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Features of Synthesis and Antimicrobial Properties of Guanidine-Containing Carboxymethylcellulose Derivatives

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Abstract

The article presents data on the synthesis and antimicrobial properties of guanidine-containing carboxymethylcellulose derivatives with different physical and chemical characteristics. The regularities of the reaction of nucleophilic substitution of the aldehyde groups of modified Na-carboxymethylcellulose (Na-CMC) by guanidine under different conditions have been studied. It has been found that the maximal replacement of reactive electrophilic groups by nucleophilic reagent depends on the pH value of the medium, molar ratio of guanidine, and the degree of oxidation of cellulose ester. The azomethine derivatives with different content of nitrogen-containing fragments in the polymer chain have been synthesized by varying the reaction conditions and the number of aldehyde groups in oxidized Na-CMC. Chemical reduction of labile azomethine bonds has led to water-soluble derivatives that contain strong amino-bound guanidine groups. The study shows and substantiates the influence of structural parameters (degree of substitution, quantitative guanidine content, pKα values, and nature of counterions) of macromolecular systems on antibacterial and antifungal properties. The developed approach to the synthesis opens up prospects for the creation of antimicrobial derivatives with regulated physical and chemical characteristics and specified biologically active properties.

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Authors and Affiliations

  1. Institute of Bioorganic Chemistry, Uzbek Academy of Sciences, 100125, Tashkent, Uzbekistan

    O. R. Akhmedov, Sh. A. Shomurotov & A. S. Turaev

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  1. O. R. Akhmedov
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  2. Sh. A. Shomurotov
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  3. A. S. Turaev
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Correspondence to O. R. Akhmedov.

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Translated by A. Levina

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Akhmedov, O.R., Shomurotov, S.A. & Turaev, A.S. Features of Synthesis and Antimicrobial Properties of Guanidine-Containing Carboxymethylcellulose Derivatives. Russ J Bioorg Chem 48, 1379–1386 (2022). https://doi.org/10.1134/S1068162022070020

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