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Antibacterial Amphiphilic Composities of Poly(Diethylamino Eethyl Methacrylate-co-Ethyl Methacrylate)/Polyindole Controlling Biofilm Adhesion for Antifouling Investigations

Year 2025, Volume: 12 Issue: 2, 167 - 175, 01.05.2025
https://doi.org/10.31202/ecjse.1557919

Abstract

Amphiphilic and conductive composites are considered notable biomaterials and used as antibacterial agents because they effectively inhibit bacterial growth. In the current study; In the first stage, amphiphilic poly(DEAEMA-co-EMA) copolymers were synthesized from the hydrophilic monomer 2-diethylamino ethylmethacrylate (DEAEMA) and the hydrophobic monomer ethyl methacrylate (EMA) using free radical polymerization. In the second stage, five series composites were prepared at different concentrations using indole conductive monomer in the presence of iron(III) chloride (FeCl3) using the in situ oxidative polymerization technique in poly(DEAEMA-co-EMA) copolymer. The structures of the polymer composites (PCs) were elucidated using FTIR, TGA, SEM, AFM characterization techniques. PCs exhibited significant performance on bacterial biofilm adhesion tested using the Streptococcus mutans by the test tube method (TM). In this study, the 0.006 mg/ml concentration of PC1 reduced the biofilm formation of Streptococcus mutans by 83.199%; PC5, 89.218%; PC3 inhibited 86.078%. 0.003 mg/ml concentration of PC1 prevented S. mutans from forming biofilm by 47.055%; PC5, 71.285%; PC3 was found to inhibit 68.139%. As the concentration and amounth of poly(indole) in the CPs increases, the % antibiofilm effect also increases.
From these results, it can be said that PCs as biofilms may be useful materials in antifouling research.

Ethical Statement

The authors have no conflicts of interest to declare regarding the content of this article.

