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New, stronger nucleophiles for nucleic acid-templated chemistry: Synthesis and application in fluorescence detection of cellular RNA.

Abstract：

:Nucleic acid-templated chemistry is a promising strategy for imaging genetic sequences in living cells. Here we describe the synthesis of two new nucleophiles for use in templated nucleophilic displacements with DNA probes. The nucleophilic groups are phosphorodithioate and phosphorotrithioate; we report on synthetic methods for introducing these groups at the 3'-terminus of oligonucleotides. Both new nucleophiles are found to be more highly reactive than earlier phosphoromonothioates. This increased nucleophilicity is shown to result in more rapid templated reactions with electrophilic DNA probes. The new probes were demonstrated in detection of specific genetic sequences in solution, with clear signal over background being generated in as little as 20 min. The probes were also tested for imaging ribosomal RNA sequences in live Escherichia coli; useful signal was generated in 20 min to 1h, approximately one quarter to one-half the time of earlier monothioate probes, and the signal-to-noise ratio was increased as well.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Miller GP,Silverman AP,Kool ET

doi

10.1016/j.bmc.2007.04.051

subject

Has Abstract

pub_date

2008-01-01 00:00:00

pages

56-64

issue

1

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(07)00379-3

journal_volume

16

pub_type

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