Synthesis and Characterisation of PVP-AAm Hydrogels via Hybrid Process: Morphological, Physical, and Antibacterial Activity

Abstract

Hydrogels are three dimentional networks that constitute of either chemical or physical crosslinks. In this study, preparation of polyvinyl pyrolidone/polyacrylamide (PVA/PAAm) hydrogels exhibiting antibacterial property was demonstrated. Bio-derived α-bisabolol, d-limonene, and geraniol were utilized as antibacterial agents, whereas stabilization of PVA/PAAm hydrogels was achieved by using beta-cyclodextrin (β-CD). PVA/AAm polyblend solutions were polymerizided via UV-irradiation. Then freeze-thawing and anneal-swelling were respectively carried out. Once the morphological, physical properties of the resulting hydrogels was characterized antibacterial efficiency tests were also performed. In the end, it was demonstrated that PVP/PAAm/α-bisabolol and PVP/PAAm/geraniol hydrogels have good antibacterial properties against Escherichia coli with 9 mm zone inhibition.

Keywords

• PVP-PAAm
• antibacterial efficiency
• bio-derived antibacterial agent
• hydrogels
• photopolymerization
• freeze-thawing

References

1. Agra, I. K., Pires, L. L., Carvalho, P. S., Silva-Filho, E. A., Smaniotto, S., & Barreto, E. (2013). Evalua-tion of wound healing and antimicrobial properties of aqueous extract from Bowdichia virgilioides stem barks in mice. Anais da Academia Brasileira de Ciências, 85, 945-954. https://doi.org/10.1590/S0001-37652013005000049 Al-Azzam, N., & Alazzam, A. (2022). Micropatterning of cells via adjusting surface wettability using plasma treatment and graphene oxide deposition. Plos one, 17(6), e0269914. https://doi.org/10.1371/journal.pone.0269914
2. Altaf, F., Niazi, M. B. K., Jahan, Z., Ahmad, T., Akram, M. A., Safdar, A., ... & Sher, F. (2021). Synt-hesis and characterization of PVA/starch hydrogel membranes incorporating essential oils aimed to be used in wound dressing applications. Journal of Polymers and the Environment, 29, 156-174. https://doi.org/10.1007/s10924-020-01866-w
3. Álvarez-Martínez, F. J., Barrajón-Catalán, E., Herranz-López, M., & Micol, V. (2021). Antibacterial plant compounds, extracts and essential oils: An updated review on their effects and putative mec-hanisms of action. Phytomedicine, 90, 153626. https://doi.org/10.1016/j.phymed.2021.153626
4. Bhavsar, V., & Tripathi, D. (2018). Structural, optical, and aging studies of biocompatible PVC-PVP blend films. Journal of Polymer Engineering, 38(5), 419-426. https://doi.org/10.1515/polyeng-2017-0184
5. Burt, S. (2004). Essential oils: their antibacterial properties and potential applications in foods—a re-view. International journal of food microbiology, 94(3), 223-253. https://doi.org/10.1016/j.ijfoodmicro.2004.03.022
6. Cahyana, Y., Putri, Y. S. E., Solihah, D. S., Lutfi, F. S., Alqurashi, R. M., & Marta, H. (2022). Pickering Emulsions as Vehicles for Bioactive Compounds from Essential Oils. Molecules, 27(22), 7872. https://doi.org/10.3390/molecules27227872
7. Chang, H. W., Lin, Y. S., Tsai, Y. D., & Tsai, M. L. (2013). Effects of chitosan characteristics on the physicochemical properties, antibacterial activity, and cytotoxicity of chitosan/2‐glycerophosphate/nanosilver hydrogels. Journal of Applied Polymer Science, 127(1), 169-176. https://doi.org/10.1002/app.37855
