Contact-Killing Antibacterial Polystyrene Polymerized Using a Quaternized Cationic Initiator

Overview

Journal ACS Omega

Publisher American Chemical Society

Specialty Chemistry

Date 2024 Mar 4

PMID 38434858

Authors

Akiko Jitsuhiro

Tomoki Maeda

Akiko Ogawa

Sayuri Yamada

Yuki Konoeda

Hiroki Maruyama

Fuyuaki Endo

Midori Kitagawa

Keishi Tanimoto

Atsushi Hotta

Toshikazu Tsuji

Affiliations

Soon will be listed here.

Abstract

Contact-killing antibacterial materials are attracting attention owing to their ability for sustained antibacterial activity. However, contact-killing antibacterial polystyrene (PS) has not been extensively studied because its chemically stable structure impedes chemical modification. In this study, we developed an antibacterial PS sheet with a contact-killing surface using PS synthesized from 2,2'-azobis-[2-(1,3-dimethyl-4,5-dihydro-1-imidazol-3-ium-2-yl)]propane triflate (ADIP) as a radical initiator with cationic moieties. The PS sheet synthesized with ADIP (ADIP-PS) exhibited antibacterial activity in contrast to PS synthesized with other azo radical initiators. Surface ζ-potential measurements revealed that only ADIP-PS had a cationic surface, which contributed to its contact-killing antibacterial activity. The ADIP-PS sheets also exhibited antibacterial activity after washing. In contrast, PS sheets containing silver, a typical leachable antibacterial agent, lost all antibacterial activity after the same washing treatment. The antibacterial ADIP-PS sheet demonstrated strong broad-spectrum activity against both Gram-positive and Gram-negative bacteria, including drug-resistant bacteria. Cytotoxicity tests using L929 cells showed that the ADIP-PS sheets were noncytotoxic. This contact-killing antibacterial PS synthesized with ADIP thus demonstrated good prospects as an easily producible antimicrobial material.

Citing Articles

Quantitative Characterization of Localized Hydrophobicity Surrounding Polymer Particle Surfaces for Aqueous Antibacterial Colloids.

Nagasawa A, Fujishima K, Suga K, Watanabe K, Nagao D Langmuir. 2025; 41(1):654-662.

PMID: 39810361 PMC: 11736841. DOI: 10.1021/acs.langmuir.4c03896.

Antibacterial, Transparency, and Mechanical Properties of Cationic Radical Initiator Triggered Polystyrene Sheets Obtained by Thermal Blending.

Maruyama H, Kishi A, Konoeda Y, Ito H, Tsuji T Polymers (Basel). 2024; 16(22).

PMID: 39599258 PMC: 11598219. DOI: 10.3390/polym16223167.

References

Elena P, Miri K . Formation of contact active antimicrobial surfaces by covalent grafting of quaternary ammonium compounds. Colloids Surf B Biointerfaces. 2018; 169:195-205. DOI: 10.1016/j.colsurfb.2018.04.065. View

Suga K, Murakami M, Nakayama S, Watanabe K, Yamada S, Tsuji T . Surface Characteristics of Antibacterial Polystyrene Nanoparticles Synthesized Using Cationic Initiator and Comonomers. ACS Appl Bio Mater. 2022; 5(5):2202-2211. DOI: 10.1021/acsabm.2c00046. View

Yazdani-Ahmadabadi H, Felix D, Yu K, Yeh H, Luo H, Khoddami S . Durable Surfaces from Film-Forming Silver Assemblies for Long-Term Zero Bacterial Adhesion without Toxicity. ACS Cent Sci. 2022; 8(5):546-561. PMC: 9136974. DOI: 10.1021/acscentsci.1c01556. View

Huang K, Yang C, Huang S, Chen C, Lu Y, Lin Y . Recent Advances in Antimicrobial Polymers: A Mini-Review. Int J Mol Sci. 2016; 17(9). PMC: 5037843. DOI: 10.3390/ijms17091578. View

Balasubramanian P, Prabhakaran M, Kai D, Ramakrishna S . Human cardiomyocyte interaction with electrospun fibrinogen/gelatin nanofibers for myocardial regeneration. J Biomater Sci Polym Ed. 2013; 24(14):1660-75. DOI: 10.1080/09205063.2013.789958. View

