Study of the antimicrobial activity of ethyl S-ester of 4-acetylaminobenzenethiosulfonic acid
Abstract
S-alkyl esters of thiosulfonic acids (R-S(O)2S-R') are structural analogs of natural sulfur-containing substances and have a broad spectrum of biological activity. The results of studying the sensitivity of microorganisms to ethyl S-ester of 4-acetylamino benzenethiosulfonic acid obtained using new “green” methods, particularly environmentally safe reactions under the influence of ultrasound, are presented. It was established that the studied substance's antimicrobial activity changed with a change in the m e dium's pH. In particular, with a decrease in the pH of the medium from 7.0 to 5.2 units, the minimum inhibitory concentration of the studied substance also decreased. Thus, the minimum inhibitory concentrations of ethyl ester of thiosulfonic acid against S taphylococcus aureus ATCC 6538 and E nterococcus faecalis IMB B-7497 decreased from 62.5 to 31.2 μg/cm 3 , and A lcal i genes faecalis GISK 242484 – LI 415 from 62.5 to – 15.6 μg/cm 3 . It is also necessary to note the decrease in the minimum inhib i tory concentration of ethyl S-ester of 4-acetylaminobenzenethiosulfonic acid against isolates of E nterobacter сloacae and P se u domonas aeruginosa , respectively, from 250 and 500 to 62.5 and 125 μg/cm 3 . At a pH of 8.8 units, the minimum inhibitory concentration of the tested substance increased, compared to pH of 7.0 and 5.2 units. In particular, it was found that the min i mum inhibitory concentration against S. aureus ATCC 6538 was 250 μg/cm 3 , while at pH values of the medium of 5.2 and 8.8 units, respectively, it was 31.2 and 15.6 μg/cm 3 . In addition, the minimum inhibitory concentration against S almonella typhim u rium 144, E. faecalis IMB B-7497, A. faecalis GISK 242484 – LI 415, and S erratia marcescens 1 was 250 μg/cm 3 , while at pH values of the medium of 5.2 and 8.0 units, the MICs were lower. The sensitivity of gram-positive microorganisms to ethyl ester of thiosulfonic acid, in particular, S. aureus ATCC 6538 and E. faecalis IMB B-7497, with a decrease in the pH of the medium to the weakly acidic side , increased from 5.4 % to 7.1%, and in the weakly alkaline, on the contrary, decreased by 3.8%. The sens i tivity of gram-negative microorganisms, in particular, E scherichia coli ATCC 25922, S. typhimurium 144, P. aeru ginosa , E. сloacae , A. faecalis GISK 242484 – LI 415, S. marcescens 1, with a decrease in the pH of the medium to the weakly acidic side , increased from 2.3 % to 12.2%, and in the weakly alkaline medium decreased from 1.5 % to 18.2%.References
Bolibrukh, K., Polovkovych, S., Khoumeri, O., Halenova, T., Nikolaeva, I., Savchuk, O., Terme, T., Vanelle, P., Lubenets, V., & Novikov, V. (2015). Synthesis and anti-platelet activity of thiosulfonate derivatives containing a quinone moiety. Scientia Pharmaceutica, 83(2), 221–231.
Boucher, H. W., Talbot, G. H., Bradley, J. S., Edwards, J. E., Gilbert, D., Rice, L. B., Scheld, M., Spellberg, B., & Bartlett, J. (2009). Bad bugs, no drugs: No ESKAPE! An update from the Infectious Diseases Society of America. Clinical Infectious Diseases, 48(1), 1–12.
Breijyeh, Z., Jubeh, B., & Karaman, R. (2020). Resistance of Gram-negative bacteria to current antibacterial agents and approaches to resolve it. Molecules, 25(6), 1340.
Briggs, W. H., Xiao, H., Parkin, K. L., Shen, C., & Goldman, I. L. (2000). Differential inhibition of human platelet aggregation by selected Allium thiosulfinates. Journal of Agricultural and Food Chemistry, 48(11), 5731–5735.
