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Fabrication of trichlorovinylsilane-modified-chitosan film with enhanced solubility and antibacterial activity

Abstract

Here, trichlorovinylsilane-modified-chitosan (TVS-m-CS) film is synthesized and explicated by scanning electron microscopy (SEM), Fourier transform infrared spectroscopy and X-ray diffraction (XRD). The SEM micrograph of TVS-m-CS revealed smooth structure with bulge surface. The TVS-m-CS antibacterial activity was evaluated using the broth dilution and agar diffusion methods. Results herein indicated that the TVS-m-CS exhibited enhanced water solubility (67 mg/mL) compared to the cross-linked chitosan (CS) film (5.5 mg/mL). Notably, TVS-m-CS showed a significantly enhanced antibacterial activity against E. coli, S. aureus, E. faecalis, Kleb spp. and methicillin-resistant Staphylococcus aureus (minimum inhibitory concentration [MIC] = 0.078–0.156 mg/mL and minimum bactericidal concentration [MBC] = 12.5–3.12 mg/mL) than the original CS film. Unlike most quaternized chitosan derivatives, the TVS-m-CS was prepared via an easy and simple route and exhibited a comparatively high antibacterial performance. The time-kill study revealed that 5 mg/mL TVS-m-CS exposed to the bacteria cells is sufficient to give a ~ 0.08 log10 reduction (> 99.9% kill rate) within 24 h.

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References

  1. Guler S, Ozseker EE, Akkaya A (2016) Developing an antibacterial biomaterial. Eur Polym J 84:326–337. https://doi.org/10.1016/j.eurpolymj.2016.09.031

    Article  CAS  Google Scholar 

  2. Ozseker EE, Akkaya A (2016) Development of a new antibacterial biomaterial by tetracycline immobilization on calcium-alginate beads. Carbohydr Polym 151:441–451. https://doi.org/10.1016/j.carbpol.2016.05.073

    Article  CAS  PubMed  Google Scholar 

  3. Gritsch L, Lovell C, Goldmann WH, Boccaccini AR (2018) Fabrication and characterization of copper(II)-chitosan complexes as antibiotic-free antibacterial biomaterial. Carbohydr Polym 179:370–378. https://doi.org/10.1016/j.carbpol.2017.09.095

    Article  CAS  PubMed  Google Scholar 

  4. Yan T, Li C, Ouyang Q, Zhang D, Zhong Q, Li P, Li S, Yang Z, Wang T, Zhao Q (2019) Synthesis of gentamicin-grafted-chitosan with improved solubility and antibacterial activity. React Funct Polym 137:38–45. https://doi.org/10.1016/j.reactfunctpolym.2019.01.013

    Article  CAS  Google Scholar 

  5. Chylińsk M, Kaczmarek H, Burkowska-But A (2019) Preparation and characteristics of antibacterial chitosan films modified with N-halamine for biomedical application. Colloids Surf B 176:379–386. https://doi.org/10.1016/j.colsurfb.2019.01.013

    Article  CAS  Google Scholar 

  6. Ahmad N, Ahmad R, Naqvi AA, Alam MA et al (2016) Rutin-encapsulated chitosan nanoparticles targeted to the brain in the treatment of Cerebral Ischemia. Int J Biol Macromol 91:640–655. https://doi.org/10.1016/j.ijbiomac.2016.06.001

    Article  CAS  PubMed  Google Scholar 

  7. Ahmad N, Al-Subaie AM, Ahmad R et al (2019) Brain-targeted glycyrrhizic-acid-loaded surface decorated nanoparticles for treatment of cerebral ischaemia and its toxicity assessment. Artif Cells Nanomed Biotechnol 47:475–490. https://doi.org/10.1080/21691401.2018.1561458

    Article  CAS  PubMed  Google Scholar 

  8. Ahmad N, Ahmad R, Alam MA, Ahmad FJ et al (2019) Daunorubicin oral bioavailability enhancement by surface coated natural biodegradable macromolecule chitosan based polymeric nanoparticles. Int J Biol Macromol 128:825–838. https://doi.org/10.1016/j.ijbiomac.2019.01.142

    Article  CAS  PubMed  Google Scholar 

  9. Alqahtani FY, Aleanizy FS, El Tahir E, Alquadeib BT, Alsarra IA, Alanazi JS, Abdelhady HG (2019) Preparation, characterization, and antibacterial activity of diclofenac-loaded chitosan nanoparticles. Saudi Pharm J 27:82–87. https://doi.org/10.1016/j.jsps.2018.08.001

    Article  PubMed  Google Scholar 

  10. Kong M, Chen XG, Xing K, Park HJ (2010) Antimicrobial properties of chitosan and mode of action: a state of the art review. Int J Food Microbiol 144:51–63. https://doi.org/10.1016/j.ijfoodmicro.2010.09.012

    Article  CAS  PubMed  Google Scholar 

  11. Rabea EI, Badawy ME, Stevens CV, Smagghe G, Steurbaut W (2003) Chitosan as antimicrobial agent: applications and mode of action. Biomacromol 4:1457–1465. https://doi.org/10.1021/bm034130m