Sharma S, Mandhani A, Bose S, Basu B . Dynamically crosslinked polydimethylsiloxane-based polyurethanes with contact-killing antimicrobial properties as implantable alloplasts for urological reconstruction. Acta Biomater. 2021; 129:122-137. DOI: 10.1016/j.actbio.2021.04.055. View

Punyani S, Deb S, Singh H . Contact killing antimicrobial acrylic bone cements: preparation and characterization. J Biomater Sci Polym Ed. 2007; 18(2):131-45. DOI: 10.1163/156856207779116748. View

Tiller J, Liao C, Lewis K, Klibanov A . Designing surfaces that kill bacteria on contact. Proc Natl Acad Sci U S A. 2001; 98(11):5981-5. PMC: 33409. DOI: 10.1073/pnas.111143098. View

Timofeeva L, Kleshcheva N . Antimicrobial polymers: mechanism of action, factors of activity, and applications. Appl Microbiol Biotechnol. 2010; 89(3):475-92. DOI: 10.1007/s00253-010-2920-9. View

10.

Liu S, Tonggu L, Niu L, Gong S, Fan B, Wang L . Antimicrobial activity of a quaternary ammonium methacryloxy silicate-containing acrylic resin: a randomised clinical trial. Sci Rep. 2016; 6:21882. PMC: 4763235. DOI: 10.1038/srep21882. View

11.

Strassburg A, Petranowitsch J, Paetzold F, Krumm C, Peter E, Meuris M . Cross-Linking of a Hydrophilic, Antimicrobial Polycation toward a Fast-Swelling, Antimicrobial Superabsorber and Interpenetrating Hydrogel Networks with Long Lasting Antimicrobial Properties. ACS Appl Mater Interfaces. 2017; 9(42):36573-36582. DOI: 10.1021/acsami.7b10049. View

12.

Uchiyama S, Tsuji T, Kawamoto K, Okano K, Fukatsu E, Noro T . A Cell-Targeted Non-Cytotoxic Fluorescent Nanogel Thermometer Created with an Imidazolium-Containing Cationic Radical Initiator. Angew Chem Int Ed Engl. 2018; 57(19):5413-5417. DOI: 10.1002/anie.201801495. View

13.

Kara F, Aksoy E, Yuksekdag Z, Hasirci N, Aksoy S . Synthesis and surface modification of polyurethanes with chitosan for antibacterial properties. Carbohydr Polym. 2014; 112:39-47. DOI: 10.1016/j.carbpol.2014.05.019. View

14.

Ho C, Odermatt E, Berndt I, Tiller J . Long-term active antimicrobial coatings for surgical sutures based on silver nanoparticles and hyperbranched polylysine. J Biomater Sci Polym Ed. 2013; 24(13):1589-600. DOI: 10.1080/09205063.2013.782803. View

15.

Shim G, Kim S, Eom H, Kim K, Choi S . Development of a transparent, non-cytotoxic, silver ion-exchanged glass with antimicrobial activity and low ion elution. Enzyme Microb Technol. 2015; 72:65-71. DOI: 10.1016/j.enzmictec.2015.02.008. View

16.

Gao J, Huddleston N, White E, Pant J, Handa H, Locklin J . Surface Grafted Antimicrobial Polymer Networks with High Abrasion Resistance. ACS Biomater Sci Eng. 2021; 2(7):1169-1179. DOI: 10.1021/acsbiomaterials.6b00221. View

17.

Zander Z, Becker M . Antimicrobial and Antifouling Strategies for Polymeric Medical Devices. ACS Macro Lett. 2022; 7(1):16-25. DOI: 10.1021/acsmacrolett.7b00879. View

18.

Kanth S, Nagaraja A, Puttaiahgowda Y . Polymeric approach to combat drug-resistant methicillin-resistant . J Mater Sci. 2021; 56(12):7265-7285. PMC: 7831626. DOI: 10.1007/s10853-021-05776-7. View

19.

Coneski P, Rao K, Schoenfisch M . Degradable nitric oxide-releasing biomaterials via post-polymerization functionalization of cross-linked polyesters. Biomacromolecules. 2010; 11(11):3208-15. PMC: 3070196. DOI: 10.1021/bm1006823. View

20.

Sekhavat Pour Z, Makvandi P, Ghaemy M . Performance properties and antibacterial activity of crosslinked films of quaternary ammonium modified starch and poly(vinyl alcohol). Int J Biol Macromol. 2015; 80:596-604. DOI: 10.1016/j.ijbiomac.2015.07.008. View