Synthesis and characterization of pyridine-based organic salts: Their antibacterial, antibiofilm and wound healing activities

• Published in: Bioorganic chemistry Vol. 100; pp. 103937 - 103944
• Main Authors: Ali, Imdad, Burki, Samiullah, El-Haj, Babiker M., Shafiullah, Parveen, Samina, Nadeem, Hilal Şahin, Nadeem, Said, Shah, Muhammad Raza
• Format: Journal Article
• Language: English
• Published: SAN DIEGO Elsevier Inc 01.07.2020; Elsevier
• Subjects: Animals; Anti-Bacterial Agents - chemical synthesis; Anti-Bacterial Agents - chemistry; Anti-Bacterial Agents - pharmacology; Antibiofilm; Antimicrobial; Biochemistry & Molecular Biology; Biofilms - drug effects; Cationic salts; Chemistry; Chemistry, Organic; Escherichia coli - drug effects; Escherichia coli - physiology; Life Sciences & Biomedicine; Mice; Microbial Sensitivity Tests; Microscopy, Atomic Force; Physical Sciences; Pyridines - chemical synthesis; Pyridines - chemistry; Pyridines - pharmacology; Salts - chemistry; Science & Technology; Staphylococcus aureus - drug effects; Staphylococcus aureus - physiology; Structure-Activity Relationship; Synthesis; Wound Healing - drug effects; Wound healing activity; Antimicrobial; Synthesis; Antibiofilm; Cationic salts; Wound healing activity; AGENTS; QUATERNARY AMMONIUM-SALTS; EXTRACT; WATER
• ISSN: 0045-2068; 1090-2120
• DOI: 10.1016/j.bioorg.2020.103937

[Display omitted] •This study involves the antibacterial, antibiofilm and wound healing potentials screening of synthetic hydrazine based cationic salts.•Some of the synthesized organic salts showed good antibacterial, antibiofilm and wound healing activities.•Compounds QAS 2, 7 and 8 can be used for further mechanistic studies to be employed as antibacterial, antibiofilm and wound healing agents. In treating wounds, long lasting infection is considered the major impediment. Drugs are rendered ineffective by pathogenic microorganisms via antibiotic resistance and calls for designing and development of new drugs. Herein, we report synthesis of eight different N-alkylated pyridine-based organic salts QAS 1–8 and their antibacterial, antibiofilm and wound healing activities. 3-(2-R-hydrazinecarbonyl)-1-propylpyridinium Bromide was the parent compound while R group was varying in each salt composed of different aromatic aldehyde moieties. In the antibacterial activity against S. aureus and E. coli, amoxicillin shows IC50 near to 25 µg/mL inhibiting 58 ± 0.4% S. aureus while ceftriaxone inhibited 55 ± 0.5% E. coli at a concentration of 10 µg/mL. The highest IC50 (56 ± 0.5% against S. aureus; 55 ± 0.5% against E. coli) was shown by compound QAS 7 at the concentration of 100 µg/mL; followed by the QAS 6 (55 ± 0.5% against E. coli) and QAS 2 (55 ± 0.5% against E. coli). In the antibiofilm activity, QAS 6, QAS 1 and QAS 8 inhibited 58 ± 0.4% S. aureus at a concentration of 75 µg/mL, while QAS 2 inhibited E. coli at the same concentration and amount. QAS 7, 3 and 1 inhibited almost 90% while QAS 6 inhibited 95 ± 1.1%of E. coli at a concentration of 250 µg/mL. Highest MBIC was provided by QAS 7 (52 ± 0.4%) against S. aureus at a concentration of 50 µg/mL that is very near to the standard amoxicillin. Antibacterial and antibiofilm activity results were also supported by the atomic force microscopy (AFM). In the wound healing activity, QAS 8 healed 90.8 ± 4.3% of the wound in 21 days with an average period of epithelialization (POE) of 19 ± 1.4 days; that is far better than povidone iodine ointment (81.5 ± 3.3% of the wound in the 21 days with 22.4 ± 2.9 days of POE). It is concluded from this study that the synthesized compounds QAS 2, 7 and 8 can be used for further mechanistic studies to be employed as antibacterial, antibiofilm and wound healing agents.