Synthesis and Electrochemistry of Anthraquinone-Oligodeoxynucleotide Conjugates

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• 作者：Neil A. Whittemore ; Adam N. Mullenix ; Gopal B. Inamati ; Muthiah Manoharan ; P. Dan Cook ; Albert A. Tuinman ; David C. Baker ; and James Q. Chambers
• 刊名：Bioconjugate Chemistry
• 出版年：1999
• 出版时间：March 1999
• 年：1999
• 卷：10
• 期：2
• 页码：261 - 270
• 全文大小：136K
• 年卷期：v.10,no.2(March 1999)
• ISSN：1520-4812

文摘

Electroactive oligodeoxynucleotides (ODNs) with specific base sequences have a potential applicationas electrical sensors for DNA molecules. To this end, a phosphoramidite that bears a 9,10-anthraquinone (AQ) group tethered to the 2'-O of the uridine via a hexylamino linker, 2'-O-[6-[2-oxo(9,10-anthraquinon-2-yl)amino]hexyl]-5'-O-(4,4'-dimethoxytrityl)uridine 3'-[2-(cyanoethyl)bis(1-methylethyl)phosphoramidite] (3), has been synthesized and used to prepare three ODNs with tethered AQs usingstandard phosphoramidite chemistry. The synthetic methodology thus allows the synthesis of ODNswith electroactive tags attached to given locations in the base sequence. Cyclic voltammetric behaviorof these AQ-ODN conjugates was examined in aqueous buffer solutions at a hanging mercury dropelectrode. At slow sweep rates, nearly reversible two-electron waves characteristic of an adsorbedanthraquinone/hydroquinone redox couple was observed for all of the AQ-ODN conjugates. Approximate Langmuirian isotherms were found for the AQ-ODNs with molecular footprints, calculatedfrom the saturation coverages, that scaled with molecular size. The cyclic voltammetric response ofthe duplexes formed from the AQ-ODNs and their complementary ODN was complicated by thecompetitive adsorption of the individual ODNs and possibly the duplex species as well.