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In vitro antifungal activity of metal complexes of a quaternized chitosan derivative with copper ions

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Abstract

Antifungal activity of synthetic metal complexes of quaternized N-(propyl) chitosan derivatives with Сu(II) against yeastlike (Saccharomyces cereviseae, Rodothorula rubra, and Candida albicans) and mycelial fungi (Fusarium oxysporum, Alternaria alternata, Cladosporium herbarum) was studied. In vitro application (at 250‒500 μg/mL) of the metal complex of quaternized N-(propyl) derivative of low-molecular chitosan with 53% substitution and 1.3% copper ions proved efficient against F. оxysporum, one of ten most common fungal plant pathogens. Water-soluble quaternized N-(propyl) chitosan derivatives with 40−58% degree of substitution were synthesized using glycidyltrimethylammonium chloride under optimally adjusted conditions. Metal complexes of the chitosan derivative with 53% degree of substitution with Сu(II) ions were obtained by dialysis. The quantity of copper ions in the metal complexes was determined by atomic emission spectrometry. The structure of chitosan derivatives was confirmed by spectral analysis (IR, 1H NMR).

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References

  • Badawy, M.E.I. and Rabea, E.I., Synthesis and antifungal property of N-(aryl) and quaternary N-(aryl) chitosan derivatives against Botrytis cinerea, Cellulose, 2014, vol. 21, no. 4, pp. 3121–3137.

    Article  CAS  Google Scholar 

  • Badawy, M.E.I., Structure and antimicrobial activity relationship of quaternary N-alkyl chitosan derivatives against some plant pathogens, J. Appl. Polym. Sci., 2010, vol. 117, no. 2, pp. 960–969.

    Article  CAS  Google Scholar 

  • Bratskaya, S.Yu. and Pestov, A.V., Khelatiruyushchie proizvodnye khitozana (Chelating Chitosan Derivatives), Vladivostok: Dal’nauka, 2016.

    Google Scholar 

  • Cho, J., Grant, J., Piquette-Miller, M., and Allen, C., Synthesis and physicochemical and dynamic mechanical properties of a water-soluble chitosan derivative as a biomaterial, Biomacromol, 2006, vol. 7, no. 10, pp. 2845–2855.

    Article  CAS  Google Scholar 

  • de Oliveira Pedro, R., Takaki, M., Gorayeb, T.C., Bianchi, V.L., Thomeo, J.C., Tiera, M.J., and de Oliveira Tiera, V.A., Synthesis, characterization and antifungal activity of quaternary derivatives of chitosan on Aspergillus flavus, Microbiol. Res., 2013, vol. 168, no. 1, pp. 50–55.

    Article  PubMed  Google Scholar 

  • Guo, Z., Xing, R., Liu, S., Zhong, Z., Ji, X., Wang, L., and Li, P., The influence of the cationic of quaternized chitosan on antifungal activity, Int. J. Food Microbiol., 2007, vol. 118, no. 2, pp. 214–217.

    Article  CAS  PubMed  Google Scholar 

  • Il’ina, A.V., Kulikov, S.N., Chalenko, G.I., Gerasimova, N.G., and Varlamov, V.P., Obtaining and study of monosaccharide derivatives of low-molecularweight chitosan, Appl. Biochem. Microbiol., 2008, vol. 45, no. 5, pp. 551–558.

    Article  Google Scholar 

  • Kulikov, S.N., Khairullin, R.Z., Tyurin, Yu.A., Lisovskaya, S.A., Glushko, N.I., Levov, A.N., and Varlamov, V.P., Fungicidal activity of chitosan against mycelial fungi, Prakt. Med., 2010, no. 1 (40), pp. 119–120.

    Google Scholar 

  • Khaldeeva, E.V., Glushko, N.I., Lisovskaya, S.A., Parshakov, V.R., and Saifieva, O.V., Allergenic fungi in presentday dwellings, Prakt. Med., 2011, vol. 51, no. 3, pp. 122–124.

    Google Scholar 

  • Kulikov, S.N., Lisovskaya, S.A., Bezrodnykh, E.A., Zelenikhin, P.V., Shakirova, D.R., and Tikhonov, V.E., Antifungal activity of oligochitosans (short chain chitosans) against some Candida species and clinical isolates of C. albicans: molecular weight–activity relationship, Eur. J. Med. Chem., 2014, vol. 74, pp. 169–178.

    Article  CAS  PubMed  Google Scholar 

  • Kulikov, S.N., Nemtsev, S.V., Varlamov, V.P., Alimova, F.K., and Zakharova, N.G., Biological preparations with different mechanisms of action for protecting potato against fungal diseases, Appl. Biochem. Microbiol., 2006, vol. 42, no. 1, pp. 77–83.

    Article  CAS  Google Scholar 

  • Kulikov, S.N., Tyurin, Yu.A., Fassakhov, R.S., and Varlamov, V.P., Antibacterial and antifungal activity of chitosan: mechanisms of action and role of the structure, Zh. Mikrobiol. Epidemiol. Immunobiol., 2009, no. 5, pp. 91–98.

    Google Scholar 

  • Lisovskaya, S., Khaldeeva, E., Salmakova, A., and Kulikov, S.N., Evaluation of the influence of antifungal drugs on growth of Candida albicans in the biofilm, BioNanoScience, 2016, vol. 6, no. 4, p. 588–590.

