journal article·2023-05

Synthesis of acryloyl copolymer core–shell microspheres with antibacterial activity and surface cationic effects

Peng Huang, Yaping Zhang, Bin Wang, Xinhua Zhu, Yufeng He, Pengfei Song, Zeyuan Wang, Rongmin Wang

Journal of Materials Science· Volume 58· Issue 18
Publisher page

Abstract

With the increasing risk of bacterial infections, antimicrobial materials have been paid attention and rapidly becoming the main components for alleviating bacterial pathogens, while synthetic polymer antibacterial materials play a crucial role. In this work, a series of acryloyl copolymer core–shell microspheres (AcCPMs) with cationic groups on its surface were synthesized by using acrolyl cationic monomers, methyl methacrylate and styrene through two-step polymerization and in-situ assembly. The micro-morphologies, structures and sizes of AcCPMs were characterized by SEM, TEM, XPS, FT-IR and dynamic light scattering. And the antibacterial activity was also evaluated against Escherichia coli (E. coli) and Staphylococcus aureus (S. aureus). It indicated that all of AcCPMs have antibacterial activity, and the highest antibacterial rate was 97.0%, because the structure–activity relationship of AcCPMs, including alkyl chain length, cationic groups and the type of anions in quaternary ammonium salts affected their microstructure and antibacterial activity. In summary, the microstructure and antibacterial activity of the acryloyl copolymer core–shell microspheres could be adjusted by varying alkyl chain length and cationic groups. The method of preparing microspheres could be used to synthesize antibacterial coatings, and acryloyl copolymer core–shell microspheres could be applied in biomedical and environmental area.
Source: expertdata · Quality: candidate unverified · Source record ↗

Research context

OpenAlex topics: Antimicrobial agents and applications · Antimicrobial Peptides and Activities · Bacterial biofilms and quorum sensing

SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.

References (58)

