This study reports synthesis and attachment of a novel antibacterial and hydrophilic polymer onto a polyvinylchloride surface via a simple and mild surface coating technique. The compound 3,4-dichloro-5-hydroxy-2(5H)-furanone was derivatized and copolymerized with N-vinylpyrrolidone. The copolymer was then covalently coated onto polyvinylchloride surface. 3T3 mouse fibroblast cells and bacterium Pseudomonas aeruginosa were used to evaluate surface adhesion and antibacterial activity. Results showed that the polymer-modified polyvinylchloride surface not only exhibited significantly decreased 3T3 fibroblast cell adhesion with a 64–84% reduction but also demonstrated significantly decreased P. aeruginosa adhesion with a 65–84% reduction, as compared to unmodified polyvinylchloride. Furthermore, the modified polyvinylchloride surfaces exhibited significant antibacterial functions by inhibiting P. aeruginosa growth with a 58–80% reduction and killing bacteria, as compared to unmodified polyvinylchloride. These results demonstrate that covalent polymer attachment conferred cell/bacterial adhesion-resistant and antibacterial properties to the polyvinylchloride surface.
RatnerBDHoffmanASSchoenFJet al. Biomaterials science: an introduction to materials in medicine. 3rd ed.
San Diego:
Elsevier Academic Press, 2012.
2.
SheddenLOldroydKConnollyP.Current issues in coronary stent technology. Proc Inst Mech Eng H2009;
223: 515–524.
3.
DonelliG.Vascular catheter-related infection and sepsis. Surg Infect2006;
7: S25–S27.
4.
ChengXCanavanHEGrahamDJet al.
Temperature dependent activity and structure of adsorbed proteins on plasma polymerized N-isopropyl acrylamide. Biointerphases2006;
1: 61–72.
5.
HuberDLManginellRPSamaraMAet al.
Programmed adsorption and release of proteins in a microfluidic device. Science2003;
301: 352–354.
6.
YuQZhangYChenHet al.
Protein adsorption on poly(N-isopropylacrylamide)-modified silicon surfaces: effects of grafted layer thickness and protein size. Colloids Surf B Biointerfaces2010;
76: 468–474.
7.
ChenLLiuMBayHet al.
Antiplatelet and thermally responsive poly(N-isopropylacrylamide) surface with nanoscale topography. J Am Chem Soc2009;
131: 10467–10472.
AlarconCDHFarhanTOsborneVLet al.
Bioadhesion at micro-patterned stimuli-responsive polymer brushes. J Mater Chem2005;
15: 2089–2094.
10.
CunliffeDAlarconCDPetersVet al.
Thermoresponsive surface-grafted poly(N-isopropylacrylamide) copolymers: effect of phase transitions on protein and bacterial attachment. Langmuir2003;
19: 2888–2899.
11.
TanDLiZYaoXet al.
The influence of fluorocarbon chain and phosphorylcholine on the improvement of hemocompatibility: a comparative study in polyurethanes. J Mater Chem B2014;
2: 1344–1353.
12.
YouIKangSMByunYet al.
Enhancement of blood compatibility of poly(urethane) substrates by mussel-inspired adhesive heparin coating. Bioconjugate Chem2011;
22: 1264–1269.
13.
GarrettTRBhakooMZhangZ.Bacterial adhesion and biofilms on surfaces. Prog Nat Sci2008;
18: 1049–1056.
14.
RenZChenGWeiZet al.
Hemocompatibility evaluation of polyurethane film with surface-grafted poly(ethyleneglycol) and carboxymethyl-chitosan. J Appl Polym Sci2013;
127: 308–315.
15.
SaskKNBerryLRChanAKet al.
Modification of polyurethane surface with an antithrombin–heparin complex for blood contact: influence of molecular weight of polyethylene oxide used as a linker/spacer. Langmuir2011;
28: 2099–2106.
16.
ChungYCChoiJWLeeJYet al.
The control of molecular interactions between polyurethane copolymers by grafted malic acid and its impact on polymer characteristics. J Appl Polym Sci2012;
126: 225–232.
17.
