Gnaim Samer, Scomparin Anna, Eldar-Boock Anat, Bauer Christoph R, Satchi-Fainaro Ronit, Shabat Doron
School of Chemistry , Raymond and Beverly Sackler Faculty of Exact Sciences , Israel . Email:
Department of Physiology and Pharmacology , Sackler Faculty of Medicine , Tel Aviv University , Tel Aviv 69978 , Israel.
Chem Sci. 2019 Jan 16;10(10):2945-2955. doi: 10.1039/c8sc05174g. eCollection 2019 Mar 14.
Chemiluminescence offers advantages over fluorescence for bioimaging, since an external light source is unnecessary with chemiluminescent agents. This report demonstrates the first encapsulation of chemiluminescence phenoxy-adamantyl-1,2-dioxetane probes with trimethyl β-cyclodextrin. Clear proof for the formation of a 1 : 1 host-guest complex between the adamantyl-1,2-dioxetane probe and trimethyl β-cyclodextrin was provided by mass spectroscopy and NMR experiments. The calculated association constant of this host-guest system, 253 M, indicates the formation of a stable inclusion complex. The inclusion complex significantly amplified the light emission intensity relative to the noncomplexed probe under physiological conditions. Complexation of adamantyl-dioxetane with fluorogenic dye-tethered cyclodextrin resulted in light emission through energy transfer to a wavelength that corresponds to the fluorescent emission of the conjugated dye. Remarkably, the light emission intensity of this inclusion complex was approximately 1500-fold higher than that of the non-complexed adamantyl-dioxetane guest. We present the first demonstration of microscopic cell images obtained using a chemiluminescence supramolecular dioxetane probe and demonstrate the utility of these supramolecular complexes by imaging of enzymatic activity and bio-analytes and . We anticipate that the described chemiluminescence supramolecular dioxetane probes will find use in various biological applications.
与荧光成像相比，化学发光在生物成像方面具有优势，因为化学发光剂无需外部光源。本报告展示了首次将化学发光苯氧基 - 金刚烷基 - 1,2 - 二氧杂环丁烷探针与三甲基β - 环糊精进行封装。质谱和核磁共振实验为金刚烷基 - 1,2 - 二氧杂环丁烷探针与三甲基β - 环糊精之间形成1:1主客体复合物提供了明确证据。该主客体系统的计算缔合常数为253 M，表明形成了稳定的包合物。在生理条件下，包合物相对于未复合的探针显著放大了发光强度。金刚烷基二氧杂环丁烷与荧光染料连接的环糊精络合导致通过能量转移发光至与共轭染料荧光发射相对应的波长。值得注意的是，该包合物的发光强度比未复合的金刚烷基二氧杂环丁烷客体高出约1500倍。我们首次展示了使用化学发光超分子二氧杂环丁烷探针获得的微观细胞图像，并通过对酶活性和生物分析物成像证明了这些超分子复合物的实用性。我们预计所描述的化学发光超分子二氧杂环丁烷探针将在各种生物应用中得到应用。
