Design, Synthesis and Antibacterial Activity Evaluation of 9-phenyl-10-(2-phenylalkyl) acridinium bromide: A Novel Acridine Based Antibacterial Agent

Order of Publishing in Issue: 
1
Volume :8
Issue :2
April, 2014
Page No: 
114-123
Authors: 
Roshali T. de Silva[1], Rohan P. Perera[1]
Authors: 
Chandrika M.Nanayakkara[2]
Address: 
[1]Organic Research Laboratory, Department of Chemistry, Faculty of Science, University of Colombo, Sri Lanka
Address: 
[2]Department of Plant Sciences, Faculty of Science, University of Colombo, Sri Lanka
Email-ID: 
r.thavindra@gmail.com

The present study was carried out to develop an effective antibacterial agent from a new derivative of acridine. Acridine had been known as an active antibacterial agent with low toxicity since past. The novel acridine derivative, 9-phenyl-10-(2-phenylalkyl)acridinium bromide was synthesized and tested for antibacterial activity against Gram positive Staphylococcus aureus and Gram negative Escherichia coli. The combination reaction between 9-phenylacridine and alpha-(bromo) methylstyrenein THF medium was carried out to synthesize 9-phenyl-10-(2- phenylalkyl) acridinium bromide. Synthesis of 9- phenyl-10-(2-phenylalkyl) acridiniumbromide was confirmed by 1H-NMR spectroscopy. Antibacterial screening was carried out using disc diffusion and broth dilution methods. The activity was compared with protonated and unprotonated forms of 9-phenylacridine, which were the core starting materials of the novel derivative. The novel compound exerted an effective antibacterial activity against both S. aureus ATCC 25923 and E. coli ATCC 25922 with MICs (Minimum Inhibitory Concentration) of 7.48 μg/ ml and 4.41 μg/ml, also with MBCs (Minimum Bactericidal Concentration)of 375 μg/ml and 6000 μg/ml respectively. The activity against E. coli was higher than that against S. aureus. Thus, 9-phenyl-10-(2-phenylalkyl) acridinium bromide can plausibly be developed as an effective antibacterial agent with a broad spectrum of activity.

Keywords: 
Acridine derivatives, 9-phenyl-10- (2-phenylalkyl)acridinium bromide, Antibacterial activity,Minimum Inhibitory Concentration
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