    Article  Google Scholar 

  • Lun’kov, A.P., Shagdarova, B.Ts., and Il’ina, A.V., Synthesis of quaternized chitosan derivatives and investigation of their properties, Izv. Ufim. Nauch. Tsentr RAN, 2016, no. 3 (1), pp. 56–58.

    Google Scholar 

  • Mari, A., Schneider, P., Wally, V., Breitenbach, M, and Simon-Nobbe, B., Sensitization to fungi: epidemiology, comparative skin tests, and IgE reactivity of fungal extracts, Clin. Exp. Allergy, 2003, vol. 33, no. 10, pp. 1429–1438.

    Article  CAS  PubMed  Google Scholar 

  • Mekahlia, S. and Bouzid, B., Chitosan-copper (II) complex as antibacterial agent: synthesis, characterization and coordinating bond-activity correlation study, Phys. Procedia, 2009, vol. 2, no. 3, pp. 1045–1053.

    Article  CAS  Google Scholar 

  • Qin, C., Xiao, Q., Li, H., Fang, M., Liu, Y., Chen, X., and Li, Q. Calorimetric studies of the action of chitosan-N-2-hydroxypropyl trimethyl ammonium chloride on the growth of microorganisms, Int. J. Biol. Macromol., 2004, vol. 34, no. 1–2, pp. 121–126.

    Article  CAS  PubMed  Google Scholar 

  • Rahman, M.H., Hjeljord, L.G., Aam, B.B., Sørlie, M., and Tronsmo, A., Antifungal effect of chito-oligosaccharides with different degrees of polymerization, Eur. J. Plant. Pathol., 2015, vol. 141, no. 1, pp. 147–158.

    Article  CAS  Google Scholar 

  • Rahman, M.H., Shovan, L.R., Hjeljord, L.G., Aam, B.B., Eijsink, V.G.H., and Tronsmo, M.S.A., Inhibition of fungal plant pathogens by synergistic action of chito-oligosaccharides and commercially available fungicides, PLoS One, 2014, vol. 9, no. 4, e93192.

    Google Scholar 

  • Schmuhl, R., Krieg, H.M., and Keizer, K., Adsorption of Cu(II) and Cr(VI) ions by chitosan: kinetics and equilibrium studies, Water SA, 2001, vol. 27, no. 1, pp. 1–7.

    CAS  Google Scholar 

  • Seyfarth, F., Schliemann, S., Elsner, P., and Hipler, U.-C., Antifungal effect of high-and low-molecular-weight chitosan hydrochloride, carboxymethyl chitosan, chitosan oligosaccharide and N-acetyl-d-glucosamine against Candida albicans, Candida krusei and Candida glabrata, Int. J. Pharmaceut., 2008, vol. 353, no. 1–2, pp. 139–148.

    CAS  Google Scholar 

  • Shagdarova, B.Ts., Il’ina, A.V., and Varlamov, V.P., Antibacterial activity of alkylated and acylated derivatives of low-molecular weight chitosan, Appl. Biochem. Microbiol., 2016, vol. 52, no. 2, pp. 222–225.

    Article  CAS  Google Scholar 

  • Varma, A.J., Deshpande, S.V., and Kennedy, J.F., Metal complexation by chitosan and its derivatives: a review, Carbohydr. Polym., 2004, vol. 55, no. 1, pp. 77–93.

    Article  CAS  Google Scholar 

  • Xiao, B., Wan, Y., Wang, X., Zha, Q., Liu, H., Qiu, Z., and Zhang, S., Synthesis and characterization of N-(2-hydroxy)propyl-3-trimethyl ammonium chitosan chloride for potential application in gene delivery, Colloids Surf. B: Biointerfaces, 2012, vol. 91, pp. 168–174.

    Article  CAS  PubMed  Google Scholar 

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Authors and Affiliations

  1. Institute of Bioengineering, Research Center of Biotechnology Russian Academy of Sciences, Moscow, Russia

    A. V. Il’ina, B. Ts. Shagdarova, A. P. Lun’kov & V. P. Varlamov

  2. Dmitry Mendeleev University of Chemical Technology of Russia, Moscow, Russia

    A. P. Lun’kov

  3. Kazan Research Institute of Microbiology and Epidemiology, Kazan, Russia

    S. N. Kulikov

  4. Kazan Federal University, Kazan, Russia

    S. N. Kulikov

Authors
  1. A. V. Il’ina
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  2. B. Ts. Shagdarova
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  3. A. P. Lun’kov
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  4. S. N. Kulikov
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  5. V. P. Varlamov
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Corresponding author

Correspondence to B. Ts. Shagdarova.

Additional information

Original Russian Text © A.V. Il’ina, B.Ts. Shagdarova, A.P. Lun’kov, S.N. Kulikov, V.P. Varlamov, 2017, published in Mikrobiologiya, 2017, Vol. 86, No. 5, pp. 586–592.

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Il’ina, A.V., Shagdarova, B.T., Lun’kov, A.P. et al. In vitro antifungal activity of metal complexes of a quaternized chitosan derivative with copper ions. Microbiology 86, 590–595 (2017). https://doi.org/10.1134/S0026261717050101

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  • DOI: https://doi.org/10.1134/S0026261717050101

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