{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,2]],"date-time":"2026-10-02T19:43:55Z","timestamp":1790970235091,"version":"4.1.0"},"reference-count":53,"publisher":"MDPI AG","issue":"10","license":[{"start":{"date-parts":[[2023,5,20]],"date-time":"2023-05-20T00:00:00Z","timestamp":1684540800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100007835","name":"Silesian University of Technology","doi-asserted-by":"publisher","award":["04\/040\/RGJ23\/0243"],"award-info":[{"award-number":["04\/040\/RGJ23\/0243"]}],"id":[{"id":"10.13039\/501100007835","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Materials"],"abstract":"<jats:p>Using dental composite restorative materials with a copolymeric matrix chemically modified towards bioactive properties can help fight secondary caries. In this study, copolymers of 40 wt.% bisphenol A glycerolate dimethacrylate, 40 wt.% quaternary ammonium urethane-dimethacrylates (QAUDMA-m, where m represents 8, 10, 12, 14, 16 and 18 carbon atoms in the N-alkyl substituent), and 20 wt.% triethylene glycol dimethacrylate (BG:QAm:TEGs) were tested for (i) cytotoxicity on the L929 mouse fibroblast cell line; (ii) fungal adhesion, fungal growth inhibition zone, and fungicidal activity against C. albicans; and (iii) bactericidal activity against S. aureus and E. coli. BG:QAm:TEGs had no cytotoxic effects on L929 mouse fibroblasts because the reduction of cell viability was less than 30% compared to the control. BG:QAm:TEGs also showed antifungal activity. The number of fungal colonies on their surfaces depended on the water contact angle (WCA). The higher the WCA, the greater the scale of fungal adhesion. The fungal growth inhibition zone depended on the concentration of QA groups (xQA). The lower the xQA, the lower the inhibition zone. In addition, 25 mg\/mL BG:QAm:TEGs suspensions in culture media showed fungicidal and bactericidal effects. In conclusion, BG:QAm:TEGs can be recognized as antimicrobial biomaterials with negligible biological patient risk.<\/jats:p>","DOI":"10.3390\/ma16103855","type":"journal-article","created":{"date-parts":[[2023,5,22]],"date-time":"2023-05-22T02:00:27Z","timestamp":1684720827000},"page":"3855","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":9,"title":["Cytotoxicity and Microbiological Properties of Copolymers Comprising Quaternary Ammonium Urethane-Dimethacrylates with Bisphenol A Glycerolate Dimethacrylate and Triethylene Glycol Dimethacrylate"],"prefix":"10.3390","volume":"16","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-6978-2547","authenticated-orcid":false,"given":"Marta W.","family":"Chr\u00f3szcz-Por\u0119bska","sequence":"first","affiliation":[{"name":"Department of Physical Chemistry and Technology of Polymers, Faculty of Chemistry, Silesian University of Technology, Strzody 9 Str., 44-100 Gliwice, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2708-1854","authenticated-orcid":false,"given":"Izabela M.","family":"Barszczewska-Rybarek","sequence":"additional","affiliation":[{"name":"Department of Physical Chemistry and Technology of Polymers, Faculty of Chemistry, Silesian University of Technology, Strzody 9 Str., 44-100 Gliwice, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9971-7279","authenticated-orcid":false,"given":"Alicja","family":"Kazek-K\u0119sik","sequence":"additional","affiliation":[{"name":"Department of Inorganic Chemistry, Analytical Chemistry and Electrochemistry, Faculty of Chemistry, Silesian University of Technology, Krzywoustego 6 Str., 44-100 Gliwice, Poland"},{"name":"Biotechnology Centre, Silesian University of Technology, Krzywoustego 8 Str., 44-100 Gliwice, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0707-2213","authenticated-orcid":false,"given":"Izabella","family":"\u015al\u0119zak-Prochazka","sequence":"additional","affiliation":[{"name":"Biotechnology Centre, Silesian University of Technology, Krzywoustego 8 Str., 44-100 Gliwice, Poland"},{"name":"Department of Systems Biology and Engineering, Faculty of Automatic Control, Electronics and Computer Science, Silesian University of Technology, Akademicka 16 Str., 44-100 Gliwice, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2023,5,20]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"446","DOI":"10.2174\/1874210601610010446","article-title":"Bisphenol A Release: Survey of the Composition of Dental Composite Resins","volume":"10","author":"Dursun","year":"2016","journal-title":"Open Dent. J."