α-Amidoamids As New Replacements of Antibiotics-Research on the Chosen K12, R2-R4 Strains

Overview

Journal Materials (Basel)

Publisher MDPI

Date 2020 Nov 19

PMID 33207799

Citations 20

Authors

Pawel Kowalczyk

Arleta Madej

Mateusz Szymczak

Ryszard Ostaszewski

Affiliations

Soon will be listed here.

Abstract

A preliminary study of α-amidoamids as new potential antimicrobial drugs was performed. Special emphasis was placed on selection of structure of α-amidoamids with the highest biological activity against different types of Gram-stained bacteria by lipopolysaccharide (LPS). Herein, model strains K12 (without LPS in its structure) and R1-R4 (with different length LPS in its structure) were used. The presented work showed that the antibacterial activity of α-amidoamids depends on their structure and affects the LPS of bacteria. Moreover, the influence of various newly synthesized α-amidoamids on bacteria possessing smooth and rought LPS and oxidative damage of plasmid DNA caused by all newly obtained compounds was indicated. The presented studies clearly explain that α-amidoamids can be used as substitutes for antibiotics. The chemical and biological activity of the analysed α-amidoamids was associated with short alkyl chain and different isocyanides molecules in their structure such as: -butyl isocyanide or 2,5-dimethoxybenzyl isocyanide. The observed results are especially important in the case of the increasing resistance of bacteria to various drugs and antibiotics.

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References

Nair J, Barbin A, Velic I, Bartsch H . Etheno DNA-base adducts from endogenous reactive species. Mutat Res. 1999; 424(1-2):59-69. DOI: 10.1016/s0027-5107(99)00008-1. View

von Minckwitz G, Procter M, de Azambuja E, Zardavas D, Benyunes M, Viale G . Adjuvant Pertuzumab and Trastuzumab in Early HER2-Positive Breast Cancer. N Engl J Med. 2017; 377(2):122-131. PMC: 5538020. DOI: 10.1056/NEJMoa1703643. View

Tchou J, Bodepudi V, Shibutani S, Antoshechkin I, Miller J, Grollman A . Substrate specificity of Fpg protein. Recognition and cleavage of oxidatively damaged DNA. J Biol Chem. 1994; 269(21):15318-24. View

Domling A, Wang W, Wang K . Chemistry and biology of multicomponent reactions. Chem Rev. 2012; 112(6):3083-135. PMC: 3712876. DOI: 10.1021/cr100233r. View

Czene S, Harms-Ringdahl M . Detection of single-strand breaks and formamidopyrimidine-DNA glycosylase-sensitive sites in DNA of cultured human fibroblasts. Mutat Res. 1995; 336(3):235-42. DOI: 10.1016/0921-8777(94)00058-e. View

Kohanski M, Dwyer D, Collins J . How antibiotics kill bacteria: from targets to networks. Nat Rev Microbiol. 2010; 8(6):423-35. PMC: 2896384. DOI: 10.1038/nrmicro2333. View

Jurado J, Saparbaev M, Matray T, Greenberg M, Laval J . The ring fragmentation product of thymidine C5-hydrate when present in DNA is repaired by the Escherichia coli Fpg and Nth proteins. Biochemistry. 1998; 37(21):7757-63. DOI: 10.1021/bi972982z. View

Tchou J, Kasai H, Shibutani S, Chung M, Laval J, Grollman A . 8-oxoguanine (8-hydroxyguanine) DNA glycosylase and its substrate specificity. Proc Natl Acad Sci U S A. 1991; 88(11):4690-4. PMC: 51731. DOI: 10.1073/pnas.88.11.4690. View

Zadlo-Dobrowolska A, Klossowski S, Koszelewski D, Paprocki D, Ostaszewski R . Enzymatic Ugi Reaction with Amines and Cyclic Imines. Chemistry. 2016; 22(46):16684-16689. DOI: 10.1002/chem.201603412. View

10.

Sidorkina O, Laval J . Role of lysine-57 in the catalytic activities of Escherichia coli formamidopyrimidine-DNA glycosylase (Fpg protein). Nucleic Acids Res. 1998; 26(23):5351-7. PMC: 148015. DOI: 10.1093/nar/26.23.5351. View

11.

Hartwig A, Dally H, Schlepegrell R . Sensitive analysis of oxidative DNA damage in mammalian cells: use of the bacterial Fpg protein in combination with alkaline unwinding. Toxicol Lett. 1996; 88(1-3):85-90. DOI: 10.1016/0378-4274(96)03722-8. View

12.

Zhao H, Neamati N, Hong H, Mazumder A, Wang S, Sunder S . Coumarin-based inhibitors of HIV integrase. J Med Chem. 1997; 40(2):242-9. DOI: 10.1021/jm960450v. View

13.

Rabow L, Kow Y . Mechanism of action of base release by Escherichia coli Fpg protein: role of lysine 155 in catalysis. Biochemistry. 1997; 36(16):5084-96. DOI: 10.1021/bi963005a. View

14.

Klossowski S, Muchowicz A, Firczuk M, Swiech M, Redzej A, Golab J . Studies toward novel peptidomimetic inhibitors of thioredoxin-thioredoxin reductase system. J Med Chem. 2011; 55(1):55-67. DOI: 10.1021/jm201359d. View

15.

Gedey S, Van der Eycken J, Fulop F . Liquid-phase combinatorial synthesis of alicyclic beta-lactams via Ugi four-component reaction. Org Lett. 2002; 4(11):1967-9. DOI: 10.1021/ol025986r. View

16.

Zhang J, Jacobson A, Rusche J, Herlihy W . Unique Structures Generated by Ugi 3CC Reactions Using Bifunctional Starting Materials Containing Aldehyde and Carboxylic Acid. J Org Chem. 2001; 64(3):1074-1076. DOI: 10.1021/jo982192a. View

17.

Cussac C, Laval F . Reduction of the toxicity and mutagenicity of aziridine in mammalian cells harboring the Escherichia coli fpg gene. Nucleic Acids Res. 1996; 24(9):1742-6. PMC: 145839. DOI: 10.1093/nar/24.9.1742. View

18.

Appelmelk B, An Y, Hekker T, Thijs L, MACLAREN D, de Graaf J . Frequencies of lipopolysaccharide core types in Escherichia coli strains from bacteraemic patients. Microbiology (Reading). 1994; 140 ( Pt 5):1119-24. DOI: 10.1099/13500872-140-5-1119. View

19.

Saparbaev M, Sidorkina O, Jurado J, Privezentzev C, Greenberg M, Laval J . Repair of oxidized purines and damaged pyrimidines by E. coli Fpg protein: different roles of proline 2 and lysine 57 residues. Environ Mol Mutagen. 2002; 39(1):10-7. DOI: 10.1002/em.10041. View

20.

Tsetlin V . Snake venom alpha-neurotoxins and other 'three-finger' proteins. Eur J Biochem. 1999; 264(2):281-6. DOI: 10.1046/j.1432-1327.1999.00623.x. View