Issue 7, 2012

Synthesis, photophysical, photochemical, DNA cleavage/binding and cytotoxic properties of pyrene oxime ester conjugates

Abstract

A new series of (E)-pyrene oxime ester conjugates of carboxylic acids including amino acids were synthesized by coupling with an environment sensitive fluorophore 1-acetylpyrene. (E)-Pyrene oxime esters exhibited strong fluorescence properties and interestingly their fluorescence properties were found to be highly sensitive to the surrounding environment. Direct irradiation of the (E)-pyrene oxime esters by UV light (≥350 nm) resulted in both the photo-Beckmann rearrangement product and products resulting from N–O bond homolysis. Photoproduct formation and their distribution were found to be solvent dependent. Further, we also showed (E)-pyrene oxime esters intercalated into DNA efficiently and photo-cleaved DNA. Finally we also showed these oxime esters can permeate cells efficiently and may cause cytotoxicity upon irradiation of light.

Graphical abstract: Synthesis, photophysical, photochemical, DNA cleavage/binding and cytotoxic properties of pyrene oxime ester conjugates

Supplementary files

Article information

Article type
Paper
Submitted
12 Feb 2012
Accepted
31 Mar 2012
First published
13 Apr 2012

Photochem. Photobiol. Sci., 2012,11, 1239-1250

Synthesis, photophysical, photochemical, DNA cleavage/binding and cytotoxic properties of pyrene oxime ester conjugates

N. Chowdhury, S. Dutta, S. Dasgupta, N. D. P. Singh, M. Baidya and S. K. Ghosh, Photochem. Photobiol. Sci., 2012, 11, 1239 DOI: 10.1039/C2PP25033K

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