Development of a Biodegradable, Cytocompatible, Antibacterial, and Biofilm-Controlling Chitosan Sulfobetaine Derivative Film as a Biological Material

Maoli Yin; Yingfeng Wang; Xuehong Ren; Tung-Shi Huang

doi:10.1016/j.eng.2023.06.020

PDF(2075 KB)

Engineering ›› 2024, Vol. 35 ›› Issue (4) : 95-103. DOI: 10.1016/j.eng.2023.06.020

Research

Article

Development of a Biodegradable, Cytocompatible, Antibacterial, and Biofilm-Controlling Chitosan Sulfobetaine Derivative Film as a Biological Material

Author information +

History +

Abstract

The purpose of this research was to develop a chitosan sulfobetaine (CS-SNCC) film via the solution-casting method as a biodegradable antibacterial material for biomedical applications. Chitosan and monochloro-triazine sulfobetaine were used as the raw materials for CS-SNCC preparation, and Fourier-transform infrared (FTIR), ultraviolet-visible (UV-Vis), energy-dispersive X-ray (EDX), and X-ray photoelectron spectroscopy (XPS) spectra were used to characterize and analyze the structure of the synthesized CS-SNCC. Furthermore, the swelling property, thermal stability, biodegradability, cytocompatibility, and antibacterial properties of the CS-SNCC film were comprehensively investigated and compared with those of the chitosan film. The results for the film’s enzymatic biodegradation behavior show that the CS-SNCC film undergoes a weight loss of 45.54% after 21 days of incubation. In addition, the CS-SNCC film effectively resists bacterial adhesion, prevents the formation of bacteria biofilms, and exhibits high antibacterial activity, with inactivation rates of 93.43% for Escherichia coli and 91.00% for Staphylococcus aureus. Moreover, the CS-SNCC film shows good cellular activity and cytocompatibility according to the cytotoxicity results. Therefore, the prepared biodegradable, cytocompatible, antibacterial, and biofilm-controlling CS-SNCC film has potential for biomedical applications.

Graphical abstract

Keywords

Chitosan / Sulfobetaine / Antibacterial / Biofilm-controlling / Film

Cite this article

EndNote

Ris (Procite)

Bibtex

Download citation ▾

Maoli Yin, Yingfeng Wang, Xuehong Ren, Tung-Shi Huang. Development of a Biodegradable, Cytocompatible, Antibacterial, and Biofilm-Controlling Chitosan Sulfobetaine Derivative Film as a Biological Material. Engineering, 2024, 35(4): 95‒103 https://doi.org/10.1016/j.eng.2023.06.020

References

Publishing order | Descend order by publishing year | Descend order by cited within

[1]

Zhao

, Y.P.

Liang

, Y.

Huang

, J.H.

, Y.

Han

, B.L.

Guo

. Physical double-network hydrogel adhesives with rapid shape adaptability, fast self-healing, antioxidant and NIR/pH stimulus-responsiveness for multidrug-resistant bacterial infection and removable wound dressing. Adv Funct Mater, 30 (17) (2020), p. 1910748.

[2]	M.L. Yin, S.S. Wan, X.H. Ren, C.C. Chu. Development of inherently antibacterial, biodegradable, and biologically active chitosan/pseudo-protein hybrid hydrogels as biofunctional wound dressings. ACS Appl Mater Interfaces, 13 (12) (2021), pp. 14688-14699.

[3]	M.L. Yin, Y.F. Wang, Y. Zhang, X.H. Ren, Y.Y. Qiu, T.S. Huang. Novel quaternarized N-halamine chitosan and polyvinyl alcohol nanofibrous membranes as hemostatic materials with excellent antibacterial properties. Carbohydr Polym, 232 (2020), p. 115823.

[4]	M. Li, J. Aveyard, K.G. Doherty, R.C. Deller, R.L. Williams, K.N. Kolegraff, et al. Antimicrobial nitric oxide-releasing electrospun dressings for wound healing applications. ACS Mater Au, 2 (2) (2022), pp. 190-203.

[5]	Y.P. Liang, J.H. He, B.L. Guo. Functional hydrogels as wound dressing to enhance wound healing. ACS Nano, 15 (8) (2021), pp. 12687-12722.

[6]	L. Li, X. Cao, X. Shen, S.T. Yu, F. Su, S.W. Liu, et al. Alkyl chitosan film—high strength, functional biomaterials. J Biomed Mater Res Part A, 105 (11) (2017), pp. 3034-3041.

[7]	S.M. Zhang, L. Li, X.H. Ren, T.S. Huang. N-Halamine modified multiporous bacterial cellulose with enhanced antibacterial and hemostatic properties. Int J Biol Macromol, 161 (2020), pp. 1070-1078.

