'Click' synthesized non-substituted triazole modified chitosan from CaC.sub.2 as a novel antibacterial and antioxidant polymer

Herein, the biopolymer chitosan has been modified via click chemistry using the robust copper catalyzed azide-alkyne cycloaddition (CuAAC) reaction. CuAAC reaction on chitosan skeleton is an interesting way for its modification and chitosan is prone to be modified at C-2, C-3 and C-6 positions where...

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Bibliographic Details
Published in:Journal of polymer research 2022-05, Vol.29 (5)
Main Authors: D., Pal Manisha, Chawla, Ruchi, Dutta, Pradip Kumar
Format: Article
Language:English
Subjects:
Antibacterial agents
Antioxidants
Copper
Polymer industry
Polymers
Triazoles
Online Access:Get full text
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Summary:Herein, the biopolymer chitosan has been modified via click chemistry using the robust copper catalyzed azide-alkyne cycloaddition (CuAAC) reaction. CuAAC reaction on chitosan skeleton is an interesting way for its modification and chitosan is prone to be modified at C-2, C-3 and C-6 positions where free amino and hydroxyl groups are present. Initially, N-azidated chitosan was prepared and then CuAAC click reaction was carried out to synthesize chitosan-1,2,3-triazole derivative (CS-triazole derivative) by a novel facile method starting from CaC.sub.2. The synthesized polymer derivative has been well characterized by FT-IR, .sup.1H NMR and .sup.13C NMR spectroscopic analyses. FT-IR spectra of N-azidated chitosan shows a peak at 2115 cm.sup.-1 which confirms the presence of azide functionality whereas the peak at 1560 cm.sup.-1 confirms the presence of unsaturation in the triazole moiety of final product. Proton NMR signal at 8.28 ppm and carbon NMR signal at 130 ppm and 144 ppm confirm the presence of = C-H protons and unsaturation in the triazole ring respectively for the synthesized derivative. On biological evaluation, CS-triazole derivative showed antibacterial activity against gram-negative (E. coli) and gram-positive (B. subtilis) bacteria (using the agar diffusion method). The antibacterial results were interpreted in terms of zone of inhibition (ZOI) which depicted that chitosan triazole derivative showed better ZOI than pristine chitosan and N-azidated chitosan. Also, ZOI for gram-negative bacteria was better than that of gram-positive bacteria. Moreover, synthesized chitosan triazole derivative also exhibited significant antioxidant property (tested using DPPH assay method).
ISSN:1022-9760
DOI:10.1007/s10965-022-03032-3