Synthesis and properties of triplex-forming oligonucleotides containing 2'-O-(2-methoxyethyl)-5-(3-aminoprop-1-ynyl)-uridine

Chenguang Lou; Qiang Xiao; Lavinia Brennan; Mark E Light; Nuria Vergara-Irigaray; Elizabeth M Atkinson; Lindy M Holden-Dye; Keith R Fox; Tom Brown

doi:10.1016/j.bmc.2010.07.005

Synthesis and properties of triplex-forming oligonucleotides containing 2'-O-(2-methoxyethyl)-5-(3-aminoprop-1-ynyl)-uridine

Chenguang Lou, Qiang Xiao, Lavinia Brennan, Mark E Light, Nuria Vergara-Irigaray, Elizabeth M Atkinson, Lindy M Holden-Dye, Keith R Fox, Tom Brown

Institut for Fysik, Kemi og Farmaci

Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › peer review

Abstract

2'-O-(2-Methoxyethyl)-5-(3-aminoprop-1-ynyl)-uridine phosphoramidite (MEPU) has been synthesized from d-ribose and 5-iodouracil and incorporated into triplex-forming oligonucleotides (TFOs) by automated solid-phase oligonucleotide synthesis. The TFOs gave very high triplex stability with their target duplexes as measured by ultraviolet/fluorescence melting and DNase I footprinting. The incorporation of MEPU into TFOs renders them resistant to degradation by serum nucleases.

Originalsprog	Engelsk
Tidsskrift	Bioorganic & Medicinal Chemistry Letters
Vol/bind	18
Udgave nummer	17
Sider (fra-til)	6389-6397
ISSN	0960-894X
DOI	https://doi.org/10.1016/j.bmc.2010.07.005
Status	Udgivet - 2010

Dokumenter og links

10.1016/j.bmc.2010.07.005

Citationsformater

@article{1eb038c9eaca4c67902c6dcf2b36f528,

title = "Synthesis and properties of triplex-forming oligonucleotides containing 2'-O-(2-methoxyethyl)-5-(3-aminoprop-1-ynyl)-uridine",

abstract = "2'-O-(2-Methoxyethyl)-5-(3-aminoprop-1-ynyl)-uridine phosphoramidite (MEPU) has been synthesized from d-ribose and 5-iodouracil and incorporated into triplex-forming oligonucleotides (TFOs) by automated solid-phase oligonucleotide synthesis. The TFOs gave very high triplex stability with their target duplexes as measured by ultraviolet/fluorescence melting and DNase I footprinting. The incorporation of MEPU into TFOs renders them resistant to degradation by serum nucleases.",

keywords = "DNA Footprinting, Humans, Nucleic Acid Conformation, Oligodeoxyribonucleotides, Structure-Activity Relationship, Uridine",

author = "Chenguang Lou and Qiang Xiao and Lavinia Brennan and Light, {Mark E} and Nuria Vergara-Irigaray and Atkinson, {Elizabeth M} and Holden-Dye, {Lindy M} and Fox, {Keith R} and Tom Brown",

year = "2010",

doi = "10.1016/j.bmc.2010.07.005",

language = "English",

volume = "18",

pages = "6389--6397",

journal = "Bioorganic & Medicinal Chemistry Letters",

issn = "0960-894X",

publisher = "Elsevier",

number = "17",

}

TY - JOUR

T1 - Synthesis and properties of triplex-forming oligonucleotides containing 2'-O-(2-methoxyethyl)-5-(3-aminoprop-1-ynyl)-uridine

AU - Lou, Chenguang

AU - Xiao, Qiang

AU - Brennan, Lavinia

AU - Light, Mark E

AU - Vergara-Irigaray, Nuria

AU - Atkinson, Elizabeth M

AU - Holden-Dye, Lindy M

AU - Fox, Keith R

AU - Brown, Tom

PY - 2010

Y1 - 2010

N2 - 2'-O-(2-Methoxyethyl)-5-(3-aminoprop-1-ynyl)-uridine phosphoramidite (MEPU) has been synthesized from d-ribose and 5-iodouracil and incorporated into triplex-forming oligonucleotides (TFOs) by automated solid-phase oligonucleotide synthesis. The TFOs gave very high triplex stability with their target duplexes as measured by ultraviolet/fluorescence melting and DNase I footprinting. The incorporation of MEPU into TFOs renders them resistant to degradation by serum nucleases.

AB - 2'-O-(2-Methoxyethyl)-5-(3-aminoprop-1-ynyl)-uridine phosphoramidite (MEPU) has been synthesized from d-ribose and 5-iodouracil and incorporated into triplex-forming oligonucleotides (TFOs) by automated solid-phase oligonucleotide synthesis. The TFOs gave very high triplex stability with their target duplexes as measured by ultraviolet/fluorescence melting and DNase I footprinting. The incorporation of MEPU into TFOs renders them resistant to degradation by serum nucleases.

KW - DNA Footprinting

KW - Humans

KW - Nucleic Acid Conformation

KW - Oligodeoxyribonucleotides

KW - Structure-Activity Relationship

KW - Uridine

U2 - 10.1016/j.bmc.2010.07.005

DO - 10.1016/j.bmc.2010.07.005

M3 - Journal article

C2 - 20674370

SN - 0960-894X

VL - 18

SP - 6389

EP - 6397

JO - Bioorganic & Medicinal Chemistry Letters

JF - Bioorganic & Medicinal Chemistry Letters

IS - 17

ER -

Synthesis and properties of triplex-forming oligonucleotides containing 2'-O-(2-methoxyethyl)-5-(3-aminoprop-1-ynyl)-uridine

Abstract

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