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"1243","DOI":"10.1177\/0022034514550039","article-title":"Proteins, Pathogens, and Failure at the Composite-Tooth Interface","volume":"93","author":"Spencer","year":"2014","journal-title":"J. Dent. Res."},{"key":"ref_3","doi-asserted-by":"crossref","unstructured":"Zhang, N., Melo, M.A.S., Weir, M.D., Reynolds, M.A., Bai, Y., and Xu, H.H.K. (2016). Do Dental Resin Composites Accumulate More Oral Biofilms and Plaque than Amalgam and Glass Ionomer Materials?. Materials, 9.","DOI":"10.3390\/ma9110888"},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"524","DOI":"10.1007\/s10266-020-00569-x","article-title":"Morpho-Functional Effects of Different Universal Dental Adhesives on Human Gingival Fibroblasts: An in Vitro Study","volume":"109","author":"Pagano","year":"2021","journal-title":"Odontology"},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"202","DOI":"10.1111\/prd.12337","article-title":"A Public Health Approach for Prevention of Periodontal Disease","volume":"84","author":"Janakiram","year":"2020","journal-title":"Periodontology 2000"},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"1789","DOI":"10.1016\/S0140-6736(18)32279-7","article-title":"Global, Regional, and National Incidence, Prevalence, and Years Lived with Disability for 354 Diseases and Injuries for 195 Countries and Territories, 1990-2017: A Systematic Analysis for the Global Burden of Disease Study 2017","volume":"392","author":"James","year":"2018","journal-title":"Lancet"},{"key":"ref_7","doi-asserted-by":"crossref","unstructured":"Carli, E., Pasini, M., Pardossi, F., Capotosti, I., Narzisi, A., and Lardani, L. (2022). Oral Health Preventive Program in Patients with Autism Spectrum Disorder. Children, 9.","DOI":"10.3390\/children9040535"},{"key":"ref_8","unstructured":"World Heath Organisation (2023, January 27). Global Oral Health Status Report: Towards Universal Health Coverage for Oral Health by 2030, Available online: https:\/\/www.who.int\/publications\/i\/item\/9789240061484."},{"key":"ref_9","doi-asserted-by":"crossref","unstructured":"Ramburrun, P., Pringle, N.A., Dube, A., Adam, R.Z., D\u2019souza, S., and Aucamp, M. (2021). Recent Advances in the Development of Antimicrobial and Antifouling Biocompatible Materials for Dental Applications. Materials, 14.","DOI":"10.3390\/ma14123167"},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"183","DOI":"10.4012\/dmj.2017-096","article-title":"Quaternary Ammonium Compounds in Dental Restorative Materials","volume":"37","author":"Zhang","year":"2018","journal-title":"Dent. Mater. J."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"115","DOI":"10.1016\/j.jdsr.2012.02.003","article-title":"Antibacterial Resin Monomers Based on Quaternary Ammonium and Their Benefits in Restorative Dentistry","volume":"48","author":"Imazato","year":"2012","journal-title":"Jpn. Dent. Sci. Rev."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"851","DOI":"10.1016\/j.dental.2018.03.014","article-title":"Antibacterial Quaternary Ammonium Compounds in Dental Materials: A Systematic Review","volume":"34","author":"Makvandi","year":"2018","journal-title":"Dent. Mater."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"1019","DOI":"10.1016\/S0079-6700(97)00055-5","article-title":"Model Networks Based on \u2018endlinking\u2019 Processes: Synthesis, Structure and Properties","volume":"23","author":"Hild","year":"1998","journal-title":"Prog. Polym. Sci."