Studies of new biocidal polyguanidines: antibacterial action and toxicity

Стельмах, С А; Grigor’eva, M. N.; Garkusheva, N. M.; Лебедева, С. Н.; Ochirov, O. S.; Могнонов, Д. М.; Жамсаранова, С. Д.; Batoev, Valeriy

doi:10.1007/s00289-020-03197-1

Cited by 6 publications

(7 citation statements)

References 9 publications

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“…This difference may be attributed to differences in the cell wall structures and to the different defense mechanisms of the two bacteria types. Also compared with Gram-negative bacteria, the cell wall of Gram-positive bacteria has a higher content of teichoic acids, which bind to the guanidine units. , …”

Section: Resultsmentioning

confidence: 99%

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Optimizing the Bacteriostatic and Cytocompatibility Properties of Poly(hexamethylene guanidine) Hydrochloride (PHMG) via the Guanidine/Alkane Ratio

Rao

Wang

et al. 2022

Biomacromolecules

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The emergence of “superbugs” is not only problematic and potentially lethal for infected subjects but also poses serious challenges for the healthcare system. Although existing antibacterial agents have been effective in some cases, the side effects and biocompatibility generally present difficulties. The development of new antibacterial agents is therefore urgently required. In this work, we have adapted a strategy for the improvement of poly(hexamethylene guanidine) hydrochloride (PHMG), a common antibacterial agent. This involves copolymerization of separate monomer units in varying ratios to find the optimum ratio of the hydrocarbon to guanidine units for antibacterial activity. A series of these copolymers, designated as PGB, was synthesized. By varying the guanidine/hydrophobic ratio and the copolymer molecular weight, a structure-optimized PGB was identified that showed broad-spectrum antibacterial activity and excellent biocompatibility in solution. In an antibacterial assay, the copolymer with the optimum composition (hydrophobic unit content 25%) inhibited >99% Staphylococcus aureus and was compatible with mammalian cells. A polyurethane emulsion containing this PGB component formed transparent, flexible films (PGB-PU films) on a wide range of substrate surfaces, including soft polymers and metals. The PGB-PU films showed excellent bacteriostatic efficiency against nosocomial drug-resistant bacteria, such as Pseudomonas aeruginosa and methicillin-resistant S. aureus (MRSA). It is concluded that our PGB polymers can be used as bacteriostatic agents generally and in particular for the design of antibacterial surfaces in medical devices.

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Section: Resultsmentioning

confidence: 99%

“…Also compared with Gram-negative bacteria, the cell wall of Gram-positive bacteria has a higher content of teichoic acids, which bind to the guanidine units. 32,33 3.4. Preparation and Characterization of PGB-PU Films.…”

Section: Hemolytic Activitymentioning

confidence: 99%

Optimizing the Bacteriostatic and Cytocompatibility Properties of Poly(hexamethylene guanidine) Hydrochloride (PHMG) via the Guanidine/Alkane Ratio

Rao

Wang

et al. 2022

Biomacromolecules

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“…Полигексаметиленгуанидин гидрохло рид (ПГМГгх) и его N-фенил-и N-октилзамещенные производные были синтезированы и исследованы с помощью методов, описанных в работе [7].…”

Section: материалы и методыunclassified

“…Так, ранее были проведены работы по синтезу новых производных ПГМГгх [7] для получения эффективных и безопасных антимикробных агентов. Проведенные работы показали, что наиболее чувствительными ко всем представленным препаратам являются дрожжеподобные грибы Candida albicans (полное угнетение), а также метициллин-резистентный S. aureus, причем замещенные образцы практически полностью подавляли его рост.…”

Section: результаты и обсуждениеunclassified

Antimicrobial activity of polyhexamethylene guanidine hydrochloride derivatives against multiresistant microbial strains