8. Chauhan, A. K., & Kang, S. C. (2014). Thymol disrupts the membrane integrity of Salmonella ser. typ-himurium in vitro and recovers infected macrophages from oxidative stress in an ex vivo mo-del. Research in microbiology, 165(7), 559-565. https://doi.org/10.1016/j.resmic.2014.07.001

9. Dafader, N. C., Akter, T., Haque, M. 1., Swapna, S. P., Islam, S., & Huq, D. (2012). Effect of acrylic acid on the properties of polyvinylpyrrolidone hydrogel prepared by the application of gamma ra-diation. African Journal of Biotechnology, 11(66), 13049-13057. https://doi.org/10.5897/AJB-11-2333
10. Derdar, H., Belbachir, M., & Harrane, A. (2019). A green synthesis of polylimonene using Maghnite-H+, an exchanged montmorillonite clay, as eco-catalyst. Bulletin of Chemical Reaction Engineering & Catalysis, 14(1), 69-78. https://doi.org/10.9767/bcrec.14.1.2692.69-78
11. Djefal-Kerrar, A., Abdoun, K. O., Chouikrat, R., El-Kahina, R. G., Khodja, A. J., & Mahlous, M. (2011). Study of bacterium fixation stability on Gamma radiation synthesized carriers to improve degradation. J. Bioremed. Biodegrad, 2, 117-124. https://doi.org/10.4172/2155-6199.1000117
12. Doğan, E. E., Tokcan, P., Diken, M. E., Yilmaz, B., Kizilduman, B. K., & Sabaz, P. (2019). Synthesis, characterization and some biological properties of PVA/PVP/PN hydrogel nanocomposites: Anti-bacterial and biocompatibility. Advances in Materials Science, 19(3), 32-45. https://doi.org/10.2478/adms-2019-0015
13. Edikresnha, D., Sriyanti, I., & Munir, M. M. (2017, May). Synthesis of polyvinylpyrrolidone (PVP)-Green tea extract composite nanostructures using electrohydrodynamic spraying technique. In IOP Conference Series: Materials Science and Engineering (Vol. 202, No. 1, p. 012043). IOP Publis-hing. https://doi.org/10.1088/1757-899X/202/1/012043
14. Ersoy, E., Ozkan, E. E., Boga, M., & Mat, A. (2020). Evaluation of in vitro biological activities of three Hypericum species (H. calycinum, H. confertum, and H. perforatum) from Turkey. South African Journal of Botany, 130, 141-147. https://doi.org/10.1016/j.sajb.2019.12.017
15. Evingür, G. A., Kaygusuz, H., Erim, F. B., & Pekcan, Ö. (2014). Gelation of PAAm-PVP composites: A fluorescence study. International Journal of Modern Physics B, 28(20), 1450122. https://doi.org/10.1142/S0217979214501227
16. Fasihi, H., Noshirvani, N., & Hashemi, M. (2023). Novel bioactive films integrated with Pickering emul-sion of ginger essential oil for food packaging application. Food Bioscience, 51, 102269. https://doi.org/10.1016/j.fbio.2022.102269
17. Fletcher, M., & Pringle, J. H. (1985). The effect of surface free energy and medium surface tension on bacterial attachment to solid surfaces. Journal of Colloid and Interface Science, 104(1), 5-14. https://doi.org/10.1016/0021-9797(85)90004-9
18. Gad, Y. H., Salah, M., & Abdel-Ghaffar, A. M. (2021). Preparation of poly (PVP/acrylamide/glycerol/bentonite clay) nanocomposite films by gamma radiation for removal of Sandolane Rubinole Acid Red 37 dye. International Journal of Environmental Analytical Che-mistry, 1-20. https://doi.org/10.1080/03067319.2021.2011256
19. Gavini, E., Bonferoni, M. C., Rassu, G., Sandri, G., Rossi, S., Salis, A., ... & Giunchedi, P. (2016). En-gineered microparticles based on drug–polymer coprecipitates for ocular-controlled delivery of Ciprofloxacin: influence of technological parameters. Drug Development and Industrial Phar-macy, 42(4), 554-562. https://doi.org/10.3109/03639045.2015.1100201
