title: 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.
authors.affiliation: Department of Chemistry, Indian Institute of Technology Kharagpur, Kharagpur-721302, India.
authors.forename: Nilanjana
authors.initials: N
authors.lastname: Chowdhury
authors.forename: Sansa
authors.initials: S
authors.lastname: Dutta
authors.forename: Swagata
authors.initials: S
authors.lastname: Dasgupta
authors.forename: N D Pradeep
authors.initials: ND
authors.lastname: Singh
authors.forename: Mithu
authors.initials: M
authors.lastname: Baidya
authors.forename: S K
authors.initials: SK
authors.lastname: Ghosh
mesh_terms: D016475:3T3 Cells; D000818:Animals; D001665:Binding Sites; D045744:Cell Line, Tumor; D002463:Cell Membrane Permeability / Q000187:drug effects; D002470:Cell Survival / Q000187:drug effects / Q000528:radiation effects; D003198:Computer Simulation; D004247:DNA / Q000378:metabolism*; D053837:DNA Cleavage / Q000187:drug effects* / Q000528:radiation effects; D004952:Esters; D006801:Humans; D007364:Intercalating Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity; D051379:Mice; D010091:Oximes / Q000737:chemistry*; D010782:Photolysis; D011721:Pyrenes / Q000737:chemistry*; D013050:Spectrometry, Fluorescence; D014466:Ultraviolet Rays
chemical_list: D004952:Esters; D007364:Intercalating Agents; D010091:Oximes; D011721:Pyrenes; D004247:DNA; C030984:pyrene