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"1897","DOI":"10.1016\/S0142-9612(00)00067-3","article-title":"Analysis of a Dimethacrylate Copolymer (Bis-GMA and TEGDMA) Network by DSC and 13C Solution and Solid-State NMR Spectroscopy","volume":"21","author":"Morgan","year":"2000","journal-title":"Biomaterials"},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"1437","DOI":"10.1177\/00220345940730080701","article-title":"Incorporation of Bacterial Inhibitor into Resin Composite","volume":"73","author":"Imazato","year":"1994","journal-title":"J. Dent. Res."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"932","DOI":"10.1177\/0022034513502053","article-title":"Effects of Quaternary Ammonium Chain Length on Antibacterial Bonding Agents","volume":"92","author":"Li","year":"2013","journal-title":"J. Dent. Res."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"143","DOI":"10.1016\/j.dental.2017.09.020","article-title":"Physical and Chemical Properties of Model Composites Containing Quaternary Ammonium Methacrylates","volume":"34","author":"Vidal","year":"2018","journal-title":"Dent. Mater."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"1161","DOI":"10.1016\/j.dental.2020.05.006","article-title":"Structural Stability of DHMAI Antibacterial Dental Composite Following in Vitro Biological Aging","volume":"36","author":"Cherchali","year":"2020","journal-title":"Dent. Mater."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"1381","DOI":"10.1016\/j.dental.2017.09.004","article-title":"Effectiveness of the DHMAI Monomer in the Development of an Antibacterial Dental Composite","volume":"33","author":"Cherchali","year":"2017","journal-title":"Dent. Mater."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"9755","DOI":"10.3390\/molecules16119755","article-title":"Synthesis of Methacrylate Monomers with Antibacterial Effects against S. Mutans","volume":"16","author":"He","year":"2011","journal-title":"Molecules"},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"184","DOI":"10.14219\/jada.archive.2011.0062","article-title":"The Effect of an Antibacterial Monomer on the Antibacterial Activity and Mechanical Properties of a Pit-and-Fissure Sealant","volume":"142","author":"Li","year":"2011","journal-title":"J. Am. Dent. Assoc."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"33858","DOI":"10.1038\/srep33858","article-title":"Antibacterial Activity of a Modified Unfilled Resin Containing a Novel Polymerizable Quaternary Ammonium Salt MAE-HB","volume":"6","author":"Huang","year":"2016","journal-title":"Sci. Rep."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"1295","DOI":"10.1007\/s00289-018-2414-y","article-title":"Synthesis and Characterization of Novel Polymerizable Bis-Quaternary Ammonium Dimethacrylate Monomers with Antibacterial Activity as an Efficient Adhesive System for Dental Restoration","volume":"76","author":"Manouchehri","year":"2019","journal-title":"Polym. Bull."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"1387","DOI":"10.1007\/s10856-014-5156-x","article-title":"Optimizing the Concentration of Quaternary Ammonium Dimethacrylate Monomer in Bis-GMA\/TEGDMA Dental Resin System for Antibacterial Activity and Mechanical Properties","volume":"25","author":"Liang","year":"2014","journal-title":"J. Mater. Sci. Mater. Med."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"68","DOI":"10.1016\/j.jmbbm.2015.10.028","article-title":"Physical and Chemical Properties of an Antimicrobial Bis-GMA Free Dental Resin with Quaternary Ammonium Dimethacrylate Monomer","volume":"56","author":"Huang","year":"2016","journal-title":"J. Mech. Behav. Biomed. Mater."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"21395","DOI":"10.1002\/adv.21395","article-title":"Preparation and Characterization of Antibacterial Dental Resin with UDMQA-12","volume":"33","author":"Huang","year":"2014","journal-title":"Adv. Polym. Technol."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"3373","DOI":"10.1002\/app.39113","article-title":"Synthesis of Novel Antibacterial Monomers (UDMQA) and Their Potential Application in Dental Resin","volume":"129","author":"Liang","year":"2013","journal-title":"J. Appl. Polym. Sci."