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References

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  • [22] K.-S. Huang, C.-H. Yang, S.-L. Huang, C.-Y. Chen, Y.-Y. Lu, and Y.-S. Lin, ‘‘Recent advances in antimicrobial polymers: a mini-review,’’ International journal of molecular sciences, vol. 17, no. 9, p. 1578, 2016.
  • [23] P. Elena and K. Miri, ‘‘Formation of contact active antimicrobial surfaces by covalent grafting of quaternary ammonium compounds,’’ Colloids and Surfaces B: Biointerfaces, vol. 169, pp. 195–205, 2018.
  • [24] E.-R. Kenawy, S. Worley, and R. Broughton, ‘‘The chemistry and applications of antimicrobial polymers: a state-of-the-art review,’’ Biomacromolecules, vol. 8, no. 5, pp. 1359–1384, 2007.
  • [25] A. M. Carmona-Ribeiro and L. D. de Melo Carrasco, ‘‘Cationic antimicrobial polymers and their assemblies,’’ International journal of molecular sciences, vol. 14, no. 5, pp. 9906–9946, 2013.
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  • [27] R. Vasudevan, ‘‘Biofilms: microbial cities of scientific significance,’’ J Microbiol Exp, vol. 1, no. 3, p. 00014, 2014.
  • [28] Y.Wang, X. Shen, S. Ma, Q. Guo,W. Zhang, L. Cheng, L. Ding, Z. Xu, J. Jiang, and L. Gao, ‘‘Oral biofilm elimination by combining iron-based nanozymes and hydrogen peroxide-producing bacteria,’’ Biomaterials science, vol. 8, no. 9, pp. 2447–2458, 2020.
  • [29] W. Krzyściak, A. Jurczak, D. Kościelniak, B. Bystrowska, and A. Skalniak, ‘‘The virulence of streptococcus mutans and the ability to form biofilms,’’ European Journal of Clinical Microbiology & Infectious Diseases, vol. 33, pp. 499–515, 2014.
  • [30] S. M. Zayed, M. M. Aboulwafa, A. M. Hashem, and S. E. Saleh, ‘‘Biofilm formation by streptococcus mutans and its inhibition by green tea extracts,’’ AMB Express, vol. 11, no. 1, p. 73, 2021.
  • [31] D. Billaud, E. Maarouf, and E. Hannecart, ‘‘Chemical oxidation and polymerization of indole,’’ Synthetic Metals, vol. 69, no. 1-3, pp. 571–572, 1995.
  • [32] M. Degirmenci, ‘‘Synthesis and characterization of novel well-defined end-functional macrophotoinitiator of poly (mma) by atrp,’’ Journal of Macromolecular Science, Part A, vol. 42, no. 1, pp. 21–30, 2005.
  • [33] D. Zielińska, D. Stawski, and A. Komisarczyk, ‘‘Producing a poly (n, n-dimethylaminoethyl methacrylate) nonwoven by using the blowing out method,’’ Textile Research Journal, vol. 86, no. 17, pp. 1837–1846, 2016.
  • [34] N. S. Okten, C. C. Canakci, and N. Orakdogen, ‘‘Hertzian elasticity and triggered swelling kinetics of poly (amino ester)-based gel beads with controlled hydrophilicity and functionality: A mild and convenient synthesis via dropwise freezing into cryogenic liquid,’’ European Polymer Journal, vol. 114, pp. 176–188, 2019.
  • [35] J. Li, T.-T. Jiang, J.-n. Shen, and H.-M. Ruan, ‘‘Preparation and characterization of pmma and its derivative via raft technique in the presence of disulfide as a source of chain transfer agent,’’ Journal of Membrane and Separation Technology, vol. 1, no. 2, p. 117, 2012.
  • [36] Z. Lin, ‘‘Analysis and identification of infrared spectrum of the polymer,’’ 1989.
  • [37] M. T. Hunley, J. P. England, and T. E. Long, ‘‘Influence of counteranion on the thermal and solution behavior of poly (2-(dimethylamino) ethyl methacrylate)-based polyelectrolytes,’’ Macromolecules, vol. 43, no. 23, pp. 9998–10 005, 2010.
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  • [40] K. Guo, S. Freguia, P. G. Dennis, X. Chen, B. C. Donose, J. Keller, J. J. Gooding, and K. Rabaey, ‘‘Effects of surface charge and hydrophobicity on anodic biofilm formation, community composition, and current generation in bioelectrochemical systems,’’ Environmental science & technology, vol. 47, no. 13, pp. 7563–7570, 2013.
  • [41] D. Raafat and H.-G. Sahl, ‘‘Chitosan and its antimicrobial potential–a critical literature survey,’’ Microbial biotechnology, vol. 2, no. 2, pp. 186–201, 2009.
  • [42] L.-A. B. Rawlinson, S. M. Ryan, G. Mantovani, J. A. Syrett, D. M. Haddleton, and D. J. Brayden, ‘‘Antibacterial effects of poly (2-(dimethylamino ethyl) methacrylate) against selected gram-positive and gram-negative bacteria,’’ Biomacromolecules, vol. 11, no. 2, pp. 443–453, 2010.
  • [43] S. Mushtaq, N. M. Ahmad, A. Mahmood, and M. Iqbal, ‘‘Antibacterial amphiphilic copolymers of dimethylamino ethyl methacrylate and methyl methacrylate to control biofilm adhesion for antifouling applications,’’ Polymers, vol. 13, no. 2, p. 216, 2021.
  • [44] M. Sandberg, A. Määttänen, J. Peltonen, P. M. Vuorela, and A. Fallarero, ‘‘Automating a 96-well microtitre plate model for staphylococcus aureus biofilms: an approach to screening of natural antimicrobial compounds,’’ International journal of antimicrobial agents, vol. 32, no. 3, pp. 233–240, 2008.
  • [45] H. Takahashi, E. F. Palermo, K. Yasuhara, G. A. Caputo, and K. Kuroda, ‘‘M olecular design, structures, and activity of antimicrobial peptide-m imetic polymers,’’ Macromolecular bioscience, vol. 13, no. 10, pp. 1285–1299, 2013.
  • [46] W. Ren, W. Cheng, G. Wang, and Y. Liu, ‘‘Developments in antimicrobial polymers,’’ Journal of Polymer Science Part A: Polymer Chemistry, vol. 55, no. 4, pp. 632–639, 2017.
  • [47] W. Yandi, S. Mieszkin, M. E. Callow, J. A. Callow, J. A. Finlay, B. Liedberg, and T. Ederth, ‘‘Antialgal activity of poly (2-(dimethylamino) ethyl methacrylate)(pdmaema) brushes against the marine alga ulva,’’ Biofouling, vol. 33, no. 2, pp. 169–183, 2017.