20. Guimarães, A. C., Meireles, L. M., Lemos, M. F., Guimarães, M. C. C., Endringer, D. C., Fronza, M., & Scherer, R. (2019). Antibacterial activity of terpenes and terpenoids present in essential oils. Molecules, 24(13), 2471. https://doi.org/10.3390/molecules24132471
21. Hu, J. W., Yen, M. W., Wang, A. J., & Chu, I. M. (2018). Effect of oil structure on cyclodextrin-based Pickering emulsions for bupivacaine topical application. Colloids and Surfaces B: Biointerfa-ces, 161, 51-58. https://doi.org/10.1016/j.colsurfb.2017.10.001
22. Huang, M., Hou, Y., Li, Y., Wang, D., & Zhang, L. (2017). High performances of dual network PVA hydrogel modified by PVP using borax as the structure-forming accelerator. Designed monomers and polymers, 20(1), 505-513. https://doi.org/10.1080/15685551.2017.1382433
23. Kamoun, E. A., El-Betany, A., Menzel, H., & Chen, X. (2018). Influence of photoinitiator concentra-tion and irradiation time on the crosslinking performance of visible-light activated pullulan-HEMA hydrogels. International journal of biological macromolecules, 120, 1884-1892. https://doi.org/10.1016/j.ijbiomac.2018.10.011
24. Kędzierska, M., Kudłacik-Kramarczyk, S., Jamroży, M., Bańkosz, M., Walter, J., Potemski, P., & Drabczyk, A. (2023). Verification of the Influence of the 2-Hydroxy-2-methylpropiophenone (Photoinitiator) Content in Hydrogel Materials on Their Physicochemical Properties and Surface Morphology. Coatings, 13(1), 40. https://doi.org/10.3390/coatings13010040
25. Kędzierska, M., Bańkosz, M., & Potemski, P. (2022). Studies on the Impact of the Photoinitiator Amo-unt Used during the PVP-Based Hydrogels’ Synthesis on Their Physicochemical Proper-ties. Materials, 15(17), 6089. https://doi.org/10.3390/ma15176089
26. Kekevi, B. Synthesis and Characterization of Bio-Derived Monoliths. Bilecik Şeyh Edebali Üniversitesi Fen Bilimleri Dergisi, 8(2), 826-832. https://doi.org/10.35193/bseufbd.963141 Krainer, S., & Hirn, U. (2021). Contact angle measurement on porous substrates: Effect of liquid ab-sorption and drop size. Colloids and Surfaces A: Physicochemical and Engineering Aspects, 619, 126503. https://doi.org/10.1016/j.colsurfa.2021.126503
27. Langeveld, W. T., Veldhuizen, E. J., & Burt, S. A. (2014). Synergy between essential oil components and antibiotics: a review. Critical reviews in microbiology, 40(1), 76-94. https://doi.org/10.3109/1040841X.2013.763219
28. Lasoń, E. (2020). Topical Administration of Terpenes Encapsulated in Nanostructured Lipid-Based Sys-tems. Molecules, 25(23), 5758. https://doi.org/10.3390/molecules25235758
29. Li, C., Luo, X., Li, L., Cai, Y., Kang, X., & Li, P. (2022). Carboxymethyl chitosan-based electrospun nanofibers with high citral-loading for potential anti-infection wound dressings. International Jour-nal of Biological Macromolecules, 209, 344-355. https://doi.org/10.1016/j.ijbiomac.2022.04.025
30. Li, S., Dong, S., Xu, W., Tu, S., Yan, L., Zhao, C., ... & Chen, X. (2018). Antibacterial hydro-gels. Advanced science, 5(5), 1700527. https://doi.org/10.1002/advs.201700527
31. Lopérgolo, L. C., Lugao, A. B., & Catalani, L. H. (2003). Direct UV photocrosslinking of poly (N-vinyl-2-pyrrolidone)(PVP) to produce hydrogels. Polymer, 44(20), 6217-6222. https://doi.org/10.1016/S0032-3861(03)00686-4
32. Lopez-Romero, J.C.; González-Ríos, H.; Borges, A.; Simões, M. Antibacterial Effects and Mode of Ac-tion of Selected Essential Oils Components against Escherichia coli and Staphylococcus aureus. Evid.-Based Complement. Altern. Med. 2015. https://doi.org/10.1155/2015/795435
