Synthesis and antibacterial evaluation of amino acid–antibiotic conjugates

• Published in: Bioorganic & medicinal chemistry letters Vol. 24; no. 7; pp. 1856 - 1861
• Main Authors: Ibrahim, Mohamed A., Panda, Siva S., Birs, Antoinette S., Serrano, Juan C., Gonzalez, Claudio F., Alamry, Khalid A., Katritzky, Alan R.
• Format: Journal Article
• Language: English
• Published: England Elsevier Ltd 01-04-2014
• Subjects: Amino Acids - chemistry; Anti-Bacterial Agents - chemical synthesis; Anti-Bacterial Agents - chemistry; Anti-Bacterial Agents - pharmacology; Antibacterial; Antibiotics; Bacillus subtilis; Bacillus subtilis - drug effects; Benzotriazole; Conjugates; Dose-Response Relationship, Drug; Escherichia coli; Escherichia coli - drug effects; Lipophilicity; Metronidazole - chemical synthesis; Metronidazole - chemistry; Metronidazole - pharmacology; Microbial Sensitivity Tests; Molecular Structure; Pseudomonas aeruginosa; Pseudomonas aeruginosa - drug effects; Quinolones - chemical synthesis; Quinolones - chemistry; Quinolones - pharmacology; Staphylococcus aureus; Staphylococcus aureus - drug effects; Structure-Activity Relationship; Sulfadiazine - chemical synthesis; Sulfadiazine - chemistry; Sulfadiazine - pharmacology; Conjugates; Antibacterial; Antibiotics; Benzotriazole; Lipophilicity
• ISSN: 0960-894X; 1464-3405
• DOI: 10.1016/j.bmcl.2014.01.065

Amino acid conjugates of quinolone, metronidazole and sulfadiazine antibiotics were synthesized in good yields using benzotriazole methodology. All the conjugates were screened for their antibacterial activity using methods adapted from the Clinical and Laboratory Standards Institute. Antibiotic conjugates were tested for activity in four medically relevant organisms; Staphylococcus aureus (RN4220), Escherichia coli (DH5α), Pseudomonas aeruginosa (PAO1), and Bacillus subtilis (168). Several antibiotic conjugates show promising results against several of the strains screened.