Year 2025, Volume: 12 Issue: 2, 167 - 175, 01.05.2025
https://doi.org/10.31202/ecjse.1557919

Abstract

Project Number

-

References

  • [1] T. Pal, S. Banerjee, P. Manna, and K. K. Kar, ‘‘Characteristics of conducting polymers,’’ Handbook of Nanocomposite Supercapacitor Materials I: Characteristics, pp. 247–268, 2020.
  • [2] K. Namsheer and C. S. Rout, ‘‘Conducting polymers: a comprehensive review on recent advances in synthesis, properties and applications,’’ RSC advances, vol. 11, no. 10, pp. 5659–5697, 2021.
  • [3] B. Guo and P. X. Ma, ‘‘Conducting polymers for tissue engineering,’’ Biomacromolecules, vol. 19, no. 6, pp. 1764–1782, 2018.
  • [4] R. Dong, P. X. Ma, and B. Guo, ‘‘Conductive biomaterials for muscle tissue engineering,’’ Biomaterials, vol. 229, p. 119584, 2020.
  • [5] Y. Park, J. Jung, and M. Chang, ‘‘Research progress on conducting polymer-based biomedical applications,’’ Applied Sciences, vol. 9, no. 6, p. 1070, 2019.
  • [6] S. S. Nair, S. K. Mishra, and D. Kumar, ‘‘Recent progress in conductive polymeric materials for biomedical applications,’’ Polymers for Advanced Technologies, vol. 30, no. 12, pp. 2932–2953, 2019.
  • [7] K. Krukiewicz, B. Bednarczyk-Cwynar, R. Turczyn, and J. K. Zak, ‘‘Eqcm verification of the concept of drug immobilization and release from conducting polymer matrix,’’ Electrochimica Acta, vol. 212, pp. 694–700, 2016.
  • [8] C. Boehler, F. Oberueber, and M. Asplund, ‘‘Tuning drug delivery from conducting polymer films for accurately controlled release of charged molecules,’’ Journal of Controlled Release, vol. 304, pp. 173–180, 2019.
  • [9] S. Lakard, N. Morrand-Villeneuve, E. Lesniewska, B. Lakard, G. Michel, G. Herlem, T. Gharbi, and B. Fahys, ‘‘Synthesis of polymer materials for use as cell culture substrates,’’ Electrochimica Acta, vol. 53, no. 3, pp. 1114–1126, 2007.
  • [10] P. Humpolíček, V. Kašpárková, J. Pacherník, J. Stejskal, P. Bober, Z. Capáková, K. A. Radaszkiewicz, I. Junkar, and M. Lehock`y, ‘‘The biocompatibility of polyaniline and polypyrrole: A comparative study of their cytotoxicity, embryotoxicity and impurity profile,’’ Materials Science and Engineering: C, vol. 91, pp. 303–310, 2018.
  • [11] S. Ramanavicius and A. Ramanavicius, ‘‘Charge transfer and biocompatibility aspects in conducting polymer-based enzymatic biosensors and biofuel cells,’’ Nanomaterials, vol. 11, no. 2, p. 371, 2021.
  • [12] H. He, L. Zhang, X. Guan, H. Cheng, X. Liu, S. Yu, J.Wei, and J. Ouyang, ‘‘Biocompatible conductive polymers with high conductivity and high stretchability,’’ ACS applied materials & interfaces, vol. 11, no. 29, pp. 26 185–26 193, 2019.
  • [13] D. N. Nguyen and H. Yoon, ‘‘Recent advances in nanostructured conducting polymers: from synthesis to practical applications,’’ Polymers, vol. 8, no. 4, p. 118, 2016.
  • [14] Y. Fan, W. Bai, P. Mu, Y. Su, Z. Zhu, H. Sun, W. Liang, and A. Li, ‘‘Conductively monolithic polypyrrole 3-d porous architecture with micron-sized channels as superior salt-resistant solar steam generators,’’ Solar Energy Materials and Solar Cells, vol. 206, p. 110347, 2020.
  • [15] S. Nie, Z. Li, Y. Yao, and Y. Jin, ‘‘Progress in synthesis of conductive polymer poly (3, 4-ethylenedioxythiophene),’’ Frontiers in chemistry, vol. 9, p. 803509, 2021.
  • [16] M. Fadel, D. A. Fadeel, M. Ibrahim, R. M. Hathout, and A. I. El-Kholy, ‘‘One-step synthesis of polypyrrole-coated gold nanoparticles for use as a photothermally active nano-system,’’ International Journal of Nanomedicine, pp. 2605–2615, 2020.
  • [17] N. K. Jangid, S. Jadoun, and N. Kaur, ‘‘Retracted: A review on high-throughput synthesis, deposition of thin films and properties of polyaniline,’’ 2020.
