Abstract
Lactones are among the well-known organic substances with a specific taste and smell. They are characterized by antibacterial, antiviral, anti-inflammatory, and anti-cancer properties. In recent years, among this group of compounds, new biologically active substances have been searched by modifying the main (leading) structure with new analogs with stronger or different responses that may have a toxic effect on the cells of pathogenic bacteria and constitute an alternative to commonly used antibiotics. A preliminary study of δ-lactone derivatives as new potential candidates for antibacterial drugs was conducted. Particular emphasis was placed on the selection of the structure of lactones with the highest biological activity, especially those with fluorine in their structure as a substituent in terms of action on bacterial lipopolysaccharide (LPS) in the model strains of Escherichia coli K12 (without LPS in its structure) and R2–R4 (LPS of different lengths in its structure). In the presented studies, on the basis of the conducted MIC and MBC tests, it was shown that the antibacterial (toxic) activity of lactones depends on their structure and the length of the bacterial LPS in the membrane of specific strains. Moreover, oxidative damage of bacterial DNA isolated from bacteria after modification with newly synthesized compounds after application of the repair enzyme Fpg glycosylase was analyzed. The analyzed damage values were compared with the modification with appropriate antibiotics: ciprofloxacin, bleomycin, and cloxacillin. The presented research clearly shows that lactone derivatives can be potential candidates as substitutes for drugs, e.g., the analyzed antibiotics. Their chemical and biological activity is related to coumarin derivatives and the corresponding δ-lactone groups in the structure of the substituent. The observed results are of particular importance in the case of increasing bacterial resistance to various drugs and antibiotics, especially in nosocomial infections and neoplasms, and in the era of a microbial pandemic.
Highlights
Lactones are a group of cyclic esters formed as a result of intramolecular esterification of hydroxy acids (Figure 1)
The aim of the study is to analyze the potential antibacterial activity of lactones as potential antibiotics in terms of their structure, especially those containing fluorine as a substituent, in terms of cytotoxic effect on bacterial lipopolysaccharides (LPS) in model strains used in this type of research of Escherichia coli K12 and
In the analyzed lactones, which contain various types of substituents in their structure, we observed a significant increase in cytotoxicity in relation to the analyzed model strains of E. coli according to R2 < R3 < R4 orders differing in LPS length
Summary
Lactones are a group of cyclic esters formed as a result of intramolecular esterification of hydroxy acids (Figure 1). General structure of lactones A (depicted in Figure 1) shows the most important structural features of these molecules. Depending on the mutual position of the hydroxyl and carboxyl groups in the starting hydroxy acid, basic four types 4.0/). Materials 2021, 14, 2956 shows the most important structural features of these molecules. It is important to note the presence of endocyclic ester group in target structure (Figure 1) [1]. Depending on the mutual position of the hydroxyl and carboxyl groups in the starting hydroxy acid, basic of lactones distinguished: α, β, γ (structure δ (structure and ε (structure four types are of lactones are distinguished: α, β, B), γ
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