Ochirov

Бурасова

Стельмах

et al. 2021

Russian Journal of Infection and Immunity

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The resistance of bacteria to the disinfectants used is one of the pressing health problems that need to be addressed in order to prevent the formation and spread of resistant strains. This leads to a sharp decrease in the effectiveness of anti-epidemic measures and contributes to maintaining a high level of morbidity. In the context of the growing incidence of HAIs, their polyetiology, the large adaptive potential of opportunistic microorganisms, and the growing resistance to antimicrobial drugs, it is necessary to search for new or modify the corresponding substances of plant or synthetic origin that have antimicrobial action and are used as antimicrobial agents. One of the representatives of this class of compounds are polyguanidines, characterized by high antimicrobial activity and low toxicity. Due to the high reactivity of the guanidine group, as well as the ease of synthesis and the relative availability of raw materials, N-phenyl- and N-octyl-substituted derivatives of polyhexamethylene guanidine hydrochloride were obtained by melt polycondensation, their molecular weight characteristics were determined, and the structure was investigated by IR spectroscopy. An earlier study of the acute toxicity of polyhexamethylene guanidine hydrochloride derivatives after a single oral intake of drugs into the body of laboratory animals (white mice) made it possible to establish the following LD50 values: polyhexamethylene guanidine hydrochloride - 850.0 ± 112.02 mg / kg; N-phenyl-substituted polyhexamethylene guanidine hydrochloride - 1399.9 ± 120.51 mg / kg; N-octyl-substituted polyhexamethylene guanidine hydrochloride - 1150.0 ± 137.40 mg / kg. The obtained values, according to the tabulation of hazard classes, allow the synthesized derivatives to be classified into the fourth hazard class and open up the possibility of using disinfectants as active components. The evaluation of the antibacterial properties of the samples was carried out by the method of serial dilutions in agar on hospital strains of bacteria and fungi isolated from the biomaterial of patients of the Republican Clinical Hospital named after N.A. Semashko, according to the clinical guidelines "Laboratory diagnosis of community-acquired pneumonia" 2014; "Bacteriological analysis of urine" 2014; "Determination of the susceptibility of microorganisms to antimicrobial drugs" 2015 It was found that N-substituted derivatives exhibit a greater antimicrobial effect in comparison with an unsubstituted polymer. The most sensitive to all the drugs presented are the yeast-like fungi Candida albicans (No. 2495) (complete suppression), as well as methicillin-resistant St. aureus (no. 2544), and the substituted samples almost completely suppress its growth. The most resistant strains are P. aeruginosa (No. 2281), A. Baumannii (No. 2806) and K. Pneumoniae (No. 3023), the percentage of reduction of these bacteria under the action of substituted samples does not exceed 41%, which is explained by their multi-resistance.

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“…Surprisingly, the approach for obtaining water-soluble biocides via radical polymerization of guanidine-containing vinyl monomers has not become as widespread as the classical polycondensation and melt-mixing methods, described, e.g., in [ 9 , 10 ]. This is mostly due to the prevalence of biocide polyhexamethyleneguanidine (PHMG), which is easily synthesized from guanidine salts and hexamethylenediamine (in melt, via microfluidic methods [ 11 ], etc.).…”

Section: Introductionmentioning

confidence: 99%

Cyclic Methacrylate Tetrahydropyrimidinones: Synthesis, Properties, (Co)Polymerization

et al. 2021

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During radical polymerization of novel biocidal methacrylate guanidine monomers, a cyclic byproduct was discovered and identified as 2-imino-5-methyltetrahydropyrimidin-4(1H)-one (THP). Its methacrylate salt (MTHP) was synthesized and characterized via 1H and 13C NMR and pyrolysis chromatography. Synthesis conditions of both THP and MTHP were optimized to high yields, and both MTHP homopolymerization (in aqua) and copolymerization with diallyldimethylammonium chloride (in aqua in salt form) were successfully carried out with middle to high yields, providing a promising platform for potential tailored biocide polymers.

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Studies of new biocidal polyguanidines: antibacterial action and toxicity

Cited by 6 publications

References 9 publications

Optimizing the Bacteriostatic and Cytocompatibility Properties of Poly(hexamethylene guanidine) Hydrochloride (PHMG) via the Guanidine/Alkane Ratio

Optimizing the Bacteriostatic and Cytocompatibility Properties of Poly(hexamethylene guanidine) Hydrochloride (PHMG) via the Guanidine/Alkane Ratio

Antimicrobial activity of polyhexamethylene guanidine hydrochloride derivatives against multiresistant microbial strains

Cyclic Methacrylate Tetrahydropyrimidinones: Synthesis, Properties, (Co)Polymerization

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