Polymerase-mediated high-density incorporation of amphiphilic functionalities into DNA: Enhancement of nuclease resistance and stability in human serum

被引：16

作者：

Fujita, Hiroto ^{[1
]}

Nakajima, Kohsuke ^{[1
]}

Kasahara, Yuuya ^{[1
,2
]}

Ozaki, Hiroaki ^{[1
]}

Kuwahara, Masayasu ^{[1
]}

机构：

[1] Gunma Univ, Grad Sch Sci & Technol, Kiryu, Gunma 3768515, Japan

[2] Natl Inst Biomed Innovat NIBIO, Ibaraki, Osaka 5670085, Japan

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2015年 / 25卷 / 02期

基金：

日本学术振兴会; 日本科学技术振兴机构;

关键词：

Amphiphilic functionality; Biostability; DNA polymerase; High-density incorporation; Modified nucleoside triphosphate; CHAIN FATTY-ACIDS; ENZYMATIC PRODUCTION; TARGET BINDING; LIVING CELLS; OLIGONUCLEOTIDES; APTAMERS; ANALOGS; BASE; NANOPARTICLES; NUCLEOTIDES;

D O I：

10.1016/j.bmcl.2014.11.037

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Modified oligodeoxyribonucleotides (mdODNs) bearing multiple copies of an amphiphilic functional group were enzymatically synthesized by simultaneous incorporation of base-modified 5'-triphosphate analogs of 2'-deoxyguanosine (dG(am)TP), 2'-deoxyuridine (dU(am)TP), 2'-deoxyadenosine (dA(am)TP), and 2'-deoxycytosine (dC(am)TP). The amphiphilic functionality, that is, (E)-38,53-dioxo-2,5,8,11,14,17, 20,23,26,29,32,35-dodecaoxa-39,52-diazapentapentacont-54-en-55-yl group, consists of the water soluble dodeca(ethylene glycol) chain and the hydrophobic dodecyl chain. An enzymatically synthesized ODN, composed of a 20-mer 5'-terminal segment containing 2'-O,4'-C-methylene-bridged/linked bicyclic ribonucleotide (B/L nucleotide) and a 12-mer 3'-terminal segment containing the nucleobase-modified analogs, exhibits very high resistance against phosphodiesterase I and is stable in human serum for a longer period when compared with ODN, where the 12-mer 3'-terminal segment contains unmodified nucleotides. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：333 / 336

页数：4

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