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<p>A series of guanidinium (het)arylchalcogenylacetates, (Het)Ar-X-CH<sub>2</sub>COO<sup>−<b>.</b></sup> H<sub>2</sub><sup>+</sup>N = C[NH(R)]<sub>2</sub>, where X = O, S, SO<sub>2</sub>, was synthesized by the reaction of biologically active arylchalcogenylacetic acids with biogenic guanidines. The structure of these salts were established by FT-IR-, <sup>1</sup>H, <sup>13</sup>C NMR-spectroscopy, and X-ray single crystal diffraction analysis. In silico (SwissADME, PASS, and ProTox) calculations showed that synthesized salts possess bioavailability, synthetic accessibility, druglikeness (Lipinski rule) and can effectively inhibit the activity of specific enzymes (up to 89%). It was found that obtained compounds are harmless (LD<sub>50</sub> 500&#xa0;mg/kg). At the same time, with a probability up to 99%, they do not have hepato-, neuro-, immune-, cyto-toxicity, and mutagenicity. The effect of these salts on the growth of pathogenic bacteria: listeria (<i>Listeria monocytogenes</i>), staphylococci (<i>Staphylococcus aureus</i>), plague sticks (<i>Yersinia enterocolitica</i>, <i>Yersinia pseudotuberculosis</i>, <i>Yersinia pestis</i>), and the cholera vibrio (<i>Vibrio cholerae</i>) was studied in vitro. It was established that salts in high concentrations (400–200&#xa0;µg/cm<sup>3</sup>) exerted a slight inhibitory effect (up to 40–50%), however, in low concentrations (3.00–1.5&#xa0;µg/cm<sup>3</sup>) exhibited the high stimulating activity (up to 90%). The efficiency of obtained compounds depends on their composition and structure. Maximum activity is observed at X = S and SO<sub>2</sub>, universal activity is manifested at Ar = indolyl. Thus, cheap and available these salts can find application in biotech as biomass growth stimulators pathogenic bacteria for express diagnostics of dangerous diseases.</p> Graphical abstract <p></p>

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Design, synthesis, structure, and biological evaluation of guanidinium (het)arylchalcogenylacetates as growth inhibitors/stimulators of pathogenic bacteria

  • 期刊论文

  • 发表日期：

    2025年8月2日

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  • Sergey N. Adamovich,
  • Svetlana V. Lukyanova,
  • Elizaveta N. Oborina,
  • Igor A. Ushakov,
  • Natalia A. Voichenko,
  • Igor B. Rozentsveig

摘要

A series of guanidinium (het)arylchalcogenylacetates, (Het)Ar-X-CH2COO−. H2+N = C[NH(R)]2, where X = O, S, SO2, was synthesized by the reaction of biologically active arylchalcogenylacetic acids with biogenic guanidines. The structure of these salts were established by FT-IR-, 1H, 13C NMR-spectroscopy, and X-ray single crystal diffraction analysis. In silico (SwissADME, PASS, and ProTox) calculations showed that synthesized salts possess bioavailability, synthetic accessibility, druglikeness (Lipinski rule) and can effectively inhibit the activity of specific enzymes (up to 89%). It was found that obtained compounds are harmless (LD50 500 mg/kg). At the same time, with a probability up to 99%, they do not have hepato-, neuro-, immune-, cyto-toxicity, and mutagenicity. The effect of these salts on the growth of pathogenic bacteria: listeria (Listeria monocytogenes), staphylococci (Staphylococcus aureus), plague sticks (Yersinia enterocolitica, Yersinia pseudotuberculosis, Yersinia pestis), and the cholera vibrio (Vibrio cholerae) was studied in vitro. It was established that salts in high concentrations (400–200 µg/cm3) exerted a slight inhibitory effect (up to 40–50%), however, in low concentrations (3.00–1.5 µg/cm3) exhibited the high stimulating activity (up to 90%). The efficiency of obtained compounds depends on their composition and structure. Maximum activity is observed at X = S and SO2, universal activity is manifested at Ar = indolyl. Thus, cheap and available these salts can find application in biotech as biomass growth stimulators pathogenic bacteria for express diagnostics of dangerous diseases.

Graphical abstract