesis of hydroxytyrosol and its lipophilic derivatives from tyrosol or homovanillyl alcohol. J Agric Food Chem 56:8897–8904
Biesalski HK (2007) Polyphenols and inflammation: basic interactions. Curr Opin Clin Nutr Metab Care 10:724–728
Boles BR, Singh PK (2008) Endogenous oxidative stress produces diversity and adaptability in biofilm communities. Proc Natl Acad Sci U S A 105:12503–12508
Boudreaux CJ, Bunyard WC, McCormick CL (1996) Controlled activity polymers. 8. Copolymers of acrylic acid and isomeric N-akylacrylamide with pendent beta-naphthol esters moieties: synthesis and characterization. J Control Release 40:223–233
Brandwilliams W, Cuvelier ME, Berset C (1995) Use of a free-radical method to evaluate antioxidant activity. LWT-Food Sci Technol 28:25–30
Campoccia D, Montanaro L, Arciola CR (2013) A review of the biomaterials technologies for infection-resistant surfaces. Biomaterials 34:8533–8554
Cap M, Vachova L, Palkova Z (2012) Reactive oxygen species in the signaling and adaptation of multicellular microbial communities. Oxid Med Cell Longev 2012:976753
Chernousova S, Epple M (2013) Silver as antibacterial agent: ion, nanoparticle, and metal. Angew Chem Int Ed Engl 52:1636–1653
Ciofu O, Riis B, Pressler T et al (2005) Occurrence of hypermutable Pseudomonas aeruginosa in cystic fibrosis patients is associated with the oxidative stress caused by chronic lung inflammation. Antimicrob Agents Chemother 49:2276–2282
Cirillo G, Curcio M, Vittorio O et al (2014) Polyphenol conjugates and human health: a perspective review. Crit Rev Food Sci Nutr. doi:10.1080/10408398.2012.752342
Correa JAG, Lopez-Villodres JA, Asensi R et al (2009) Virgin olive oil polyphenol hydroxytyrosol acetate inhibits in vitro platelet aggregation in human whole blood: comparison with hydroxytyrosol and acetylsalicylic acid. Br J Nutr 101:1157–1164
Costerton JW, Montanaro L, Arciola CR (2007) Bacterial communications in implant infections: a target for an intelligence war. Int J Artif Organs 30:757–763
Curcio M, Puoci F, Iemma F et al (2009) Covalent insertion of antioxidant molecules on chitosan by a free radical grafting procedure. J Agric Food Chem 57:5933–5938
de Pinedo AT, Penalver P, Morales JC (2007) Synthesis and evaluation of new phenolic-based antioxidants: structure-activity relationship. Food Chem 103:55–61
Dhall S, Do D, Garcia M et al (2014a) A novel model of chronic wounds: importance of redox imbalance and biofilm-forming bacteria for establishment of chronicity. Plos One 9:e109848
Dhall S, Do DC, Garcia M et al (2014b) Generating and reversing chronic wounds in diabetic mice by manipulating wound redox parameters. J Diabetes Res http://dx.doi.org/10.1155/2014/562625
Donelli G, Vuotto C (2014) Biofilm-based infections in long-term care facilities. Future Microbiol 9:175–188
Donelli G, Francolini I, Romoli D et al (2007) Synergistic activity of dispersin B and cefamandole nafate in inhibition of staphylococcal biofilm growth on polyurethanes. Antimicrob Agents Chemother 51:2733–2740
Fialkow L, Wang Y, Downey GP (2007) Reactive oxygen and nitrogen species as signaling molecules regulating neutrophil function. Free Radic Biol Med 42:153–164
Francolini I, Donelli G (2010) Prevention and control of biofilm-based medical-device-related infections. FEMS Immunol Med Microbiol 59:227–238
Francolini I, D’Ilario L, Guaglianone E et al (2010) Polyurethane anionomers containing metal ions with antimicrobial properties: thermal, mechanical and biological characterization. Acta Biomater 6:3482–3490
Francolini I, Taresco V, Crisante F et al (2013) Water soluble usnic acid-polyacrylamide complexes with enhanced antimicrobial activity against staphylococcus epidermidis. Int J Mol Sci 14:7356–7369
Francolini I, Donelli G, Vuotto C et al (2014a) Antifouling polyurethanes to fight device-related staphylococcal infections: synthesis, characterization, and antibiofilm efficacy. Pathog Dis 70:401–407