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"81","DOI":"10.1016\/j.eurpolymj.2015.11.011","article-title":"Synthesis and Characterization of Photo-Curable Bis-Quaternary Ammonium Dimethacrylate with Antimicrobial Activity for Dental Restoration Materials","volume":"74","author":"Makvandi","year":"2016","journal-title":"Eur. Polym. J."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"219","DOI":"10.1016\/j.dental.2011.10.004","article-title":"Synthesis and Characterization of Dimethacrylates Containing Quaternary Ammonium Functionalities for Dental Applications","volume":"28","author":"Antonucci","year":"2012","journal-title":"Dent. Mater."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"450","DOI":"10.1016\/j.dental.2013.01.012","article-title":"Comparison of Quaternary Ammonium-Containing with Nano-Silver-Containing Adhesive in Antibacterial Properties and Cytotoxicity","volume":"29","author":"Li","year":"2013","journal-title":"Dent. Mater."},{"key":"ref_31","doi-asserted-by":"crossref","unstructured":"Chr\u00f3szcz, M.W., and Barszczewska-Rybarek, I.M. (2021). Synthesis and Characterization of Novel Quaternary Ammonium Urethane-Dimethacrylate Monomers\u2014A Pilot Study. Int. J. Mol. Sci., 22.","DOI":"10.3390\/ijms22168842"},{"key":"ref_32","doi-asserted-by":"crossref","unstructured":"Chr\u00f3szcz, M.W., Barszczewska-Rybarek, I.M., and Kazek-K, A. (2022). Novel Antibacterial Copolymers Based on Quaternary Ammonium Urethane-Dimethacrylate Analogues and Triethylene Glycol Dimethacrylate. Int. J. Mol. Sci., 23.","DOI":"10.3390\/ijms23094954"},{"key":"ref_33","doi-asserted-by":"crossref","unstructured":"Chr\u00f3szcz-Por\u0119bska, M.W., Barszczewska-Rybarek, I.M., and Chladek, G. (2022). Characterization of the Mechanical Properties, Water Sorption, and Solubility of Antibacterial Copolymers of Quaternary Ammonium Urethane-Dimethacrylates and Triethylene Glycol Dimethacrylate. Materials, 15.","DOI":"10.3390\/ma15165530"},{"key":"ref_34","doi-asserted-by":"crossref","unstructured":"Chr\u00f3szcz-Por\u0119bska, M.W., Barszczewska-Rybarek, I.M., and Chladek, G. (2023). Physicochemical Properties of Novel Copolymers of Quaternary Ammonium UDMA Analogues, Bis-GMA, and TEGDMA. Int. J. Mol. Sci., 24.","DOI":"10.3390\/ijms24021400"},{"key":"ref_35","unstructured":"(2019). Dentistry\u2014Polymer Based Restorative Materials (Standard No. ISO 4049:2019)."},{"key":"ref_36","unstructured":"(2009). Biological Evaluation of Medical Devices\u2014Part 5: Tests for In Vivo Cytotoxicity (Standard No. ISO 10993-5:2009)."},{"key":"ref_37","doi-asserted-by":"crossref","unstructured":"Lee, M.J., Kim, M.J., Kwon, J.S., Lee, S.B., and Kim, K.M. (2017). Cytotoxicity of Light-Cured Dental Materials According to Different Sample Preparation Methods. Materials, 10.","DOI":"10.3390\/ma10030288"},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"618","DOI":"10.1016\/j.dental.2013.03.009","article-title":"Quantification of Elutable Substances from Methacrylate Based Sealers and Their Cytotoxicity Effect on with Human Gingival Fibroblasts","volume":"29","author":"Furche","year":"2013","journal-title":"Dent. Mater."},{"key":"ref_39","first-page":"261","article-title":"Biology and Cytotoxicity of Dental Materials: An in Vitro Study","volume":"54","author":"Gociu","year":"2013","journal-title":"Rom. J. Morphol. Embryol."},{"key":"ref_40","doi-asserted-by":"crossref","unstructured":"Hampe, T., Wiessner, A., Frauendorf, H., Alhussein, M., Karlovsky, P., B\u00fcrgers, R., and Krohn, S. (2022). Monomer Release from Dental Resins: The Current Status on Study Setup, Detection and Quantification for In Vitro Testing. Polymers, 14.","DOI":"10.3390\/polym14091790"},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"1535","DOI":"10.1016\/j.dental.2006.12.011","article-title":"Elution of Monomers from Two Conventional Dental Composite Materials","volume":"23","author":"Polydorou","year":"2007","journal-title":"Dent. Mater."