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. 2024 Feb 9;9(7):7910-7922.
doi: 10.1021/acsomega.3c07836. eCollection 2024 Feb 20.

First In Vitro- In Silico Analysis for the Determination of Antimicrobial and Antioxidant Properties of 2-(4-Methoxyphenylamino)-2-oxoethyl Methacrylate and p-Acetamide

Mehmet Mürşit Temüz  1 , Nevin Çankaya  2 , Safiye Elif Korcan  2 , Serap Yalçin Azarkan  3 , Tuğba Kahraman  4
Affiliations

First In Vitro- In Silico Analysis for the Determination of Antimicrobial and Antioxidant Properties of 2-(4-Methoxyphenylamino)-2-oxoethyl Methacrylate and p-Acetamide

Mehmet Mürşit Temüz et al. ACS Omega. .

Abstract

The antibacterial, antifungal, and antioxidant activities of 2-chloro-N-(4-methoxyphenyl)acetamide (p-acetamide) and 2-(4-methoxyphenylamino)-2-oxoethyl methacrylate (MPAEMA) were investigated by in vitro experiments and in silico analyses. MPAEMA has an antibacterial effect only against Gram-positive Staphylococcus aureus. It was determined that this did not affect any other bacteria and Candida glabrata yeast. On the other hand, p-acetamide showed antimicrobial activity against S. aureus ATCC 25923, C. glabrata ATCC 90030, Bacillus subtilis NRRL 744, Enterococcus faecalis ATCC 551289, Escherichia coli ATCC 25922, Klebsiella pneumoniae NRLLB4420, Pseudomonas aeruginosa ATCC 27853, and Listeria monocytogenes ATCC 1911. p-Acetamide showed the greatest antifungal effect by inhibiting the colony growth of Trichoderma longibrachiatum (98%). This was followed by Mucor plumbeus with 83% and Fusarium solani with 21%. MPAEMA inhibited colony growth of T. longibrachiatum by 95% and that of M. plumbeus by 91%. Also, p-acetamide and MPAEMA had a scavenging effect on free radicals. According to results of the in silico analysis, the antimicrobial effect of these compounds is due to their effect on DNA ligase. Based on drug-likeness analysis, they were found to be consistent with the Lipinski, Veber, or Ghose rule. p-Acetamide and MPAEMA may be used as drugs.

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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Figure 1
Figure 1
Synthesis of p-acetamide and MPAEMA.
Figure 2
Figure 2
Gel image of target DNA regions of isolates varying between 500 and 700 bp.
Figure 3
Figure 3
Microscopic views of fungal isolates. PDA: Potato Dextrose Agar; CA: Czapek Agar; MEA: Malt Extract Agar.
Figure 4
Figure 4
Fungal isolates on agar.
Figure 5
Figure 5
p-Acetamide and DNA ligase interaction.
Figure 6
Figure 6
MPAEMA and DNA ligase interaction.
Figure 7
Figure 7
p-Acetamide and glucoamylase interaction.
Figure 8
Figure 8
MPAEMA and glucoamylase interaction.
Figure 9
Figure 9
MD simulations of the stability and fluctuations of glucoamylase-p-acetamide (RMSD, RMSF, and hydrogen bonds).
Figure 10
Figure 10
MD simulations of the stability and fluctuations of glucoamylase–MPAEMA (RMSD, RMSF, and hydrogen bonds).
Figure 11
Figure 11
MD simulations of the stability and fluctuations of DNA ligase–p-acetamide (RMSD, RMSF, and hydrogen bonds).
Figure 12
Figure 12
MD simulations of the stability and fluctuations of DNA ligase–MPAEMA (RMSD, RMSF, and hydrogen bonds).
See this image and copyright information in PMC

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