  • [18] R. B. Choudhary, S. Ansari, and M. Majumder, ‘‘Recent advances on redox active composites of metal-organic framework and conducting polymers as pseudocapacitor electrode material,’’ Renewable and Sustainable Energy Reviews, vol. 145, p. 110854, 2021.
  • [19] C. I. Idumah, E. Ezeani, and I. Nwuzor, ‘‘A review: advancements in conductive polymers nanocomposites,’’ Polymer-Plastics Technology and Materials, vol. 60, no. 7, pp. 756–783, 2021.
  • [20] J. Chapman, ‘‘The development of novel antifouling materials-a multi-disciplinary approach,’’ Ph.D. dissertation, Dublin City University, 2011.
  • [21] G. Lu, D.Wu, and R. Fu, ‘‘Studies on the synthesis and antibacterial activities of polymeric quaternary ammonium salts from dimethylaminoethyl methacrylate,’’ Reactive and Functional Polymers, vol. 67, no. 4, pp. 355–366, 2007.
  • [22] K.-S. Huang, C.-H. Yang, S.-L. Huang, C.-Y. Chen, Y.-Y. Lu, and Y.-S. Lin, ‘‘Recent advances in antimicrobial polymers: a mini-review,’’ International journal of molecular sciences, vol. 17, no. 9, p. 1578, 2016.
  • [23] P. Elena and K. Miri, ‘‘Formation of contact active antimicrobial surfaces by covalent grafting of quaternary ammonium compounds,’’ Colloids and Surfaces B: Biointerfaces, vol. 169, pp. 195–205, 2018.
  • [24] E.-R. Kenawy, S. Worley, and R. Broughton, ‘‘The chemistry and applications of antimicrobial polymers: a state-of-the-art review,’’ Biomacromolecules, vol. 8, no. 5, pp. 1359–1384, 2007.
  • [25] A. M. Carmona-Ribeiro and L. D. de Melo Carrasco, ‘‘Cationic antimicrobial polymers and their assemblies,’’ International journal of molecular sciences, vol. 14, no. 5, pp. 9906–9946, 2013.
  • [26] Z. Zhou, D. R. Calabrese, W. Taylor, J. A. Finlay, M. E. Callow, J. A. Callow, D. Fischer, E. J. Kramer, and C. K. Ober, ‘‘Amphiphilic triblock copolymers with pegylated hydrocarbon structures as environmentally friendly marine antifouling and fouling-release coatings,’’ Biofouling, vol. 30, no. 5, pp. 589–604, 2014.
  • [27] R. Vasudevan, ‘‘Biofilms: microbial cities of scientific significance,’’ J Microbiol Exp, vol. 1, no. 3, p. 00014, 2014.
  • [28] Y.Wang, X. Shen, S. Ma, Q. Guo,W. Zhang, L. Cheng, L. Ding, Z. Xu, J. Jiang, and L. Gao, ‘‘Oral biofilm elimination by combining iron-based nanozymes and hydrogen peroxide-producing bacteria,’’ Biomaterials science, vol. 8, no. 9, pp. 2447–2458, 2020.
  • [29] W. Krzyściak, A. Jurczak, D. Kościelniak, B. Bystrowska, and A. Skalniak, ‘‘The virulence of streptococcus mutans and the ability to form biofilms,’’ European Journal of Clinical Microbiology & Infectious Diseases, vol. 33, pp. 499–515, 2014.
  • [30] S. M. Zayed, M. M. Aboulwafa, A. M. Hashem, and S. E. Saleh, ‘‘Biofilm formation by streptococcus mutans and its inhibition by green tea extracts,’’ AMB Express, vol. 11, no. 1, p. 73, 2021.
  • [31] D. Billaud, E. Maarouf, and E. Hannecart, ‘‘Chemical oxidation and polymerization of indole,’’ Synthetic Metals, vol. 69, no. 1-3, pp. 571–572, 1995.
  • [32] M. Degirmenci, ‘‘Synthesis and characterization of novel well-defined end-functional macrophotoinitiator of poly (mma) by atrp,’’ Journal of Macromolecular Science, Part A, vol. 42, no. 1, pp. 21–30, 2005.
  • [33] D. Zielińska, D. Stawski, and A. Komisarczyk, ‘‘Producing a poly (n, n-dimethylaminoethyl methacrylate) nonwoven by using the blowing out method,’’ Textile Research Journal, vol. 86, no. 17, pp. 1837–1846, 2016.
  • [34] N. S. Okten, C. C. Canakci, and N. Orakdogen, ‘‘Hertzian elasticity and triggered swelling kinetics of poly (amino ester)-based gel beads with controlled hydrophilicity and functionality: A mild and convenient synthesis via dropwise freezing into cryogenic liquid,’’ European Polymer Journal, vol. 114, pp. 176–188, 2019.