33. Luthfianti, H. R., Waresindo, W. X., Edikresnha, D., Chahyadi, A., Suciati, T., Noor, F. A., & Khairurri-jal, K. (2023). Physicochemical Characteristics and Antibacterial Activities of Freeze-Thawed Poly-vinyl Alcohol/Andrographolide Hydrogels. ACS Omega. https://doi.org/10.1021/acsomega.2c05110
34. Magiatis, P., Skaltsounis, A. L., Chinou, I., & Haroutounian, S. A. (2002). Chemical composition and in-vitro antimicrobial activity of the essential oils of three Greek Achillea species. Zeitschrift für Naturforschung C, 57(3-4), 287-290. https://doi.org/10.1515/znc-2002-3-415
35. Mahizan, N. A., Yang, S. K., Moo, C. L., Song, A. A. L., Chong, C. M., Chong, C. W., ... & Lai, K. S. (2019). Terpene derivatives as a potential agent against antimicrobial resistance (AMR) patho-gens. Molecules, 24(14), 2631. https://doi.org/10.3390/molecules24142631
36. Mao, L., Wang, D., Liu, F., & Gao, Y. (2018). Emulsion design for the delivery of β-carotene in comp-lex food systems. Critical Reviews in Food Science and Nutrition, 58(5), 770-784. https://doi.org/10.1080/10408398.2016.1223599
37. Masyita, A., Sari, R. M., Astuti, A. D., Yasir, B., Rumata, N. R., Emran, T. B., ... & Simal-Gandara, J. (2022). Terpenes and terpenoids as main bioactive compounds of essential oils, their roles in hu-man health and potential application as natural food preservatives. Food chemistry: X, 100217. https://doi.org/10.1016/j.fochx.2022.100217
38. Moo, C. L., Yang, S. K., Yusoff, K., Ajat, M., Thomas, W., Abushelaibi, A., ... & Lai, K. S. (2020). Mechanisms of antimicrobial resistance (AMR) and alternative approaches to overcome AMR. Current drug discovery technologies, 17(4), 430-447. https://doi.org/10.2174/1570163816666190304122219
39. Okay, O. (2020). Self-Healing and Shape-Memory Hydrogels. Hacettepe Journal of Biology and Che-mistry, The 100 Year of Polymers, 507-525. https://doi.org/10.15671/hjbc.797525
40. Ouattara, B., Simard, R. E., Holley, R. A., Piette, G. J. P., & Bégin, A. (1997). Antibacterial activity of selected fatty acids and essential oils against six meat spoilage organisms. International journal of food microbiology, 37(2-3), 155-162. https://doi.org/10.1016/S0168-1605(97)00070-6
41. Owonubi, S. J., Agwuncha, S. C., Malima, N. M., Sadiku, E. R., & Revaprasadu, N. (2021). Develop-ment of bacterial resistant acrylamide-polyvinylpyrrolidone-metal oxide hydrogel nanocomposi-tes. Materials Today: Proceedings, 38, 982-987. https://doi.org/10.1016/j.matpr.2020.05.502
42. Panahi, Y., Gharekhani, A., Hamishehkar, H., Zakeri-Milani, P., & Gharekhani, H. (2019). Stomach-specific drug delivery of clarithromycin using a semi interpenetrating polymeric network hydrogel made of montmorillonite and chitosan: Synthesis, characterization and in vitro drug release study. Advanced pharmaceutical bulletin, 9(1), 159. https://doi.org/10.15171/apb.2019.019
43. Perveen, S., & Al-Taweel, A. (2018). Introductory chapter: Terpenes and terpenoids. Terpenes and ter-penoids, 1, 1-12. https://doi.org/10.15171/apb.2019.019
44. Qureshi, M. A., Nishat, N., & Ahmed, S. (2023). Environmentally Benign Green Synthesized Chitosan-pNIPAm Composite Hydrogel. Advanced Chemicobiology Research, 45-53. https://doi.org/10.37256/acbr.2120231775