Dmitryjuk, M., Szczotko, M., Kubiak, K., Trojanowicz, R., Parashchyn, Z., Khomitska, H., & Lubenets, V. (2020). S-methyl-(2-methoxycarbonylamino-benzimidazole-5) thiosulfonate as a potential antiparasitic agent – its action on the development of Ascaris suum eggs in vitro. Pharmaceuticals, 13(11), 332.
El Bcheraoui, C., Mokdad, A. H., Dwyer-Lindgren, L., Bertozzi-Villa, A., Stubbs, R. W., Morozoff, C., Shirude, S., Naghavi, M., & Murray, C. J. L. (2018). Trends and patterns of differences in infectious disease mortality among US counties, 1980–2014. Journal of the American Medical Association, 319(12), 1248–1260.
Gu, X., Wu, H., & Fu, P. (2013). Allicin attenuates inflammation and suppresses HLA-B27 protein expression in ankylosing spondylitis mice. BioMed Research International, 2013, 171573.
Guillamón, E., Mut-Salud, N., Rodríguez-Sojo, M. J., Ruiz-Malagón, A. J., Cuberos-Escobar, A., Martínez-Férez, A., Rodríguez-Nogales, A., Gálvez, J., & Baños, A. (2023). In vitro antitumor and anti-inflammatory activities of allium-derived compounds propyl propane thiosulfonate (PTSO) and propyl propane thiosulfinate (PTS). Nutrients, 15(6), 1363.
Haase, H., Hieke, N., Plum, L. M., Gruhlke, M. C., Slusarenko, A. J., & Rink, L. (2012). Impact of allicin on macrophage activity. Food Chemistry, 134(1), 141–148.
Halenova, T. I., Nikolaeva, I. V., Nakonechna, A. V., Bolibrukh, K. B., Monka, N. Y., Lubenets, V. I., & Ostapchenko, L. I. (2015). The search of compounds with antiaggregation activity among S-esters of thiosulfonic acids. The Ukrainian Biochemical Journal, 87(5), 83–92.
Halenova, T. I., Nikolaeva, I. V., Stasevych, M. V., Zvarych, V. I., Lunin, V. V., Novikov, V. P., & Savchuk, O. M. (2017). Platelet aggregation under the influence of some dithiocarbamate derivatives of 9,10-anthracenedione. Research Journal of Pharmaceutical, Biological and Chemical Sciences, 8, 1626–1632.
Heydari, S., Habibi, D., & Faraji, A. A. (2022). Green and efficient solventand catalyst-free ultrasonic dibenzylation procedure. Chemistry and Chemical Technology, 16(1), 126–132.
Isko, O. Y., & Sychov, M. Y. (2022). Vplyv riznykh rivniv chasnyka (Allium sativum) na pokaznyky zaboyu molodnyaka kroliv [The influence of different levels of garlic (Allium sativum) on slaughter indicators of young rabbits]. Tavriiskyi Naukovyi Visnyk Silskohospodarskoyi Nauky, 128, 251–256 (in Ukrainian).
Khaytovych, M. V., & Polyakova, D. S. (2023). Antymikrobna rezystentnistʹ ta orhanizatsiyni pytannya administruvannya antymikrobnykh preparativ v Ukrayini [Antimicrobial resistance and organizational issues of antimicrobial drug administration in Ukraine]. Ukrainskyi Medychnyi Chasopys, 153(1), 5–9 (in Ukrainian).
Liubas, N., Iskra, R., Stadnytska, N., Monka N., Havryliak, V., & Lubenets, V. (2022). Antioxidant activity of thiosulfonate compounds in experiments in vitro and in vivo. Biointerface Research in Applied Chemistry, 12(3), 3106–3116.
Lubenets, V., Karpenko, O., Ponomarenko, M., Zahoriy, G., Krychkovska, A., & Novikov, V. (2013). Development of new antimicrobial compositions of thiosulfonate structure. Chemistry and Chemical Technology, 7(2), 119–124.
