Instituto de Química Médica (CSIC). Juan de la Cierva 3, 28006, Madrid, Spain.
Instituto de Ciencia y Tecnología de Polímeros (CSIC), CIBER-BBN, Juan de la Cierva 3, 28006, Madrid, Spain.
Eur J Med Chem. 2020 Aug 15;200:112407. doi: 10.1016/j.ejmech.2020.112407. Epub 2020 May 16.
The photophysical properties of naphthalimide-based fluorophores can be easily tuned by chemical manipulation of the substituents on that privileged scaffold. Replacement of a OMe group at position 6 in 2-(hydroxyl)ethyl-naphthalimide derivatives by diverse amines, including 2-(hydroxyl)ethylamine, trans-(4-acetamido)cyclohexylamine and azetidine increases the solvatochromic (ICT) character, while this replacement in 2-(dimethylamino)ethyl-naphthalimide analogues (PET fluorophores) decrease their solvent polarity sensitivity or even reversed them to solvatochromic fluorophores. These fluorophores resulted macrophage nucleus imaging probes, which bind DNA as intercalants and showed low cytotoxicity in human cancer cells.
萘酰亚胺类荧光团的光物理性质可以通过对该优势骨架上取代基的化学修饰来轻松调节。在 2-（羟乙基）萘酰亚胺衍生物中，将 6 位的 OMe 基团替换为各种胺，包括 2-（羟乙基）胺、反式-（4-乙酰氨基）环己胺和氮杂环丁烷，会增加溶剂致变色（ICT）特性，而在 2-（二甲基氨基）乙基-萘酰亚胺类似物（PET 荧光团）中进行这种取代会降低它们对溶剂极性的敏感性，甚至将其反转成溶剂致变色荧光团。这些荧光团被用作巨噬细胞核成像探针，它们作为嵌入剂与 DNA 结合，并在人类癌细胞中表现出低细胞毒性。