Francolini I, Piozzi A, Donelli G (2014b) Efficacy evaluation of antimicrobial drug-releasing polymer matrices. Methods Mol Biol 1147:215–225
Francolini I, Donelli G, Crisante F et al (2015) Antimicrobial polymers for anti-biofilm medical devices: state-of-art and perspectives. Adv Exp Med Biol 831:93–117
Frigerio M, Santagostino M, Sputore S (1999) A user-friendly entry to 2-iodoxybenzoic acid (IBX). J Org Chem 64:4537–4538
Geier H, Mostowy S, Cangelosi GA et al (2008) Autoinducer-2 triggers the oxidative stress response in Mycobacterium avium, leading to biofilm formation. Appl Environ Microbiol 74:1798–1804
Granados-Principal S, Quiles JL, Ramirez-Tortosa CL et al (2010) Hydroxytyrosol: from laboratory investigations to future clinical trials. Nutr Rev 68:191–206
Gristina AG (1994) Implant failure and the immuno-incompetent fibro-inflammatory zone. Clin Orthop Relat Res 298:106–118
Habash M, Reid G (1999) Microbial biofilms: their development and significance for medical device-related infections. J Clin Pharmacol 39:887–898
Hanna HA, Raad II, Hackett B et al (2003) Antibiotic-impregnated catheters associated with significant decrease in nosocomial and multidrug-resistant bacteremias in critically ill patients. Chest 124:1030–1038
Hoiby N, Bjarnsholt T, Givskov M et al (2010) Antibiotic resistance of bacterial biofilms. Int J Antimicrob Agents 35:322–332
Iemma F, Puoci F, Curcio M et al (2010) Ferulic acid as a comonomer in the synthesis of a novel polymeric chain with biological properties. J Appl Polym Sci 115:784–789
Jamal MA, Rosenblatt JS, Hachem RY et al (2014) Prevention of biofilm colonization by Gram-negative bacteria on minocycline-rifampin-impregnated catheters sequentially coated with chlorhexidine. Antimicrob Agents Chemother 58:1179–1182
Jung LS, He X, Song C et al (2012) Antioxidant, antibiofilm, and anticholinesterase activities of fermented Deodeok (Codonopsis lanceolata) extracts. Food Sci Biotechnol 21:1413–1419
Mack D, Rohde H, Harris LG et al (2006) Biofilm formation in medical device-related infection. Int J Artif Organs 29:343–359
Mah TF (2012) Biofilm-specific antibiotic resistance. Future Microbiol 7:1061–1072
Manea AM, Vasile BS, Meghea A (2014) Antioxidant and antimicrobial activities of green tea extract loaded into nanostructured lipid carriers. C R Chim 17:331–341
Mansouri MD, Hull RA, Stager CE et al (2013) In vitro activity and durability of a combination of an antibiofilm and an antibiotic against vascular catheter colonization. Antimicrob Agents Chemother 57:621–625
Monzillo V, Corona S, Lanzarini P et al (2012) Chlorhexidine-silver sulfadiazine-impregnated central venous catheters: in vitro antibacterial activity and impact on bacterial adhesion. New Microbiol 35:175–182
Ortiz C, Vazquez B, San RJ (1999) Hydrophilic acrylic biomaterials derived from vitamin E with antioxidant properties. J Biomed Mater Res 45:184–191
Piozzi A, Francolini I, Occhiaperti L et al (2004) Polyurethanes loaded with antibiotics: influence of polymer-antibiotic interactions on in vitro activity against Staphylococcus epidermidis. J Chemother 16:446–452
Raad II, Darouiche RO, Hachem R et al (1998) Antimicrobial durability and rare ultrastructural colonization of indwelling central catheters coated with minocycline and rifampin. Crit Care Med 26:219–224
Ramos ER, Reitzel R, Jiang Y et al (2011) Clinical effectiveness and risk of emerging resistance associated with prolonged use of antibiotic-impregnated catheters: more than 0.5 million catheter days and 7 years of clinical experience. Crit Care Med 39:245–251
Rupp ME, Lisco SJ, Lipsett PA et al (2005) Effect of a second-generation venous catheter impregnated with chlorhexidine and silver sulfadiazine on central catheter-related infections: a randomized, controlled trial. Ann Intern Med 143:570–580