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"1556","DOI":"10.1016\/j.dental.2009.07.009","article-title":"Non-Irradiated Campherquinone Induces DNA Damage in Human Gingival Fibroblasts","volume":"25","author":"Volk","year":"2009","journal-title":"Dent. Mater."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"143","DOI":"10.1007\/s00204-010-0558-0","article-title":"Induction of DNA Strand Breaks by Dental Composite Components Compared to X-ray Exposure in Human Gingival Fibroblasts","volume":"85","author":"Durner","year":"2011","journal-title":"Arch. Toxicol."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"72","DOI":"10.1111\/j.1365-2591.2007.01321.x","article-title":"Toxicity Evaluation of Root Canal Sealers in Vitro","volume":"41","author":"Lodiene","year":"2008","journal-title":"Int. Endod. J."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"362","DOI":"10.1016\/j.dental.2007.06.009","article-title":"The Induction of Oxidative Stress, Cytotoxicity, and Genotoxicity by Dental Adhesives","volume":"24","author":"Demirci","year":"2008","journal-title":"Dent. Mater."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"646","DOI":"10.1016\/j.toxrep.2021.03.006","article-title":"Altered Toxicological Endpoints in Humans from Common Quaternary Ammonium Compound Disinfectant Exposure","volume":"8","author":"Hrubec","year":"2021","journal-title":"Toxicol. Rep."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"352","DOI":"10.1016\/j.scitotenv.2015.03.007","article-title":"Quaternary Ammonium Compounds (QACs): A Review on Occurrence, Fate and Toxicity in the Environment","volume":"518\u2013519","author":"Zhang","year":"2015","journal-title":"Sci. Total Environ."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"633","DOI":"10.1128\/EC.4.4.633-638.2005","article-title":"Candida Biofilms: An Update","volume":"4","author":"Ramage","year":"2005","journal-title":"Eukaryot. Cell"},{"key":"ref_49","doi-asserted-by":"crossref","unstructured":"Bertolini, M., Costa, R.C., Bar\u00e3o, V.A.R., Cunha Villar, C., Retamal-Valdes, B., Feres, M., and Silva Souza, J.G. (2022). Oral Microorganisms and Biofilms: New Insights to Defeat the Main Etiologic Factor of Oral Diseases. Microorganisms, 10.","DOI":"10.3390\/microorganisms10122413"},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"681","DOI":"10.1517\/13543771003720491","article-title":"Novel Technologies for the Prevention and Treatment of Dental Caries: A Patent Survey","volume":"20","author":"Chen","year":"2010","journal-title":"Expert Opin. Ther. Pat."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"1072","DOI":"10.1111\/odi.13319","article-title":"In Vitro Adherence of Candida Albicans to Zirconia Surfaces","volume":"26","author":"Dvorak","year":"2020","journal-title":"Oral Dis."},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"1391","DOI":"10.3389\/fmicb.2015.01391","article-title":"Clinical Appearance of Oral Candida Infection and Therapeutic Strategies","volume":"6","author":"Patil","year":"2015","journal-title":"Front. Microbiol."},{"key":"ref_53","first-page":"e576","article-title":"Current Treatment of Oral Candidiasis: A Literature Review","volume":"6","year":"2014","journal-title":"J. Clin. Exp. Dent."}],"container-title":["Materials"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1996-1944\/16\/10\/3855\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T19:38:58Z","timestamp":1760125138000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1996-1944\/16\/10\/3855"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2023,5,20]]},"references-count":53,"journal-issue":{"issue":"10","published-online":{"date-parts":[[2023,5]]}},"alternative-id":["ma16103855"],"URL":"https:\/\/doi.org\/10.3390\/ma16103855","relation":{},"ISSN":["1996-1944"],"issn-type":[{"value":"1996-1944","type":"electronic"}],"subject":[],"published":{"date-parts":[[2023,5,20]]}}}