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Synthesis, primary photophysical and antibacterial properties of naphthyl ester cinoxacin and nalidixic acid derivatives

Paper ID Volume ID Publish Year Pages File Format Full-Text
30555 44486 2008 8 PDF Available
Title
Synthesis, primary photophysical and antibacterial properties of naphthyl ester cinoxacin and nalidixic acid derivatives
Abstract

We have synthesized two naphthyl ester quinolone derivates and determined their ability to generate reactive oxygen species (ROS) such as 1O2, OH, H2O2 upon photolysis with UV-A light. The ability of cinoxacin (1) and nalidixic acid (2), and their naphthyl ester derivatives (3 and 4) to generate a dose-dependent amount of singlet oxygen and ROS (−O2, OH) in cell-free systems was detected by histidine assay and by luminol-enhanced chemiluminescence (LCL), respectively. Their electronic absorption and emission spectra were quantified and their photostability was determined. Their tendency to generate peroxidic derivative species showed the following order: 3 > 4; in contrast, their ability to generate singlet oxygen was 4 > 3 and these were better sensitizers than their parent quinolones 1 and 2. The antibacterial activity in darkness and under irradiation of compounds 3 and 4 was tested on Escherichia coli and compared with that of their parent compounds. An enhanced antibacterial activity by irradiation of the naphthyl esters of cinoxacin and nalidixic acid on E. coli was observed.

Keywords
Antibacterial; Cinoxacin; Nalidixic acid; Photostability; Photochemical activity; Quinolone
First Page Preview
Synthesis, primary photophysical and antibacterial properties of naphthyl ester cinoxacin and nalidixic acid derivatives
Publisher
Database: Elsevier - ScienceDirect
Journal: Journal of Photochemistry and Photobiology B: Biology - Volume 92, Issue 2, 21 August 2008, Pages 83–90
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Bioengineering