Serpen A, Capuano E, Fogliano V et al (2007) A new procedure to measure the antioxidant activity of insoluble food components. J Agric Food Chem 55:7676–7681
Siedenbiedel F, Tiller J (2012) Antimicrobial polymers in solution and on surfaces: overview and functional principles. Polymers 4:46–71
Stickler DJ, Morris NS, Williams TJ (1996) An assessment of the ability of a silver-releasing device to prevent bacterial contamination of urethral catheter drainage systems. Br J Urol 78:579–588
Stutz H, Illers KH, Mertes J (1990) A generalized theory for the glass-transition temperature of cross-linked and uncrosslinked polymers. J Polym Sci Polym Phys 28:1483–1498
Sutherland K, Mahoney JR, Coury AJ et al (1993) Degradation of biomaterials by phagocyte-derived oxidants. J Clin Invest 92:2360–2367
Tang L, Sheu MS, Chu T et al (1999) Anti-inflammatory properties of triblock siloxane copolymer-blended materials. Biomaterials 20:1365–1370
Taresco V, Crisante F, Francolini I, Martinelli A, D’Ilario L, Ricci-Vitiani L, Buccarelli M, Pietrelli L, Piozzi A (2015a) Antimicrobial and antioxidant amphiphilic random copolymers to address medical device-centered infections. Acta Biomater 22:131–140
Taresco V, Gontrani L, Crisante F, Francolini I, Martinelli A, D’Ilario L, Bordi F, Piozzi A (2015b) Self-assembly of catecholic moiety-containing cationic random acrylic copolymers. J Phys Chem B 119:8369–8379
Tuck KL, Hayball PJ (2002) Major phenolic compounds in olive oil: metabolism and health effects. J Nutr Biochem 13:636–644
Villa F, Remelli W, Forlani F et al (2012) Effects of chronic sub-lethal oxidative stress on biofilm formation by Azotobacter vinelandii. Biofouling 28:823–833
Visioli F, Poli A, Galli C (2002) Antioxidant and other biological activities of phenols from olives and olive oil. Med Res Rev 22:65–75
Wang R, Neoh KG, Kang ET et al (2015) Antifouling coating with controllable and sustained silver release for long-term inhibition of infection and encrustation in urinary catheters. J Biomed Mater Res B Appl Biomater 103:519–528
Wattamwar PP, Biswal D, Cochran DB et al (2012) Synthesis and characterization of poly(antioxidant beta-amino esters) for controlled release of polyphenolic antioxidants. Acta Biomater 8:2529–2537
Williams SR, Lepene BS, Thatcher CD et al (2009) Synthesis and characterization of poly(ethylene glycol)-glutathione conjugate self-assembled nanoparticles for antioxidant delivery. Biomacromolecules 10:155–161
Wolcott R, Costerton JW, Raoult D et al (2013) The polymicrobial nature of biofilm infection. Clin Microbiol Infect 19:107–112
Xu CM, Yagiz Y, Hsu WY et al (2014) Antioxidant, antibacterial, and antibiofilm activities of muscadine grape (Vitis rotundifolia) polyphenols against selected foodborne pathogens. J Agric Food Chem 62:6640–6649
Yu ME, Hwang JY, Deming TJ (1999) Role of L-3,4-dihydroxyphenylalanine in mussel adhesive proteins. J Am Chem Soc 121:5825–5826
Acknowledgments
The work was financially supported by the Italian Ministry of Education, University and Research.
Author information
Authors and Affiliations
Corresponding authors
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2015 Springer International Publishing Switzerland
About this chapter
Cite this chapter
Crisante, F. et al. (2015). Antioxidant Hydroxytyrosol-Based Polyacrylate with Antimicrobial and Antiadhesive Activity Versus Staphylococcus Epidermidis . In: Donelli, G. (eds) Advances in Microbiology, Infectious Diseases and Public Health. Advances in Experimental Medicine and Biology(), vol 901. Springer, Cham. https://doi.org/10.1007/5584_2015_5013
Download citation
DOI: https://doi.org/10.1007/5584_2015_5013
Published:
Publisher Name: Springer, Cham
Print ISBN: 978-3-319-27934-3
Online ISBN: 978-3-319-27935-0
eBook Packages: Biomedical and Life SciencesBiomedical and Life Sciences (R0)