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

Chowdhury, Nilanjana ; Dutta, Sansa ; Dasgupta, Swagata ; Pradeep Singh, N. D. ; Baidya, Mithu ; Ghosh, S. K. (2012) Synthesis, photophysical, photochemical, DNA cleavage/binding and cytotoxic properties of pyrene oxime ester conjugates Photochemical and Photobiological Sciences, 11 (7). pp. 1239-1250. ISSN 1474-905X

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Official URL: http://pubs.rsc.org/en/content/articlelanding/2012...

Related URL: http://dx.doi.org/10.1039/C2PP25033K

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.

Item Type:Article
Source:Copyright of this article belongs to Royal Society of Chemistry.
ID Code:113014
Deposited On:15 May 2018 09:17
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