Antioxidant hydroxytyrosol-based polyacrylate with antimicrobial and antiadhesive activity versus Staphylococcus epidermidis

Advances in Experimental Medicine and Biology

Volumn 901, Issue , 2016, Pages 25-36

  Crisante, Fernanda ^a   Taresco, Vincenzo ^b   Donelli, Gianfranco ^c   Vuotto, Claudia ^c   Martinelli, Andrea ^a   D’Ilario, Lucio ^a   Pietrelli, Loris ^d   Francolini, Iolanda ^a   Piozzi, Antonella ^a  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

^b UNIVERSITY OF NOTTINGHAM   (United Kingdom)

^c IRCCS FONDAZIONE SANTA LUCIA   (Italy)

^d ENEA C R CASACCIA   (Italy)

Author keywords

Antioxidant polymers; Hydroxytyrosol; Medical device related infections; Microbial biofilm; Nanoparticles

Indexed keywords

2 (3',4' DIHYDROXYPHENYL)ETHANOL; 2 (3,4 HYDROXYPHENYL)ETHYL ACRYLIC ACID; HYDROXYTYROSOL; NANOPARTICLE; POLYACRYLIC ACID; TYROSOL; UNCLASSIFIED DRUG; 3,4-DIHYDROXYPHENYLETHANOL; ANTIINFECTIVE AGENT; ANTIOXIDANT; PHENETHYL ALCOHOL;

ANTIADHESIVE ACTIVITY; ANTIMICROBIAL ACTIVITY; ARTICLE; BACTERIAL STRAIN; BACTERIUM ADHERENCE; BIOFILM; CHRONIC WOUND; CONTROLLED STUDY; DPPH RADICAL SCAVENGING ASSAY; DRUG ACTIVITY; DRUG DETERMINATION; DRUG SYNTHESIS; EC50; NONHUMAN; PRIORITY JOURNAL; STAPHYLOCOCCUS EPIDERMIDIS; ANALOGS AND DERIVATIVES; CHEMISTRY; DRUG EFFECTS; GROWTH, DEVELOPMENT AND AGING; MICROBIAL SENSITIVITY TEST; PHYSIOLOGY;

ANTI-BACTERIAL AGENTS; ANTIOXIDANTS; BACTERIAL ADHESION; BIOFILMS; MICROBIAL SENSITIVITY TESTS; PHENYLETHYL ALCOHOL; STAPHYLOCOCCUS EPIDERMIDIS;

EID: 84990246172     PISSN: 00652598     EISSN: 22148019     Source Type: Book Series    
DOI: 10.1007/5584_2015_5013     Document Type: Article

References (65)

1. Al Mohajer M, Darouiche RO (2012) Sepsis syndrome, bloodstream infections, and device-related infections. Med Clin N Am 96:1203-1223
2. Anderson JM, Rodriguez A, Chang DT (2008) Foreign body reaction to biomaterials. Semin Immunol 20:86-100
3. 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
4. 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
5. Biesalski HK (2007) Polyphenols and inflammation: basic interactions. Curr Opin Clin Nutr Metab Care 10:724-728
6. 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
7. 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
8. Brandwilliams W, Cuvelier ME, Berset C (1995) Use of a free-radical method to evaluate antioxidant activity. LWT-Food Sci Technol 28:25-30
9. Campoccia D, Montanaro L, Arciola CR (2013) A review of the biomaterials technologies for infection-resistant surfaces. Biomaterials 34:8533-8554
10. 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
11. Chernousova S, Epple M (2013) Silver as antibacterial agent: ion, nanoparticle, and metal. Angew Chem Int Ed Engl 52:1636-1653
12. 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
13. 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
14. 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
15. 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
16. 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
17. de Pinedo AT, Penalver P, Morales JC (2007) Synthesis and evaluation of new phenolic-based antioxidants: structure-activity relationship. Food Chem 103:55-61
18. 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
19. 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
20. Donelli G, Vuotto C (2014) Biofilm-based infections in long-term care facilities. Future Microbiol 9:175-188
21. 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
22. 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
23. Francolini I, Donelli G (2010) Prevention and control of biofilm-based medical-device-related infections. FEMS Immunol Med Microbiol 59:227-238
24. 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
25. Francolini I, Taresco V, Crisante F et al (2013) Water soluble usnic acid-polyacrylamide complexes wiThenhanced antimicrobial activity against staphylococcus epidermidis. Int J Mol Sci 14:7356-7369
26. 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
27. Francolini I, Piozzi A, Donelli G (2014b) Efficacy evaluation of antimicrobial drug-releasing polymer matrices. Methods Mol Biol 1147:215-225
28. 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
29. Frigerio M, Santagostino M, Sputore S (1999) A userfriendly entry to 2-iodoxybenzoic acid (IBX). J Org Chem 64:4537-4538
30. 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
31. Granados-Principal S, Quiles JL, Ramirez-Tortosa CL et al (2010) Hydroxytyrosol: from laboratory investigations to future clinical trials. Nutr Rev 68:191-206
32. Gristina AG (1994) Implant failure and the immunoincompetent fibro-inflammatory zone. Clin Orthop Relat Res 298:106-118
33. Habash M, Reid G (1999) Microbial biofilms: their development and significance for medical device-related infections. J Clin Pharmacol 39:887-898
34. Hanna HA, Raad II, Hackett B et al (2003) Antibioticimpregnated catheters associated with significant decrease in nosocomial and multidrug-resistant bacteremias in critically ill patients. Chest 124:1030-1038
35. Hoiby N, Bjarnsholt T, Givskov M et al (2010) Antibiotic resistance of bacterial biofilms. Int J Antimicrob Agents 35:322-332
36. 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
37. 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
38. 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
39. Mack D, Rohde H, Harris LG et al (2006) Biofilm formation in medical device-related infection. Int J Artif Organs 29:343-359
40. Mah TF (2012) Biofilm-specific antibiotic resistance. Future Microbiol 7:1061-1072
41. 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
42. 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
43. 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
44. Ortiz C, Vazquez B, San RJ (1999) Hydrophilic acrylic biomaterials derived from vitamin E with antioxidant properties. J Biomed Mater Res 45:184-191
45. 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
46. 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
47. 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
48. 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
49. 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
50. Siedenbiedel F, Tiller J (2012) Antimicrobial polymers in solution and on surfaces: overview and functional principles. Polymers 4:46-71
51. 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
52. 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
53. Sutherland K, Mahoney JR, Coury AJ et al (1993) Degradation of biomaterials by phagocyte-derived oxidants. J Clin Invest 92:2360-2367
54. Tang L, Sheu MS, Chu T et al (1999) Anti-inflammatory properties of triblock siloxane copolymer-blended materials. Biomaterials 20:1365-1370
55. 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 devicecentered infections. Acta Biomater 22:131-140
56. 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
57. Tuck KL, Hayball PJ (2002) Major phenolic compounds in olive oil: metabolism and healTheffects. J Nutr Biochem 13:636-644
58. 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
59. 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
60. 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
61. Wattamwar PP, Biswal D, Cochran DB et al (2012) Synthesis and characterization of poly(antioxidant betaamino esters) for controlled release of polyphenolic antioxidants. Acta Biomater 8:2529-2537
62. 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
63. Wolcott R, Costerton JW, Raoult D et al (2013) The polymicrobial nature of biofilm infection. Clin Microbiol Infect 19:107-112
64. 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
65. Yu ME, Hwang JY, Deming TJ (1999) Role of L-3,4-dihydroxyphenylalanine in mussel adhesive proteins. J Am Chem Soc 121:5825-5826