[8]	B. Demir, R.M. Broughton, M.Y. Qiao, T.H. Huang, S.D. Worley. N-Halamine biocidal materials with superior antimicrobial efficacies for wound dressings. Molecules, 22 (10) (2017), p. 1582.

[9]	M.G.A. Vieira, M.A. da Silva, L.O. dos Santos, M.M. Beppu. Natural-based plasticizers and biopolymer films: a review. Eur Polym J, 47 (3) (2011), pp. 254-263.

[10]	S. Patel, S. Srivastava, M.R. Singh, D. Singh. Preparation and optimization of chitosan-gelatin films for sustained delivery of lupeol for wound healing. Int J Biol Macromol, 107 (2018), pp. 1888-1897.

[11]	C. Liu, H.R. Shan, X.X. Chen, Y. Si, X. Yin, J.Y. Yu, et al. Novel inorganic-based N-halamine nanofibrous membranes as highly effective antibacterial agent for water disinfection. ACS Appl Mater Interfaces, 10 (51) (2018), pp. 44209-44215.

[12]	J.H. Li, S.L. Zhuang. Antibacterial activity of chitosan and its derivatives and their interaction mechanism with bacteria: current state and perspectives. Eur Polym J, 138 (2020), p. 109984.

[13]	P.S. Bakshi, D. Selvakumar, K. Kadirvelu, N.S. Kumar. Chitosan as an environment friendly biomaterial—a review on recent modifications and applications. Int J Biol Macromol, 150 (2020), pp. 1072-1083.

[14]	P. Sahariah, M. Masson. Antimicrobial chitosan and chitosan derivatives: a review of the structure-activity relationship. Biomacromolecules, 18 (11) (2017), pp. 3846-3868.

[15]	M.L. Yin, X.H. Lin, T. Ren, Z.G. Li, X.H. Ren, T.S. Huang. Cytocompatible quaternized carboxymethyl chitosan/poly(vinyl alcohol) blend film loaded copper for antibacterial application. Int J Biol Macromol, 120 (Pt A) (2018), pp. 992-998.

[16]	P. Sahariah, B.E. Benediktssdottir, M.A. Hjalmarsdottir, O.E. Sigurjonsson, K.K. Sorensen, M.B. Thygesen, et al. Impact of chain length on antibacterial activity and hemocompatibility of quaternary N-alkyl and N,N-dialkyl chitosan derivatives. Biomacromolecules, 16 (5) (2015), pp. 1449-1460.

[17]	V. Patrulea, B.H. Gan, K. Perron, X. Cai, P. Abdel-Sayed, E. Sublet, et al. Synergistic effects of antimicrobial peptide dendrimer-chitosan polymer conjugates against Pseudomonas aeruginosa. Carbohydr Polym, 280 (2022), p. 119025.

[18]	Y.Z. Ma, K. Gao, H.H. Yu, W.X. Liu, Y.K. Qin, R.G. Xing, et al. C-coordinated O-carboxymethyl chitosan Cu(II) complex exerts antifungal activity by disrupting the cell membrane integrity of Phytophthora capsici Leonian. Carbohydr Polym, 261 (2021), p. 117821.

[19]	D.D. Li, X. Gao, X.C. Huang, P.L. Liu, W. Xiong, S.T. Wu, et al. Preparation of organic-inorganic chitosan@silver/sepiolite composites with high synergistic antibacterial activity and stability. Carbohydr Polym, 249 (2020), p. 116858.

[20]	H.C. He, Z.C. Xiao, Y.J. Zhou, A.Q. Chen, X. Xuan, Y.Y. Li, et al. Zwitterionic poly(sulfobetaine methacrylate) hydrogels with optimal mechanical properties for improving wound healing in vivo. J Mater Chem B, 7 (10) (2019), pp. 1697-1707.

[21]	H.T. Lin, A. Venault, Y. Chang. Zwitterionized chitosan based soft membranes for diabetic wound healing. J Membr Sci, 591 (2019), p. 117319.

[22]	Y.X. Chen, J.N. Li, Q.Q. Li, Y.Y. Shen, Z.C. Ge, W.W. Zhang, et al. Enhanced water-solubility, antibacterial activity and biocompatibility upon introducing sulfobetaine and quaternary ammonium to chitosan. Carbohydr Polym, 143 (2016), pp. 246-253.

[23]	X.H. Chu, M. Zhang, N.L. Zhou, F. Wu, B.H. Sun, J. Shen. Synthesis and characterization of a novel antibacterial material containing poly(sulfobetaine) using reverse atom transfer radical polymerization. RSC Adv, 8 (58) (2018), pp. 33000-33009.

