TY - JOUR

T1 - Water-soluble chitotriazolans derived from cationic, neutral, and anionic common chitosan derivatives

T2 - Synthesis, characterization, and antibacterial activity

AU - Rathinam, Sankar

AU - Hjálmarsdóttir, Martha

AU - Thygesen, Mikkel B.

AU - Másson, Már

N1 - Funding Information: Már Másson (MM) designed the research plan in collaboration and was the principal supervisor for Sankar Rathinam. The synthesis work and the characterization were done by Sankar Rathinam (SR). The antimicrobial assay was done by SR, supervised by Martha Á. Hjálmarsdóttir (MAH). SR and MM prepared the manuscript, and all co-authors participated in interpreting the results and approved the final version. MM and MBT were responsible for funding. This work presents no conflict of interest for any of the authors. In summary: Conceptualization; MM, SR, Data curation; SR,MM, Formal analysis; SR, MM, Funding acquisition; MM, MBT Investigation; SR Methodology; SR,MM, MAH Project administration; MM Resources; MM, MAH, Software; MM, Supervision; MM, MAH Validation; MM, MAH, MBT, Visualization; SR Roles/Writing - original draft; SR, and Writing - review & editing, MM, MAH, MBT, SR. Publisher Copyright: © 2023 Elsevier Ltd

PY - 2023

Y1 - 2023

N2 - Partially substituted N,N,N-trimethyl chitosan (TMC), N-(2-(N,N,N-trimethylammoniumyl))acetyl chitosan (TAC), 2-hydroxy-3-(N,N,N-trimethylammoniumyl)propyl chitosan (HTC), N-(2-hydroxy)propyl chitosan (HPC), and N-carboxymethyl chitosan (CMC) were reacted with the diazo transfer reagent, imidazole-1-sulfonyl azide, to convert the 2-amino groups to azides. Subsequent reaction via copper-catalyzed azide-alkyne cycloaddition (CuAAC) with N-propargyl-N,N,N-trimethylammonium bromide provided water-soluble “mixed” chitotriazolan derivatives. The NMR data was generally consistent with the complete conversion of all primary amines in the polymer to triazole moieties, except in the case of TAC, where the conversion was ∼50 %. The mixed chitotriazolans derived from cationic TMC, TAC, and HTC and neutral HPC were active against Gram-positive S. aureus and E. faecalis and Gram-negative bacteria E. coli and P. aeruginosa, but chitotriazolans derived from anionic CMC were inactive.

AB - Partially substituted N,N,N-trimethyl chitosan (TMC), N-(2-(N,N,N-trimethylammoniumyl))acetyl chitosan (TAC), 2-hydroxy-3-(N,N,N-trimethylammoniumyl)propyl chitosan (HTC), N-(2-hydroxy)propyl chitosan (HPC), and N-carboxymethyl chitosan (CMC) were reacted with the diazo transfer reagent, imidazole-1-sulfonyl azide, to convert the 2-amino groups to azides. Subsequent reaction via copper-catalyzed azide-alkyne cycloaddition (CuAAC) with N-propargyl-N,N,N-trimethylammonium bromide provided water-soluble “mixed” chitotriazolan derivatives. The NMR data was generally consistent with the complete conversion of all primary amines in the polymer to triazole moieties, except in the case of TAC, where the conversion was ∼50 %. The mixed chitotriazolans derived from cationic TMC, TAC, and HTC and neutral HPC were active against Gram-positive S. aureus and E. faecalis and Gram-negative bacteria E. coli and P. aeruginosa, but chitotriazolans derived from anionic CMC were inactive.

KW - Antimicrobials

KW - Chitosan

KW - Chitotriazolan

KW - Click reaction

KW - TMC

U2 - 10.1016/j.eurpolymj.2023.112311

DO - 10.1016/j.eurpolymj.2023.112311

M3 - Journal article

AN - SCOPUS:85165369939

VL - 196

JO - European Polymer Journal

JF - European Polymer Journal

SN - 0014-3057

M1 - 112311

ER -