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

Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology
Nilanjana ChowdhuryS K Ghosh

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.

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Citations

Mar 8, 2016·Journal of Photochemistry and Photobiology. B, Biology·Nicolaos-Panagiotis AndreouKonstantina C Fylaktakidou
Mar 10, 2016·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·A PapastergiouK C Fylaktakidou
Apr 2, 2016·Molecular BioSystems·Atanu Singha RoySwagata Dasgupta
Nov 9, 2019·Chemical Communications : Chem Comm·Karthik SambathYuanwei Zhang
Jul 5, 2016·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Milena PasolliKonstantina C Fylaktakidou
Apr 8, 2020·Beilstein Journal of Organic Chemistry·Panagiotis S GritzapisKonstantina C Fylaktakidou
Oct 31, 2020·Chemical Reviews·Roy WeinstainPetr Klán

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