硝酰花青酰胺是一种多功能近红外荧光探针。
Norcyanine-Carbamates Are Versatile Near-Infrared Fluorogenic Probes.
机构信息
Chemical Biology Laboratory, Center for Cancer Research, National Cancer Institute, Frederick, Maryland 21702, United States.
Molecular Imaging Branch, Center for Cancer Research, National Cancer Institute, National Institutes of Health, Bethesda, Maryland 20892, United States.
出版信息
J Am Chem Soc. 2021 Apr 21;143(15):5674-5679. doi: 10.1021/jacs.1c02112. Epub 2021 Apr 12.
Abstract
Fluorogenic probes in the near-infrared (NIR) region have the potential to provide stimuli-dependent information in living organisms. Here, we describe a new class of fluorogenic probes based on the heptamethine cyanine scaffold, the most broadly used NIR chromophore. These compounds result from modification of heptamethine norcyanines with stimuli-responsive carbamate linkers. The resulting cyanine carbamates (CyBams) exhibit exceptional turn-ON ratios (∼170×) due to dual requirements for NIR emission: carbamate cleavage through 1,6-elimination and chromophore protonation. Illustrating their utility in complex settings, a γ-glutamate substituted CyBam was applied to imaging γ-glutamyl transpeptidase (GGT) activity in a metastatic model of ovarian cancer. Overall, CyBams have significant potential to extend the reach of fluorogenic strategies to intact tissue and live animal imaging applications.
摘要
近红外（NIR）区域的荧光探针具有在活生物体中提供依赖于刺激的信息的潜力。在这里，我们描述了一类基于七甲川菁染料骨架的新型荧光探针，这是最广泛使用的 NIR 生色团。这些化合物是通过用对刺激响应的氨基甲酸酯连接子修饰七甲川正电荷菁染料得到的。所得的菁氨基甲酸酯（CyBams）由于 NIR 发射的双重要求，表现出异常的开比值（约 170×）：氨基甲酸酯通过 1,6-消除和生色团质子化断裂。为了说明它们在复杂环境中的应用，将一个γ-谷氨酸取代的 CyBam 应用于卵巢癌转移模型中γ-谷氨酰转肽酶（GGT）活性的成像。总的来说，CyBams 具有将荧光探针策略扩展到完整组织和活体动物成像应用的巨大潜力。
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