Show source-provided references
1. Zhao Z, Ma X, Chen R, Xue H, Lei J, Du H, Chen H (2020) Universal antibacterial surfaces fabricated from quaternary ammonium salt-based PNIPAM microgels. ACS Appl Mater Interfaces 12(17):19268–1927610.1021/acsami.0c00791 ↗
2. Rahma H, Asghari S, Logsetty S, Gu X, Liu S (2015) Preparation of hollow N-chloramine-functionalized hemispherical silica particles with enhanced efficacy against bacteria in the presence of organic load: synthesis, characterization, and antibacterial activity. ACS Appl Mater Interfaces 7(21):11536–1154610.1021/acsami.5b02486 ↗
3. Zhang L, Ning C, Zhou T, Liu X, Yeung KWK, Zhang T, Xu Z, Wang X, Wu S, Chu PK (2014) Polymeric nanoarchitectures on Ti-based implants for antibacterial applications. ACS Appl Mater Interfaces 6(20):17323–1734510.1021/am5045604 ↗
4. Ivanova K, Fernandes MM, Francesko A, Mendoza E, Guezguez J, Burnet M, Tzanov T (2015) Quorum-quenching and matrix-degrading enzymes in multilayer coatings synergistically prevent bacterial biofilm formation on urinary catheters. ACS Appl Mater Interfaces 7(49):27066–2707710.1021/acsami.5b09489 ↗
5. Perelshtein I, Applerot G, Perkas N, Wehrschetz-Sigl E, Hasmann A, Guebitz GM, Gedanken A (2009) Antibacterial properties of an in situ generated and simultaneously deposited nanocrystalline ZnO on fabrics. ACS Appl Mater Interfaces 1(2):361–36610.1021/am8000743 ↗
6. Schiffman JD, Elimelech M (2011) Antibacterial activity of electrospun polymer mats with incorporated narrow diameter single-walled carbon nanotubes. ACS Appl Mater Inter 3(2):462–46810.1021/am101043y ↗
7. Kayser FH (2003) Safety aspects of enterococci from the medical point of view. Int J Food Microbiol 88:255–26210.1016/S0168-1605(03)00188-0 ↗
8. Rychlik I, Barrow PA (2005) Salmonella stress management and its relevance to behaviour during intestinal colonisation and infection. FEMS Microbiol Rev 29(5):1021–104010.1016/j.femsre.2005.03.005 ↗
9. Jiang MM, Zhang B, Tang XN, Liu QL, Tian XL (2018) Preparation and characterization of hybrid antimicrobial materials based on Zn–Lu composites. J Mater Sci 53:14922–14932. https://doi.org/10.1007/s10853-018-2688-310.1007/s10853-018-2688-3 ↗
10. Cheng G, Zhang Z, Chen SF, Bryers JD, Jiang S (2007) Inhibition of bacterial adhesion and biofilm formation on Zwitterionic surfaces. Biomaterials 28(29):4192–419910.1016/j.biomaterials.2007.05.041 ↗
11. Chen Y, Chen Q, Wang ZD, Yan ZQ, Zhang Q, Han QX (2022) Bactericidal silicone with one quaternary ammonium salt and two N-halamine sites in the repeating unit for improved biocidability on magnetic submicrospheres. J Mater Sci 57:2100–2114. https://doi.org/10.1007/s10853-021-06647-x10.1007/s10853-021-06647-x ↗
12. Chong YB, Sun DW, Zhang X, Yue CY, Yang JL (2019) Robust multifunctional microcapsules with antibacterial and anticorrosion features. Chem Eng J 372:496–50810.1016/j.cej.2019.04.139 ↗
13. Han XF, Leng C, Shao Q, Jiang SY, Chen Z (2019) Absolute orientations of water molecules at Zwitterionic polymer interfaces and interfacial dynamics after salt exposure. Langmuir 35(5):1327–133410.1021/acs.langmuir.8b01515 ↗
14. Leng C, Sun SW, Zhang K, Jiang SY, Chen Z (2016) Molecular level studies on interfacial hydration of zwitterionic and other antifouling polymers in situ. Acta Biomater 40:6–1510.1016/j.actbio.2016.02.030 ↗
15. Cai CC, Ma RJ, Duan MW, Lu DJ (2019) Preparation and antimicrobial activity of thyme essential oil microcapsules prepared with gum Arabic. RSC Adv 9:19740–1974710.1039/C9RA03323H ↗
16. Ma CC, Wang W, Kong DB, Li W, Chen SG (2023) A novel all-organic microcapsule with excellent long-term antibacterial and anti-corrosion performances. J Colloid Interface Sci 634:553–56210.1016/j.jcis.2022.12.074 ↗
17. Julaeh E, Eddy DR, Wahyudi T, Ningsih BA, Nurzaman M, Permadi N, Herlina T, Anshori JA (2022) Coacervate microcapsules of citrus aurantifolia essential oil (LOs): optimization and their antibacterial activity study. ChemistrySelect 7(15):e202200187
18. Gabriel GJ, Pool JG, Som A, Dabkowski JM, Coughlin EB, Muthukurnar M (2008) Interactions between antimicrobial polynorbornenes and phospholipid vesicles monitored by light scattering and microcalorimetry. Langmuir 24(21):12489–1249510.1021/la802232p ↗
19. Yin JJ, Wahid F, Zhang Q, Tao YC, Zhong C, Chu LQ (2017) Facile incorporation of silver nanoparticles into quaternized poly(2-(dimethylamino)ethyl methacrylate) brushes as bifunctional antibacterial coatings. Macromol Mater Eng 302:170006910.1002/mame.201700069 ↗
