Gutiérrez Sara, Martínez-López David, Morón María, Sucunza David, Sampedro Diego, Domingo Alberto, Salgado Antonio, Vaquero Juan J
Departamento de Química Orgánica y Química Inorgánica, Universidad de Alcalá, Edificio de Farmacia, 28871, Alcalá de Henares, Madrid (Spain).
Departamento de Química, Centro de Investigación en Síntesis Química (CISQ), Universidad de La Rioja, Madre de Dios, 53, 26006, Logroño, La Rioja (Spain).
Chemistry. 2015 Dec 14;21(51):18758-63. doi: 10.1002/chem.201502929. Epub 2015 Nov 3.
The synthesis and photophysical behavior of an unexplored family of green fluorescent protein (GFP)-like chromophore analogues is reported. The compound (Z)-4-(4-hydroxybenzylidene)-1-propyl-2-(propylamino)-1H-imidazol-5(4 H)-one (p-HBDNI, 2 a) exhibits significantly enhanced fluorescence properties relative to the parent compound (Z)-5-(4-hydroxybenzylidene)-2,3-dimethyl-3,5-dihydro-4H-imidazol-4-one (p-HBDI, 1). p-HBDNI was considered as a model system and the photophysical properties of other novel 2-amino-3,5-dihydro-4H-imidazol-4-one derivatives were evaluated. Time-dependent DFT calculations were carried out to rationalize the results. The analogue AIDNI (2 c), in which the 4-hydroxybenzyl group of p-HBDNI was replaced by an azaindole group, showed improved photophysical properties and potential for cell staining. The uptake and intracellular distribution of 2 c in living cells was investigated by confocal microscopy imaging.
报道了一类尚未探索的绿色荧光蛋白（GFP）类发色团类似物的合成及其光物理行为。化合物（Z）-4-（4-羟基亚苄基）-1-丙基-2-（丙基氨基）-1H-咪唑-5（4H）-酮（p-HBDNI，2a）相对于母体化合物（Z）-5-（4-羟基亚苄基）-2,3-二甲基-3,5-二氢-4H-咪唑-4-酮（p-HBDI，1）表现出显著增强的荧光性质。将p-HBDNI视为模型体系，并评估了其他新型2-氨基-3,5-二氢-4H-咪唑-4-酮衍生物的光物理性质。进行了含时密度泛函理论计算以解释结果。类似物AIDNI（2c）中p-HBDNI的4-羟基苄基被氮杂吲哚基团取代，显示出改善的光物理性质和细胞染色潜力。通过共聚焦显微镜成像研究了2c在活细胞中的摄取和细胞内分布。