WangYXuWChenY.Surface modification on polyurethanes by using bioactive carboxymethylated fungal glucan from Poriacocos. Colloid Surf B Biointerfaces2010;
81: 629–633.
18.
LuYShenLGongFet al.
Polycarbonate urethane films modified by heparin to enhance hemocompatibility and endothelialization. Polym Int2012;
61: 1433–1438.
19.
TanMFengYWangHet al.
Immobilized bioactive agents onto polyurethane surface with heparin and phosphorylcholine group. Macromol Res2013;
21: 541–549.
20.
JiangJFuYZhangQet al.
Novel amphiphilic poly(dimethylsiloxane) based polyurethanenetworks tethered with carboxybetaine and their combinedantibacterial and anti-adhesive property. Appl Surf Sci2017;
412: 1–9.
21.
YuanSLiYLuanSet al.
Infection-resistant styrenic thermoplastic elastomers that can switch from bactericidal capability to anti-adhesion. J Mater Chem B2016;
4: 1081–1089.
22.
MuzzioNEPasqualeMADiamantiEet al.
Enhanced antiadhesive properties of chitosan/hyaluronic acid polyelectrolyte multilayers driven by thermal annealing: low adherence for mammalian cells and selective decrease in adhesion for Gram-positive bacteria. Mater Sci Eng C2017;
80: 677–687.
23.
CraigRGPowerJM.Restorative dental materials. 11th ed.
St Louis:
Mosby-Year Book, Inc., 2002, pp. 614–618.
24.
OsinagaPWGrandeRHBallesterRYet al.
Zinc sulfate addition to glass-ionomer-based cements: influence on physical and antibacterial properties, zinc and fluoride release. Dent Mater2003;
19: 212–217.
25.
TakahashiYImazatoSKaneshiroAVet al.
Antibacterial effects and physical properties of glass-ionomer cements containing chlorhexidine for the ART approach. Dent Mater2006;
22: 452–467.
26.
YamamotoKOhashiSAonoMet al.
Antibacterial activity of silver ions implanted in SiO2 filler on oral streptococci. Dent Mater1996;
12: 227–229.
27.
ImazatoSRussellRRMcCabeJF.Antibacterial activity of MDPB polymer incorporated in dental resin. J Dent1995;
23: 177–181.
28.
GottenbosBvan der MeiHCKlatterFet al.
In vitro and in vivo antimicrobial activity of covalently coupled quaternary ammonium silane coatings on silicone rubber. Biomaterials2002;
23: 1417–1423.
29.
MurataH.Permanent, non-leaching antibacterial surfaces – 2: how high density cationic surfaces kill bacterial cells. Biomaterials2007;
28: 4870–4879.
30.
XieDWengYGuoXet al.
Preparation and evaluation of a novel glass-ionomer cement with antibacterial functions. Dent Mater2011;
27: 487–496.
31.
EbiNImazatoSNoiriYet al.
Inhibitory effects of resin composite containing bactericide-immobilized filler on plaque accumulation. Dent Mater2001;
17: 485–491.
32.
ImazatoSEbiNTakahashiYet al.
Antibacterial activity of bactericide-immobilized filler for resin-based restoratives. Biomaterials2003;
24: 3605–3609.
WengYHowardLChongVJet al.
A novel antibacterial dental resin composite. J Mater Sci Mater Med2012;
23: 1553–1561.
35.
XieDHowardLAlmousaR.Surface modification of polyurethane with a hydrophilic, antibacterial polymer for improved antifouling and antibacterial function. J Biomater Appl2018;
33: 340–351.
36.
BanoriyaDPurohitRDwivediRK.Advanced application of polymer based biomaterials. Mater Today2017;
4: 3534–3541.
37.
KaczmarekHKowalonekJSzallaAet al.
Surface modification of thin polymeric films by air-plasma or UV-irradiation. Surf Sci2002;
507–510: 883–888.
38.
HosseiniSMMadaeniSSKhodabakhshiARet al.
Preparation and surface modification of PVC/SBR heterogeneous cation exchange membrane with silver nanoparticles by plasma treatment. J Membr Sci2010;
365: 438–446.
