Department of Chemistry, Indian Institute of Technology Kharagpur, Kharagpur-721302, India.
Photochem Photobiol Sci. 2012 Jul;11(7):1239-50. doi: 10.1039/c2pp25033k. Epub 2012 May 8.
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.
一系列新的（E）-蒽酮肟酯羧酸化合物包括氨基酸，通过与环境敏感荧光团 1-乙酰基蒽结合而合成。（E）-蒽酮肟酯表现出强烈的荧光性质，有趣的是，它们的荧光性质对周围环境高度敏感。（E）-蒽酮肟酯的直接紫外线（≥350nm）照射导致光贝克曼重排产物和 N-O 键均裂产物的形成。光产物的形成及其分布发现与溶剂有关。此外，我们还表明（E）-蒽酮肟酯可以有效地插入 DNA 并进行光解。最后，我们还表明这些肟酯可以有效地穿透细胞，并在光照下引起细胞毒性。
