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Synthesis, binding, nuclease resistance and cellular uptake properties of 2'-O-acetalester-modified oligonucleotides containing cationic groups.

Abstract：

:We report on the synthesis and properties of oligonucleotides (ONs) with 2'-O-acetalester modifications containing cationic side chains in a prodrug-like approach. In the aim to improve cell penetration and nuclease resistance, various different amino- or guanidino-acetalester were grafted to 2'-OH of uridine and the corresponding phosphoramidites were incorporated into ONs. Introduction of 2'-O-(2-aminomethyl-2-ethyl)butyryloxymethyl (AMEBuOM) modification into 2'-OMe ONs leads to high resistance towards enzymatic degradation and to destabilization of duplexes with complementary RNA strand. Spontaneous uptake experiments of a twelve-mer containing ten 2'-O-AMEBuOM-U units into A673 cells showed moderate internalization of ON within the cells whereas substantial internalization of the corresponding lipophilic 2'-O-pivaloyloxymethyl ON was observed for the first time.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Biscans A,Rouanet S,Bertrand JR,Vasseur JJ,Dupouy C,Debart F

doi

10.1016/j.bmc.2015.07.054

subject

Has Abstract

pub_date

2015-09-01 00:00:00

pages

5360-8

issue

17

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(15)00638-0

journal_volume

23

pub_type

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