20. Wu ZL, Wang JM, Pei DF, Li L, Mu YB, Wan XB (2018) A simple strategy to achieve mussel-inspired highly effective antibacterial coating. Macromol Mater Eng 303:170043010.1002/mame.201700430 ↗
21. Zhu ZM, Hu JF, Zhong ZC (2022) Preparation and characterization of long-term antibacterial and pH-responsive polylactic acid/octenyl succinic anhydride-chitosan @ tea tree oil microcapsules. Int J Biol Macromol 220:1318–132810.1016/j.ijbiomac.2022.09.038 ↗
22. Yu Q, Ista LK, López GP (2014) Nanopatterned antimicrobial enzymatic surfaces combining biocidal and fouling release properties. Nanoscale 6:4750–475710.1039/C3NR06497B ↗
23. Wang Y, Ying ML, Zhang M, Ren XH, Kim LS (2021) Development of antibacterial and hemostatic PCL/Zein/ZnO-quaternary ammonium salts NPs composite mats as wound dressings. Macromol Mater Eng 306:210058710.1002/mame.202100587 ↗
24. Chen MJ, Hu Y, Zhou J, Xie YR, Wu H, Yuan T, Yang ZH (2016) Facile fabrication of tea tree oil-loaded antibacterial microcapsules by complex coacervation of sodium alginate/quaternary ammonium salt of chitosan. RSC Adv 6:13032–1303910.1039/C5RA26052C ↗
25. Huang JY, Koepsel RR, Murata H, Wu W, Lee SB, Kowalewski T, Russell AJ, Matyjaszewski K (2008) Nonleaching antibacterial glass surfaces via “grafting onto”: the effect of the number of quaternary ammonium groups on biocidal activity. Langmuir 24(13):6785–679510.1021/la8003933 ↗
26. Kang CK, Kim SS, Kim S, Lee J, Lee JH, Roh C, Lee J (2016) Antibacterial cotton fibers treated with silver nanoparticles and quaternary ammonium salts. Carbohyd Polym 151:1012–101810.1016/j.carbpol.2016.06.043 ↗
27. Ye X, Feng J, Zhang J, Yang X, Liao X, Shi Q, Tan S (2017) Controlled release and long-term antibacterial activity of reduced graphene oxide/quaternary ammonium salt nanocomposites prepared by non-covalent modification. Colloids Surf B 149:322–32910.1016/j.colsurfb.2016.10.016 ↗
28. Yu Q, Wu ZQ, Chen H (2015) Dual-function antibacterial surfaces for biomedical applications. Acta Biomater 16:1–1310.1016/j.actbio.2015.01.018 ↗
29. Torkelson AA, Da Silva AK, Love DC, Kim JY, Alper JP, Coox B, Dahm J, Kozodoy P, Maboudian R, Nelson KL (2012) Investigation of quaternary ammonium silane-coated sand filter for the removal of bacteria and viruses from drinking water. J Appl Microbiol 113(5):1196–120710.1111/j.1365-2672.2012.05411.x ↗
30. Belalia R, Grelier S, Benaissa M, Coma V (2008) New bioactive biomaterials based on quaternized chitosan. J Agric Food Chem 56:1582–158810.1021/jf071717+ ↗
31. Song Z, Wang H, Wu Y, Gu J, Li S, Han H (2018) Fabrication of bis-quaternary ammonium salt as an efficient bactericidal weapon against Escherichia coli and Staphylococcus aureus. ACS Omega 3(10):14517–1452510.1021/acsomega.8b01265 ↗
32. Wang Y, Chen R, Li T, Ma PM, Zhang HJ, Du ML, Chen MQ, Dong WF (2020) Antimicrobial waterborne polyurethanes based on quaternary ammonium compounds. Ind Eng Chem Res 59(1):458–46310.1021/acs.iecr.9b04828 ↗
33. Wang B, Wang F, Kong Y, Wu Z, Wang RM, Song PF, He YF (2018) Polyurea-crosslinked cationic acrylate copolymer for antibacterial coating. Colloids Surf A 549:122–12910.1016/j.colsurfa.2018.04.012 ↗
34. Chen A, Peng H, Blakey I, Whittaker AK (2016) Biocidal polymers: a mechanistic overview. Polym Rev 57:276–31010.1080/15583724.2016.1223131 ↗
35. Kenawy ER, Worley SD, Broughton R (2007) The chemistry and applications of antimicrobial polymers: a state-of-the-art review. Biomacromol 8(5):1359–138410.1021/bm061150q ↗
36. Cao WW, Peng XF, Chen XQ, Wang X, Jin F, Li Q, Chen HN, Jiang C, Ye ZW, Xing XD (2016) Facile synthesis of cationic polymer functionalized nanodiamond with high dispersity and antibacterial activity. J Mater Sci 52:1856–1867. https://doi.org/10.1007/s10853-016-0475-610.1007/s10853-016-0475-6 ↗
37. Wang X, Deng AP, Cao WW, Li Q, Wang LN, Zhou J, Hu BC, Xing XD (2018) Synthesis of chitosan/poly (ethylene glycol)-modified magnetic nanoparticles for antibiotic delivery and their enhanced anti-biofilm activity in the presence of magnetic field. J Mater Sci 53:6433–6449. https://doi.org/10.1007/s10853-018-1998-910.1007/s10853-018-1998-9 ↗
38. Huang JH, Murata H, Koepsel RR, Russell AJ, Matyjaszewski K (2007) Antibacterial polypropylene via surface-initiated atom transfer radical polymerization. Biomacromol 8(5):1396–139910.1021/bm061236j ↗
