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Synthesis of new water-soluble polyarene-substituted naphtho[1,2-d]oxazole-based fluorophores as fluorescent dyes and biological photosensitizers
Dyes and Pigments ( IF 4.1 ) Pub Date : 2022-05-18 , DOI: 10.1016/j.dyepig.2022.110410
Nataliya V. Slovesnova , Artem S. Minin , Leonid T. Smolyuk , Olga S. Taniya , Anton N. Tsmokalyuk , Grigory A. Kim , Igor S. Kovalev , Varvara A. Pozdina , Dmitry S. Kopchuk , Alexey P. Krinochkin , Grigory V. Zyryanov , Alexander Yu Petrov , Valery N. Charushin

Two new water-soluble PAH-substituted (PAH - polyaromatic hydrocarbon) naphtho[1,2-d] [1,3]oxazole dyes 12 were synthesized and investigated for intramolecular charge transfer (ICT) behavior, aggregation, and ability to fluorescent staining and photosensitization on living cancer cells of HeLa and Vero cultures. To make clear this behavior a detailed analysis of the relationship between the structure and photophysical properties 12 were carried out based on experimental and computation data. As a result of the staining experiment, there was a diffuse distribution in the cytoplasm of 2-(9-anthracenyl)-containing naphthoxazole 1 as a hydrophilic fluorophore. Whereas 2-(1-pyrenyl)-derivative 2 showed accumulation in the endoplasmic reticulum, as well as additional distribution in lipid bilayers. Photodynamic activity of type II was confirmed for the cationic exogenous photosensitizer 2: the IC50 value in the case of HeLa cell culture was 0.50 μM. The radical mechanism of photodynamic activity was determined by the EPR method.



中文翻译:

新型水溶性聚芳烃取代萘并[1,2-d]恶唑基荧光团作为荧光染料和生物光敏剂的合成

合成了两种新型水溶性 PAH 取代(PAH - 多环芳烃)萘并[1,2- d ] [1,3] 恶唑染料12 ,并研究了其分子内电荷转移 (ICT) 行为、聚集和HeLa 和 Vero 培养的活癌细胞的荧光染色和光敏作用。为了弄清这种行为,我们根据实验和计算数据对结构和光物理特性1-2之间的关系进行了详细分析。染色实验的结果是,含有 2-(9-蒽基)的萘恶唑1作为亲水性分子在细胞质中呈弥散分布。荧光团。而 2-(1-芘基)-衍生物2显示在内质网中的积累,以及在脂质双层中的额外分布。对于阳离子外源光敏剂2 ,证实了II型光动力活性:在HeLa细胞培养的情况下IC 50值为0.50μM。光动力活性的自由基机理由EPR方法确定。

更新日期:2022-05-18
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