A Mild Aqueous Sonogashira Reaction as a Fluorescent Labeling Strategy for 5-Bromide-2′-Deoxyuridine
AbstractC5-modified uridines are a valuable class of nucleoside analogues, both as potent chemotherapy agents and through their use as the conjunction site in DNA labeling strategies. As an important C5-modified uridine, BrdU has been used in cell proliferation assays since the 1980s. Currently, the detection of BrdU relies on traditional immunostaining; however, this approach has its limitations. Thus, it is desirable, albeit difficult, to develop chemistry methods to fluorescently label BrdU in a cellular context. In the present study, we report our efforts toward developing a robust chemistry methodology for BrdU fluorescent labeling. The Sonogashira reaction was chosen as the key reaction, and various alkynyl groups (aliphatic or aryl) containing fluorescent dyes were synthesized to cross-couple with BrdU. Various bases and catalyst systems were screened to evaluate the optimum conditions. A mild aqueous Sonogashira reaction (K2PdCl4, S-Phos, n-Bu4N+OH−, Sodium d-isoascorbate, EtOH/H2O = 1:1, 37 °C, Ar) was obtained to enable high-yielding BrdU fluorescent labeling. View Full-Text
Share & Cite This Article
Wang, S.; Gao, Y.; Shen, S.; Wen, H.; Cui, H. A Mild Aqueous Sonogashira Reaction as a Fluorescent Labeling Strategy for 5-Bromide-2′-Deoxyuridine. Molecules 2018, 23, 154.
Wang S, Gao Y, Shen S, Wen H, Cui H. A Mild Aqueous Sonogashira Reaction as a Fluorescent Labeling Strategy for 5-Bromide-2′-Deoxyuridine. Molecules. 2018; 23(1):154.Chicago/Turabian Style
Wang, Shufang; Gao, Yongxin; Shen, Shigang; Wen, Hui; Cui, Huaqing. 2018. "A Mild Aqueous Sonogashira Reaction as a Fluorescent Labeling Strategy for 5-Bromide-2′-Deoxyuridine." Molecules 23, no. 1: 154.
Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.