    Article  CAS  Google Scholar 

  12. Verlee A, Mincke S, Stevens CV (2017) Recent developments in antibacterial and antifungal chitosan and its derivatives. Carbohydr Polym 164:268–283. https://doi.org/10.1016/j.carbpol.2017.02.001

    Article  CAS  PubMed  Google Scholar 

  13. Abureesh MA, Oladipo AA, Gazi M (2016) Facile synthesis of glucose-sensitive chitosan–poly (vinyl alcohol) hydrogel: drug release optimization and swelling properties. Int J Biol Macromol 90:75–80. https://doi.org/10.1016/j.ijbiomac.2015.10.001

    Article  CAS  PubMed  Google Scholar 

  14. Bakshi PS, Selvakumar D, Kadirvelu K, Kumar NS (2018) Comparative study on antimicrobial activity and biocompatibility of N-selective chitosan derivatives. React Funct Polym 124:149–155. https://doi.org/10.1016/j.reactfunctpolym.2018.01.016

    Article  CAS  Google Scholar 

  15. Chen Y, Li J, Li Q, Shen Y, Ge Z, Zhang W, Chen S (2016) Enhanced water solubility, antibacterial activity and biocompatibility upon introducing sulfobetaine and quaternary ammonium to chitosan. Carbohydr Polym 143:246–253. https://doi.org/10.1016/j.carbpol.2016.01.073

    Article  CAS  PubMed  Google Scholar 

  16. Wen Y, Yao FL, Sun F, Tan ZL, Tian L, Xie L et al (2015) Antibacterial action mode of quaternized carboxymethyl chitosan/poly(amidoamine) dendrimer core-shell nanoparticles against Escherichia coli correlated with molecular chain conformation. Mater Sci Eng C 48:220–227. https://doi.org/10.1016/j.msec.2014.11.066

    Article  CAS  Google Scholar 

  17. Guo AJ, Wang FH, Lin WT, Xu XF, Tang TT, Shen YY et al (2014) Evaluation of antibacterial activity of N-phosphonium chitosan as a novel polymeric antibacterial agent. Int J Biol Macromol 67:163–171. https://doi.org/10.1016/j.ijbiomac.2014.03.024

    Article  CAS  PubMed  Google Scholar 

  18. Jou CH (2011) Antibacterial activity and cytocompatibility of chitosan-N-hydroxy-2,3-propyl-N methyl-N, N-diallylammonium methyl sulfate. Colloids Surf B 88:448–454. https://doi.org/10.1016/j.colsurfb.2011.07.028

    Article  CAS  Google Scholar 

  19. Dang Q, Liu K, Liu C, Xu T, Yan J, Yan F, Cha D, Zhang Q, Cao Y (2018) Preparation, characterization, and evaluation of 3,6-O-N-acetylethylenediamine modified chitosan as potential antimicrobial wound dressing material. Carbohydr Polym 180:1–12. https://doi.org/10.1016/j.carbpol.2017.10.019

    Article  CAS  PubMed  Google Scholar 

  20. Komata Y, Yoshikawa M, Tamura Y, Wada H, Shimojima A, Kuroda K (2016) Selective formation of alkoxychlorosilanes and organotrialkoxysilane with four different substituents by intermolecular exchange reaction. Chem Asian J 11:3225–3233. https://doi.org/10.1002/asia.201601120

    Article  CAS  PubMed  Google Scholar 

  21. Shin HK, Park M, Chung YS, Kim HY, Jin FL, Choi HS, Park SJ (2013) Preparation and characterization of chlorinated cross-linked chitosan/cotton knit for biomedical applications. Macromol Res 21:1241–1246. https://doi.org/10.1007/s13233-013-1164-9

    Article  CAS  Google Scholar 

  22. Sluszny A, Silverstein MS, Kababya S, Schmidt A, Narkis M (2001) Novel Semi-IPN through vinyl silane polymerization and crosslinking within PVC films. J Polym Sci Part A 39:8–22. https://doi.org/10.1002/1099-0518(20010101)39

    Article  CAS  Google Scholar 

  23. Gazi M, Shahmohammadi S (2012) Removal of trace boron from aqueous solution using iminobis-(propylene glycol) modified chitosan beads. React Funct Polym 72:680–686. https://doi.org/10.1016/j.reactfunctpolym.2012.06.016

    Article  CAS  Google Scholar 

  24. Aleanizy FS, Alqahtani FY, Shazly G, Alfaraj R, Alsarra I, Alshamsan A, Abdulhady HG (2018) Measurement and evaluation of the effects of pH gradients on the antimicrobial and antivirulence activities of chitosan nanoparticles in Pseudomonas aeruginosa. Saudi Pharm J 26:79–83. https://doi.org/10.1016/j.jsps.2017.10.009

    Article  PubMed  Google Scholar 

  25. Oladipo AA, Gazi M, Yilmaz E (2015) Single and binary adsorption of azo and anthraquinone dyes by chitosan-based hydrogel: selectivity factor and Box-Behnken process design. Chem Eng Res Des 104:264–279. https://doi.org/10.1016/j.cherd.2015.08.018

