Mikrobiol. Z. 2020; 82(6):54-63.
doi: https://doi.org/10.15407/microbiolj82.06.054

Fungicidal and Bactericidal Activity of the Alkyl-Substituted Guanidine-Containing Oligomers

M.Ya. Vortman1, Yu.B. Pysmenna2, A.I. Chuenko2, D.R. Abdulina2, Zh.P. Kopteva2, A.E. Kopteva2,
A.V. Rudenko3, V.V.Tretyak3, V.N. Lemeshko1, V.V. Shevchenko1

1Institute of Macromolecular Chemistry, NAS of Ukraine
48 Kharkivske Highway, Kyiv, 02160, Ukraine

2Zabolotny Institute of Microbiology and Virology, NAS of Ukraine
154 Akad. Zabolotny Str., Kyiv, 03143, Ukraine

3Institute of Urology, NAMS of Ukraine
9A Vinnichenka Str., Kyiv, 04053, Ukraine

Biocides are widely used in medicine and various industries to protect against a number of harmful microorganisms. Organic quaternary ammonium and guanidine-containing compounds, the biological action of which is based on membrane-toxic properties, are used as bactericidal preparations. The aim of this work was to study the bactericidal and fungicidal activities of the synthesized oligomeric alkylsubstituted guanidinium bromides with different radicals -C3H7, -C7H15, -C10H21, against different isolates of heterotrophic bacteria and microscopic fungi. Methods. The synthesis of alkyl-substituted guanidiniumcontaining oligomers was performed in two stages. In the first stage, alkyl-substituted guanidine was obtained by the reaction of guanidine, previously converted by alkali from the salt form to the base form by the base and alkyl bromides (Alk=-C3H7 (propyl), -C7H15 (heptyl), -C10H21 (decyl)) in methanol at a temperature of 50°C and a molar ratio of 1:1. The second carried out the reaction between aromatic oligoepoxide DER-331 and alkyl-substituted guanidine in methanol at a temperature of 50°C for 2–3 hours and a molar ratio of 1:2. Bacteria were grown on meat-peptone agar for 48 hours at a temperature of 28±2°С. Test cultures of micromycetes were cultured on agar beer wort (6°B), incubated for 14 days in a thermostat at a temperature of 28±2°C. Antimicrobial activity of newly synthesized alkyl-substituted guanidinium-containing oligomers was determined by standard disco-diffusion method (method of disks on agar) and fungicidal activity was determined by the method of holes in agar. Results. Oligomeric alkylsubstituted guanidinium bromides with different radicals composed -C3H7, -C7H15, -C10H21- synthesized by the reaction of guanidine alkyl bromides with aromatic oligoepoxydes. It was found that alkyl-substituted guanidinium-containing oligomers at a concentration of 1–3% inhibited the growth of Escherichia coli 475, Pseudomonas aeruginosa 465, Klebsiella pneumonia 479, Pseudomonas pseudoalcaligenes 109, Staphylococcus aureus 451, E. faecalis 422, Rhodococcus erythropolis 102, Bacillus subtilis 138 and most of the studied micromycetes – Aureobasidium pullulans F-41430, Paecilomyces variotii F-41432, Penicillium funiculosum F-41435, Penicillium ochrochloron F-41431, Scopulariopsis brevicaulis F-41434, Trichoderma viride F-41437, Candida albicans F-41441, Aspergillus flavus F-41442, Aspergillus niger F-41448, Penicillium sp. F-41447. Conclusions. Antimicrobial and fungicidal properties significantly depend on the length of the alkyl radical, with increasing of its length the diameter of the zone of bacterial and micromycetes growth retardation increases.

Keywords: alkyl-substituted guanidinium-containing oligomers, heterotrophic bacteria, micromycetes, bactericidal and fungicidal activity.

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