Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2022 Apr 29;23(9):4954.
doi: 10.3390/ijms23094954.

Novel Antibacterial Copolymers Based on Quaternary Ammonium Urethane-Dimethacrylate Analogues and Triethylene Glycol Dimethacrylate

Marta W Chrószcz  1 , Izabela M Barszczewska-Rybarek  1 , Alicja Kazek-Kęsik  2   3
Affiliations

Novel Antibacterial Copolymers Based on Quaternary Ammonium Urethane-Dimethacrylate Analogues and Triethylene Glycol Dimethacrylate

Marta W Chrószcz et al. Int J Mol Sci. .

Abstract

The growing scale of secondary caries and occurrence of antibiotic-resistant bacterial strains require the development of antibacterial dental composites. It can be achieved by the chemical introduction of quaternary ammonium dimethacrylates into dental composites. In this study, physicochemical and antibacterial properties of six novel copolymers consisting of 60 wt. % quaternary ammonium urethane-dimethacrylate analogues (QAUDMA) and 40 wt. % triethylene glycol dimethacrylate (TEGDMA) were investigated. Uncured compositions had suitable refractive index (RI), density (dm), and glass transition temperature (Tgm). Copolymers had low polymerization shrinkage (S), high degree of conversion (DC) and high glass transition temperature (Tgp). They also showed high antibacterial effectiveness against S. aureus and E. coli bacterial strains. It was manifested by the reduction in cell proliferation, decrease in the number of bacteria adhered on their surfaces, and presence of growth inhibition zones. It can be concluded that the copolymerization of bioactive QAUDMAs with TEGDMA provided copolymers with high antibacterial activity and rewarding physicochemical properties.

Keywords: antibacterial activity; photocurable copolymers; physicochemical properties; quaternary ammonium compounds; urethane-dimethacrylates.

PubMed Disclaimer

Conflict of interest statement

The authors declare no conflict of interest. The funders had no role in the design of the study, in the collection, analyses, or interpretation of data, in the writing of the manuscript, or in the decision to publish the results.

Figures

Figure 1
Figure 1
The synthesis route and chemical structure of the QAUDMA resins used in this study (n = 7–17). Stage 1—Synthesis of HAMA, Stage 2—Synthesis of QAHAMAS, Stage 3—Synthesis of QAUDMAs.
Figure 2
Figure 2
DSC thermograms of the liquid monomer compositions showing their glass transition temperatures.
Figure 3
Figure 3
The representative FT IR spectra of the QA16:TEG: (a) liquid monomer composition and (b) copolymer.
Figure 4
Figure 4
DSC thermograms of copolymers showing their glass transition temperatures.
Figure 5
Figure 5
The images of deionized water droplets on the studied copolymer surfaces obtained from the goniometry camera. Lower case letters indicate statistically insignificant differences (p > 0.05) (non-parametric Wilcoxon test).
Figure 6
Figure 6
The results of the bacterial adhesion tests with (a) S. aureus (ATCC 25923) and (b) E. coli (ATCC 25922) on the studied copolymer surfaces after 18 h of incubation. An asterisk (*) indicates that no adhered bacteria were observed. Lower case letters indicate statistically insignificant differences (p > 0.05) (non-parametric Wilcoxon test).
Figure 7
Figure 7
Images showing (a) S. aureus (ATCC 25923) and (b) E. coli (ATCC 25922) growth inhibition zones.
Figure 7
Figure 7
Images showing (a) S. aureus (ATCC 25923) and (b) E. coli (ATCC 25922) growth inhibition zones.
Figure 8
Figure 8
Images of the bacteria colonies (a) S. aureus (ATCC 25923) and (b) E. coli (ATCC 25922) that grew at the copolymer concentrations of 25 mg/mL.
Figure 8
Figure 8
Images of the bacteria colonies (a) S. aureus (ATCC 25923) and (b) E. coli (ATCC 25922) that grew at the copolymer concentrations of 25 mg/mL.
See this image and copyright information in PMC

Similar articles

See all similar articles

Cited by

See all "Cited by" articles

References

    1. Bowen R.L. Dental Filling Material Comprising Vinyl Silane Treated Fused Silica and a Binder Consisting of the Reaction Product of Bis Phenol and Glycidyl Acrylate. 3,066,112A. U.S. Patent. 1692 June 26;
    1. Dursun E., Fron-Chabouis H., Attal J.P., Raskin A. Bisphenol A Release: Survey of the Composition of Dental Composite Resins. Open Dent. J. 2016;10:446–453. doi: 10.2174/1874210601610010446. - DOI - PMC - PubMed
    1. Watts D.C. Adhesives and Sealants. In: Ratner B., Hoffman A., Schoen F., Lemons J., editors. Biomaterials Science: An Introduction to Materials. 3rd ed. Elsevier Inc.; Amsterdam, The Netherlands: 2013. pp. 889–904.
    1. Lin G.S.S., Abdul Ghani N.R.N., Ismail N.H., Singbal K.P., Yusuff N.M.M. Polymerization Shrinkage and Degree of Conversion of New Zirconia-Reinforced Rice Husk Nanohybrid Composite. Eur. J. Dent. 2020;14:448–455. doi: 10.1055/s-0040-1713951. - DOI - PMC - PubMed
    1. Pratap B., Gupta R.K., Bhardwaj B., Nag M. Resin Based Restorative Dental Materials: Characteristics and Future Perspectives. Jpn. Dent. Sci. Rev. 2019;55:126–138. doi: 10.1016/j.jdsr.2019.09.004. - DOI - PMC - PubMed

LinkOut - more resources