Combining Aminocyanine Dyes with Polyamide Dendrons: A Promising Strategy for Imaging in the Near-Infrared Region
Combining Aminocyanine Dyes with Polyamide Dendrons: A Promising Strategy for Imaging in the Near-Infrared Region
复制标题
DOI：
10.1002/chem.201002268
复制
发表时间：
2011-03-01
影响因子：
4.3
通讯作者：
Weck, Marcus
中科院分区：
文献类型：
--
作者：
Ornelas, Catia;Lodescar, Rachelle;Weck, Marcus
菁染料以其在近红外(NIR)区域的荧光而闻名，这是生物应用的理想选择。我们报道了一系列含有末端官能团的氨基菁染料的合成，如酸、叠氮和环辛基，用于进一步的官能化，例如通过点击化学。这些氨基菁染料可以通过铜催化的叠氮炔环加成反应、应变促进的叠氮炔环加成反应、多肽偶联反应或直接的S(NR)1反应等方式连接到多官能团的树枝上。所得到的树枝状染料偶联物的产率很高，并且具有很高的化学稳定性和光稳定性。用紫外-可见光谱和荧光光谱研究了新化合物的光学性质。所有化合物在近红外区都表现出大的斯托克斯位移和强的荧光，具有高的量子产率，这是在体内光学成像的最佳性质。
Cyanine dyes are known for their fluorescence in the near-IR (NIR) region, which is desirable for biological applications. We report the synthesis of a series of aminocyanine dyes containing terminal functional groups such as acid, azide, and cyclooctyne groups for further functionalization through, for example, click chemistry. These aminocyanine dyes can be attached to polyfunctional dendrons by copper-catalyzed azide alkyne cycloaddition (CuAAC), strain-promoted azide alkyne cycloaddition (SPAAC), peptide coupling, or direct S(NR)1 reactions. The resulting dendron-dye conjugates were obtained in high yields and displayed high chemical stability and photostability. The optical properties of the new compounds were studied by UV/Vis and fluorescence spectroscopy. All compounds show large Stokes shifts and strong fluorescence in the NIR region with high quantum yields, which are optimal properties for in vivo optical imaging.