2. Academic Validation
  3. Synthesis, biofilm formation inhibitory, and inflammation inhibitory activities of new coumarin derivatives

Synthesis, biofilm formation inhibitory, and inflammation inhibitory activities of new coumarin derivatives

  • Sci Rep. 2024 Apr 20;14(1):9106. doi: 10.1038/s41598-024-59072-w.
Ghada E Ahmed 1,  Zeinab A Elshahid 2,  Eslam Reda El-Sawy 3,  Mohamed S Abdel-Aziz 4,  Anhar Abdel-Aziem 5
Affiliations

Affiliations

  • 1 High Canal Institute of Engineering & Technology, Suez, Egypt.
  • 2 Chemistry of Natural and Microbial Products Department, Pharmaceutical and Drug Industries Research Institute, National Research Centre, Giza, Egypt.
  • 3 Chemistry of Natural Compounds Department, National Research Centre, Dokki, Giza, 12622, Egypt.
  • 4 Microbial Chemistry Department, Genetic Engineering and Biotechnology Institute, National Research Centre, Dokki, Giza, 12622, Egypt.
  • 5 Chemistry Department, Faculty of Science (Girl's Branch), Al-Azhar University, Cairo, 11754, Egypt. anhar@azhar.edu.eg.
PMID: 38643226 DOI: 10.1038/s41598-024-59072-w
Abstract

Coumarins are heterocycles of great interest in the development of valuable active structures in chemistry and biological domains. The ability of Coumarins to inhibit biofilm formation of Gram positive bacterium (Staphylococcus aureus), Gram negative bacterium (Escherichia coli) as well as the methicillin-resistant S. aureus (MRSA) has been previously described. In the present work, new hybrid coumarin-heterocycles have been synthesized via the reaction of coumarin-6-sulfonyl chloride and 6-aminocoumarin with different small heterocycle moieties. The biological efficacy of the new compounds was evaluated towards their ability to inhibit biofilm formation and their anti-inflammatory properties. The antimicrobial activities of the newly synthesized compounds were tested against Gram positive bacterium (S. aureus ATCC 6538), Gram negative bacterium (E. coli ATCC 25922), yeast (Candida albicans ATCC 10231) and the fungus (Aspergillus niger NRRL-A326). Compounds 4d, 4e, 4f, 6a and 9 showed significant MIC and MBC values against S. aureus, E. coli, C. albicans, and methicillin-resistant S. aureus (MRSA) with especial incidence on compound 9 which surpasses all the Other compounds giving MIC and MBC values of (4.88 and 9.76 µg/mL for S. aureus), (78.13 and 312.5 µg/mL for E. coli), (9.77 and 78.13 µg/mL for C. albicans), and (39.06 and 76.7 µg/mL for MRSA), respectively. With reference to the antibiofilm activity, compound 9 exhibited potent antibiofilm activity with IC50 of 60, 133.32, and 19.67 µg/mL against S. aureus, E. coli, and MRSA, (respectively) considering the reference drug (neomycin). Out of all studied compounds, the anti-inflammatory results indicated that compound 4d effectively inhibited nitric oxide production in lipopolysaccharide-(LPS-) stimulated RAW264.7 macrophage cells, giving NO% inhibition of 70% compared to Sulindac (55.2%).

Keywords

6-aminocoumarin; Anti-inflammatory; Antimicrobial; Biofilm; Coumarin-6-sulfonyl chloride; Heterocycles.

Figures
Products