39.
BazakaKJacobMVCrawfordRJet al.
Plasma-assisted surface modification of organic biopolymers to prevent bacterial attachment. Acta Biomater2011;
7: 2015–2028.
40.
MaoCZhaoWBZhuAPet al.
A photochemical method for the surface modification of poly(vinyl chloride) with O-butyrylchitosan to improve blood compatibility. Proc Biochem2004;
39: 1151–1157.
41.
Meléndez-OrtizHIAlvarez-LorenzoCConcheiroAet al.
Modification of medical grade PVC with N-vinylimidazole to obtain bactericidal surface. Rad Phys Chem2016;
119: 37–43.
42.
MoulayS.Chemical modification of poly(vinyl chloride) – still on the run. Prog Polym Sci2010;
35: 303–331.
43.
McCoyCPIrwinNJHardyJGet al.
Systematic optimization of poly(vinyl chloride) surface modification with an aromatic thiol. Eur Polym J2017;
97: 40–48.
44.
LafargeJKébirKSchapmanDet al.
Design of self-disinfecting PVC surfaces using the click chemistry. React Funct Polym2013;
73: 1464–1472.
45.
JamesNRJayakrishnanA.Surface thiocyanation of plasticized poly(vinyl chloride) and its effect on bacterial adhesion. Biomaterials2003;
24: 2205–2212.
46.
JayakrishnanASunnyMC.Phase transfer catalysed surface modification of plasticized poly(vinyl chloride) in aqueous media to retard plasticizer migration. Polymer1996;
37: 5213–5218.
47.
XieDSmythCAEcksteinCet al.
Cytoprotection of PEG-modified adult porcine pancreatic islets for improved xenotransplantation. Biomaterials2005;
26: 403–412.
XieD. Surface coating for biological implants and prostheses. Patent 9,550,011 B2, USA, 2017.
50.
YuanHQianBChenHet al.
The influence of conditioning film on antifouling properties of the polyurethane film modified by chondroitin sulfate in urine. Appl Sur Sci2017;
426: 587–596.
51.
KimYFarrahSBaneyRH.Membrane damage of bacteria by silanols treatment. Electron J Biotechnol2007;
10: 252–259.
52.
GuelcherSAHollingerJO.An introduction to biomaterials.
Boca Raton:
CRC Press, 2006, pp.161–183.
53.
Wei Q, Becherer T, Angioletti-Uberti S, et al. Protein interactions with polymer coatings and biomaterials. Angew Chem Int Ed 2014; 53: 8004–8031.
54.
Wei Q, Haag R. Universal polymer coatings and their representative biomedical applications. Mater Horiz 2015; 2: 567–577.
55.
LattmannEDunnSNiamsanitSet al.
Synthesis and antibacterial activities of 5-hydroxy-4-amino-2(5H)-furanones. Bioorg Med Chem Lett2005;
15: 919–921.
56.
MoffittEA.Blood substitutes. Can Anaesth Soc J1975;
22: 12–19.
57.
TeodorescuMBerceaM.Poly(vinylpyrrolidone) – a versatile polymer for biomedical and beyond medical applications.Polym Plast Technol Eng2015;
54: 923–943.
58.
MattsonGConklinEDesaiSet al.
A practical approach to crosslinking. Mol Biol Rep1993;
17: 167–183.
59.
GibneyKSovadinovaILopezAIet al.
Poly(ethylene imine)s as antimicrobial agents with selective activity. Macromol Biosci2012;
12: 1279–1289.
60.
ShimaSMatsuokaHIwamotoTet al.
Antimicrobial action of epsilon-poly-L-lysine. J Antibiot1984;
37: 1449–1455.
61.
ZoumpoulakisPCamoutsisCPairasGet al.
Synthesis of novel sulfonamide-1,2,4-triazoles, 1,3,4-thiadiazoles and 1,3,4-oxadiazoles, as potential antibacterial and antifungal agents. Biological evaluation and conformational analysis studies. Bioorg Med Chem2012;
20: 1569–1583.
