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10.3390/ma14185401
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Article

Pyridine Derivatives—A New Class of Compounds That Are Toxic to E. coli K12, R2–R4 Strains

by
Dominik Koszelewski
1,
Ryszard Ostaszewski
1,
Paweł Śmigielski
1,
Anastasiia Hrunyk
1,
Karol Kramkowski
2,
Łukasz Laskowski
3,
Magdalena Laskowska
3,
Rafał Lizut
4,
Mateusz Szymczak
5,
Jacek Michalski
6,
Kamil Gawin
6 and
Paweł Kowalczyk
6,*
1
Institute of Organic Chemistry PAS, Kasprzaka 44/52, 01-224 Warsaw, Poland
2
Department of Physical Chemistry, Medical University of Bialystok, Kilińskiego 1 Str., 15-089 Białystok, Poland
3
Institute of Nuclear Physics Polish Academy of Sciences, 31-342 Krakow, Poland
4
The John Paul II Catholic University of Lublin, Institute of Mathematics, Informatics and Landscape Architecture ul. Konstantynów 1 H, 20-708 Lublin, Poland
5
Department of Molecular Virology, Institute of Microbiology, Faculty of Biology, University of Warsaw, Miecznikowa 1, 02-096 Warsaw, Poland
6
Department of Animal Nutrition, The Kielanowski Institute of Animal Physiology and Nutrition, Polish Academy of Sciences, 05-110 Jabłonna, Poland
*
Author to whom correspondence should be addressed.
Materials 2021, 14(18), 5401; https://doi.org/10.3390/ma14185401
Submission received: 17 July 2021 / Revised: 15 September 2021 / Accepted: 16 September 2021 / Published: 18 September 2021
(This article belongs to the Special Issue Analysis of Peptidomimetic Toxicity in E. coli Bacterial Cells—Studies on Selected Strains)
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Abstract

A preliminary study of 2-amino-4-aryl-3,5-dicarbonitrile-6-thiopyridines as new potential antimicrobial drugs was performed. Special emphasis was placed on the selection of the structure of target pyridine derivatives with the highest biological activity against different types of Gram-stained bacteria by lipopolysaccharide (LPS). Herein, Escherichia coli model strains K12 (without LPS in its structure) and R2–R4 (with different lengths of LPS in its structure) were used. Studied target compounds were provided with yields ranging from 53% to 91% by the lipase-catalyzed one pot multicomponent reaction of various aromatic aldehydes with malononitrile, and thiols. The presented work showed that the antibacterial activity of the studied pyridines depends on their structure and affects the LPS of bacteria. Moreover, the influence of the pyridines on bacteria possessing smooth and rough LPS and oxidative damage to plasmid DNA caused by investigated compounds was indicated. Additionally, the modification of the bacterial DNA with the tested compounds was performed to detect new potential oxidative damages, which are recognized by the Fpg protein. The obtained damage modification values of the analyzed compounds were compared with the modifications after antibiotics were used in this type of research. The presented studies demonstrate that 2-amino-4-aryl-3,5-dicarbonitrile-6-thiopyridines can be used as substitutes for known antibiotics. The observed results are especially important in the case of the increasing resistance of bacteria to various drugs and antibiotics.
Keywords: pyridine derivatives; E. coli strains; oxidative stress; antibiotics; lipopolysaccharide pyridine derivatives; E. coli strains; oxidative stress; antibiotics; lipopolysaccharide

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MDPI and ACS Style

Koszelewski, D.; Ostaszewski, R.; Śmigielski, P.; Hrunyk, A.; Kramkowski, K.; Laskowski, Ł.; Laskowska, M.; Lizut, R.; Szymczak, M.; Michalski, J.; et al. Pyridine Derivatives—A New Class of Compounds That Are Toxic to E. coli K12, R2–R4 Strains. Materials 2021, 14, 5401. https://doi.org/10.3390/ma14185401

AMA Style

Koszelewski D, Ostaszewski R, Śmigielski P, Hrunyk A, Kramkowski K, Laskowski Ł, Laskowska M, Lizut R, Szymczak M, Michalski J, et al. Pyridine Derivatives—A New Class of Compounds That Are Toxic to E. coli K12, R2–R4 Strains. Materials. 2021; 14(18):5401. https://doi.org/10.3390/ma14185401

Chicago/Turabian Style

Koszelewski, Dominik, Ryszard Ostaszewski, Paweł Śmigielski, Anastasiia Hrunyk, Karol Kramkowski, Łukasz Laskowski, Magdalena Laskowska, Rafał Lizut, Mateusz Szymczak, Jacek Michalski, and et al. 2021. "Pyridine Derivatives—A New Class of Compounds That Are Toxic to E. coli K12, R2–R4 Strains" Materials 14, no. 18: 5401. https://doi.org/10.3390/ma14185401

APA Style

Koszelewski, D., Ostaszewski, R., Śmigielski, P., Hrunyk, A., Kramkowski, K., Laskowski, Ł., Laskowska, M., Lizut, R., Szymczak, M., Michalski, J., Gawin, K., & Kowalczyk, P. (2021). Pyridine Derivatives—A New Class of Compounds That Are Toxic to E. coli K12, R2–R4 Strains. Materials, 14(18), 5401. https://doi.org/10.3390/ma14185401

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