Lubenets, V., Vasylyuk, S., Monka, N., Bolibrukh, K., Komarovska-Porokhnyavets, O., Baranovych, D., Musyanovych, R., Zaczynska, E., Czarny, A., Nawrot, U., & Novikov, V. (2017). Synthesis and antimicrobial properties of 4-acylaminobenzenethiosulfoacid S-esters. Saudi Pharmaceutical Journal, 25(2), 266–274.
Martini, H., & Passos, J. F. (2023). Cellular senescence: all roads lead to mitochondria. The FEBS Journal, 290(5), 1186–1202.
Martirosyan, I., Pakholiuk, E., Lubenets, V., Komarovska-Porokhnyavets, O., Monka, N., Nakonechna, A., Peredriy, O., & Lutskova, V. (2021). Innovative approach to the creation of textile materials with antimicrobial properties. Science and Innovation, 17(3), 56–66.
Martirosyan, I., Pakholiuk, O., Golodyuk, G., Lutskova, V., & Lubenets, V. (2022). Investigation of antimicrobial properties of textile materials after washing. Fibres and Textiles, 29(1), 28–35.
Martyrosian, I. A., Pakholiuk, O. V., Semak, B. D., Komarovska-Porokhniavets, O. Z., Lubenets, V. I., & Pambuk, S. A. (2019). New technologies of effective protection of textiles against microbiological damage. Nanosistemy, Nanomateriali, Nanotehnologii, 17(4), 621–636.
Patya, M., Zahalka, M. A., Vanichkin, A., Rabinkov, A., Miron, T., Mirelman, D., Wilchek, M., Lander, H. M., & Novogrodsky, A. (2004). Allicin stimulates lymphocytes and elicits an antitumor effect: A possible role of p21ras. International Immunology, 16(2), 275–281.
Pham, H. T., Nguyen, N. T., Duus, F., & Luu, T. X. T. (2015). Ultrasound-accelerated synthesis of asymmetrical thiosulfonate S-esters by base-promoted reaction of sulfonyl chlorides with thiols. Phosphorus, Sulfur, and Silicon and the Related Elements, 190(11), 1934–1941.
Prager-Khoutorsky, M., Goncharov, I., Rabinkov, A., Mirelman, D., Geiger, B., & Bershadsky, A. D. (2007). Allicin inhibits cell polarization, migration and division via its direct effect on microtubules. Cell Motility and the Cytoskeleton, 64(5), 321–337.
Salmanov, A. H., Shchehlov, D. V., Artomenko, V. V., Mamonova, M. Y., & Ushkalov, V. O. (2022). Strymuvannia antymikrobnoyi rezystentnosti na pidkhodakh “Yedyne zdorovia” [Suppression of antimicrobial resistance in the “One health” approach]. AhrarMediaHrup, Kyiv (in Ukrainian).
Sela, U., Ganor, S., Hecht, I., Brill, A., Miron, T., Rabinkov, A., Wilchek, M., Mirelman, D., Lider, O., & Hershkoviz, R. (2004). Allicin inhibits SDF-1alphainduced T cell interactions with fibronectin and endothelial cells by downregulating cytoskeleton rearrangement, Pyk-2 phosphorylation and VLA-4 expression. Immunology, 111(4), 391–399.
Vasylyuk, S. V., Shyyan, H. B., Monka, N. Y., Shyyan, A. V., & Lubenets, V. I. (2018). Syntez tiosulfoesteriv iz sym-tryazynovym frahmentom [Synthesis of thiosulfoesters with a sym-tryazine fragment]. Chemistry, Technology and Application of Substances, 2(1), 98–104 (in Ukrainian).
Yip, J., Shen, Y., Berndt, M. C., & Andrews, R. K. (2005). Primary platelet adhesion receptors. IUBMB Life, 57(2), 103–108.
Zaczynska, E., Czarny, A., Karpenko, О., Vasylyuk, S., Monka, N., Stadnytska, N., Fizer, L., Komarovska-Porokhnyavets, O., Jaranowski, M., Lubenets, V., & Zimecki, M. (2023). Obtaining and determining antiviral and antibacterial activity of S-esters of 4-r-aminobenzenethiosulfonic acid. Chemistry and Chemical Technology, 17(2), 315–324.
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