CEA, LETI-MINATEC, Departement des Technologies pour la Biologie et la Sante, 17 rue des Martyrs, F-38054 Grenoble, France.
Bioconjug Chem. 2010 Apr 21;21(4):583-8. doi: 10.1021/bc900564w.
Quantum dots (QD) are inorganic nanocrystals with outstanding optical properties, specially suited for biological imaging applications. Their attachment to biomolecules in mild aqueous conditions for the design of bioconjugates is therefore highly desirable. 1,3-dipolar [3 + 2] cycloaddition between azides and terminal alkynes ("click chemistry") could represent an attractive QD functionalization method. Unfortunately, the use of the popular Cu(I)-catalyzed version of this reaction is not applicable for achieving this goal, since the presence of copper dramatically alters the luminescence properties of QD dispersions. We demonstrate here that copper-free click chemistry, between strained cyclooctyne functionalized QD and azido-biomolecules, leads to highly luminescent conjugates. In addition, we show that QD-cyclooctyne can be used at previously unreported low concentration (250 nM) for imaging the incorporation of azido-modified sialic acid in cell membrane glycoproteins.
量子点（QD）是具有出色光学性能的无机纳米晶体，特别适合生物成像应用。因此，非常希望在温和的水相条件下将其附着到生物分子上，以设计生物缀合物。叠氮化物和末端炔烃之间的 1,3-偶极子 [3 + 2] 环加成（“点击化学”）可以代表一种有吸引力的 QD 功能化方法。不幸的是，由于铜的存在会极大地改变 QD 分散体的发光性质，因此不能使用这种反应的流行 Cu（I）催化版本来实现这一目标。我们在这里证明，在不存在铜的情况下，应变环辛炔官能化的 QD 与叠氮基生物分子之间的点击化学反应会导致高发光的缀合物。此外，我们还表明，QD-环辛炔可以以前所未有的低浓度（250 nM）用于成像细胞膜糖蛋白中叠氮修饰的唾液酸的掺入。
