A Mild Aqueous Sonogashira Reaction as a Fluorescent Labeling Strategy for 5-Bromide-2'-Deoxyuridine.
Molecules
; 23(1)2018 Jan 12.
Article
em En
| MEDLINE
| ID: mdl-29329267
ABSTRACT
C5-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-Bu4NâºOH-, Sodium d-isoascorbate, EtOH/H2O = 11, 37 °C, Ar) was obtained to enable high-yielding BrdU fluorescent labeling.
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Texto completo:
1
Base de dados:
MEDLINE
Assunto principal:
Bromodesoxiuridina
/
Alcinos
/
Corantes Fluorescentes
Limite:
Humans
Idioma:
En
Ano de publicação:
2018
Tipo de documento:
Article