Bioinspired large Stokes shift small molecular dyes for biomedical fluorescence imaging

用于生物医学荧光成像的仿生大斯托克斯位移小分子染料

主讲人：文正

Sci. Adv., 8 (31), eabo3289. • DOI: 10.1126/sciadv.abo3289

Abstract:

         Long Stokes shift dyes that minimize cross-talk between the excitation source and fluorescent emission to improve the signal-to-background ratio are highly desired for fluorescence imaging. However, simple small molecular dyes with large Stokes shift (more than 120 nanometers) and near-infrared (NIR) emissions have been rarely reported so far. Here, inspired by the chromophore chemical structure of fluorescent proteins, we designed and synthesized a series of styrene oxazolone dyes (SODs) with simple synthetic methods, which show NIR emissions (>650 nanometers) with long Stokes shift (ranged from 136 to 198 nanometers) and small molecular weight (<450 daltons). The most promising SOD9 shows rapid renal excretion and blood-brain barrier passing properties. After functioning with the mitochondrial-targeted triphenylphosphonium (TPP) group, the resulting SOD9-TPP can be engineered for head-neck tumor imaging, fluorescence image–guided surgery, brain neuroimaging, and on-site pathologic analysis. In summary, our findings add an essential small molecular dye category to the classical dyes.

摘要：

长斯托克斯移位染料，最大限度地减少激发源和荧光发射之间的串扰，以提高信号与背景比是荧光成像非常需要的。然而，具有大斯托克斯位移(大于120纳米)和近红外(NIR)发射的简单小分子染料迄今为止很少报道。本研究以荧光蛋白的发色团化学结构为灵感，采用简单的合成方法设计并合成了一系列苯乙烯-奥唑酮染料(SODs)，这些染料具有近红外发射(>650纳米)、长斯托克斯位移(136 ~ 198纳米)和小分子量(<450道尔顿)。最有希望的SOD9具有快速肾排泄和血脑屏障通过的特性。在与线粒体靶向三苯磷(TPP)基团一起发挥作用后，所得SOD9-TPP可用于头颈部肿瘤成像、荧光图像引导手术、脑神经成像和现场病理分析。总之，我们的发现为传统染料增加了一个重要的小分子染料类别。