Kim Eunha, Koh Minseob, Ryu Jihoon, Park Seung Bum
Department of Chemistry, Seoul National University, Seoul 151-747, Korea.
J Am Chem Soc. 2008 Sep 17;130(37):12206-7. doi: 10.1021/ja8020268. Epub 2008 Aug 23.
We developed a novel fluorescent core skeleton, 1,2-dihydropyrrolo[3,4-beta]indolizin-3-one, by complexity-generating one-pot reactions through 1,3-dipolar cyclization followed by oxidative aromatization. This fluorescent core skeleton can accommodate various wavelengths of emission maxima by changing the electronic properties of substituents, which was postulated by computational studies. The full-color-tunable emission maxima were achieved with a single core skeleton by changing the substituents using the combinatorial approach. These novel fluorophores have excellent photophysical and photochemical properties: moderate to excellent quantum yields, resistance to the photobleaching, pH-independent fluorescence, large Stokes shifts, druglike lipophilicity for membrane permeability, etc. Further, we successfully demonstrated the bioapplication of fluorophores B1 and B5 in the immunofluorescence for visualizing cellular compartments of HeLa cells.
我们通过1,3-偶极环化随后氧化芳构化的一锅法反应生成复杂结构，开发了一种新型荧光核心骨架——1,2-二氢吡咯并[3,4-β]中氮茚-3-酮。这种荧光核心骨架可通过改变取代基的电子性质来适应各种发射最大值波长，这是通过计算研究推测出来的。通过组合方法改变取代基，用单一核心骨架实现了全色可调发射最大值。这些新型荧光团具有优异的光物理和光化学性质：量子产率适中至优异、抗光漂白、pH无关荧光、大斯托克斯位移、具有类似药物的亲脂性以实现膜通透性等。此外，我们成功证明了荧光团B1和B5在免疫荧光中用于可视化HeLa细胞的细胞区室的生物应用。