[24]	X. Yang, D. Sha, H. Jiang, K. Shi, J.D. Xu, C. Yu, et al. Preparation of antibacterial poly(sulfobetaine methacrylate) grafted on poly(vinyl alcohol)-formaldehyde sponges and their properties. J Appl Polym Sci, 136 (6) (2019), p. 47047.

[25]	R. Wang, K.G. Neoh, E.T. Kang. Integration of antifouling and bactericidal moieties for optimizing the efficacy of antibacterial coatings. J Colloid Interface Sci, 438 (2015), pp. 138-148.

[26]	X. Zhao, B.L. Guo, H. Wu, Y.P. Liang, P.X. Ma. Injectable antibacterial conductive nanocomposite cryogels with rapid shape recovery for noncompressible hemorrhage and wound healing. Nat Commun, 9 (1) (2018), p. 2784.

[27]	L. He, C. Gao, S. Li, C.T.W. Chung, J.H. Xin. Non-leaching and durable antibacterial textiles finished with reactive zwitterionic sulfobetaine. J Ind Eng Chem, 46 (2017), pp. 373-378.

[28]	C. Chen, S.G. Yang, Y.P. Guo, C. Sun, C.G. Gu, B. Xu. Photolytic destruction of endocrine disruptor atrazine in aqueous solution under UV irradiation: products and pathways. J Hazard Mater, 172 (2-3) (2009), pp. 675-684.

[29]	S. Chen, L. Yuan, Q. Li, J. Li, X. Zhu, Y. Jiang, et al. Durable antibacterial and nonfouling cotton textiles with enhanced comfort via zwitterionic sulfopropylbetaine coating. Small, 12 (26) (2016), pp. 3516-3521.

[30]	Y.J. Chen, W. Wang, Y. Qiu, L.S. Li, L.J. Qian, F. Xin. Terminal group effects of phosphazene-triazine bi-group flame retardant additives in flame retardant polylactic acid composites. Polym Degrad Stabil, 140 (2017), pp. 166-175.

[31]	D.W. Yuan, K. Cadien, Q. Liu, H.B. Zeng. Adsorption characteristics and mechanisms of O-carboxymethyl chitosan on chalcopyrite and molybdenite. J Colloid Interface Sci, 552 (2019), pp. 659-670.

[32]	R.L. Tang, Y. Zhang, Y. Zhang, Z.M. Yu. Synthesis and characterization of chitosan based dye containing quaternary ammonium group. Carbohydr Polym, 139 (2016), pp. 191-196.

[33]	M.L. Yin, X.L. Chen, R. Li, D. Huang, X.Y. Fan, X.H. Ren, et al. Preparation and characterization of antimicrobial PVA hybrid films with N-halamine modified chitosan nanospheres. J Appl Polym Sci, 133 (46) (2016), p. 44204.

[34]	R. Li, P. Hu, X.H. Ren, S.D. Worley, T.S. Huang. Antimicrobial N-halamine modified chitosan films. Carbohydr Polym, 92 (1) (2013), pp. 534-539.

[35]	M. Nieto-Suárez, M.A. López-Quintela, M. Lazzari. Preparation and characterization of crosslinked chitosan/gelatin scaffolds by ice segregation induced self-assembly. Carbohydr Polym, 141 (2016), pp. 175-183.

[36]	S. Ganguly, P.P. Maity, S. Mondal, P. Das, P. Bhawal, S. Dhara, et al. Polysaccharide and poly(methacrylic acid) based biodegradable elastomeric biocompatible semi-IPN hydrogel for controlled drug delivery. Mater Sci Eng C, 92 (2018), pp. 34-51.

[37]	M.Y. He, A. Potuck, Y. Zhang, C.C. Chu. Arginine-based polyester amide/polysaccharide hydrogels and their biological response. Acta Biomater, 10 (6) (2014), pp. 2482-2494.

[38]	Y. Ma, J.Y. Li, Y. Si, K. Huang, N. Nitin, G. Sun. Rechargeable antibacterial N-halamine films with antifouling function for food packaging applications. ACS Appl Mater Interfaces, 11 (19) (2019), pp. 17814-17822.

[39]	A.M. Heimbuck, T.R. Priddy-Arrington, M.L. Padgett, C.B. Llamas, H.H. Barnett, B.A. Bunnell, et al. Development of responsive chitosan-genipin hydrogels for the treatment of wounds. ACS Appl Bio Mater, 2 (7) (2019), pp. 2879-2888.

[40]	W.Y. Li, B.X. Wang, M.H. Zhang, Z.T. Wu, J.X. Wei, Y. Jiang, et al. All-natural injectable hydrogel with self-healing and antibacterial properties for wound dressing. Cellulose, 27 (5) (2020), pp. 2637-2650.