Effect of C-5 position on the photochemical properties and phototoxicity of antofloxacin and levofloxacin: A stable and transient study.

Abstract

The photochemistry of two structure-related fluoroquinolones (FQs), antofloxacin (ANT) and levofloxacin (LEV), was studied in aqueous solution using stable and transient methods. The properties for energy transfer and electron transfer of these two FQs were also studied. The transient absorption spectra of FQs were observed, and transient species were assigned. The LEV triplet state ((3)LEV(⁎)) spectra (λmax = 610 nm) were determined, whereas the transient absorption of ANT could not be observed. The decay rate constant of (3)LEV(⁎) via unimolecular attenuation, self-quenching, and quenching by oxygen was 3.2 × 10(5) s(-1), 6.72 × 10(8) M(-1) s(-1), and 1.01 × 10(9) M(-1) s(-1), respectively. A reasonable diagram showing the decay of (1)FQs* consisting of various substituents at the C-5 position was proposed. The phototoxicity of LEV and ANT was investigated and compared. Insertion of an amino group at the C-5 position made ANT relatively photostable and non-phototoxic compared with LEV.

• Authors: Jianfeng Zhao, Yancheng Liu, Xingxing Jiang, Ping Guo, Yulie Xu, Peng Zhang, Tianyi Ji, Zheshuai Lin, Wenfeng Wang
• Journal: Journal of photochemistry and photobiology. B, Biology (J Photochem Photobiol B) Vol. 155 Pg. 122-9 (Feb 2016) ISSN: 1873-2682 [Electronic] Switzerland
• PMID: 26746788 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
• Copyright: Copyright © 2015 Elsevier B.V. All rights reserved.

Chemical References

• Fluoroquinolones
• antofloxacin
• Levofloxacin
• Ofloxacin

Topics

• Electron Transport
• Electrophoresis, Polyacrylamide Gel
• Energy Transfer
• Fluoroquinolones (chemistry)
• Lasers, Solid-State
• Levofloxacin (chemistry)
• Ofloxacin (analogs & derivatives, chemistry)
• Photolysis (radiation effects)
• Quantum Theory