    Article  CAS  Google Scholar 

  26. Yusof NAA, Zain NM, Pauzi N (2019) Synthesis of ZnO nanoparticles with chitosan as stabilizing agent and their antibacterial properties against Gram-positive and Gram-negative bacteria. Int J Biol Macromol 124:1132–1136. https://doi.org/10.1016/j.ijbiomac.2018.11.228

    Article  CAS  PubMed  Google Scholar 

  27. Tabriz A, Alvi MAU, Niazi MBK, Batool M, Bhatti MF, Khan AL, Khan AU, Jamil T, Ahmad NM (2019) Quaternized trimethyl functionalized chitosan based antifungal membranes for drinking water treatment. Carbohydr Polym 207:17–25. https://doi.org/10.1016/j.carbpol.2018.11.066

    Article  CAS  PubMed  Google Scholar 

  28. Li K, Guan G, Zhu J, Wu H, Sun Q (2019) Antibacterial activity and mechanism of a laccase-catalyzed chitosan–gallic acid derivative against Escherichia coli and Staphylococcus aureus. Food Control 96:234–243. https://doi.org/10.1016/j.foodcont.2018.09.021

    Article  CAS  Google Scholar 

  29. Abureesh MA, Oladipo AA, Mizwari ZM, Berksel E (2018) Engineered mixed oxide-based polymeric composites for enhanced antimicrobial activity and sustained release of antiretroviral drug. Int J Biol Macromol 116:417–425. https://doi.org/10.1016/j.ijbiomac.2018.05.065

    Article  CAS  PubMed  Google Scholar 

  30. El-Shahawy AAG, El-Ela FIA, Mohamed NA, Eldine ZE, El Rouby WMA (2018) Synthesis and evaluation of layered double hydroxide/doxycycline and cobalt ferrite/chitosan nanohybrid efficacy on gram positive and gram negative bacteria. Mater Sci Eng C 91:361–371. https://doi.org/10.1016/j.msec.2018.05.042

    Article  CAS  Google Scholar 

  31. Blondeau JM, Shebelski SD, Hesje CK (2015) Killing of Streptococcus pneumoniae by azithromycin, clarithromycin, erythromycin, telithromycin and gemifloxacin using drug minimum inhibitory concentrations and mutant prevention concentrations. Int J Antimicrob Agents 45:594–599. https://doi.org/10.1016/j.ijantimicag.2014.12.034

    Article  CAS  PubMed  Google Scholar 

  32. Pan C, Qian J, Fan J, Guo H, Gou L, Yang H, Liang C (2019) Preparation nanoparticle by ionic cross-linked emulsified chitosan and its antibacterial activity. Colloids Surf A 568:362–370. https://doi.org/10.1016/j.colsurfa.2019.02.039

    Article  CAS  Google Scholar 

  33. Cao W, Yue L, Wang Z (2019) High antibacterial activity of chitosan–molybdenum disulfide nanocomposite. Carbohydr Polym 215:226–234. https://doi.org/10.1016/j.carbpol.2019.03.085

    Article  CAS  PubMed  Google Scholar 

  34. Bharathi D, Ranjithkumar R, Chandarshekar B, Bhuvaneshwari V (2019) Preparation of chitosan coated zinc oxide nanocomposite for enhanced antibacterial and photocatalytic activity: as a bionanocomposite. Int J Biol Macromol 129:989–996. https://doi.org/10.1016/j.ijbiomac.2019.02.061

    Article  CAS  PubMed  Google Scholar 

  35. Karpuraranjith M, Thambidurai S (2017) Chitosan/zinc oxide-polyvinylpyrrolidone (CS/ZnO-PVP) nanocomposite for better thermal and antibacterial activity. Int J Biol Macromol 104:1753–1761. https://doi.org/10.1016/j.ijbiomac.2017.02.079

    Article  CAS  PubMed  Google Scholar 

  36. Merlusca IP, Matiut DS, Lisa G, Silion M, Gradinaru L, Oprea S, Popa IM (2018) Preparation and characterization of chitosan–poly(vinyl alcohol)–neomycin sulfate films. Polym Bull 75:3971–3986. https://doi.org/10.1007/s00289-017-2246-1

    Article  CAS  Google Scholar 

  37. Yu Z, Liu W, Huo P (2019) Preparation, characterization, and antimicrobial activity of poly(γ-glutamic acid)/chitosan blends. Polym Bull 76:2163–2178. https://doi.org/10.1007/s00289-018-2485-9

    Article  CAS  Google Scholar 

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Correspondence to Akeem Adeyemi Oladipo or Mustafa Gazi.

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Awode, A.U., Oladipo, A.A., Guran, M. et al. Fabrication of trichlorovinylsilane-modified-chitosan film with enhanced solubility and antibacterial activity. Polym. Bull. 77, 5811–5824 (2020). https://doi.org/10.1007/s00289-019-03056-8

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  • DOI: https://doi.org/10.1007/s00289-019-03056-8

Keywords

  • Chitosan antibacterial activity
  • Time-kill study
  • Vinylsilane
  • Minimum bactericidal concentration
  • Water solubility