  • [35] J. Li, T.-T. Jiang, J.-n. Shen, and H.-M. Ruan, ‘‘Preparation and characterization of pmma and its derivative via raft technique in the presence of disulfide as a source of chain transfer agent,’’ Journal of Membrane and Separation Technology, vol. 1, no. 2, p. 117, 2012.
  • [36] Z. Lin, ‘‘Analysis and identification of infrared spectrum of the polymer,’’ 1989.
  • [37] M. T. Hunley, J. P. England, and T. E. Long, ‘‘Influence of counteranion on the thermal and solution behavior of poly (2-(dimethylamino) ethyl methacrylate)-based polyelectrolytes,’’ Macromolecules, vol. 43, no. 23, pp. 9998–10 005, 2010.
  • [38] D. Stawski and A. Nowak, ‘‘Thermal properties of poly (n, n-dimethylaminoethyl methacrylate),’’ PLoS One, vol. 14, no. 6, p. e0217441, 2019.
  • [39] P. S. Abthagir, K. Dhanalakshmi, and R. Saraswathi, ‘‘Thermal studies on polyindole and polycarbazole,’’ Synthetic metals, vol. 93, no. 1, pp. 1–7, 1998.
  • [40] K. Guo, S. Freguia, P. G. Dennis, X. Chen, B. C. Donose, J. Keller, J. J. Gooding, and K. Rabaey, ‘‘Effects of surface charge and hydrophobicity on anodic biofilm formation, community composition, and current generation in bioelectrochemical systems,’’ Environmental science & technology, vol. 47, no. 13, pp. 7563–7570, 2013.
  • [41] D. Raafat and H.-G. Sahl, ‘‘Chitosan and its antimicrobial potential–a critical literature survey,’’ Microbial biotechnology, vol. 2, no. 2, pp. 186–201, 2009.
  • [42] L.-A. B. Rawlinson, S. M. Ryan, G. Mantovani, J. A. Syrett, D. M. Haddleton, and D. J. Brayden, ‘‘Antibacterial effects of poly (2-(dimethylamino ethyl) methacrylate) against selected gram-positive and gram-negative bacteria,’’ Biomacromolecules, vol. 11, no. 2, pp. 443–453, 2010.
  • [43] S. Mushtaq, N. M. Ahmad, A. Mahmood, and M. Iqbal, ‘‘Antibacterial amphiphilic copolymers of dimethylamino ethyl methacrylate and methyl methacrylate to control biofilm adhesion for antifouling applications,’’ Polymers, vol. 13, no. 2, p. 216, 2021.
  • [44] M. Sandberg, A. Määttänen, J. Peltonen, P. M. Vuorela, and A. Fallarero, ‘‘Automating a 96-well microtitre plate model for staphylococcus aureus biofilms: an approach to screening of natural antimicrobial compounds,’’ International journal of antimicrobial agents, vol. 32, no. 3, pp. 233–240, 2008.
  • [45] H. Takahashi, E. F. Palermo, K. Yasuhara, G. A. Caputo, and K. Kuroda, ‘‘M olecular design, structures, and activity of antimicrobial peptide-m imetic polymers,’’ Macromolecular bioscience, vol. 13, no. 10, pp. 1285–1299, 2013.
  • [46] W. Ren, W. Cheng, G. Wang, and Y. Liu, ‘‘Developments in antimicrobial polymers,’’ Journal of Polymer Science Part A: Polymer Chemistry, vol. 55, no. 4, pp. 632–639, 2017.
  • [47] W. Yandi, S. Mieszkin, M. E. Callow, J. A. Callow, J. A. Finlay, B. Liedberg, and T. Ederth, ‘‘Antialgal activity of poly (2-(dimethylamino) ethyl methacrylate)(pdmaema) brushes against the marine alga ulva,’’ Biofouling, vol. 33, no. 2, pp. 169–183, 2017.
There are 47 citations in total.

Details

Primary Language English
Subjects Engineering Design, Engineering Practice, Engineering Practice and Education (Other)
Journal Section Research Articles
Authors

Cengiz Soykan 0000-0002-5802-5097

Burak Tüfekçi This is me 0000-0001-8695-8604

Project Number -
Publication Date May 1, 2025
Submission Date September 29, 2024
Acceptance Date March 29, 2025
Published in Issue Year 2025 Volume: 12 Issue: 2

Cite

IEEE C. Soykan and B. Tüfekçi, “Antibacterial Amphiphilic Composities of Poly(Diethylamino Eethyl Methacrylate-co-Ethyl Methacrylate)/Polyindole Controlling Biofilm Adhesion for Antifouling Investigations”, El-Cezeri Journal of Science and Engineering, vol. 12, no. 2, pp. 167–175, 2025, doi: 10.31202/ecjse.1557919.
Creative Commons License El-Cezeri is licensed to the public under a Creative Commons Attribution 4.0 license.
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