Ultrabright and bioorthogonal labeling of cellular targets using semiconducting polymer dots and click chemistry.
Ultrabright and bioorthogonal labeling of cellular targets using semiconducting polymer dots and click chemistry.
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DOI：
10.1002/anie.201004260
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发表时间：
2010-12-03
影响因子：
16.6
通讯作者：
Chiu, Daniel T.
中科院分区：
文献类型：
--
作者：
Wu, Changfeng;Jin, Yuhui;Schneider, Thomas;Burnham, Daniel R.;Smith, Polina B.;Chiu, Daniel T.
点击化学描述了一组强大的化学反应，快速，选择性和高产率。[1]这些反应中最被认可的是铜（I）催化的叠氮化物-炔环加成反应，其已被应用于从材料科学到化学生物学的各个领域。[2-8]对于生物学应用，叠氮基和炔基都被认为是生物正交化学报告分子，因为它们不与任何天然生物官能团相互作用。因此，这些生物正交报告分子可以使用细胞的生物合成机制掺入靶生物分子中，以提供随后可以用外源探针标记的化学手柄。生物正交报告基因与遗传编码标签（例如绿色荧光蛋白（GFP））互补，[9]并提供了一种强大的标记生物分子的方法，而无需直接遗传编码。尽管细胞环境复杂，但通过点击化学进行的生物正交标记具有高灵敏度和低背景。然而，在实践中，灵敏度受到目标分子的丰度、化学报告物的标记效率和外源探针的性能的限制。[7]在几乎所有的情况下，明亮且光稳定的探针都是非常理想的，特别是对于低丰度生物分子的长期跟踪和灵敏检测。荧光纳米颗粒如量子点（Qdot）与传统荧光染料相比，具有更高的亮度和光稳定性。[10-12]然而，在点击化学的背景下，铜催化剂不可逆地淬灭Qdot荧光并阻止它们在基于铜催化的点击化学的各种应用中的使用。[13]由于铜的细胞毒性，无铜的生物正交方法，如施陶丁格连接和应变促进的叠氮化物-炔环加成，已被开发用于活细胞和体内应用。[7]量子点可以用于无铜方法中，[13，14]其中由铜引起的它们的不稳定性不是问题。然而，量子点的内在毒性，所造成的重金属离子的浸出，仍然是一个关键的问题。
Click chemistry describes a powerful set of chemical reactions that are rapid, selective, and produce high yields.[1] The most recognized of these reactions is the copper (I)-catalyzed azide-alkyne cycloaddition, which has been applied to diverse areas, ranging from materials science to chemical biology.[2–8] For biological applications, both azido and alkyne groups are considered to be bioorthogonal chemical reporters because they do not interact with any native biological functional groups. As a result, these bioorthogonal reporters can be incorporated into a target biomolecule using the cell’s biosynthetic machinery to provide chemical handles that can be subsequently tagged with exogenous probes. The bioorthogonal reporters are complementary to genetically encoded tags, such as green fluorescent protein (GFP),[9] and provide a powerful approach to tag biomolecules without the need of direct genetic encoding. Bioorthogonal labeling via click chemistry is highly sensitive with low background despite the complex cellular environment. In practice, however, the sensitivity is constrained by the abundance of the target molecules, the labeling efficiency of the chemical reporters, and the performance of the exogenous probes.[7] In almost all cases, bright and photostable probes are highly desirable, particularly for longterm tracking and sensitive detection of low-abundance biomolecules.Fluorescent nanoparticles such as quantum dots (Qdots) exhibit improved brightness and photostability over traditional fluorescent dyes.[10–12] In the context of click chemistry, however, the copper catalyst irreversibly quenches Qdot fluorescence and prevents their usage in the various applications based on copper-catalyzed click chemistry.[13] Because of copper’s cytotoxicity, copper-free bioorthogonal approaches, such as the Staudinger ligation and the strain-promoted azide-alkyne cycloaddition, have been developed for live cell and in vivo applications.[7] Qdots can be employed in the copper-free methods,[13, 14] where their instability caused by copper is not an issue. However, Qdots’ intrinsic toxicity, caused by the leaching of heavy metal ions, is still a critical concern.
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影响因子：
16.6
作者：
Moon, Joong Ho;McDaniel, William;Hancock, Lawrence E.
通讯作者：
Hancock, Lawrence E.
DOI：
10.1073/pnas.0911247107
发表时间：
2010-03-02
影响因子：
11.1
作者：
Breidenbach, Mark A.;Gallagher, Jennifer E. G.;Bertozzi, Carolyn R.
通讯作者：
Bertozzi, Carolyn R.
影响因子：
15
作者：
Howes, Philip;Green, Mark;Hughes, Mary
通讯作者：
Hughes, Mary
DOI：
10.1073/pnas.0811481106
发表时间：
2009-01-06
影响因子：
11.1
作者：
Laughlin, Scott T.;Bertozzi, Carolyn R.
通讯作者：
Bertozzi, Carolyn R.
影响因子：
56.9
作者：
Bruchez, M;Moronne, M;Alivisatos, AP
通讯作者：
Alivisatos, AP