39. Timofeeva LM, Kleshcheva NA, Moroz AF, Didenko LV (2009) Secondary and tertiary polydiallylammonium salts: novel polymers with high antimicrobial activity. Biomacromol 10(11):2976–298610.1021/bm900435v ↗
40. Palermo EF, Vemparala S, Kuroda K (2012) Cationic spacer arm design strategy for control of antimicrobial activity and conformation of amphiphilic methacrylate random copolymers. Biomacromolcules 13(5):1632–164110.1021/bm300342u ↗
41. Punia A, He E, Lee K, Banerjee P, Yang NL (2014) Cationic amphiphilic non-hemolytic polyacrylates with superior antibacterial activity. Chem Commun 50:7071–707410.1039/c4cc01583e ↗
42. Chin W, Yang CA, Ng VWL, Huang Y, Cheng JC, Tong YW, Coady DJ, Fan WM, Hedrick JL, Yang YY (2013) Biodegradable broad-spectrum antimicrobial polycarbonates: investigating the role of chemical structure on activity and selectivity. Macromolecules 46(22):8797–880710.1021/ma4019685 ↗
43. Punia A, Mancuso A, Banerjee P, Yang NL (2015) Nonhemolytic and antibacterial acrylic copolymers with hexamethyleneamine and poly (ethylene glycol) side chains. ACS Macro Lett 4(4):426–43010.1021/acsmacrolett.5b00102 ↗
44. Waschinski CJ, Barnert S, Theobald A, Schubert R, Kleinschmidt F, Hoffmann A, Saalwachter K, Tiller JC (2008) Insights in the antibacterial action of poly(methyloxazoline)s with a biocidal end group and varying satellite groups. Biomacromol 9(7):1764–177110.1021/bm7013944 ↗
45. Waschinski CJ, Zimmermann J, Salz U, Hutzler R, Sadowski G, Tiller JC (2008) Design of contact-active antimicrobial acrylate-based materials using biocidal macromers. Adv Mater 20(1):104–10810.1002/adma.200701095 ↗
46. Waschinski CJ, Herdes V, Schueler F, Tiller JC (2005) Influence of satellite groups on telechelic antimicrobial functions of polyoxazolines. Macromol Biosci 5:149–15610.1002/mabi.200400169 ↗
47. Krumm C, Harmuth S, Hijazi M, Neugebauer B, Kampmann AL, Geltenpoth H, Sickmann A, Tiller JC (2014) Antimicrobial poly(2-methyloxazoline)s with bioswitchable activity through satellite group modification. Angew Chem Int Ed 53(15):3830–383410.1002/anie.201311150 ↗
48. Mizutani M, Palermo EF, Thoma LM, Satoh K, Kamigaito M, Kuroda K (2012) Design and synthesis of self-degradable antibacterial polymers by simultaneous chain- and step-growth radical copolymerization. Biomacromol 13(5):1554–156310.1021/bm300254s ↗
49. Wang H, Shi X, Yu D, Zhang J, Yang G, Cui Y, Yan H (2015) Antibacterial activity of geminized amphiphilic cationic homopolymers. Langmuir 31(50):13469–1347710.1021/acs.langmuir.5b03182 ↗
50. Negm N, Abd-Elaal AAA, Mohamed DE, El-Farargy AF, Mohamed S (2015) Synthesis and evaluation of silver nanoparticles loaded with Gemini surfactants: surface and antimicrobial activity. J Ind Eng Chem 24:34–4110.1016/j.jiec.2014.09.006 ↗
51. Salehi M, Johnson SJ, Liang JT (2010) Enhanced wettability alteration by surfactants with multiple hydrophilic moieties. J Surfactants Deterg 13(3):243–24610.1007/s11743-010-1193-8 ↗
52. Tawfik SM, Abd-Elaal AA, Shaban SM, Roshdy AA (2015) Surface, thermodynamic and biological activities of some synthesized Gemini quaternary ammonium salts based on polyethylene glycol. J Ind Eng Chem 30:112–11910.1016/j.jiec.2015.05.011 ↗
53. Obłak E, Piecuch A, Krasowska A (2013) Antifungal activity of Gemini quaternary ammonium salts. J Luczynski Microbiol Res 168(10):630–63810.1016/j.micres.2013.06.001 ↗
54. Liu XQ, Huang P, Wang JQ, Wang XY, He YF, Song PF, Wang RM (2022) Rational design of polycationic hydrogel with excellent combination functions for flexible wearable electronic devices. Macromol Mater Eng 307(1):210059310.1002/mame.202100593 ↗
55. Conte P, Agretto A, Spaccini R, Piccolo A (2005) Soil remediation: humic acids as natural surfactants in the washings of highly contaminated soils. Environ Pollut 135(3):515–52210.1016/j.envpol.2004.10.006 ↗
56. Li T, Huang P, Li XM, Wang RM, Lu ZX, Song PF, He, YF (2022) Synthesis of Polymer nanospheres conjugated Ce (IV) complexes for constructing double antibacterial centers. J Inorg Organomet Polym 32:883–89410.1007/s10904-021-02165-0 ↗
57. Dai F, Liu W (2011) Enhanced gene transfection and serum stability of polyplexes by PDMAEMA-polysulfobetaine diblock copolymers. Biomaterials 32(2):628–63810.1016/j.biomaterials.2010.09.021 ↗
58. Li XM, Wang B, Liang TY, Wang RM, Song PF, He YF (2020) Synthesis of cationic acrylate copolyvidone-iodine nanoparticles with double active centers and their antibacterial application. Nanoscale 12:21940–2195010.1039/D0NR05462C ↗