45. Rahma, A., Munir, M. M., Prasetyo, A., Suendo, V., & Rachmawati, H. (2016). Intermolecular interacti-ons and the release pattern of electrospun curcumin-polyvinyl (pyrrolidone) fiber. Biological and Pharmaceutical Bulletin, 39(2), 163-173. https://doi.org/10.1248/bpb.b15-00391
46. Roy, N., Saha, N., Kitano, T., & Saha, P. (2012). Biodegradation of PVP–CMC hydrogel film: A useful food packaging material. Carbohydrate polymers, 89(2), 346-353. https://doi.org/10.1016/j.carbpol.2012.03.008 Roy, N., Saha, N., Kitano, T., & Saha, P. (2010). Novel hydrogels of PVP–CMC and their swelling ef-fect on viscoelastic properties. Journal of Applied Polymer Science, 117(3), 1703-1710. https://doi.org/10.1002/app.32056
47. Saroj, A. L., Singh, R. K., & Chandra, S. (2013). Studies on polymer electrolyte poly (vinyl) pyrrolidone (PVP) complexed with ionic liquid: Effect of complexation on thermal stability, conductivity and relaxation behaviour. Materials Science and Engineering: B, 178(4), 231-238. https://doi.org/10.1016/j.mseb.2012.11.007
48. Sheik, S., Nagaraja, G. K., & Prashantha, K. (2018). Effect of silk fiber on the structural, thermal, and mechanical properties of PVA/PVP composite films. Polymer Engineering & Science, 58(11), 1923-1930. https://doi.org/10.1002/pen.24801
49. Silva, A. P. (2009). Síntese e avaliação da atividade antitumoral de tiossemicarbazonas derivadas do alfa-(-)-bisabolol (Doctoral dissertation, Master Thesis, Department of Chemistry, State University of Maringá-Maringá).
50. Souza, F. C., Souza, R. F., & Moraes, Â. M. (2016). Incorporation and release kinetics of alpha-bisabolol from PCL and chitosan/guar gum membranes. Brazilian Journal of Chemical Enginee-ring, 33, 453-467. https://doi.org/10.1590/0104-6632.20160333s20150083
51. Tang, H., Lu, A., Li, L., Zhou, W., Xie, Z., & Zhang, L. (2013). Highly antibacterial materials construc-ted from silver molybdate nanoparticles immobilized in chitin matrix. Chemical Engineering Jour-nal, 234, 124-131. https://doi.org/10.1016/j.cej.2013.08.096
52. Torres, E., Vallés‐Lluch, A., Fombuena, V., Napiwocki, B., & Lih‐Sheng, T. (2017). Influence of the hydrophobic–hydrophilic nature of biomedical polymers and nanocomposites on in vitro biological development. Macromolecular Materials and Engineering, 302(12), 1700259.
53. Van Loosdrecht, M. C., Norde, W., Lyklema, J., & Zehnder, A. J. (1990). Hydrophobic and electrostatic parameters in bacterial adhesion: Dedicated to Werner Stumm for his 65 th birthday. Aquatic scien-ces, 52, 103-114. https://doi.org/10.1007/BF00878244
54. Vogler, E. A. (1998). Structure and reactivity of water at biomaterial surfaces. Advances in colloid and interface science, 74(1-3), 69-117. https://doi.org/10.1016/S0001-8686(97)00040-7
55. Worzakowska, M., & Ścigalski, P. (2013). TG/DSC/FTIR characterization of linear geranyl dies-ters. Journal of thermal analysis and calorimetry, 113, 53-60. https://doi.org/10.1007/s10973-012-2865-6
56. Wu, S., & Shanks, R. A. (2004). Solubility study of polyacrylamide in polar solvents. Journal of app-lied polymer science, 93(3), 1493-1499. https://doi.org/10.1002/app.20608
57. Yang, K., Han, Q., Chen, B., Zheng, Y., Zhang, K., Li, Q., & Wang, J. (2018). Antimicrobial hydrogels: promising materials for medical application. International Journal of Nanomedicine, 13, 2217. https://doi/epdf/10.2147/IJN.S154748
58. Xiao, K., Wen, L., & Jiang, L. (2016). Bioinspired Superwettability Materials. Kirk‐Othmer Encyclope-dia of Chemical Technology, 1-34. https://doi.org/10.1002/0471238961.koe00013